# 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_CEA5164P
_database_code_depnum_ccdc_archive 'CCDC 1057455'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 O3'
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1 '
_symmetry_space_group_name_H-M   'P -1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2616(10)
_cell_length_b                   9.3550(15)
_cell_length_c                   11.752(2)
_cell_angle_alpha                87.526(10)
_cell_angle_beta                 88.241(10)
_cell_angle_gamma                86.453(9)
_cell_volume                     686.18(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7899
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      32.50

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23967
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         32.59
_reflns_number_total             4973
_reflns_number_gt                3715
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.2257P] 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_number_reflns         4973
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93583(13) 0.29814(10) 0.22438(7) 0.01898(19) Uani 1 1 d . . .
O2 O 0.49090(13) 0.27005(9) 0.50999(7) 0.01499(17) Uani 1 1 d . . .
O3 O 0.18233(14) 0.32718(10) 0.60465(8) 0.0221(2) Uani 1 1 d . . .
C1 C 0.75462(16) 0.22423(11) 0.22098(9) 0.01128(19) Uani 1 1 d . . .
C2 C 0.66298(17) 0.17469(11) 0.33569(9) 0.01084(19) Uani 1 1 d . . .
C3 C 0.47526(18) 0.08789(12) 0.30187(9) 0.0145(2) Uani 1 1 d . . .
H3A H 0.3458 0.1131 0.3490 0.017 Uiso 1 1 calc R . .
H3B H 0.5120 -0.0161 0.3130 0.017 Uiso 1 1 calc R . .
C4 C 0.43520(18) 0.12663(12) 0.17510(9) 0.0143(2) Uani 1 1 d . . .
H4A H 0.4096 0.0400 0.1332 0.017 Uiso 1 1 calc R . .
H4B H 0.3104 0.1962 0.1667 0.017 Uiso 1 1 calc R . .
C5 C 0.63918(17) 0.19228(11) 0.13211(9) 0.01152(19) Uani 1 1 d . . .
C6 C 0.58990(17) 0.30905(12) 0.40106(9) 0.0126(2) Uani 1 1 d . . .
H6 H 0.7180 0.3641 0.4147 0.015 Uiso 1 1 calc R . .
C7 C 0.42456(19) 0.40745(12) 0.34482(10) 0.0149(2) Uani 1 1 d . . .
H7 H 0.4393 0.4508 0.2706 0.018 Uiso 1 1 calc R . .
C8 C 0.25370(18) 0.42554(12) 0.41373(10) 0.0153(2) Uani 1 1 d . . .
H8 H 0.1279 0.4840 0.3975 0.018 Uiso 1 1 calc R . .
C9 C 0.29316(18) 0.33946(12) 0.51931(10) 0.0143(2) Uani 1 1 d . . .
C10 C 0.68822(17) 0.21143(11) 0.00925(9) 0.0119(2) Uani 1 1 d . . .
C11 C 0.89458(18) 0.18071(12) -0.03579(10) 0.0148(2) Uani 1 1 d . . .
H11 H 1.0073 0.1519 0.0141 0.018 Uiso 1 1 calc R . .
C12 C 0.93669(19) 0.19180(13) -0.15255(10) 0.0173(2) Uani 1 1 d . . .
H12 H 1.0777 0.1708 -0.1818 0.021 Uiso 1 1 calc R . .
C13 C 0.7735(2) 0.23343(12) -0.22672(10) 0.0171(2) Uani 1 1 d . . .
H13 H 0.8028 0.2414 -0.3065 0.021 Uiso 1 1 calc R . .
C14 C 0.56732(19) 0.26327(12) -0.18344(10) 0.0165(2) Uani 1 1 d . . .
H14 H 0.4551 0.2914 -0.2338 0.020 Uiso 1 1 calc R . .
C15 C 0.52489(19) 0.25210(12) -0.06682(10) 0.0153(2) Uani 1 1 d . . .
H15 H 0.3832 0.2723 -0.0381 0.018 Uiso 1 1 calc R . .
C16 C 0.82849(19) 0.08570(13) 0.40663(10) 0.0177(2) Uani 1 1 d . . .
H16A H 0.8852 0.0037 0.3635 0.027 Uiso 1 1 calc R . .
H16B H 0.7604 0.0512 0.4779 0.027 Uiso 1 1 calc R . .
H16C H 0.9457 0.1453 0.4238 0.027 Uiso 1 1 calc R . .
C17 C 0.9495(2) 0.42317(13) 0.15092(11) 0.0207(2) Uani 1 1 d . . .
H17A H 1.0199 0.3968 0.0785 0.031 Uiso 1 1 calc R . .
H17B H 1.0327 0.4930 0.1872 0.031 Uiso 1 1 calc R . .
H17C H 0.8051 0.4654 0.1367 0.031 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 C1 1.3672(13) . ?
O1 C17 1.4288(15) . ?
O2 C9 1.3657(14) . ?
O2 C6 1.4474(13) . ?
O3 C9 1.2074(14) . ?
C1 C5 1.3426(15) . ?
C1 C2 1.5142(15) . ?
C2 C16 1.5325(16) . ?
C2 C6 1.5395(15) . ?
C2 C3 1.5407(15) . ?
C3 C4 1.5424(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5148(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.4725(15) . ?
C6 C7 1.4925(16) . ?
C6 H6 1.0000 . ?
C7 C8 1.3287(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4687(16) . ?
C8 H8 0.9500 . ?
C10 C11 1.3992(16) . ?
C10 C15 1.4031(15) . ?
C11 C12 1.3900(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3898(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3896(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3888(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C1 O1 C17 117.54(9) . . ?
C9 O2 C6 109.42(8) . . ?
C5 C1 O1 130.39(10) . . ?
C5 C1 C2 114.14(9) . . ?
O1 C1 C2 115.43(9) . . ?
C1 C2 C16 112.23(9) . . ?
C1 C2 C6 107.72(9) . . ?
C16 C2 C6 108.42(9) . . ?
C1 C2 C3 102.29(8) . . ?
C16 C2 C3 113.01(9) . . ?
C6 C2 C3 113.01(9) . . ?
C2 C3 C4 106.67(9) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 104.17(9) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C1 C5 C10 129.27(10) . . ?
C1 C5 C4 109.57(9) . . ?
C10 C5 C4 121.16(9) . . ?
O2 C6 C7 103.90(9) . . ?
O2 C6 C2 110.91(9) . . ?
C7 C6 C2 115.68(9) . . ?
O2 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C2 C6 H6 108.7 . . ?
C8 C7 C6 110.04(10) . . ?
C8 C7 H7 125.0 . . ?
C6 C7 H7 125.0 . . ?
C7 C8 C9 108.11(10) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
O3 C9 O2 121.54(11) . . ?
O3 C9 C8 129.94(11) . . ?
O2 C9 C8 108.51(9) . . ?
C11 C10 C15 118.12(10) . . ?
C11 C10 C5 121.29(10) . . ?
C15 C10 C5 120.45(10) . . ?
C12 C11 C10 120.84(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.34(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.55(10) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.19(11) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.95(11) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C17 O1 C1 C5 40.44(17) . . . . ?
C17 O1 C1 C2 -136.92(10) . . . . ?
C5 C1 C2 C16 127.56(11) . . . . ?
O1 C1 C2 C16 -54.64(12) . . . . ?
C5 C1 C2 C6 -113.16(10) . . . . ?
O1 C1 C2 C6 64.64(11) . . . . ?
C5 C1 C2 C3 6.16(12) . . . . ?
O1 C1 C2 C3 -176.05(9) . . . . ?
C1 C2 C3 C4 -14.75(11) . . . . ?
C16 C2 C3 C4 -135.63(10) . . . . ?
C6 C2 C3 C4 100.78(10) . . . . ?
C2 C3 C4 C5 17.94(11) . . . . ?
O1 C1 C5 C10 8.7(2) . . . . ?
C2 C1 C5 C10 -173.87(10) . . . . ?
O1 C1 C5 C4 -172.01(11) . . . . ?
C2 C1 C5 C4 5.37(13) . . . . ?
C3 C4 C5 C1 -14.54(12) . . . . ?
C3 C4 C5 C10 164.78(9) . . . . ?
C9 O2 C6 C7 -1.49(11) . . . . ?
C9 O2 C6 C2 -126.41(9) . . . . ?
C1 C2 C6 O2 177.32(8) . . . . ?
C16 C2 C6 O2 -61.00(11) . . . . ?
C3 C2 C6 O2 65.08(11) . . . . ?
C1 C2 C6 C7 59.34(12) . . . . ?
C16 C2 C6 C7 -178.98(9) . . . . ?
C3 C2 C6 C7 -52.89(12) . . . . ?
O2 C6 C7 C8 1.29(12) . . . . ?
C2 C6 C7 C8 123.09(11) . . . . ?
C6 C7 C8 C9 -0.62(13) . . . . ?
C6 O2 C9 O3 -177.68(10) . . . . ?
C6 O2 C9 C8 1.18(12) . . . . ?
C7 C8 C9 O3 178.40(12) . . . . ?
C7 C8 C9 O2 -0.34(13) . . . . ?
C1 C5 C10 C11 41.28(17) . . . . ?
C4 C5 C10 C11 -137.88(11) . . . . ?
C1 C5 C10 C15 -142.99(12) . . . . ?
C4 C5 C10 C15 37.85(15) . . . . ?
C15 C10 C11 C12 0.70(16) . . . . ?
C5 C10 C11 C12 176.53(10) . . . . ?
C10 C11 C12 C13 -0.16(17) . . . . ?
C11 C12 C13 C14 -0.33(17) . . . . ?
C12 C13 C14 C15 0.26(17) . . . . ?
C13 C14 C15 C10 0.30(17) . . . . ?
C11 C10 C15 C14 -0.78(16) . . . . ?
C5 C10 C15 C14 -176.64(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
####################################################################### 
# 
# 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_NDange3
_database_code_depnum_ccdc_archive 'CCDC 1057456'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O'
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_weight         306.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_Hall  '-R 3 '
_symmetry_space_group_name_H-M   'R -3   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   25.0795(18)
_cell_length_b                   25.0795(18)
_cell_length_c                   13.9752(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7612.5(10)
_cell_formula_units_Z            18
_cell_measurement_temperature    135.0(5)
_cell_measurement_reflns_used    3430
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.39

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2952
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      135.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12232
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         27.09
_reflns_number_total             3678
_reflns_number_gt                2685
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+4.8033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3678
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13148(5) 0.75077(5) 0.75722(7) 0.0357(3) Uani 1 1 d . . .
N1 N 0.05284(6) 0.54941(6) 0.71803(9) 0.0321(3) Uani 1 1 d . . .
H1N H 0.0617(8) 0.5341(8) 0.6669(12) 0.038 Uiso 1 1 d . . .
C1 C 0.12714(7) 0.72767(6) 0.83534(10) 0.0255(3) Uani 1 1 d . . .
C2 C 0.06738(6) 0.67531(6) 0.87654(9) 0.0238(3) Uani 1 1 d . . .
C3 C 0.08496(7) 0.67388(7) 0.98231(10) 0.0322(4) Uani 1 1 d . . .
H3A H 0.0775 0.7023 1.0217 0.039 Uiso 1 1 calc R . .
H3B H 0.0608 0.6318 1.0090 0.039 Uiso 1 1 calc R . .
C4 C 0.15323(7) 0.69441(7) 0.97971(11) 0.0356(4) Uani 1 1 d . . .
H4A H 0.1599 0.6606 0.9582 0.043 Uiso 1 1 calc R . .
H4B H 0.1724 0.7088 1.0434 0.043 Uiso 1 1 calc R . .
C5 C 0.17933(7) 0.74747(7) 0.90695(11) 0.0298(3) Uani 1 1 d . . .
H5 H 0.1825 0.7839 0.9414 0.036 Uiso 1 1 calc R . .
C6 C 0.05331(6) 0.61658(6) 0.82517(9) 0.0232(3) Uani 1 1 d . . .
C7 C 0.08105(7) 0.61003(7) 0.74526(10) 0.0271(3) Uani 1 1 d . . .
H7 H 0.1150 0.6428 0.7132 0.032 Uiso 1 1 calc R . .
C8 C 0.00532(7) 0.51525(7) 0.77986(10) 0.0298(3) Uani 1 1 d . . .
C9 C 0.00376(7) 0.55580(6) 0.84897(9) 0.0264(3) Uani 1 1 d . . .
C10 C -0.04299(8) 0.53159(7) 0.91799(11) 0.0373(4) Uani 1 1 d . . .
H10 H -0.0450 0.5575 0.9658 0.045 Uiso 1 1 calc R . .
C11 C -0.08609(9) 0.46969(8) 0.91572(13) 0.0487(5) Uani 1 1 d . . .
H11 H -0.1182 0.4531 0.9620 0.058 Uiso 1 1 calc R . .
C12 C -0.08331(9) 0.43075(8) 0.84605(12) 0.0487(5) Uani 1 1 d . . .
H12 H -0.1138 0.3883 0.8458 0.058 Uiso 1 1 calc R . .
C13 C -0.03781(8) 0.45254(7) 0.77874(12) 0.0393(4) Uani 1 1 d . . .
H13 H -0.0356 0.4259 0.7327 0.047 Uiso 1 1 calc R . .
C14 C 0.24191(7) 0.76832(7) 0.86514(11) 0.0315(4) Uani 1 1 d . . .
C15 C 0.25418(9) 0.72863(9) 0.8152(2) 0.0789(9) Uani 1 1 d . . .
H15 H 0.2225 0.6871 0.8065 0.095 Uiso 1 1 calc R . .
C16 C 0.31172(10) 0.74794(11) 0.7773(3) 0.0972(11) Uani 1 1 d . . .
H16 H 0.3190 0.7195 0.7430 0.117 Uiso 1 1 calc R . .
C17 C 0.35865(8) 0.80755(9) 0.78824(16) 0.0535(5) Uani 1 1 d . . .
H17 H 0.3986 0.8203 0.7635 0.064 Uiso 1 1 calc R . .
C18 C 0.34667(8) 0.84780(8) 0.83529(14) 0.0455(4) Uani 1 1 d . . .
H18 H 0.3782 0.8895 0.8424 0.055 Uiso 1 1 calc R . .
C19 C 0.28847(8) 0.82830(7) 0.87306(13) 0.0421(4) Uani 1 1 d . . .
H19 H 0.2808 0.8572 0.9051 0.050 Uiso 1 1 calc R . .
C20 C 0.01443(7) 0.68826(7) 0.86432(11) 0.0324(4) Uani 1 1 d . . .
H20A H 0.0095 0.6944 0.7963 0.049 Uiso 1 1 calc R . .
H20B H 0.0235 0.7254 0.9002 0.049 Uiso 1 1 calc R . .
H20C H -0.0237 0.6533 0.8886 0.049 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 C1 1.2151(17) . ?
N1 C8 1.371(2) . ?
N1 C7 1.3714(19) . ?
N1 H1N 0.891(17) . ?
C1 C5 1.520(2) . ?
C1 C2 1.5277(19) . ?
C2 C6 1.5132(19) . ?
C2 C20 1.526(2) . ?
C2 C3 1.5481(19) . ?
C3 C4 1.522(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.537(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.503(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.3684(19) . ?
C6 C9 1.444(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.394(2) . ?
C8 C9 1.417(2) . ?
C9 C10 1.401(2) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.405(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.371(3) . ?
C14 C19 1.372(2) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C8 N1 C7 108.85(12) . . ?
C8 N1 H1N 124.2(11) . . ?
C7 N1 H1N 126.8(11) . . ?
O1 C1 C5 125.34(13) . . ?
O1 C1 C2 124.33(13) . . ?
C5 C1 C2 110.31(12) . . ?
C6 C2 C20 110.48(12) . . ?
C6 C2 C1 108.00(11) . . ?
C20 C2 C1 111.04(12) . . ?
C6 C2 C3 111.15(11) . . ?
C20 C2 C3 113.58(12) . . ?
C1 C2 C3 102.20(11) . . ?
C4 C3 C2 104.75(12) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 103.22(12) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C14 C5 C1 115.89(12) . . ?
C14 C5 C4 118.49(13) . . ?
C1 C5 C4 103.20(12) . . ?
C14 C5 H5 106.1 . . ?
C1 C5 H5 106.1 . . ?
C4 C5 H5 106.1 . . ?
C7 C6 C9 106.39(12) . . ?
C7 C6 C2 128.24(13) . . ?
C9 C6 C2 125.25(12) . . ?
C6 C7 N1 110.37(13) . . ?
C6 C7 H7 124.8 . . ?
N1 C7 H7 124.8 . . ?
N1 C8 C13 129.77(15) . . ?
N1 C8 C9 107.96(13) . . ?
C13 C8 C9 122.21(15) . . ?
C10 C9 C8 118.40(14) . . ?
C10 C9 C6 135.11(14) . . ?
C8 C9 C6 106.42(13) . . ?
C11 C10 C9 119.17(16) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.00(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 121.42(16) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C8 117.78(16) . . ?
C12 C13 H13 121.1 . . ?
C8 C13 H13 121.1 . . ?
C15 C14 C19 117.40(16) . . ?
C15 C14 C5 121.34(15) . . ?
C19 C14 C5 121.23(14) . . ?
C14 C15 C16 121.10(18) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 118.41(18) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 120.37(17) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 121.54(16) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 C1 C2 C6 74.14(17) . . . . ?
C5 C1 C2 C6 -107.39(13) . . . . ?
O1 C1 C2 C20 -47.13(18) . . . . ?
C5 C1 C2 C20 131.34(12) . . . . ?
O1 C1 C2 C3 -168.58(14) . . . . ?
C5 C1 C2 C3 9.90(15) . . . . ?
C6 C2 C3 C4 83.72(14) . . . . ?
C20 C2 C3 C4 -150.95(12) . . . . ?
C1 C2 C3 C4 -31.28(14) . . . . ?
C2 C3 C4 C5 41.31(14) . . . . ?
O1 C1 C5 C14 -35.6(2) . . . . ?
C2 C1 C5 C14 145.97(12) . . . . ?
O1 C1 C5 C4 -166.76(14) . . . . ?
C2 C1 C5 C4 14.79(15) . . . . ?
C3 C4 C5 C14 -163.57(13) . . . . ?
C3 C4 C5 C1 -33.95(15) . . . . ?
C20 C2 C6 C7 111.22(16) . . . . ?
C1 C2 C6 C7 -10.40(19) . . . . ?
C3 C2 C6 C7 -121.74(15) . . . . ?
C20 C2 C6 C9 -64.22(17) . . . . ?
C1 C2 C6 C9 174.17(13) . . . . ?
C3 C2 C6 C9 62.82(18) . . . . ?
C9 C6 C7 N1 -0.69(16) . . . . ?
C2 C6 C7 N1 -176.81(13) . . . . ?
C8 N1 C7 C6 0.68(16) . . . . ?
C7 N1 C8 C13 176.94(15) . . . . ?
C7 N1 C8 C9 -0.37(16) . . . . ?
N1 C8 C9 C10 177.37(13) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
N1 C8 C9 C6 -0.05(15) . . . . ?
C13 C8 C9 C6 -177.61(13) . . . . ?
C7 C6 C9 C10 -176.34(16) . . . . ?
C2 C6 C9 C10 -0.1(3) . . . . ?
C7 C6 C9 C8 0.45(15) . . . . ?
C2 C6 C9 C8 176.72(12) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C6 C9 C10 C11 175.71(17) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
N1 C8 C13 C12 -175.71(15) . . . . ?
C9 C8 C13 C12 1.3(2) . . . . ?
C1 C5 C14 C15 -64.5(2) . . . . ?
C4 C5 C14 C15 59.0(2) . . . . ?
C1 C5 C14 C19 113.49(17) . . . . ?
C4 C5 C14 C19 -122.99(17) . . . . ?
C19 C14 C15 C16 2.1(4) . . . . ?
C5 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C15 C14 C19 C18 -2.5(3) . . . . ?
C5 C14 C19 C18 179.42(16) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?

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
N1 H1N O1 0.891(17) 2.033(18) 2.8570(16) 153.4(15) 15_556

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.041

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.333 0.667 0.167 328 60 ' '
2 0.667 0.333 -0.167 328 60 ' '
3 0.000 0.000 0.500 324 60 ' '
_platon_squeeze_details          
;
The 179 electrons removed by SQUEEZE correspond to 3.6 molecules
of disordered hexane per unit cell or 0.2 per main molecule. This
solvent is included in the density, FW, etc., but is not in the model.
;
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
####################################################################### 
# 
# 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_NSD-1131
_database_code_depnum_ccdc_archive 'CCDC 1057457'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O2'
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc '
_symmetry_space_group_name_H-M   'P 21/c  '

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

_cell_length_a                   14.0542(10)
_cell_length_b                   15.9871(11)
_cell_length_c                   7.7187(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.974(4)
_cell_angle_gamma                90
_cell_volume                     1733.25(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    3184
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      61.15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6184
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2004)'

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13157
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         61.15
_reflns_number_total             2537
_reflns_number_gt                1965
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          Twin

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1411P)²+0.3725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2098
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80629(17) 0.60700(14) 0.1714(2) 0.0396(6) Uani 1 1 d . . .
O2 O 0.43063(16) 0.51840(15) 0.2137(3) 0.0432(6) Uani 1 1 d . . .
N1 N 0.6418(2) 0.75114(19) 0.5822(4) 0.0433(8) Uani 1 1 d . . .
H1N H 0.628(3) 0.798(3) 0.636(5) 0.052 Uiso 1 1 d . . .
C1 C 0.8095(2) 0.5447(2) 0.2939(4) 0.0357(8) Uani 1 1 d . . .
C2 C 0.8064(2) 0.5774(2) 0.4780(4) 0.0370(8) Uani 1 1 d . . .
C3 C 0.7893(2) 0.4943(2) 0.5787(4) 0.0385(8) Uani 1 1 d . . .
H3A H 0.8305 0.4921 0.6853 0.046 Uiso 1 1 calc R . .
H3B H 0.7220 0.4903 0.6120 0.046 Uiso 1 1 calc R . .
C4 C 0.8138(3) 0.4225(2) 0.4564(4) 0.0397(8) Uani 1 1 d . . .
H4A H 0.8760 0.3974 0.4904 0.048 Uiso 1 1 calc R . .
H4B H 0.7643 0.3784 0.4574 0.048 Uiso 1 1 calc R . .
C5 C 0.8174(2) 0.4625(2) 0.2801(4) 0.0346(8) Uani 1 1 d . . .
C6 C 0.7261(2) 0.63932(19) 0.5008(4) 0.0360(8) Uani 1 1 d . . .
C7 C 0.7296(3) 0.7139(2) 0.5890(4) 0.0395(8) Uani 1 1 d . . .
H7 H 0.7848 0.7363 0.6463 0.047 Uiso 1 1 calc R . .
C8 C 0.5787(3) 0.7014(2) 0.4894(4) 0.0389(8) Uani 1 1 d . . .
C9 C 0.6300(2) 0.63013(19) 0.4369(4) 0.0356(8) Uani 1 1 d . . .
C10 C 0.5815(2) 0.5667(2) 0.3414(4) 0.0365(8) Uani 1 1 d . . .
H10 H 0.6143 0.5182 0.3045 0.044 Uiso 1 1 calc R . .
C11 C 0.4862(2) 0.5768(2) 0.3034(4) 0.0373(8) Uani 1 1 d . . .
C12 C 0.4364(3) 0.6486(2) 0.3550(4) 0.0410(9) Uani 1 1 d . . .
H12 H 0.3705 0.6539 0.3256 0.049 Uiso 1 1 calc R . .
C13 C 0.4825(3) 0.7113(2) 0.4478(4) 0.0429(9) Uani 1 1 d . . .
H13 H 0.4492 0.7599 0.4824 0.051 Uiso 1 1 calc R . .
C14 C 0.8377(2) 0.4080(2) 0.1271(4) 0.0357(8) Uani 1 1 d . . .
C15 C 0.9285(2) 0.4048(2) 0.0629(4) 0.0385(8) Uani 1 1 d . . .
H15 H 0.9772 0.4390 0.1137 0.046 Uiso 1 1 calc R . .
C16 C 0.9497(3) 0.3527(2) -0.0738(4) 0.0446(9) Uani 1 1 d . . .
H16 H 1.0121 0.3518 -0.1171 0.054 Uiso 1 1 calc R . .
C17 C 0.8790(3) 0.3018(2) -0.1473(4) 0.0442(9) Uani 1 1 d . . .
H17 H 0.8930 0.2654 -0.2403 0.053 Uiso 1 1 calc R . .
C18 C 0.7883(3) 0.3044(2) -0.0848(4) 0.0414(9) Uani 1 1 d . . .
H18 H 0.7397 0.2702 -0.1358 0.050 Uiso 1 1 calc R . .
C19 C 0.7676(3) 0.3568(2) 0.0526(4) 0.0392(8) Uani 1 1 d . . .
H19 H 0.7052 0.3576 0.0958 0.047 Uiso 1 1 calc R . .
C20 C 0.9036(2) 0.6158(2) 0.5286(4) 0.0440(9) Uani 1 1 d . . .
H20A H 0.9536 0.5738 0.5151 0.066 Uiso 1 1 calc R . .
H20B H 0.9035 0.6344 0.6496 0.066 Uiso 1 1 calc R . .
H20C H 0.9157 0.6638 0.4534 0.066 Uiso 1 1 calc R . .
C21 C 0.7936(3) 0.5828(2) -0.0057(4) 0.0410(9) Uani 1 1 d . . .
H21A H 0.8522 0.5568 -0.0451 0.062 Uiso 1 1 calc R . .
H21B H 0.7788 0.6322 -0.0766 0.062 Uiso 1 1 calc R . .
H21C H 0.7411 0.5426 -0.0172 0.062 Uiso 1 1 calc R . .
C22 C 0.4733(3) 0.4386(2) 0.1842(4) 0.0426(9) Uani 1 1 d . . .
H22A H 0.5245 0.4447 0.1022 0.064 Uiso 1 1 calc R . .
H22B H 0.4250 0.4000 0.1362 0.064 Uiso 1 1 calc R . .
H22C H 0.4995 0.4163 0.2941 0.064 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 C1 1.373(4) . ?
O1 C21 1.426(4) . ?
O2 C11 1.387(4) . ?
O2 C22 1.432(4) . ?
N1 C7 1.369(5) . ?
N1 C8 1.375(5) . ?
N1 H1N 0.87(4) . ?
C1 C5 1.323(5) . ?
C1 C2 1.516(4) . ?
C2 C6 1.516(5) . ?
C2 C20 1.536(5) . ?
C2 C3 1.561(5) . ?
C3 C4 1.533(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.503(4) . ?
C6 C7 1.372(5) . ?
C6 C9 1.430(5) . ?
C7 H7 0.9500 . ?
C8 C13 1.387(5) . ?
C8 C9 1.415(5) . ?
C9 C10 1.415(5) . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(5) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C14 C19 1.390(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 O1 C21 117.6(3) . . ?
C11 O2 C22 116.6(3) . . ?
C7 N1 C8 109.4(3) . . ?
C7 N1 H1N 124(3) . . ?
C8 N1 H1N 126(3) . . ?
C5 C1 O1 131.8(3) . . ?
C5 C1 C2 115.0(3) . . ?
O1 C1 C2 113.2(3) . . ?
C6 C2 C1 112.3(3) . . ?
C6 C2 C20 111.5(3) . . ?
C1 C2 C20 108.8(3) . . ?
C6 C2 C3 111.7(3) . . ?
C1 C2 C3 100.6(3) . . ?
C20 C2 C3 111.4(3) . . ?
C4 C3 C2 106.7(3) . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 104.7(3) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C1 C5 C14 131.1(3) . . ?
C1 C5 C4 110.1(3) . . ?
C14 C5 C4 118.5(3) . . ?
C7 C6 C9 106.1(3) . . ?
C7 C6 C2 127.7(3) . . ?
C9 C6 C2 126.2(3) . . ?
N1 C7 C6 110.0(3) . . ?
N1 C7 H7 125.0 . . ?
C6 C7 H7 125.0 . . ?
N1 C8 C13 131.4(3) . . ?
N1 C8 C9 106.8(3) . . ?
C13 C8 C9 121.8(3) . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 C6 133.3(3) . . ?
C8 C9 C6 107.7(3) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 O2 123.8(3) . . ?
C10 C11 C12 121.8(3) . . ?
O2 C11 C12 114.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 118.3(3) . . ?
C12 C13 H13 120.9 . . ?
C8 C13 H13 120.9 . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C5 120.3(3) . . ?
C19 C14 C5 121.1(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.5(3) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C21 O1 C1 C5 11.8(5) . . . . ?
C21 O1 C1 C2 -170.3(3) . . . . ?
C5 C1 C2 C6 -132.1(3) . . . . ?
O1 C1 C2 C6 49.6(4) . . . . ?
C5 C1 C2 C20 103.9(3) . . . . ?
O1 C1 C2 C20 -74.4(3) . . . . ?
C5 C1 C2 C3 -13.2(4) . . . . ?
O1 C1 C2 C3 168.5(3) . . . . ?
C6 C2 C3 C4 135.8(3) . . . . ?
C1 C2 C3 C4 16.4(3) . . . . ?
C20 C2 C3 C4 -98.7(3) . . . . ?
C2 C3 C4 C5 -14.9(3) . . . . ?
O1 C1 C5 C14 8.6(6) . . . . ?
C2 C1 C5 C14 -169.3(3) . . . . ?
O1 C1 C5 C4 -177.9(3) . . . . ?
C2 C1 C5 C4 4.2(4) . . . . ?
C3 C4 C5 C1 7.1(4) . . . . ?
C3 C4 C5 C14 -178.5(3) . . . . ?
C1 C2 C6 C7 -136.4(3) . . . . ?
C20 C2 C6 C7 -13.9(4) . . . . ?
C3 C2 C6 C7 111.4(4) . . . . ?
C1 C2 C6 C9 45.2(4) . . . . ?
C20 C2 C6 C9 167.7(3) . . . . ?
C3 C2 C6 C9 -66.9(4) . . . . ?
C8 N1 C7 C6 0.2(4) . . . . ?
C9 C6 C7 N1 -0.3(3) . . . . ?
C2 C6 C7 N1 -179.0(3) . . . . ?
C7 N1 C8 C13 179.5(3) . . . . ?
C7 N1 C8 C9 0.1(3) . . . . ?
N1 C8 C9 C10 178.6(3) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?
N1 C8 C9 C6 -0.3(3) . . . . ?
C13 C8 C9 C6 -179.8(3) . . . . ?
C7 C6 C9 C10 -178.2(3) . . . . ?
C2 C6 C9 C10 0.4(5) . . . . ?
C7 C6 C9 C8 0.4(3) . . . . ?
C2 C6 C9 C8 179.1(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C6 C9 C10 C11 178.5(3) . . . . ?
C9 C10 C11 O2 -178.8(3) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C22 O2 C11 C10 9.9(4) . . . . ?
C22 O2 C11 C12 -169.6(2) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
O2 C11 C12 C13 179.0(3) . . . . ?
C11 C12 C13 C8 -0.3(4) . . . . ?
N1 C8 C13 C12 -178.3(3) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
C1 C5 C14 C15 73.5(5) . . . . ?
C4 C5 C14 C15 -99.6(4) . . . . ?
C1 C5 C14 C19 -109.8(4) . . . . ?
C4 C5 C14 C19 77.1(4) . . . . ?
C19 C14 C15 C16 0.8(5) . . . . ?
C5 C14 C15 C16 177.6(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C5 C14 C19 C18 -177.6(3) . . . . ?
C17 C18 C19 C14 0.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        61.15
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.072
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
####################################################################### 
# 
# 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_NSD-1189P
_database_code_depnum_ccdc_archive 'CCDC 1057458'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 N O2'
_chemical_formula_sum            'C23 H25 N O2'
_chemical_formula_weight         347.44

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab '
_symmetry_space_group_name_H-M   'P b c a '

loop_
_symmetry_equiv_pos_as_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'
'-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                   7.5352(3)
_cell_length_b                   16.1007(6)
_cell_length_c                   30.3669(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3684.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.50

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8998
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50544
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         30.51
_reflns_number_total             5627
_reflns_number_gt                4736
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0562P)²+1.5053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5627
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14716(9) 0.61972(5) 0.66120(2) 0.01365(15) Uani 1 1 d . . .
O2 O 0.55810(12) 0.89891(5) 0.62757(3) 0.02121(18) Uani 1 1 d . . .
N1 N 0.64117(12) 0.64350(6) 0.74545(3) 0.01605(18) Uani 1 1 d . . .
H1N H 0.682(2) 0.6398(9) 0.7727(5) 0.019 Uiso 1 1 d . . .
C1 C 0.25741(12) 0.59221(6) 0.62789(3) 0.01040(17) Uani 1 1 d . . .
C2 C 0.42193(12) 0.55042(6) 0.64702(3) 0.01118(17) Uani 1 1 d . . .
C3 C 0.56127(13) 0.53718(6) 0.61032(3) 0.01336(18) Uani 1 1 d . . .
H3A H 0.6209 0.5907 0.6040 0.016 Uiso 1 1 calc R . .
H3B H 0.6525 0.4976 0.6208 0.016 Uiso 1 1 calc R . .
C4 C 0.47885(14) 0.50382(7) 0.56802(3) 0.01488(19) Uani 1 1 d . . .
H4A H 0.5731 0.4935 0.5460 0.018 Uiso 1 1 calc R . .
H4B H 0.4180 0.4505 0.5741 0.018 Uiso 1 1 calc R . .
C5 C 0.34635(13) 0.56636(7) 0.54988(3) 0.01506(19) Uani 1 1 d . . .
H5A H 0.4122 0.6129 0.5362 0.018 Uiso 1 1 calc R . .
H5B H 0.2751 0.5393 0.5265 0.018 Uiso 1 1 calc R . .
C6 C 0.22179(12) 0.60093(6) 0.58464(3) 0.01096(17) Uani 1 1 d . . .
C7 C 0.50345(12) 0.60453(6) 0.68264(3) 0.01141(18) Uani 1 1 d . . .
C8 C 0.56507(13) 0.57853(7) 0.72313(3) 0.01464(19) Uani 1 1 d . . .
H8 H 0.5561 0.5234 0.7340 0.018 Uiso 1 1 calc R . .
C9 C 0.62790(13) 0.71391(7) 0.72013(3) 0.01433(19) Uani 1 1 d . . .
C10 C 0.54284(12) 0.69191(6) 0.68019(3) 0.01195(18) Uani 1 1 d . . .
C11 C 0.51621(13) 0.75333(6) 0.64762(3) 0.01338(18) Uani 1 1 d . . .
H11 H 0.4607 0.7402 0.6204 0.016 Uiso 1 1 calc R . .
C12 C 0.57335(14) 0.83315(7) 0.65658(3) 0.0163(2) Uani 1 1 d . . .
C13 C 0.65557(15) 0.85429(7) 0.69694(4) 0.0197(2) Uani 1 1 d . . .
H13 H 0.6914 0.9100 0.7021 0.024 Uiso 1 1 calc R . .
C14 C 0.68442(14) 0.79498(7) 0.72894(3) 0.0187(2) Uani 1 1 d . . .
H14 H 0.7406 0.8087 0.7560 0.022 Uiso 1 1 calc R . .
C15 C 0.06761(12) 0.64799(6) 0.56679(3) 0.01131(18) Uani 1 1 d . . .
C16 C 0.03336(14) 0.72979(6) 0.57977(3) 0.01550(19) Uani 1 1 d . . .
H16 H 0.1056 0.7550 0.6016 0.019 Uiso 1 1 calc R . .
C17 C -0.10530(15) 0.77471(7) 0.56101(4) 0.0191(2) Uani 1 1 d . . .
H17 H -0.1270 0.8302 0.5702 0.023 Uiso 1 1 calc R . .
C18 C -0.21232(14) 0.73882(7) 0.52884(4) 0.0181(2) Uani 1 1 d . . .
H18 H -0.3055 0.7699 0.5157 0.022 Uiso 1 1 calc R . .
C19 C -0.18187(14) 0.65731(7) 0.51613(3) 0.0163(2) Uani 1 1 d . . .
H19 H -0.2560 0.6320 0.4947 0.020 Uiso 1 1 calc R . .
C20 C -0.04299(13) 0.61248(6) 0.53477(3) 0.01383(19) Uani 1 1 d . . .
H20 H -0.0227 0.5568 0.5256 0.017 Uiso 1 1 calc R . .
C21 C 0.36532(14) 0.46621(7) 0.66690(3) 0.0170(2) Uani 1 1 d . . .
H21A H 0.4691 0.4386 0.6797 0.026 Uiso 1 1 calc R . .
H21B H 0.3146 0.4311 0.6437 0.026 Uiso 1 1 calc R . .
H21C H 0.2764 0.4755 0.6899 0.026 Uiso 1 1 calc R . .
C22 C -0.03964(13) 0.60171(7) 0.65837(3) 0.0164(2) Uani 1 1 d . . .
H22A H -0.1008 0.6480 0.6439 0.025 Uiso 1 1 calc R . .
H22B H -0.0880 0.5941 0.6881 0.025 Uiso 1 1 calc R . .
H22C H -0.0574 0.5508 0.6413 0.025 Uiso 1 1 calc R . .
C23 C 0.47364(16) 0.88257(7) 0.58672(4) 0.0195(2) Uani 1 1 d . . .
H23A H 0.5427 0.8414 0.5703 0.029 Uiso 1 1 calc R . .
H23B H 0.4659 0.9341 0.5696 0.029 Uiso 1 1 calc R . .
H23C H 0.3540 0.8610 0.5921 0.029 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 C1 1.3818(11) . ?
O1 C22 1.4397(12) . ?
O2 C12 1.3821(13) . ?
O2 C23 1.4189(13) . ?
N1 C8 1.3721(14) . ?
N1 C9 1.3735(14) . ?
N1 H1N 0.886(15) . ?
C1 C6 1.3479(13) . ?
C1 C2 1.5254(13) . ?
C2 C7 1.5188(13) . ?
C2 C21 1.5443(14) . ?
C2 C3 1.5458(13) . ?
C3 C4 1.5245(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5212(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5182(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C15 1.4893(13) . ?
C7 C8 1.3793(13) . ?
C7 C10 1.4398(14) . ?
C8 H8 0.9500 . ?
C9 C14 1.3988(15) . ?
C9 C10 1.4168(13) . ?
C10 C11 1.4129(14) . ?
C11 C12 1.3824(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.4148(15) . ?
C13 C14 1.3798(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3987(14) . ?
C15 C20 1.4025(13) . ?
C16 C17 1.3925(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3924(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3870(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.3915(14) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 O1 C22 118.66(8) . . ?
C12 O2 C23 116.91(8) . . ?
C8 N1 C9 108.80(8) . . ?
C8 N1 H1N 123.8(9) . . ?
C9 N1 H1N 127.2(9) . . ?
C6 C1 O1 124.07(9) . . ?
C6 C1 C2 125.36(8) . . ?
O1 C1 C2 110.57(7) . . ?
C7 C2 C1 110.29(8) . . ?
C7 C2 C21 109.68(8) . . ?
C1 C2 C21 108.16(8) . . ?
C7 C2 C3 108.53(8) . . ?
C1 C2 C3 109.78(8) . . ?
C21 C2 C3 110.39(8) . . ?
C4 C3 C2 112.29(8) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 109.83(8) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C4 113.37(8) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C1 C6 C15 124.26(9) . . ?
C1 C6 C5 121.08(9) . . ?
C15 C6 C5 114.57(8) . . ?
C8 C7 C10 105.86(9) . . ?
C8 C7 C2 126.65(9) . . ?
C10 C7 C2 127.38(8) . . ?
N1 C8 C7 110.47(9) . . ?
N1 C8 H8 124.8 . . ?
C7 C8 H8 124.8 . . ?
N1 C9 C14 129.86(9) . . ?
N1 C9 C10 107.81(9) . . ?
C14 C9 C10 122.33(9) . . ?
C11 C10 C9 119.24(9) . . ?
C11 C10 C7 133.70(9) . . ?
C9 C10 C7 107.05(9) . . ?
C12 C11 C10 117.95(9) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
O2 C12 C11 124.11(9) . . ?
O2 C12 C13 113.84(9) . . ?
C11 C12 C13 122.04(10) . . ?
C14 C13 C12 120.84(10) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 117.58(9) . . ?
C13 C14 H14 121.2 . . ?
C9 C14 H14 121.2 . . ?
C16 C15 C20 118.01(9) . . ?
C16 C15 C6 121.37(9) . . ?
C20 C15 C6 120.56(9) . . ?
C17 C16 C15 120.82(10) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.40(10) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.47(10) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.14(10) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 121.15(10) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C22 O1 C1 C6 46.49(14) . . . . ?
C22 O1 C1 C2 -132.97(9) . . . . ?
C6 C1 C2 C7 132.23(10) . . . . ?
O1 C1 C2 C7 -48.32(10) . . . . ?
C6 C1 C2 C21 -107.82(11) . . . . ?
O1 C1 C2 C21 71.63(10) . . . . ?
C6 C1 C2 C3 12.69(13) . . . . ?
O1 C1 C2 C3 -167.86(8) . . . . ?
C7 C2 C3 C4 -164.76(8) . . . . ?
C1 C2 C3 C4 -44.15(11) . . . . ?
C21 C2 C3 C4 75.00(10) . . . . ?
C2 C3 C4 C5 62.29(11) . . . . ?
C3 C4 C5 C6 -46.20(12) . . . . ?
O1 C1 C6 C15 5.83(16) . . . . ?
C2 C1 C6 C15 -174.79(9) . . . . ?
O1 C1 C6 C5 -177.81(9) . . . . ?
C2 C1 C6 C5 1.57(15) . . . . ?
C4 C5 C6 C1 15.60(14) . . . . ?
C4 C5 C6 C15 -167.70(9) . . . . ?
C1 C2 C7 C8 135.83(10) . . . . ?
C21 C2 C7 C8 16.81(13) . . . . ?
C3 C2 C7 C8 -103.87(11) . . . . ?
C1 C2 C7 C10 -48.51(13) . . . . ?
C21 C2 C7 C10 -167.54(9) . . . . ?
C3 C2 C7 C10 71.79(12) . . . . ?
C9 N1 C8 C7 1.03(12) . . . . ?
C10 C7 C8 N1 -0.68(11) . . . . ?
C2 C7 C8 N1 175.73(9) . . . . ?
C8 N1 C9 C14 179.43(11) . . . . ?
C8 N1 C9 C10 -0.93(11) . . . . ?
N1 C9 C10 C11 -178.60(9) . . . . ?
C14 C9 C10 C11 1.06(15) . . . . ?
N1 C9 C10 C7 0.51(11) . . . . ?
C14 C9 C10 C7 -179.82(9) . . . . ?
C8 C7 C10 C11 179.03(11) . . . . ?
C2 C7 C10 C11 2.65(18) . . . . ?
C8 C7 C10 C9 0.09(11) . . . . ?
C2 C7 C10 C9 -176.28(9) . . . . ?
C9 C10 C11 C12 -0.71(14) . . . . ?
C7 C10 C11 C12 -179.54(10) . . . . ?
C23 O2 C12 C11 1.82(15) . . . . ?
C23 O2 C12 C13 -178.79(10) . . . . ?
C10 C11 C12 O2 179.07(9) . . . . ?
C10 C11 C12 C13 -0.28(16) . . . . ?
O2 C12 C13 C14 -178.42(10) . . . . ?
C11 C12 C13 C14 0.98(17) . . . . ?
C12 C13 C14 C9 -0.63(16) . . . . ?
N1 C9 C14 C13 179.21(11) . . . . ?
C10 C9 C14 C13 -0.38(16) . . . . ?
C1 C6 C15 C16 52.17(14) . . . . ?
C5 C6 C15 C16 -124.40(10) . . . . ?
C1 C6 C15 C20 -130.82(11) . . . . ?
C5 C6 C15 C20 52.61(12) . . . . ?
C20 C15 C16 C17 -0.71(15) . . . . ?
C6 C15 C16 C17 176.38(10) . . . . ?
C15 C16 C17 C18 -0.13(17) . . . . ?
C16 C17 C18 C19 1.17(17) . . . . ?
C17 C18 C19 C20 -1.36(16) . . . . ?
C18 C19 C20 C15 0.52(16) . . . . ?
C16 C15 C20 C19 0.52(15) . . . . ?
C6 C15 C20 C19 -176.59(9) . . . . ?

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
N1 H1N O1 0.886(15) 2.050(15) 2.8607(11) 151.6(13) 6_657

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.051
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
####################################################################### 
# 
# 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_NSD-1183-F1
_database_code_depnum_ccdc_archive 'CCDC 1057459'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab '
_symmetry_space_group_name_H-M   'P 21 21 21 '

loop_
_symmetry_equiv_pos_as_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                   7.2261(3)
_cell_length_b                   13.4245(5)
_cell_length_c                   18.9990(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1843.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7072
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      60.92

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8372
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18058
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         61.22
_reflns_number_total             2831
_reflns_number_gt                2333
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.8243P] 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 '1174 Friedel pairs (Flack, 1983) '
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_number_reflns         2831
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1154
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4610(3) 0.46844(17) 0.62253(14) 0.0625(7) Uani 1 1 d . . .
O2 O 0.6491(3) 0.44203(16) 0.72455(12) 0.0560(6) Uani 1 1 d . . .
O3 O 0.6346(4) 0.75636(17) 0.37777(12) 0.0588(7) Uani 1 1 d . . .
N1 N 0.6480(4) 0.70144(18) 0.49084(14) 0.0462(7) Uani 1 1 d . . .
C1 C 0.6063(5) 0.4995(2) 0.66414(18) 0.0523(9) Uani 1 1 d . . .
C2 C 0.6150(5) 0.6120(2) 0.67643(17) 0.0505(9) Uani 1 1 d . . .
C3 C 0.7995(5) 0.6221(3) 0.7166(2) 0.0557(10) Uani 1 1 d . . .
H3A H 0.8570 0.6876 0.7069 0.067 Uiso 1 1 calc R . .
H3B H 0.7789 0.6160 0.7679 0.067 Uiso 1 1 calc R . .
C4 C 0.9250(5) 0.5372(2) 0.69003(19) 0.0541(9) Uani 1 1 d . . .
H4A H 0.9993 0.5590 0.6490 0.065 Uiso 1 1 calc R . .
H4B H 1.0097 0.5143 0.7276 0.065 Uiso 1 1 calc R . .
C5 C 0.7907(5) 0.4557(3) 0.6694(2) 0.0536(9) Uani 1 1 d . . .
C6 C 0.6251(5) 0.6674(2) 0.60702(18) 0.0466(8) Uani 1 1 d . . .
C7 C 0.6317(5) 0.6274(2) 0.54184(18) 0.0496(8) Uani 1 1 d . . .
H7 H 0.6259 0.5581 0.5321 0.060 Uiso 1 1 calc R . .
C8 C 0.6539(5) 0.7935(2) 0.52544(17) 0.0470(9) Uani 1 1 d . . .
C9 C 0.6416(5) 0.7735(2) 0.59808(18) 0.0494(9) Uani 1 1 d . . .
C10 C 0.6484(5) 0.8539(2) 0.6448(2) 0.0589(10) Uani 1 1 d . . .
H10 H 0.6393 0.8431 0.6941 0.071 Uiso 1 1 calc R . .
C11 C 0.6684(5) 0.9485(3) 0.6187(2) 0.0641(11) Uani 1 1 d . . .
H11 H 0.6720 1.0032 0.6504 0.077 Uiso 1 1 calc R . .
C12 C 0.6835(5) 0.9664(3) 0.5466(2) 0.0626(11) Uani 1 1 d . . .
H12 H 0.6991 1.0326 0.5301 0.075 Uiso 1 1 calc R . .
C13 C 0.6762(5) 0.8896(2) 0.4994(2) 0.0552(9) Uani 1 1 d . . .
H13 H 0.6860 0.9016 0.4502 0.066 Uiso 1 1 calc R . .
C14 C 0.8539(5) 0.3652(3) 0.6314(2) 0.0533(9) Uani 1 1 d . . .
C15 C 0.8754(5) 0.2749(3) 0.6653(2) 0.0607(10) Uani 1 1 d . . .
H15 H 0.8473 0.2692 0.7139 0.073 Uiso 1 1 calc R . .
C16 C 0.9383(5) 0.1924(3) 0.6281(2) 0.0626(10) Uani 1 1 d . . .
H16 H 0.9520 0.1302 0.6514 0.075 Uiso 1 1 calc R . .
C17 C 0.9811(5) 0.2007(3) 0.5572(2) 0.0624(11) Uani 1 1 d . . .
H17 H 1.0247 0.1443 0.5319 0.075 Uiso 1 1 calc R . .
C18 C 0.9600(5) 0.2912(2) 0.5235(2) 0.0611(10) Uani 1 1 d . . .
H18 H 0.9886 0.2971 0.4748 0.073 Uiso 1 1 calc R . .
C19 C 0.8976(5) 0.3729(3) 0.5603(2) 0.0571(10) Uani 1 1 d . . .
H19 H 0.8842 0.4350 0.5369 0.069 Uiso 1 1 calc R . .
C20 C 0.4505(5) 0.6464(3) 0.7209(2) 0.0637(11) Uani 1 1 d . . .
H20A H 0.3352 0.6333 0.6954 0.096 Uiso 1 1 calc R . .
H20B H 0.4613 0.7180 0.7301 0.096 Uiso 1 1 calc R . .
H20C H 0.4496 0.6101 0.7656 0.096 Uiso 1 1 calc R . .
C21 C 0.3832(6) 0.3741(3) 0.6361(2) 0.0671(11) Uani 1 1 d . . .
H21A H 0.4799 0.3231 0.6332 0.101 Uiso 1 1 calc R . .
H21B H 0.2868 0.3600 0.6012 0.101 Uiso 1 1 calc R . .
H21C H 0.3287 0.3737 0.6834 0.101 Uiso 1 1 calc R . .
C22 C 0.6482(5) 0.6864(3) 0.41727(19) 0.0507(9) Uani 1 1 d . . .
C23 C 0.6673(5) 0.5806(2) 0.39377(18) 0.0594(10) Uani 1 1 d . . .
H23A H 0.5537 0.5440 0.4049 0.089 Uiso 1 1 calc R . .
H23B H 0.7722 0.5496 0.4181 0.089 Uiso 1 1 calc R . .
H23C H 0.6887 0.5787 0.3428 0.089 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 C1 1.379(4) . ?
O1 C21 1.410(4) . ?
O2 C1 1.417(4) . ?
O2 C5 1.476(4) . ?
O3 C22 1.206(4) . ?
N1 C7 1.393(4) . ?
N1 C8 1.400(4) . ?
N1 C22 1.412(4) . ?
C1 C5 1.460(5) . ?
C1 C2 1.530(5) . ?
C2 C6 1.516(4) . ?
C2 C20 1.530(5) . ?
C2 C3 1.542(5) . ?
C3 C4 1.541(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.514(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.485(5) . ?
C6 C7 1.350(4) . ?
C6 C9 1.439(4) . ?
C7 H7 0.9500 . ?
C8 C13 1.392(4) . ?
C8 C9 1.409(4) . ?
C9 C10 1.399(5) . ?
C10 C11 1.372(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.381(5) . ?
C14 C19 1.391(5) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.496(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 O1 C21 118.1(3) . . ?
C1 O2 C5 60.6(2) . . ?
C7 N1 C8 107.8(3) . . ?
C7 N1 C22 125.9(3) . . ?
C8 N1 C22 126.2(3) . . ?
O1 C1 O2 117.8(3) . . ?
O1 C1 C5 127.8(3) . . ?
O2 C1 C5 61.7(2) . . ?
O1 C1 C2 114.7(3) . . ?
O2 C1 C2 113.9(3) . . ?
C5 C1 C2 110.5(3) . . ?
C6 C2 C20 111.7(3) . . ?
C6 C2 C1 110.7(3) . . ?
C20 C2 C1 110.5(3) . . ?
C6 C2 C3 110.2(3) . . ?
C20 C2 C3 111.9(3) . . ?
C1 C2 C3 101.4(3) . . ?
C4 C3 C2 106.4(3) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 104.0(3) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C1 C5 O2 57.7(2) . . ?
C1 C5 C14 125.2(3) . . ?
O2 C5 C14 117.2(3) . . ?
C1 C5 C4 108.1(3) . . ?
O2 C5 C4 110.5(3) . . ?
C14 C5 C4 121.4(3) . . ?
C7 C6 C9 106.4(3) . . ?
C7 C6 C2 127.2(3) . . ?
C9 C6 C2 126.3(3) . . ?
C6 C7 N1 110.9(3) . . ?
C6 C7 H7 124.5 . . ?
N1 C7 H7 124.5 . . ?
C13 C8 N1 130.9(3) . . ?
C13 C8 C9 122.2(3) . . ?
N1 C8 C9 106.8(3) . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 C6 133.8(3) . . ?
C8 C9 C6 108.0(3) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 118.0(4) . . ?
C12 C13 H13 121.0 . . ?
C8 C13 H13 121.0 . . ?
C15 C14 C19 119.5(4) . . ?
C15 C14 C5 121.7(3) . . ?
C19 C14 C5 118.8(3) . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 N1 120.3(3) . . ?
O3 C22 C23 124.1(3) . . ?
N1 C22 C23 115.6(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C21 O1 C1 O2 -9.7(5) . . . . ?
C21 O1 C1 C5 64.6(5) . . . . ?
C21 O1 C1 C2 -147.9(3) . . . . ?
C5 O2 C1 O1 120.2(4) . . . . ?
C5 O2 C1 C2 -101.3(4) . . . . ?
O1 C1 C2 C6 -57.1(4) . . . . ?
O2 C1 C2 C6 163.1(3) . . . . ?
C5 C1 C2 C6 95.9(4) . . . . ?
O1 C1 C2 C20 67.2(4) . . . . ?
O2 C1 C2 C20 -72.6(4) . . . . ?
C5 C1 C2 C20 -139.8(3) . . . . ?
O1 C1 C2 C3 -174.1(3) . . . . ?
O2 C1 C2 C3 46.1(4) . . . . ?
C5 C1 C2 C3 -21.0(4) . . . . ?
C6 C2 C3 C4 -87.0(3) . . . . ?
C20 C2 C3 C4 148.1(3) . . . . ?
C1 C2 C3 C4 30.3(3) . . . . ?
C2 C3 C4 C5 -29.0(4) . . . . ?
O1 C1 C5 O2 -104.6(4) . . . . ?
C2 C1 C5 O2 106.8(3) . . . . ?
O1 C1 C5 C14 -2.1(6) . . . . ?
O2 C1 C5 C14 102.5(4) . . . . ?
C2 C1 C5 C14 -150.7(3) . . . . ?
O1 C1 C5 C4 152.1(3) . . . . ?
O2 C1 C5 C4 -103.3(3) . . . . ?
C2 C1 C5 C4 3.6(4) . . . . ?
C1 O2 C5 C14 -116.2(4) . . . . ?
C1 O2 C5 C4 99.0(3) . . . . ?
C3 C4 C5 C1 15.7(4) . . . . ?
C3 C4 C5 O2 -45.8(4) . . . . ?
C3 C4 C5 C14 171.1(3) . . . . ?
C20 C2 C6 C7 -125.5(4) . . . . ?
C1 C2 C6 C7 -1.9(5) . . . . ?
C3 C2 C6 C7 109.5(4) . . . . ?
C20 C2 C6 C9 58.7(5) . . . . ?
C1 C2 C6 C9 -177.6(4) . . . . ?
C3 C2 C6 C9 -66.2(4) . . . . ?
C9 C6 C7 N1 -1.1(4) . . . . ?
C2 C6 C7 N1 -177.5(3) . . . . ?
C8 N1 C7 C6 0.5(4) . . . . ?
C22 N1 C7 C6 -176.2(3) . . . . ?
C7 N1 C8 C13 177.3(4) . . . . ?
C22 N1 C8 C13 -6.0(6) . . . . ?
C7 N1 C8 C9 0.3(4) . . . . ?
C22 N1 C8 C9 177.0(3) . . . . ?
C13 C8 C9 C10 1.3(5) . . . . ?
N1 C8 C9 C10 178.7(3) . . . . ?
C13 C8 C9 C6 -178.2(3) . . . . ?
N1 C8 C9 C6 -0.9(4) . . . . ?
C7 C6 C9 C10 -178.2(4) . . . . ?
C2 C6 C9 C10 -1.8(7) . . . . ?
C7 C6 C9 C8 1.2(4) . . . . ?
C2 C6 C9 C8 177.7(3) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
C6 C9 C10 C11 178.8(4) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C8 -0.2(6) . . . . ?
N1 C8 C13 C12 -177.5(4) . . . . ?
C9 C8 C13 C12 -0.9(5) . . . . ?
C1 C5 C14 C15 -105.5(5) . . . . ?
O2 C5 C14 C15 -37.4(5) . . . . ?
C4 C5 C14 C15 103.4(4) . . . . ?
C1 C5 C14 C19 76.5(5) . . . . ?
O2 C5 C14 C19 144.6(3) . . . . ?
C4 C5 C14 C19 -74.6(5) . . . . ?
C19 C14 C15 C16 -0.7(6) . . . . ?
C5 C14 C15 C16 -178.7(3) . . . . ?
C14 C15 C16 C17 0.6(6) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C14 -0.5(6) . . . . ?
C15 C14 C19 C18 0.7(6) . . . . ?
C5 C14 C19 C18 178.7(4) . . . . ?
C7 N1 C22 O3 168.6(3) . . . . ?
C8 N1 C22 O3 -7.6(6) . . . . ?
C7 N1 C22 C23 -11.8(5) . . . . ?
C8 N1 C22 C23 172.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        61.22
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
####################################################################### 
# 
# 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_NSD-1207major
_database_code_depnum_ccdc_archive 'CCDC 1057460'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0196(11)
_cell_length_b                   12.4522(11)
_cell_length_c                   14.0202(14)
_cell_angle_alpha                94.894(4)
_cell_angle_beta                 114.290(4)
_cell_angle_gamma                113.544(4)
_cell_volume                     1673.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    6801
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20648
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         26.54
_reflns_number_total             20352
_reflns_number_gt                14935
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          Twin

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1362P)²+0.2759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         20352
_refine_ls_number_parameters     426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61829(11) 0.17554(10) 0.37206(9) 0.0170(3) Uani 1 1 d . . .
N1 N 0.48670(16) 0.06857(14) 0.61515(12) 0.0211(3) Uani 1 1 d . . .
H1N H 0.4608(19) -0.0058(17) 0.6293(15) 0.025 Uiso 1 1 d . . .
C1 C 0.56680(17) 0.26201(15) 0.36260(13) 0.0156(4) Uani 1 1 d . . .
H1 H 0.6438 0.3471 0.4076 0.019 Uiso 1 1 calc R . .
C2 C 0.45279(18) 0.22411(15) 0.39711(14) 0.0184(4) Uani 1 1 d . . .
C3 C 0.32442(18) 0.11983(16) 0.29429(15) 0.0247(4) Uani 1 1 d . . .
H3A H 0.3146 0.0389 0.3028 0.030 Uiso 1 1 calc R . .
H3B H 0.2389 0.1224 0.2835 0.030 Uiso 1 1 calc R . .
C4 C 0.34723(18) 0.13978(17) 0.19592(15) 0.0268(4) Uani 1 1 d . . .
H4A H 0.2729 0.1527 0.1417 0.032 Uiso 1 1 calc R . .
H4B H 0.3463 0.0674 0.1597 0.032 Uiso 1 1 calc R . .
C5 C 0.49032(17) 0.25470(15) 0.24100(14) 0.0181(4) Uani 1 1 d . . .
H5 H 0.4742 0.3275 0.2388 0.022 Uiso 1 1 calc R . .
C6 C 0.49358(17) 0.18467(15) 0.49983(14) 0.0171(4) Uani 1 1 d . . .
C7 C 0.42118(18) 0.07348(15) 0.50993(15) 0.0204(4) Uani 1 1 d . . .
H7 H 0.3367 0.0081 0.4520 0.024 Uiso 1 1 calc R . .
C8 C 0.60802(19) 0.17693(15) 0.67508(15) 0.0192(4) Uani 1 1 d . . .
C9 C 0.61530(18) 0.25386(15) 0.60647(14) 0.0178(4) Uani 1 1 d . . .
C10 C 0.72979(18) 0.37149(15) 0.65151(14) 0.0200(4) Uani 1 1 d . . .
H10 H 0.7372 0.4260 0.6083 0.024 Uiso 1 1 calc R . .
C11 C 0.8320(2) 0.40783(16) 0.75923(15) 0.0233(4) Uani 1 1 d . . .
H11 H 0.9104 0.4873 0.7892 0.028 Uiso 1 1 calc R . .
C12 C 0.8222(2) 0.32960(16) 0.82523(15) 0.0244(4) Uani 1 1 d . . .
H12 H 0.8937 0.3570 0.8992 0.029 Uiso 1 1 calc R . .
C13 C 0.7104(2) 0.21381(16) 0.78398(14) 0.0231(4) Uani 1 1 d . . .
H13 H 0.7032 0.1606 0.8284 0.028 Uiso 1 1 calc R . .
C14 C 0.56763(17) 0.25727(15) 0.17868(13) 0.0171(4) Uani 1 1 d . . .
C15 C 0.62876(18) 0.36394(15) 0.15253(13) 0.0205(4) Uani 1 1 d . . .
H15 H 0.6184 0.4328 0.1727 0.025 Uiso 1 1 calc R . .
C16 C 0.7040(2) 0.37153(17) 0.09798(15) 0.0271(4) Uani 1 1 d . . .
H16 H 0.7452 0.4454 0.0821 0.033 Uiso 1 1 calc R . .
C17 C 0.7191(2) 0.27232(18) 0.06665(14) 0.0290(4) Uani 1 1 d . . .
H17 H 0.7700 0.2773 0.0288 0.035 Uiso 1 1 calc R . .
C18 C 0.6589(2) 0.16473(18) 0.09105(15) 0.0283(4) Uani 1 1 d . . .
H18 H 0.6690 0.0960 0.0700 0.034 Uiso 1 1 calc R . .
C19 C 0.58385(19) 0.15787(16) 0.14636(14) 0.0221(4) Uani 1 1 d . . .
H19 H 0.5430 0.0840 0.1623 0.027 Uiso 1 1 calc R . .
C20 C 0.42630(19) 0.33308(16) 0.41746(15) 0.0248(4) Uani 1 1 d . . .
H20A H 0.5122 0.4026 0.4764 0.037 Uiso 1 1 calc R . .
H20B H 0.3536 0.3089 0.4387 0.037 Uiso 1 1 calc R . .
H20C H 0.3963 0.3569 0.3502 0.037 Uiso 1 1 calc R . .
C21 C 0.76476(18) 0.23114(17) 0.41818(15) 0.0240(4) Uani 1 1 d . . .
H21A H 0.8091 0.2770 0.4955 0.036 Uiso 1 1 calc R . .
H21B H 0.7943 0.2874 0.3783 0.036 Uiso 1 1 calc R . .
H21C H 0.7921 0.1675 0.4126 0.036 Uiso 1 1 calc R . .
O2 O 0.92748(11) 0.82071(10) 0.27949(9) 0.0168(3) Uani 1 1 d . . .
N2 N 0.91489(15) 0.93003(13) 0.58410(12) 0.0197(3) Uani 1 1 d . . .
H2N H 0.9677(19) 1.0001(16) 0.6409(16) 0.024 Uiso 1 1 d . . .
C22 C 0.78129(16) 0.73850(15) 0.22465(13) 0.0149(4) Uani 1 1 d . . .
H22 H 0.7625 0.6523 0.2225 0.018 Uiso 1 1 calc R . .
C23 C 0.71312(17) 0.77953(14) 0.28288(14) 0.0166(4) Uani 1 1 d . . .
C24 C 0.69970(19) 0.88508(15) 0.23735(14) 0.0214(4) Uani 1 1 d . . .
H24A H 0.6145 0.8862 0.2294 0.026 Uiso 1 1 calc R . .
H24B H 0.7809 0.9651 0.2878 0.026 Uiso 1 1 calc R . .
C25 C 0.6928(2) 0.86245(17) 0.12605(14) 0.0273(4) Uani 1 1 d . . .
H25A H 0.7677 0.9343 0.1251 0.033 Uiso 1 1 calc R . .
H25B H 0.6022 0.8488 0.0675 0.033 Uiso 1 1 calc R . .
C26 C 0.71035(18) 0.74762(15) 0.10734(13) 0.0189(4) Uani 1 1 d . . .
H26 H 0.6151 0.6751 0.0667 0.023 Uiso 1 1 calc R . .
C27 C 0.79869(17) 0.81770(15) 0.40620(14) 0.0165(4) Uani 1 1 d . . .
C28 C 0.84417(17) 0.92655(15) 0.47728(14) 0.0186(4) Uani 1 1 d . . .
H28 H 0.8288 0.9918 0.4555 0.022 Uiso 1 1 calc R . .
C29 C 0.92118(17) 0.82249(15) 0.58455(14) 0.0187(4) Uani 1 1 d . . .
C30 C 0.84683(17) 0.74793(15) 0.47409(13) 0.0167(4) Uani 1 1 d . . .
C31 C 0.83839(18) 0.63131(15) 0.45428(14) 0.0192(4) Uani 1 1 d . . .
H31 H 0.7880 0.5781 0.3815 0.023 Uiso 1 1 calc R . .
C32 C 0.90383(18) 0.59527(16) 0.54132(15) 0.0235(4) Uani 1 1 d . . .
H32 H 0.8999 0.5175 0.5277 0.028 Uiso 1 1 calc R . .
C33 C 0.97605(19) 0.67088(16) 0.64955(15) 0.0251(4) Uani 1 1 d . . .
H33 H 1.0191 0.6430 0.7080 0.030 Uiso 1 1 calc R . .
C34 C 0.98566(18) 0.78497(16) 0.67267(14) 0.0222(4) Uani 1 1 d . . .
H34 H 1.0345 0.8363 0.7460 0.027 Uiso 1 1 calc R . .
C35 C 0.78342(18) 0.74471(15) 0.04207(13) 0.0174(4) Uani 1 1 d . . .
C36 C 0.72642(19) 0.63856(16) -0.04105(14) 0.0209(4) Uani 1 1 d . . .
H36 H 0.6418 0.5702 -0.0563 0.025 Uiso 1 1 calc R . .
C37 C 0.7902(2) 0.62998(18) -0.10230(15) 0.0277(4) Uani 1 1 d . . .
H37 H 0.7491 0.5567 -0.1590 0.033 Uiso 1 1 calc R . .
C38 C 0.9143(2) 0.72895(19) -0.08030(16) 0.0317(5) Uani 1 1 d . . .
H38 H 0.9588 0.7235 -0.1216 0.038 Uiso 1 1 calc R . .
C39 C 0.9727(2) 0.83516(18) 0.00178(16) 0.0294(5) Uani 1 1 d . . .
H39 H 1.0575 0.9031 0.0169 0.035 Uiso 1 1 calc R . .
C40 C 0.90812(19) 0.84353(16) 0.06269(14) 0.0235(4) Uani 1 1 d . . .
H40 H 0.9493 0.9173 0.1189 0.028 Uiso 1 1 calc R . .
C41 C 0.56731(17) 0.67340(15) 0.24616(14) 0.0218(4) Uani 1 1 d . . .
H41A H 0.5245 0.6990 0.2832 0.033 Uiso 1 1 calc R . .
H41B H 0.5752 0.6019 0.2653 0.033 Uiso 1 1 calc R . .
H41C H 0.5095 0.6518 0.1666 0.033 Uiso 1 1 calc R . .
C42 C 1.00849(18) 0.76069(17) 0.28559(15) 0.0238(4) Uani 1 1 d . . .
H42A H 0.9770 0.7134 0.2116 0.036 Uiso 1 1 calc R . .
H42B H 0.9975 0.7053 0.3306 0.036 Uiso 1 1 calc R . .
H42C H 1.1066 0.8222 0.3188 0.036 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 C21 1.418(2) . ?
O1 C1 1.4315(19) . ?
N1 C8 1.371(2) . ?
N1 C7 1.378(2) . ?
N1 H1N 0.920(19) . ?
C1 C5 1.542(2) . ?
C1 C2 1.550(2) . ?
C1 H1 1.0000 . ?
C2 C6 1.513(2) . ?
C2 C20 1.542(2) . ?
C2 C3 1.548(2) . ?
C3 C4 1.534(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.546(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.509(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.366(2) . ?
C6 C9 1.446(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.393(3) . ?
C8 C9 1.418(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.395(2) . ?
C14 C15 1.401(2) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 C42 1.428(2) . ?
O2 C22 1.4296(19) . ?
N2 C28 1.371(2) . ?
N2 C29 1.372(2) . ?
N2 H2N 0.906(18) . ?
C22 C26 1.549(2) . ?
C22 C23 1.553(2) . ?
C22 H22 1.0000 . ?
C23 C27 1.510(2) . ?
C23 C41 1.541(2) . ?
C23 C24 1.546(2) . ?
C24 C25 1.523(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.543(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C35 1.514(2) . ?
C26 H26 1.0000 . ?
C27 C28 1.363(2) . ?
C27 C30 1.444(2) . ?
C28 H28 0.9500 . ?
C29 C34 1.395(2) . ?
C29 C30 1.419(2) . ?
C30 C31 1.410(2) . ?
C31 C32 1.377(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.401(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.390(2) . ?
C35 C40 1.398(2) . ?
C36 C37 1.389(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.388(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.379(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.392(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C21 O1 C1 113.42(12) . . ?
C8 N1 C7 108.33(14) . . ?
C8 N1 H1N 129.2(12) . . ?
C7 N1 H1N 119.8(12) . . ?
O1 C1 C5 109.63(13) . . ?
O1 C1 C2 109.68(12) . . ?
C5 C1 C2 104.25(13) . . ?
O1 C1 H1 111.0 . . ?
C5 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
C6 C2 C20 109.10(14) . . ?
C6 C2 C3 113.66(13) . . ?
C20 C2 C3 110.10(14) . . ?
C6 C2 C1 111.86(14) . . ?
C20 C2 C1 109.47(13) . . ?
C3 C2 C1 102.47(13) . . ?
C4 C3 C2 107.22(13) . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 C5 106.84(14) . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
C5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C14 C5 C1 115.38(14) . . ?
C14 C5 C4 115.93(14) . . ?
C1 C5 C4 103.16(13) . . ?
C14 C5 H5 107.3 . . ?
C1 C5 H5 107.3 . . ?
C4 C5 H5 107.3 . . ?
C7 C6 C9 105.55(15) . . ?
C7 C6 C2 126.21(16) . . ?
C9 C6 C2 128.24(14) . . ?
C6 C7 N1 111.17(16) . . ?
C6 C7 H7 124.4 . . ?
N1 C7 H7 124.4 . . ?
N1 C8 C13 129.58(16) . . ?
N1 C8 C9 107.84(15) . . ?
C13 C8 C9 122.57(16) . . ?
C10 C9 C8 117.94(16) . . ?
C10 C9 C6 135.01(15) . . ?
C8 C9 C6 107.05(14) . . ?
C11 C10 C9 119.56(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.28(17) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.73(17) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 117.92(16) . . ?
C12 C13 H13 121.0 . . ?
C8 C13 H13 121.0 . . ?
C19 C14 C15 117.29(16) . . ?
C19 C14 C5 123.01(15) . . ?
C15 C14 C5 119.70(15) . . ?
C16 C15 C14 121.65(17) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C15 120.31(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.37(17) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.02(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 121.35(16) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C42 O2 C22 113.38(12) . . ?
C28 N2 C29 108.32(14) . . ?
C28 N2 H2N 123.1(12) . . ?
C29 N2 H2N 126.4(12) . . ?
O2 C22 C26 110.69(13) . . ?
O2 C22 C23 109.69(13) . . ?
C26 C22 C23 103.93(13) . . ?
O2 C22 H22 110.8 . . ?
C26 C22 H22 110.8 . . ?
C23 C22 H22 110.8 . . ?
C27 C23 C41 109.20(13) . . ?
C27 C23 C24 113.69(13) . . ?
C41 C23 C24 109.61(14) . . ?
C27 C23 C22 112.20(14) . . ?
C41 C23 C22 109.40(13) . . ?
C24 C23 C22 102.53(13) . . ?
C25 C24 C23 107.27(13) . . ?
C25 C24 H24A 110.3 . . ?
C23 C24 H24A 110.3 . . ?
C25 C24 H24B 110.3 . . ?
C23 C24 H24B 110.3 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 C26 107.35(14) . . ?
C24 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 . . ?
C24 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C35 C26 C25 116.55(14) . . ?
C35 C26 C22 114.62(14) . . ?
C25 C26 C22 103.42(13) . . ?
C35 C26 H26 107.2 . . ?
C25 C26 H26 107.2 . . ?
C22 C26 H26 107.2 . . ?
C28 C27 C30 105.43(15) . . ?
C28 C27 C23 126.29(16) . . ?
C30 C27 C23 128.27(14) . . ?
C27 C28 N2 111.48(16) . . ?
C27 C28 H28 124.3 . . ?
N2 C28 H28 124.3 . . ?
N2 C29 C34 129.69(16) . . ?
N2 C29 C30 107.65(15) . . ?
C34 C29 C30 122.66(16) . . ?
C31 C30 C29 117.80(16) . . ?
C31 C30 C27 135.12(16) . . ?
C29 C30 C27 107.06(15) . . ?
C32 C31 C30 119.39(16) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C33 121.42(17) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 121.08(17) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C29 117.64(16) . . ?
C33 C34 H34 121.2 . . ?
C29 C34 H34 121.2 . . ?
C36 C35 C40 117.84(16) . . ?
C36 C35 C26 119.09(15) . . ?
C40 C35 C26 123.06(15) . . ?
C37 C36 C35 121.57(17) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C38 C37 C36 119.73(17) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C39 C38 C37 119.67(17) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.41(17) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C35 120.78(17) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
C23 C41 H41A 109.5 . . ?
C23 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C23 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O2 C42 H42A 109.5 . . ?
O2 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O2 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

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
C21 O1 C1 C5 108.16(15) . . . . ?
C21 O1 C1 C2 -137.95(14) . . . . ?
O1 C1 C2 C6 43.55(18) . . . . ?
C5 C1 C2 C6 160.86(13) . . . . ?
O1 C1 C2 C20 164.60(13) . . . . ?
C5 C1 C2 C20 -78.09(16) . . . . ?
O1 C1 C2 C3 -78.56(15) . . . . ?
C5 C1 C2 C3 38.75(16) . . . . ?
C6 C2 C3 C4 -145.12(15) . . . . ?
C20 C2 C3 C4 92.14(17) . . . . ?
C1 C2 C3 C4 -24.24(17) . . . . ?
C2 C3 C4 C5 0.93(19) . . . . ?
O1 C1 C5 C14 -48.49(18) . . . . ?
C2 C1 C5 C14 -165.83(14) . . . . ?
O1 C1 C5 C4 78.96(15) . . . . ?
C2 C1 C5 C4 -38.39(16) . . . . ?
C3 C4 C5 C14 150.06(16) . . . . ?
C3 C4 C5 C1 22.96(18) . . . . ?
C20 C2 C6 C7 116.64(18) . . . . ?
C3 C2 C6 C7 -6.6(2) . . . . ?
C1 C2 C6 C7 -122.10(18) . . . . ?
C20 C2 C6 C9 -63.9(2) . . . . ?
C3 C2 C6 C9 172.83(16) . . . . ?
C1 C2 C6 C9 57.4(2) . . . . ?
C9 C6 C7 N1 1.2(2) . . . . ?
C2 C6 C7 N1 -179.25(15) . . . . ?
C8 N1 C7 C6 -2.4(2) . . . . ?
C7 N1 C8 C13 -178.33(18) . . . . ?
C7 N1 C8 C9 2.65(18) . . . . ?
N1 C8 C9 C10 178.48(14) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
N1 C8 C9 C6 -1.93(18) . . . . ?
C13 C8 C9 C6 178.97(15) . . . . ?
C7 C6 C9 C10 179.95(18) . . . . ?
C2 C6 C9 C10 0.4(3) . . . . ?
C7 C6 C9 C8 0.47(19) . . . . ?
C2 C6 C9 C8 -179.09(15) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C6 C9 C10 C11 -178.31(18) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C8 0.2(3) . . . . ?
N1 C8 C13 C12 -178.93(16) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C1 C5 C14 C19 73.5(2) . . . . ?
C4 C5 C14 C19 -47.2(2) . . . . ?
C1 C5 C14 C15 -105.43(18) . . . . ?
C4 C5 C14 C15 133.84(17) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C5 C14 C15 C16 178.23(16) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C5 C14 C19 C18 -178.46(16) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C42 O2 C22 C26 -104.05(15) . . . . ?
C42 O2 C22 C23 141.84(14) . . . . ?
O2 C22 C23 C27 -42.53(18) . . . . ?
C26 C22 C23 C27 -160.91(13) . . . . ?
O2 C22 C23 C41 -163.88(13) . . . . ?
C26 C22 C23 C41 77.73(16) . . . . ?
O2 C22 C23 C24 79.84(15) . . . . ?
C26 C22 C23 C24 -38.55(15) . . . . ?
C27 C23 C24 C25 147.04(15) . . . . ?
C41 C23 C24 C25 -90.45(17) . . . . ?
C22 C23 C24 C25 25.69(18) . . . . ?
C23 C24 C25 C26 -3.2(2) . . . . ?
C24 C25 C26 C35 -147.53(16) . . . . ?
C24 C25 C26 C22 -20.79(19) . . . . ?
O2 C22 C26 C35 47.07(18) . . . . ?
C23 C22 C26 C35 164.77(13) . . . . ?
O2 C22 C26 C25 -80.87(16) . . . . ?
C23 C22 C26 C25 36.82(16) . . . . ?
C41 C23 C27 C28 -112.43(18) . . . . ?
C24 C23 C27 C28 10.3(2) . . . . ?
C22 C23 C27 C28 126.10(17) . . . . ?
C41 C23 C27 C30 66.0(2) . . . . ?
C24 C23 C27 C30 -171.31(15) . . . . ?
C22 C23 C27 C30 -55.5(2) . . . . ?
C30 C27 C28 N2 -0.97(19) . . . . ?
C23 C27 C28 N2 177.71(15) . . . . ?
C29 N2 C28 C27 2.13(19) . . . . ?
C28 N2 C29 C34 177.76(17) . . . . ?
C28 N2 C29 C30 -2.37(18) . . . . ?
N2 C29 C30 C31 -179.58(14) . . . . ?
C34 C29 C30 C31 0.3(2) . . . . ?
N2 C29 C30 C27 1.77(18) . . . . ?
C34 C29 C30 C27 -178.34(15) . . . . ?
C28 C27 C30 C31 -178.81(18) . . . . ?
C23 C27 C30 C31 2.5(3) . . . . ?
C28 C27 C30 C29 -0.51(18) . . . . ?
C23 C27 C30 C29 -179.15(15) . . . . ?
C29 C30 C31 C32 -1.2(2) . . . . ?
C27 C30 C31 C32 176.94(18) . . . . ?
C30 C31 C32 C33 1.5(3) . . . . ?
C31 C32 C33 C34 -0.8(3) . . . . ?
C32 C33 C34 C29 -0.1(2) . . . . ?
N2 C29 C34 C33 -179.79(16) . . . . ?
C30 C29 C34 C33 0.4(2) . . . . ?
C25 C26 C35 C36 -133.82(17) . . . . ?
C22 C26 C35 C36 105.21(18) . . . . ?
C25 C26 C35 C40 47.5(2) . . . . ?
C22 C26 C35 C40 -73.5(2) . . . . ?
C40 C35 C36 C37 -0.1(3) . . . . ?
C26 C35 C36 C37 -178.88(16) . . . . ?
C35 C36 C37 C38 0.4(3) . . . . ?
C36 C37 C38 C39 -0.4(3) . . . . ?
C37 C38 C39 C40 0.1(3) . . . . ?
C38 C39 C40 C35 0.1(3) . . . . ?
C36 C35 C40 C39 -0.1(2) . . . . ?
C26 C35 C40 C39 178.58(17) . . . . ?

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
N1 H1N O1 0.920(19) 1.935(19) 2.8423(18) 168.6(17) 2_656
N2 H2N O2 0.906(18) 1.996(18) 2.8616(18) 159.2(16) 2_776

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.086
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
