# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_sarpong38
_database_code_depnum_ccdc_archive 'CCDC 1400755'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 sarpong38 
;
_chemical_name_common            EM03-093B
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.33

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.9384(5)
_cell_length_b                   7.0246(5)
_cell_length_c                   12.9394(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.464(4)
_cell_angle_gamma                90
_cell_volume                     713.69(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7066
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      68.29

_exptl_crystal_description       blade
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.734
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_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            10468
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         68.368
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2538
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.942

_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    SIR-2011
_computing_structure_refinement  SHELXL-2012
_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)+(0.0709P)²+0.1688P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     direct
_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_abs_structure_details 
; 
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2538
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.3422(3) 0.9265(4) 0.7290(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.4152(3) 1.0654(4) 0.6533(2) 0.0252(6) Uani 1 1 d . . . . .
H2A H 0.4373 1.1907 0.6877 0.030 Uiso 1 1 calc R U . . .
H2B H 0.5247 1.0153 0.6368 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2904(3) 1.0899(5) 0.5523(2) 0.0303(6) Uani 1 1 d . . . . .
H3A H 0.3418 1.1742 0.5042 0.036 Uiso 1 1 calc R U . . .
H3B H 0.2693 0.9645 0.5179 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1232(3) 1.1738(4) 0.5726(2) 0.0272(6) Uani 1 1 d . . . . .
C5 C 0.0650(3) 1.1278(4) 0.67858(19) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.1430(3) 0.9323(4) 0.7160(2) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.1032 0.8411 0.6583 0.025 Uiso 1 1 calc R U . . .
C7 C 0.0845(3) 0.8469(4) 0.8138(2) 0.0236(5) Uani 1 1 d . . . . .
H7A H -0.0412 0.8551 0.8067 0.028 Uiso 1 1 calc R U . . .
H7B H 0.1162 0.7106 0.8185 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1608(3) 0.9456(4) 0.9136(2) 0.0251(6) Uani 1 1 d . . . . .
H8 H 0.1077 1.0742 0.9164 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1460(3) 0.8392(5) 1.0146(2) 0.0288(6) Uani 1 1 d . . . . .
H9 H 0.0307 0.8590 1.0353 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2824(4) 0.9376(5) 1.0920(2) 0.0315(6) Uani 1 1 d . . . . .
H10A H 0.3185 0.8555 1.1534 0.038 Uiso 1 1 calc R U . . .
H10B H 0.2396 1.0597 1.1162 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4310(4) 0.9715(4) 1.0300(2) 0.0278(6) Uani 1 1 d . . . . .
H11A H 0.4860 1.0961 1.0479 0.033 Uiso 1 1 calc R U . . .
H11B H 0.5175 0.8696 1.0436 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4368(3) 0.9595(4) 0.84078(19) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.3927(3) 0.7318(4) 0.7019(2) 0.0262(6) Uani 1 1 d . . . . .
C14 C 0.1176(4) 1.3004(4) 0.7498(2) 0.0298(6) Uani 1 1 d . . . . .
H14A H 0.0848 1.4182 0.7114 0.045 Uiso 1 1 calc R U . . .
H14B H 0.2412 1.2989 0.7713 0.045 Uiso 1 1 calc R U . . .
H14C H 0.0602 1.2938 0.8117 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1302(3) 1.1140(5) 0.6608(2) 0.0310(6) Uani 1 1 d . . . . .
H15A H -0.1710 1.0955 0.7279 0.047 Uiso 1 1 calc R U . . .
H15B H -0.1656 1.0060 0.6147 0.047 Uiso 1 1 calc R U . . .
H15C H -0.1785 1.2317 0.6282 0.047 Uiso 1 1 calc R U . . .
N1 N 0.3476(3) 0.9679(3) 0.92025(16) 0.0231(5) Uani 1 1 d . . . . .
N2 N 0.4323(3) 0.5815(4) 0.6786(2) 0.0397(7) Uani 1 1 d . . . . .
O1 O 0.0400(3) 1.2762(4) 0.51012(17) 0.0425(6) Uani 1 1 d . . . . .
O2 O 0.1768(3) 0.6432(3) 1.00132(16) 0.0329(5) Uani 1 1 d . . . . .
H2 H 0.2546 0.6065 1.0482 0.049 Uiso 1 1 calc R U . . .
O3 O 0.5946(2) 0.9707(3) 0.85313(14) 0.0296(5) 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 C13 1.481(4) . ?
C1 C12 1.546(3) . ?
C1 C2 1.554(4) . ?
C1 C6 1.566(3) . ?
C2 C3 1.529(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.510(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.204(4) . ?
C4 C5 1.544(4) . ?
C5 C15 1.536(3) . ?
C5 C14 1.542(4) . ?
C5 C6 1.554(4) . ?
C6 C7 1.532(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.480(3) . ?
C8 C9 1.525(4) . ?
C8 H8 1.0000 . ?
C9 O2 1.413(4) . ?
C9 C10 1.528(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.539(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.476(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.242(3) . ?
C12 N1 1.333(3) . ?
C13 N2 1.155(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 H2 0.8400 . ?

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
C13 C1 C12 104.4(2) . . ?
C13 C1 C2 106.9(2) . . ?
C12 C1 C2 108.7(2) . . ?
C13 C1 C6 107.7(2) . . ?
C12 C1 C6 116.1(2) . . ?
C2 C1 C6 112.4(2) . . ?
C3 C2 C1 110.8(2) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.7(2) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 C3 121.7(2) . . ?
O1 C4 C5 121.0(3) . . ?
C3 C4 C5 117.3(2) . . ?
C15 C5 C14 108.5(2) . . ?
C15 C5 C4 107.9(2) . . ?
C14 C5 C4 106.0(2) . . ?
C15 C5 C6 109.7(2) . . ?
C14 C5 C6 116.6(2) . . ?
C4 C5 C6 107.7(2) . . ?
C7 C6 C5 116.6(2) . . ?
C7 C6 C1 109.0(2) . . ?
C5 C6 C1 113.9(2) . . ?
C7 C6 H6 105.4 . . ?
C5 C6 H6 105.4 . . ?
C1 C6 H6 105.4 . . ?
C8 C7 C6 113.2(2) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C7 111.7(2) . . ?
N1 C8 C9 101.9(2) . . ?
C7 C8 C9 115.8(2) . . ?
N1 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
O2 C9 C8 109.7(2) . . ?
O2 C9 C10 113.7(2) . . ?
C8 C9 C10 101.7(2) . . ?
O2 C9 H9 110.5 . . ?
C8 C9 H9 110.5 . . ?
C10 C9 H9 110.5 . . ?
C9 C10 C11 104.6(2) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
N1 C11 C10 103.3(2) . . ?
N1 C11 H11A 111.1 . . ?
C10 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
O3 C12 N1 122.6(2) . . ?
O3 C12 C1 118.1(2) . . ?
N1 C12 C1 119.2(2) . . ?
N2 C13 C1 178.5(3) . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 N1 C11 121.9(2) . . ?
C12 N1 C8 126.3(2) . . ?
C11 N1 C8 111.15(19) . . ?
C9 O2 H2 109.5 . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.048

_shelxl_version_number           2012-9



####################################################################### 
# 
# 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_sarpong107
_database_code_depnum_ccdc_archive 'CCDC 1400756'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        sarpong107
_chemical_name_common            EM07-137C
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 N3 O3'
_chemical_formula_weight         431.52

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'

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

_cell_length_a                   8.7961(4)
_cell_length_b                   9.7026(5)
_cell_length_c                   35.0914(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2994.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      68.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.957
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.506
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_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            39292
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         68.506
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             5366
_reflns_number_gt                5041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.977

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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)+(0.0567P)²+3.5971P] 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_abs_structure_details 
; 
 Flack x determined using 1966 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.08(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5366
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.5760(5) 0.2190(5) 0.34561(12) 0.0316(9) Uani 1 1 d . . . . .
C2 C 0.7122(5) 0.1545(5) 0.32682(11) 0.0318(9) Uani 1 1 d . . . . .
H2A H 0.8047 0.1782 0.3415 0.038 Uiso 1 1 calc R U . . .
H2B H 0.7010 0.0530 0.3271 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7302(4) 0.2022(5) 0.28697(12) 0.0294(9) Uani 1 1 d . . . . .
C4 C 0.8333(4) 0.1546(4) 0.25814(11) 0.0255(8) Uani 1 1 d . . . . .
C5 C 0.9424(4) 0.0478(5) 0.25696(12) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.9606 -0.0074 0.2788 0.035 Uiso 1 1 calc R U . . .
C6 C 1.0229(4) 0.0243(5) 0.22349(13) 0.0331(10) Uani 1 1 d . . . . .
H6 H 1.0955 -0.0481 0.2223 0.040 Uiso 1 1 calc R U . . .
C7 C 0.9971(5) 0.1075(5) 0.19140(13) 0.0330(9) Uani 1 1 d . . . . .
C8 C 1.1049(6) 0.1892(5) 0.13293(14) 0.0419(11) Uani 1 1 d . . . . .
C9 C 0.9579(6) 0.2719(6) 0.12661(13) 0.0504(14) Uani 1 1 d . . . . .
H9 H 0.9354 0.3114 0.1025 0.060 Uiso 1 1 calc R U . . .
C10 C 0.8620(6) 0.2868(6) 0.15631(14) 0.0475(13) Uani 1 1 d . . . . .
H10 H 0.7775 0.3474 0.1543 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8870(5) 0.2119(5) 0.19078(12) 0.0347(10) Uani 1 1 d . . . . .
C12 C 0.8070(4) 0.2348(5) 0.22505(12) 0.0311(9) Uani 1 1 d . . . . .
C13 C 0.6487(4) 0.3075(5) 0.27107(12) 0.0284(9) Uani 1 1 d . . . . .
C14 C 0.5288(5) 0.3920(4) 0.28928(12) 0.0304(9) Uani 1 1 d . . . . .
C15 C 0.5500(5) 0.3696(5) 0.33350(12) 0.0331(10) Uani 1 1 d . . . . .
H15 H 0.6439 0.4213 0.3408 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4178(5) 0.4330(5) 0.35724(14) 0.0393(11) Uani 1 1 d . . . . .
H16A H 0.4563 0.5091 0.3734 0.047 Uiso 1 1 calc R U . . .
H16B H 0.3385 0.4702 0.3401 0.047 Uiso 1 1 calc R U . . .
C17 C 0.3510(5) 0.3176(5) 0.38237(13) 0.0386(11) Uani 1 1 d . . . . .
C18 C 0.2001(6) 0.3495(6) 0.40206(16) 0.0521(14) Uani 1 1 d . . . . .
H18A H 0.1928 0.3019 0.4269 0.063 Uiso 1 1 calc R U . . .
H18B H 0.1875 0.4499 0.4061 0.063 Uiso 1 1 calc R U . . .
C19 C 0.0826(6) 0.2947(7) 0.37418(16) 0.0543(14) Uani 1 1 d . . . . .
H19A H -0.0147 0.2751 0.3873 0.065 Uiso 1 1 calc R U . . .
H19B H 0.0639 0.3618 0.3535 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1515(5) 0.1648(6) 0.35879(16) 0.0480(13) Uani 1 1 d . . . . .
H20A H 0.1308 0.0854 0.3757 0.058 Uiso 1 1 calc R U . . .
H20B H 0.1130 0.1440 0.3329 0.058 Uiso 1 1 calc R U . . .
C21 C 0.4271(5) 0.1387(5) 0.33928(11) 0.0313(9) Uani 1 1 d . . . . .
C22 C 0.4808(5) 0.2694(6) 0.40887(13) 0.0409(11) Uani 1 1 d . . . . .
C23 C 1.2315(7) 0.2795(6) 0.14692(15) 0.0550(14) Uani 1 1 d . . . . .
H23A H 1.2067 0.3141 0.1724 0.083 Uiso 1 1 calc R U . . .
H23B H 1.2446 0.3574 0.1294 0.083 Uiso 1 1 calc R U . . .
H23C H 1.3259 0.2260 0.1480 0.083 Uiso 1 1 calc R U . . .
C24 C 1.1487(7) 0.1178(6) 0.09558(15) 0.0540(14) Uani 1 1 d . . . . .
H24A H 1.2372 0.0585 0.0999 0.081 Uiso 1 1 calc R U . . .
H24B H 1.1736 0.1874 0.0764 0.081 Uiso 1 1 calc R U . . .
H24C H 1.0632 0.0617 0.0866 0.081 Uiso 1 1 calc R U . . .
C25 C 0.5505(5) 0.5463(5) 0.28113(14) 0.0375(10) Uani 1 1 d . . . . .
H25A H 0.6542 0.5736 0.2880 0.056 Uiso 1 1 calc R U . . .
H25B H 0.4776 0.5997 0.2962 0.056 Uiso 1 1 calc R U . . .
H25C H 0.5337 0.5640 0.2540 0.056 Uiso 1 1 calc R U . . .
C26 C 0.3708(5) 0.3500(5) 0.27370(12) 0.0341(10) Uani 1 1 d . . . . .
H26A H 0.3682 0.3645 0.2461 0.051 Uiso 1 1 calc R U . . .
H26B H 0.2922 0.4064 0.2859 0.051 Uiso 1 1 calc R U . . .
H26C H 0.3522 0.2525 0.2793 0.051 Uiso 1 1 calc R U . . .
N1 N 0.6948(4) 0.3272(4) 0.23370(9) 0.0291(8) Uani 1 1 d . . . . .
H1 H 0.6578 0.3895 0.2180 0.035 Uiso 1 1 calc R U . . .
N2 N 0.3155(4) 0.1987(4) 0.35808(10) 0.0343(8) Uani 1 1 d . . . . .
N3 N 0.5959(4) 0.2220(4) 0.38757(10) 0.0384(9) Uani 1 1 d . . . . .
H3 H 0.6809 0.1934 0.3982 0.046 Uiso 1 1 calc R U . . .
O1 O 1.0765(4) 0.0780(3) 0.15841(9) 0.0387(8) Uani 1 1 d . . . . .
O2 O 0.4164(4) 0.0338(3) 0.31943(9) 0.0377(7) Uani 1 1 d . . . . .
O3 O 0.4792(4) 0.2780(4) 0.44338(9) 0.0544(10) 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 N3 1.483(5) . ?
C1 C2 1.504(6) . ?
C1 C15 1.539(7) . ?
C1 C21 1.540(6) . ?
C2 C3 1.482(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C13 1.367(6) . ?
C3 C4 1.435(6) . ?
C4 C5 1.413(6) . ?
C4 C12 1.416(6) . ?
C5 C6 1.391(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(6) . ?
C6 H6 0.9500 . ?
C7 O1 1.382(5) . ?
C7 C11 1.402(6) . ?
C8 O1 1.423(6) . ?
C8 C23 1.500(8) . ?
C8 C24 1.532(7) . ?
C8 C9 1.538(7) . ?
C9 C10 1.349(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.428(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(6) . ?
C12 N1 1.367(5) . ?
C13 N1 1.386(5) . ?
C13 C14 1.481(6) . ?
C14 C25 1.536(7) . ?
C14 C26 1.548(6) . ?
C14 C15 1.578(6) . ?
C15 C16 1.557(6) . ?
C15 H15 1.0000 . ?
C16 C17 1.541(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N2 1.468(6) . ?
C17 C18 1.529(6) . ?
C17 C22 1.545(7) . ?
C18 C19 1.519(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.499(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N2 1.480(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O2 1.237(5) . ?
C21 N2 1.318(6) . ?
C22 O3 1.214(5) . ?
C22 N3 1.341(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H1 0.8800 . ?
N3 H3 0.8800 . ?

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
N3 C1 C2 110.4(3) . . ?
N3 C1 C15 105.9(4) . . ?
C2 C1 C15 113.1(4) . . ?
N3 C1 C21 104.7(3) . . ?
C2 C1 C21 113.8(4) . . ?
C15 C1 C21 108.3(3) . . ?
C3 C2 C1 111.7(4) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C13 C3 C4 106.5(4) . . ?
C13 C3 C2 124.2(4) . . ?
C4 C3 C2 129.3(4) . . ?
C5 C4 C12 119.3(4) . . ?
C5 C4 C3 133.3(4) . . ?
C12 C4 C3 107.3(4) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O1 C7 C11 119.1(4) . . ?
O1 C7 C6 118.1(4) . . ?
C11 C7 C6 122.7(4) . . ?
O1 C8 C23 111.6(4) . . ?
O1 C8 C24 103.8(4) . . ?
C23 C8 C24 110.9(4) . . ?
O1 C8 C9 109.8(4) . . ?
C23 C8 C9 111.5(5) . . ?
C24 C8 C9 108.9(4) . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C7 C11 C12 116.4(4) . . ?
C7 C11 C10 119.2(4) . . ?
C12 C11 C10 124.4(4) . . ?
N1 C12 C11 130.7(4) . . ?
N1 C12 C4 107.2(4) . . ?
C11 C12 C4 122.1(4) . . ?
C3 C13 N1 109.6(4) . . ?
C3 C13 C14 127.7(4) . . ?
N1 C13 C14 122.7(4) . . ?
C13 C14 C25 111.8(4) . . ?
C13 C14 C26 110.0(3) . . ?
C25 C14 C26 107.6(4) . . ?
C13 C14 C15 105.3(4) . . ?
C25 C14 C15 107.6(4) . . ?
C26 C14 C15 114.7(3) . . ?
C1 C15 C16 109.7(4) . . ?
C1 C15 C14 114.8(3) . . ?
C16 C15 C14 112.6(4) . . ?
C1 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C14 C15 H15 106.4 . . ?
C17 C16 C15 107.7(4) . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
N2 C17 C18 103.7(4) . . ?
N2 C17 C16 108.6(4) . . ?
C18 C17 C16 116.3(4) . . ?
N2 C17 C22 105.6(4) . . ?
C18 C17 C22 115.5(4) . . ?
C16 C17 C22 106.4(4) . . ?
C19 C18 C17 103.2(4) . . ?
C19 C18 H18A 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C20 C19 C18 104.6(4) . . ?
C20 C19 H19A 110.8 . . ?
C18 C19 H19A 110.8 . . ?
C20 C19 H19B 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
N2 C20 C19 102.3(4) . . ?
N2 C20 H20A 111.3 . . ?
C19 C20 H20A 111.3 . . ?
N2 C20 H20B 111.3 . . ?
C19 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
O2 C21 N2 126.1(4) . . ?
O2 C21 C1 124.2(4) . . ?
N2 C21 C1 109.7(4) . . ?
O3 C22 N3 126.1(5) . . ?
O3 C22 C17 124.8(4) . . ?
N3 C22 C17 109.1(4) . . ?
C8 C23 H23A 109.5 . . ?
C8 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C8 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 C24 H24A 109.5 . . ?
C8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C25 H25A 109.5 . . ?
C14 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C14 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C26 H26A 109.5 . . ?
C14 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C14 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C12 N1 C13 109.3(3) . . ?
C12 N1 H1 125.3 . . ?
C13 N1 H1 125.3 . . ?
C21 N2 C17 118.7(4) . . ?
C21 N2 C20 129.5(4) . . ?
C17 N2 C20 111.9(4) . . ?
C22 N3 C1 118.1(4) . . ?
C22 N3 H3 121.0 . . ?
C1 N3 H3 121.0 . . ?
C7 O1 C8 117.3(3) . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051




