# Electronic Supplementary Material (ESI) for ChemComm.
# 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_sarpong98
_database_code_depnum_ccdc_archive 'CCDC 1048615'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound11
_chemical_name_common            Hiro-40
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O3'
_chemical_formula_weight         416.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_diffrn_refln_scan_width         0.5
_diffrn_refln_scan_rate          10
_space_group.centring_type       primitive

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2482(8)
_cell_length_b                   12.3730(13)
_cell_length_c                   24.270(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.430(2)
_cell_angle_gamma                90
_cell_volume                     2158.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.38

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            27272
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.692
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3962
_reflns_number_gt                3230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_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)+(0.0425P)²+0.9412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3962
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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
C1 C 0.47404(19) 0.31995(12) 0.53200(6) 0.0226(3) Uani 1 1 d . . . . .
H1A H 0.5104 0.3846 0.5548 0.027 Uiso 1 1 calc R U . . .
H1B H 0.4910 0.3367 0.4931 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5993(2) 0.22632(13) 0.55245(6) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.7312 0.2487 0.5546 0.031 Uiso 1 1 calc R U . . .
H2B H 0.5785 0.1652 0.5261 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5576(2) 0.19089(13) 0.60943(6) 0.0259(3) Uani 1 1 d . . . . .
H3A H 0.5914 0.2502 0.6362 0.031 Uiso 1 1 calc R U . . .
H3B H 0.6367 0.1279 0.6216 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3530(2) 0.16036(12) 0.61112(6) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.3392 0.1567 0.6515 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2253(2) 0.25500(12) 0.58814(6) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.0967 0.2248 0.5800 0.023 Uiso 1 1 calc R U . . .
C6 C 0.13859(19) 0.32194(12) 0.49430(6) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.19266(19) 0.36053(12) 0.43990(6) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.18403(19) 0.46995(12) 0.42731(6) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.1504 0.5204 0.4538 0.025 Uiso 1 1 calc R U . . .
C9 C 0.22446(19) 0.50576(12) 0.37607(6) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.2194 0.5805 0.3671 0.026 Uiso 1 1 calc R U . . .
C10 C 0.27219(19) 0.43030(12) 0.33846(6) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.2800(2) 0.32088(12) 0.34952(6) 0.0231(3) Uani 1 1 d . . . . .
H11 H 0.3119 0.2708 0.3226 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2400(2) 0.28592(12) 0.40088(6) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.2447 0.2110 0.4096 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2863(2) 0.04753(12) 0.58730(6) 0.0235(3) Uani 1 1 d . . . . .
C14 C 0.4341(2) -0.03848(13) 0.60571(7) 0.0311(4) Uani 1 1 d . . . . .
H14A H 0.3846 -0.1103 0.5951 0.047 Uiso 1 1 calc R U . . .
H14B H 0.4670 -0.0352 0.6461 0.047 Uiso 1 1 calc R U . . .
H14C H 0.5452 -0.0248 0.5876 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2400(2) 0.04370(13) 0.52382(6) 0.0273(4) Uani 1 1 d . . . . .
H15A H 0.1997 -0.0294 0.5123 0.041 Uiso 1 1 calc R U . . .
H15B H 0.3509 0.0629 0.5067 0.041 Uiso 1 1 calc R U . . .
H15C H 0.1400 0.0952 0.5119 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1092(2) 0.01615(13) 0.61240(7) 0.0285(4) Uani 1 1 d . . . . .
H16A H 0.0116 0.0697 0.6016 0.043 Uiso 1 1 calc R U . . .
H16B H 0.1366 0.0139 0.6530 0.043 Uiso 1 1 calc R U . . .
H16C H 0.0666 -0.0552 0.5986 0.043 Uiso 1 1 calc R U . . .
C17 C 0.21613(19) 0.34551(12) 0.63062(6) 0.0200(3) Uani 1 1 d . . . . .
C18 C 0.1656(2) 0.31678(12) 0.68345(6) 0.0231(3) Uani 1 1 d . . . . .
H18 H 0.1411 0.2432 0.6911 0.028 Uiso 1 1 calc R U . . .
C19 C 0.1515(2) 0.39290(12) 0.72339(6) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.1188 0.3713 0.7584 0.029 Uiso 1 1 calc R U . . .
C20 C 0.18486(19) 0.50316(12) 0.71349(6) 0.0208(3) Uani 1 1 d . . . . .
C21 C 0.1716(2) 0.58437(13) 0.75406(6) 0.0237(3) Uani 1 1 d . . . . .
H21 H 0.1427 0.5645 0.7898 0.028 Uiso 1 1 calc R U . . .
C22 C 0.1997(2) 0.69030(13) 0.74255(6) 0.0253(3) Uani 1 1 d . . . . .
H22 H 0.1924 0.7435 0.7704 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2396(2) 0.72141(13) 0.68945(6) 0.0265(3) Uani 1 1 d . . . . .
H23 H 0.2577 0.7956 0.6815 0.032 Uiso 1 1 calc R U . . .
C24 C 0.2523(2) 0.64513(12) 0.64924(6) 0.0230(3) Uani 1 1 d . . . . .
H24 H 0.2775 0.6670 0.6134 0.028 Uiso 1 1 calc R U . . .
C25 C 0.22855(19) 0.53428(12) 0.66032(6) 0.0200(3) Uani 1 1 d . . . . .
C26 C 0.24331(19) 0.45261(12) 0.61991(6) 0.0199(3) Uani 1 1 d . . . . .
H26 H 0.2730 0.4730 0.5844 0.024 Uiso 1 1 calc R U . . .
N1 N 0.27659(16) 0.29547(10) 0.53488(5) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.31560(17) 0.46827(11) 0.28421(5) 0.0256(3) Uani 1 1 d . . . . .
O1 O -0.02760(14) 0.31427(9) 0.49938(4) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.34583(16) 0.40014(10) 0.24978(4) 0.0349(3) Uani 1 1 d . . . . .
O3 O 0.32024(18) 0.56586(10) 0.27598(5) 0.0395(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4733(18) . ?
C1 C2 1.515(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.518(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.536(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.551(2) . ?
C4 C13 1.564(2) . ?
C4 H4 1.0000 . ?
C5 N1 1.4781(18) . ?
C5 C17 1.529(2) . ?
C5 H5 1.0000 . ?
C6 O1 1.2303(17) . ?
C6 N1 1.3502(18) . ?
C6 C7 1.5028(19) . ?
C7 C8 1.388(2) . ?
C7 C12 1.397(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(2) . ?
C10 N2 1.4700(18) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.535(2) . ?
C13 C14 1.535(2) . ?
C13 C16 1.540(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C26 1.369(2) . ?
C17 C18 1.424(2) . ?
C18 C19 1.365(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.411(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.419(2) . ?
C20 C25 1.421(2) . ?
C21 C22 1.361(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.410(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.413(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.422(2) . ?
C26 H26 0.9500 . ?
N2 O3 1.2250(17) . ?
N2 O2 1.2265(17) . ?

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
N1 C1 C2 111.83(12) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 109.75(12) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 113.71(12) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 109.77(12) . . ?
C3 C4 C13 117.60(12) . . ?
C5 C4 C13 113.55(12) . . ?
C3 C4 H4 104.9 . . ?
C5 C4 H4 104.9 . . ?
C13 C4 H4 104.9 . . ?
N1 C5 C17 112.28(12) . . ?
N1 C5 C4 111.35(11) . . ?
C17 C5 C4 112.73(11) . . ?
N1 C5 H5 106.7 . . ?
C17 C5 H5 106.7 . . ?
C4 C5 H5 106.7 . . ?
O1 C6 N1 123.42(13) . . ?
O1 C6 C7 118.85(13) . . ?
N1 C6 C7 117.72(12) . . ?
C8 C7 C12 120.24(13) . . ?
C8 C7 C6 119.61(13) . . ?
C12 C7 C6 120.03(13) . . ?
C9 C8 C7 120.03(14) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 118.48(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 122.84(14) . . ?
C11 C10 N2 118.67(13) . . ?
C9 C10 N2 118.49(13) . . ?
C10 C11 C12 118.26(14) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C7 120.14(14) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C15 C13 C14 108.93(12) . . ?
C15 C13 C16 107.72(13) . . ?
C14 C13 C16 107.24(13) . . ?
C15 C13 C4 114.56(12) . . ?
C14 C13 C4 109.90(13) . . ?
C16 C13 C4 108.22(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C17 C18 118.21(13) . . ?
C26 C17 C5 124.11(13) . . ?
C18 C17 C5 117.57(13) . . ?
C19 C18 C17 121.25(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.07(14) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 122.55(14) . . ?
C19 C20 C25 118.66(13) . . ?
C21 C20 C25 118.77(14) . . ?
C22 C21 C20 120.95(14) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.28(14) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.25(15) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.83(14) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C20 118.89(13) . . ?
C24 C25 C26 122.46(13) . . ?
C20 C25 C26 118.64(13) . . ?
C17 C26 C25 122.09(13) . . ?
C17 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C6 N1 C1 123.24(12) . . ?
C6 N1 C5 118.27(11) . . ?
C1 N1 C5 117.85(11) . . ?
O3 N2 O2 123.74(13) . . ?
O3 N2 C10 118.34(13) . . ?
O2 N2 C10 117.93(13) . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_sarpong100
_database_code_depnum_ccdc_archive 'CCDC 1048616'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        compound12
_chemical_name_common            Hiro-77
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H30 N2 O3'
_chemical_formula_weight         430.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_diffrn_refln_scan_width         1.0
_diffrn_refln_scan_rate          10
_space_group.centring_type       primitive

_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, -y, -z'

_cell_length_a                   7.2150(2)
_cell_length_b                   12.5739(4)
_cell_length_c                   13.1379(4)
_cell_angle_alpha                70.3580(10)
_cell_angle_beta                 86.9080(10)
_cell_angle_gamma                85.3840(10)
_cell_volume                     1118.43(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.36

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            28948
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         25.365
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4090
_reflns_number_gt                3444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_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)+(0.0275P)²+0.7502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4090
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.5163(2) 0.65801(13) 0.54833(12) 0.0186(3) Uani 1 1 d . . . . .
H1A H 0.4774 0.5832 0.5956 0.022 Uiso 1 1 calc R U . . .
H1B H 0.4951 0.6648 0.4725 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3997(2) 0.75066(13) 0.57668(12) 0.0210(3) Uani 1 1 d . . . . .
H2A H 0.2662 0.7398 0.5732 0.025 Uiso 1 1 calc R U . . .
H2B H 0.4265 0.8252 0.5233 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4416(2) 0.74918(12) 0.69025(12) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.3777 0.8190 0.6996 0.023 Uiso 1 1 calc R U . . .
C4 C 0.65190(19) 0.75253(12) 0.70700(11) 0.0152(3) Uani 1 1 d . . . . .
H4 H 0.6647 0.7256 0.7872 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7723(2) 0.66334(12) 0.66862(11) 0.0142(3) Uani 1 1 d . . . . .
H5 H 0.9019 0.6887 0.6579 0.017 Uiso 1 1 calc R U . . .
C6 C 0.3619(2) 0.64755(14) 0.77786(13) 0.0256(4) Uani 1 1 d . . . . .
H6A H 0.2287 0.6470 0.7670 0.038 Uiso 1 1 calc R U . . .
H6B H 0.3800 0.6532 0.8492 0.038 Uiso 1 1 calc R U . . .
H6C H 0.4261 0.5775 0.7734 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7341(2) 0.87187(12) 0.66633(11) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.7791(2) 0.91701(13) 0.54452(12) 0.0209(3) Uani 1 1 d . . . . .
H8A H 0.8250 0.9928 0.5252 0.031 Uiso 1 1 calc R U . . .
H8B H 0.6664 0.9209 0.5046 0.031 Uiso 1 1 calc R U . . .
H8C H 0.8747 0.8662 0.5259 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5999(2) 0.95873(13) 0.69578(12) 0.0220(3) Uani 1 1 d . . . . .
H9A H 0.5637 0.9288 0.7726 0.033 Uiso 1 1 calc R U . . .
H9B H 0.4888 0.9737 0.6521 0.033 Uiso 1 1 calc R U . . .
H9C H 0.6613 1.0292 0.6815 0.033 Uiso 1 1 calc R U . . .
C10 C 0.9141(2) 0.86408(13) 0.72682(13) 0.0242(4) Uani 1 1 d . . . . .
H10A H 1.0044 0.8091 0.7106 0.036 Uiso 1 1 calc R U . . .
H10B H 0.8864 0.8397 0.8048 0.036 Uiso 1 1 calc R U . . .
H10C H 0.9661 0.9384 0.7036 0.036 Uiso 1 1 calc R U . . .
C11 C 0.78392(19) 0.54394(12) 0.75150(11) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.8260(2) 0.53121(12) 0.85963(11) 0.0172(3) Uani 1 1 d . . . . .
H12 H 0.8432 0.5965 0.8781 0.021 Uiso 1 1 calc R U . . .
C13 C 0.8422(2) 0.42715(12) 0.93724(12) 0.0178(3) Uani 1 1 d . . . . .
H13 H 0.8685 0.4213 1.0091 0.021 Uiso 1 1 calc R U . . .
C14 C 0.82050(19) 0.32766(12) 0.91256(12) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.8377(2) 0.21808(13) 0.99140(12) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.8589 0.2102 1.0644 0.025 Uiso 1 1 calc R U . . .
C16 C 0.8243(2) 0.12407(13) 0.96332(13) 0.0241(4) Uani 1 1 d . . . . .
H16 H 0.8355 0.0511 1.0168 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7936(2) 0.13480(13) 0.85520(13) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.7863 0.0688 0.8361 0.030 Uiso 1 1 calc R U . . .
C18 C 0.7742(2) 0.23907(13) 0.77750(13) 0.0207(3) Uani 1 1 d . . . . .
H18 H 0.7531 0.2449 0.7050 0.025 Uiso 1 1 calc R U . . .
C19 C 0.78532(19) 0.33862(12) 0.80398(12) 0.0163(3) Uani 1 1 d . . . . .
C20 C 0.76705(19) 0.44857(12) 0.72554(11) 0.0155(3) Uani 1 1 d . . . . .
H20 H 0.7424 0.4561 0.6531 0.019 Uiso 1 1 calc R U . . .
C21 C 0.8479(2) 0.66456(12) 0.48560(11) 0.0156(3) Uani 1 1 d . . . . .
C22 C 0.78592(19) 0.68843(12) 0.37187(11) 0.0155(3) Uani 1 1 d . . . . .
C23 C 0.7323(2) 0.79971(13) 0.31062(12) 0.0203(3) Uani 1 1 d . . . . .
H23 H 0.7224 0.8566 0.3436 0.024 Uiso 1 1 calc R U . . .
C24 C 0.6934(2) 0.82820(13) 0.20249(12) 0.0196(3) Uani 1 1 d . . . . .
H24 H 0.6575 0.9040 0.1604 0.024 Uiso 1 1 calc R U . . .
C25 C 0.70829(19) 0.74296(13) 0.15751(11) 0.0165(3) Uani 1 1 d . . . . .
C26 C 0.7581(2) 0.63191(12) 0.21618(12) 0.0173(3) Uani 1 1 d . . . . .
H26 H 0.7651 0.5752 0.1830 0.021 Uiso 1 1 calc R U . . .
C27 C 0.79776(19) 0.60437(12) 0.32448(12) 0.0165(3) Uani 1 1 d . . . . .
H27 H 0.8329 0.5283 0.3662 0.020 Uiso 1 1 calc R U . . .
N1 N 0.71499(16) 0.66567(10) 0.56184(9) 0.0146(3) Uani 1 1 d . . . . .
N2 N 0.67218(17) 0.77290(11) 0.04168(10) 0.0213(3) Uani 1 1 d . . . . .
O1 O 1.01568(14) 0.65265(9) 0.50307(8) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.67230(18) 0.69580(10) 0.00399(9) 0.0340(3) Uani 1 1 d . . . . .
O3 O 0.64491(17) 0.87322(10) -0.01183(9) 0.0305(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4689(18) . ?
C1 C2 1.517(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C6 1.532(2) . ?
C3 C4 1.551(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.5629(19) . ?
C4 C7 1.568(2) . ?
C4 H4 1.0000 . ?
C5 N1 1.4739(17) . ?
C5 C11 1.5288(19) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.534(2) . ?
C7 C9 1.534(2) . ?
C7 C10 1.538(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C20 1.368(2) . ?
C11 C12 1.422(2) . ?
C12 C13 1.363(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.419(2) . ?
C14 C19 1.421(2) . ?
C15 C16 1.363(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.366(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.416(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.421(2) . ?
C20 H20 0.9500 . ?
C21 O1 1.2322(17) . ?
C21 N1 1.3515(18) . ?
C21 C22 1.507(2) . ?
C22 C27 1.391(2) . ?
C22 C23 1.394(2) . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(2) . ?
C25 N2 1.4722(18) . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N2 O3 1.2260(17) . ?
N2 O2 1.2277(17) . ?

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
N1 C1 C2 110.94(12) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 C3 110.92(12) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C6 C3 C2 111.53(13) . . ?
C6 C3 C4 110.24(12) . . ?
C2 C3 C4 113.06(12) . . ?
C6 C3 H3 107.2 . . ?
C2 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C3 C4 C5 111.90(12) . . ?
C3 C4 C7 116.83(12) . . ?
C5 C4 C7 112.58(12) . . ?
C3 C4 H4 104.7 . . ?
C5 C4 H4 104.7 . . ?
C7 C4 H4 104.7 . . ?
N1 C5 C11 112.67(11) . . ?
N1 C5 C4 110.97(11) . . ?
C11 C5 C4 114.42(11) . . ?
N1 C5 H5 106.0 . . ?
C11 C5 H5 106.0 . . ?
C4 C5 H5 106.0 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C9 108.66(12) . . ?
C8 C7 C10 108.36(13) . . ?
C9 C7 C10 106.52(12) . . ?
C8 C7 C4 114.47(12) . . ?
C9 C7 C4 110.23(12) . . ?
C10 C7 C4 108.29(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C11 C12 118.44(13) . . ?
C20 C11 C5 123.34(13) . . ?
C12 C11 C5 118.10(12) . . ?
C13 C12 C11 121.29(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.07(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 122.41(13) . . ?
C13 C14 C19 118.34(13) . . ?
C15 C14 C19 119.22(14) . . ?
C16 C15 C14 120.60(14) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.18(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.72(15) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.63(14) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 122.40(13) . . ?
C18 C19 C14 118.61(13) . . ?
C20 C19 C14 118.97(13) . . ?
C11 C20 C19 121.83(13) . . ?
C11 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
O1 C21 N1 123.37(13) . . ?
O1 C21 C22 118.96(12) . . ?
N1 C21 C22 117.49(12) . . ?
C27 C22 C23 119.88(13) . . ?
C27 C22 C21 121.37(13) . . ?
C23 C22 C21 118.48(13) . . ?
C24 C23 C22 120.81(14) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 117.90(14) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C26 C25 C24 122.72(13) . . ?
C26 C25 N2 118.91(13) . . ?
C24 C25 N2 118.36(13) . . ?
C25 C26 C27 118.88(13) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C26 C27 C22 119.79(13) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C21 N1 C1 123.65(12) . . ?
C21 N1 C5 118.74(12) . . ?
C1 N1 C5 117.35(11) . . ?
O3 N2 O2 123.70(13) . . ?
O3 N2 C25 118.29(12) . . ?
O2 N2 C25 118.01(13) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041

