# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_csi14_0m
_database_code_depnum_ccdc_archive 'CCDC 1471600'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration ad

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_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.9318(2)
_cell_length_b                   11.9510(3)
_cell_length_c                   16.7072(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1384.06(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7597
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      69.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.40
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4649
_exptl_absorpt_correction_T_max  0.7821
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6982
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         69.76
_reflns_number_total             2371
_reflns_number_gt                2370
_reflns_threshold_expression     >2sigma(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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0720P)²+0.6655P] 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     SHELXL
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_number_reflns         2371
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.8927(2) 1.20890(11) 0.27792(8) 0.0178(4) Uani 1 1 d . . .
O2 O 0.1665(2) 0.91288(12) 0.29796(9) 0.0180(4) Uani 1 1 d . . .
H2 H 0.1553 0.8498 0.2763 0.027 Uiso 1 1 calc R . .
N1 N 0.8186(3) 1.03736(13) 0.33121(9) 0.0140(4) Uani 1 1 d . . .
H1 H 0.9025 0.9973 0.3040 0.017 Uiso 1 1 calc R . .
C1 C 0.7962(3) 1.14822(17) 0.32232(11) 0.0148(5) Uani 1 1 d . . .
C2 C 0.6384(3) 1.18628(16) 0.37979(11) 0.0142(4) Uani 1 1 d . . .
H2A H 0.5574 1.2455 0.3555 0.017 Uiso 1 1 calc R . .
H2B H 0.6939 1.2144 0.4306 0.017 Uiso 1 1 calc R . .
C3 C 0.5217(3) 1.07782(16) 0.39336(11) 0.0136(5) Uani 1 1 d . . .
C4 C 0.4341(3) 1.05080(16) 0.47629(11) 0.0150(4) Uani 1 1 d . . .
H4 H 0.3440 1.1114 0.4938 0.018 Uiso 1 1 calc R . .
C5 C 0.6075(3) 1.04103(17) 0.53434(12) 0.0174(5) Uani 1 1 d . . .
C6 C 0.6560(4) 1.15485(18) 0.57373(12) 0.0227(5) Uani 1 1 d . . .
H6A H 0.7893 1.1536 0.5933 0.034 Uiso 1 1 calc R . .
H6B H 0.5682 1.1682 0.6187 0.034 Uiso 1 1 calc R . .
H6C H 0.6414 1.2148 0.5342 0.034 Uiso 1 1 calc R . .
C7 C 0.6872(3) 0.99051(16) 0.39144(11) 0.0125(4) Uani 1 1 d . . .
C8 C 0.7715(3) 0.99739(17) 0.47780(12) 0.0153(4) Uani 1 1 d . . .
H8A H 0.8829 1.0492 0.4791 0.018 Uiso 1 1 calc R . .
H8B H 0.8157 0.9226 0.4955 0.018 Uiso 1 1 calc R . .
C9 C 0.3259(3) 0.93818(16) 0.46676(11) 0.0156(5) Uani 1 1 d . . .
H9A H 0.2165 0.9487 0.4294 0.019 Uiso 1 1 calc R . .
H9B H 0.2721 0.9159 0.5193 0.019 Uiso 1 1 calc R . .
C10 C 0.4567(3) 0.84273(16) 0.43497(11) 0.0151(5) Uani 1 1 d . . .
H10A H 0.5282 0.8107 0.4809 0.018 Uiso 1 1 calc R . .
H10B H 0.3727 0.7829 0.4133 0.018 Uiso 1 1 calc R . .
C11 C 0.6045(3) 0.87494(16) 0.36967(11) 0.0141(5) Uani 1 1 d . . .
C12 C 0.5138(3) 0.88011(16) 0.28580(11) 0.0151(5) Uani 1 1 d . . .
H12A H 0.6161 0.9003 0.2471 0.018 Uiso 1 1 calc R . .
H12B H 0.4677 0.8043 0.2717 0.018 Uiso 1 1 calc R . .
C13 C 0.3469(3) 0.96167(16) 0.27531(12) 0.0155(4) Uani 1 1 d . . .
H13 H 0.3386 0.9803 0.2171 0.019 Uiso 1 1 calc R . .
C14 C 0.3799(3) 1.07236(17) 0.32084(12) 0.0154(5) Uani 1 1 d . . .
H14A H 0.2524 1.0980 0.3403 0.018 Uiso 1 1 calc R . .
H14B H 0.4245 1.1282 0.2812 0.018 Uiso 1 1 calc R . .
C15 C 0.7602(3) 0.78397(16) 0.36633(12) 0.0164(5) Uani 1 1 d . . .
H15A H 0.8340 0.7843 0.4164 0.025 Uiso 1 1 calc R . .
H15B H 0.8472 0.7987 0.3213 0.025 Uiso 1 1 calc R . .
H15C H 0.6991 0.7107 0.3592 0.025 Uiso 1 1 calc R . .
C16 C 0.5767(4) 0.96165(19) 0.60596(12) 0.0215(5) Uani 1 1 d . . .
H16A H 0.4606 0.9841 0.6353 0.032 Uiso 1 1 calc R . .
H16B H 0.6887 0.9655 0.6416 0.032 Uiso 1 1 calc R . .
H16C H 0.5612 0.8848 0.5865 0.032 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 1.234(3) . ?
O2 C13 1.431(3) . ?
O2 H2 0.8400 . ?
N1 C1 1.342(3) . ?
N1 C7 1.468(3) . ?
N1 H1 0.8800 . ?
C1 C2 1.525(3) . ?
C2 C3 1.545(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.547(3) . ?
C3 C7 1.551(3) . ?
C3 C14 1.561(3) . ?
C4 C5 1.548(3) . ?
C4 C9 1.549(3) . ?
C4 H4 1.0000 . ?
C5 C16 1.542(3) . ?
C5 C6 1.548(3) . ?
C5 C8 1.568(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C11 1.539(3) . ?
C7 C8 1.559(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.551(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.545(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.533(3) . ?
C11 C12 1.537(3) . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.543(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O2 H2 109.5 . . ?
C1 N1 C7 112.38(17) . . ?
C1 N1 H1 123.8 . . ?
C7 N1 H1 123.8 . . ?
O1 C1 N1 125.7(2) . . ?
O1 C1 C2 126.29(18) . . ?
N1 C1 C2 107.92(17) . . ?
C1 C2 C3 102.58(15) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C4 120.80(15) . . ?
C2 C3 C7 100.01(16) . . ?
C4 C3 C7 99.69(15) . . ?
C2 C3 C14 104.54(15) . . ?
C4 C3 C14 116.07(18) . . ?
C7 C3 C14 114.92(16) . . ?
C3 C4 C5 105.81(17) . . ?
C3 C4 C9 106.23(15) . . ?
C5 C4 C9 112.01(16) . . ?
C3 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C9 C4 H4 110.9 . . ?
C16 C5 C6 103.93(16) . . ?
C16 C5 C4 115.17(18) . . ?
C6 C5 C4 111.64(18) . . ?
C16 C5 C8 111.31(18) . . ?
C6 C5 C8 113.00(19) . . ?
C4 C5 C8 102.14(16) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C11 114.30(15) . . ?
N1 C7 C3 102.49(15) . . ?
C11 C7 C3 109.44(17) . . ?
N1 C7 C8 112.45(17) . . ?
C11 C7 C8 113.94(16) . . ?
C3 C7 C8 102.86(15) . . ?
C7 C8 C5 107.68(17) . . ?
C7 C8 H8A 110.2 . . ?
C5 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C5 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C4 C9 C10 113.00(18) . . ?
C4 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C4 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 116.50(16) . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C15 C11 C12 106.46(16) . . ?
C15 C11 C7 112.49(18) . . ?
C12 C11 C7 109.38(15) . . ?
C15 C11 C10 108.41(16) . . ?
C12 C11 C10 112.50(17) . . ?
C7 C11 C10 107.68(15) . . ?
C13 C12 C11 116.19(16) . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
O2 C13 C12 111.88(16) . . ?
O2 C13 C14 110.41(16) . . ?
C12 C13 C14 112.29(18) . . ?
O2 C13 H13 107.3 . . ?
C12 C13 H13 107.3 . . ?
C14 C13 H13 107.3 . . ?
C13 C14 C3 120.78(17) . . ?
C13 C14 H14A 107.1 . . ?
C3 C14 H14A 107.1 . . ?
C13 C14 H14B 107.1 . . ?
C3 C14 H14B 107.1 . . ?
H14A C14 H14B 106.8 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C7 N1 C1 O1 177.2(2) . . . . ?
C7 N1 C1 C2 0.2(2) . . . . ?
O1 C1 C2 C3 159.4(2) . . . . ?
N1 C1 C2 C3 -23.6(2) . . . . ?
C1 C2 C3 C4 143.25(19) . . . . ?
C1 C2 C3 C7 35.54(17) . . . . ?
C1 C2 C3 C14 -83.65(17) . . . . ?
C2 C3 C4 C5 -61.8(2) . . . . ?
C7 C3 C4 C5 46.11(18) . . . . ?
C14 C3 C4 C5 170.12(16) . . . . ?
C2 C3 C4 C9 179.01(18) . . . . ?
C7 C3 C4 C9 -73.10(19) . . . . ?
C14 C3 C4 C9 50.9(2) . . . . ?
C3 C4 C5 C16 -151.06(17) . . . . ?
C9 C4 C5 C16 -35.7(2) . . . . ?
C3 C4 C5 C6 90.7(2) . . . . ?
C9 C4 C5 C6 -153.94(17) . . . . ?
C3 C4 C5 C8 -30.28(19) . . . . ?
C9 C4 C5 C8 85.04(19) . . . . ?
C1 N1 C7 C11 141.54(19) . . . . ?
C1 N1 C7 C3 23.2(2) . . . . ?
C1 N1 C7 C8 -86.5(2) . . . . ?
C2 C3 C7 N1 -35.46(17) . . . . ?
C4 C3 C7 N1 -159.35(15) . . . . ?
C14 C3 C7 N1 75.8(2) . . . . ?
C2 C3 C7 C11 -157.13(14) . . . . ?
C4 C3 C7 C11 78.97(17) . . . . ?
C14 C3 C7 C11 -45.8(2) . . . . ?
C2 C3 C7 C8 81.40(16) . . . . ?
C4 C3 C7 C8 -42.49(18) . . . . ?
C14 C3 C7 C8 -167.31(16) . . . . ?
N1 C7 C8 C5 134.76(16) . . . . ?
C11 C7 C8 C5 -93.1(2) . . . . ?
C3 C7 C8 C5 25.2(2) . . . . ?
C16 C5 C8 C7 126.16(18) . . . . ?
C6 C5 C8 C7 -117.33(19) . . . . ?
C4 C5 C8 C7 2.7(2) . . . . ?
C3 C4 C9 C10 56.2(2) . . . . ?
C5 C4 C9 C10 -58.9(2) . . . . ?
C4 C9 C10 C11 -39.1(2) . . . . ?
N1 C7 C11 C15 65.5(2) . . . . ?
C3 C7 C11 C15 179.82(15) . . . . ?
C8 C7 C11 C15 -65.7(2) . . . . ?
N1 C7 C11 C12 -52.5(2) . . . . ?
C3 C7 C11 C12 61.7(2) . . . . ?
C8 C7 C11 C12 176.26(17) . . . . ?
N1 C7 C11 C10 -175.06(16) . . . . ?
C3 C7 C11 C10 -60.79(19) . . . . ?
C8 C7 C11 C10 53.7(2) . . . . ?
C9 C10 C11 C15 161.40(17) . . . . ?
C9 C10 C11 C12 -81.1(2) . . . . ?
C9 C10 C11 C7 39.4(2) . . . . ?
C15 C11 C12 C13 177.23(17) . . . . ?
C7 C11 C12 C13 -61.0(2) . . . . ?
C10 C11 C12 C13 58.6(2) . . . . ?
C11 C12 C13 O2 -85.6(2) . . . . ?
C11 C12 C13 C14 39.2(2) . . . . ?
O2 C13 C14 C3 103.2(2) . . . . ?
C12 C13 C14 C3 -22.4(3) . . . . ?
C2 C3 C14 C13 135.81(19) . . . . ?
C4 C3 C14 C13 -88.5(2) . . . . ?
C7 C3 C14 C13 27.2(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 H1 O2 0.88 2.09 2.888(2) 150.0 1_655
O2 H2 O1 0.84 1.94 2.7782(19) 174.8 3_645

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        69.76
_diffrn_measured_fraction_theta_full 0.931
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_150714d
_database_code_depnum_ccdc_archive 'CCDC 1471601'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            CSI28
_chemical_melting_point          188.4-188.8
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration unk

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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.4825(4)
_cell_length_b                   18.4760(9)
_cell_length_c                   6.6666(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.723(3)
_cell_angle_gamma                90.00
_cell_volume                     751.62(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1661
_cell_measurement_theta_min      4.8490
_cell_measurement_theta_max      71.7720

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7840
_exptl_absorpt_correction_T_max  0.8188
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2402
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         4.79
_diffrn_reflns_theta_max         66.17
_reflns_number_total             1829
_reflns_number_gt                1788
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0482P)²+0.1200P] 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     SHELXL
_refine_ls_extinction_coef       0.053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_number_reflns         1829
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
N1 N 0.2592(4) 0.75350(13) 0.1016(3) 0.0595(6) Uani 1 1 d . . .
H1A H 0.1461 0.7731 0.0100 0.071 Uiso 1 1 calc R . .
H1B H 0.3582 0.7339 0.0601 0.071 Uiso 1 1 calc R . .
O1 O 0.1432(3) 0.78101(12) 0.3698(3) 0.0601(5) Uani 1 1 d . . .
O2 O 0.0198(3) 0.31272(9) 0.3089(3) 0.0518(5) Uani 1 1 d . . .
H3 H -0.0216 0.2942 0.4006 0.062 Uiso 1 1 calc R . .
C1 C 0.2810(4) 0.75356(12) 0.3068(4) 0.0423(5) Uani 1 1 d . . .
C2 C 0.4943(4) 0.72080(12) 0.4559(3) 0.0412(5) Uani 1 1 d . . .
H2 H 0.6068 0.7582 0.4761 0.049 Uiso 1 1 calc R . .
C3 C 0.5728(3) 0.65566(13) 0.3624(3) 0.0390(5) Uani 1 1 d . . .
C4 C 0.4753(4) 0.58260(12) 0.3814(3) 0.0375(5) Uani 1 1 d . . .
H4 H 0.5667 0.5453 0.3487 0.045 Uiso 1 1 calc R . .
C5 C 0.2364(4) 0.57079(13) 0.2321(3) 0.0408(5) Uani 1 1 d . . .
H5A H 0.1527 0.6152 0.2174 0.049 Uiso 1 1 calc R . .
H5B H 0.2336 0.5555 0.0920 0.049 Uiso 1 1 calc R . .
C6 C 0.1412(4) 0.51212(12) 0.3353(3) 0.0393(5) Uani 1 1 d . . .
H6 H -0.0093 0.5224 0.3284 0.047 Uiso 1 1 calc R . .
C7 C 0.1795(4) 0.43049(13) 0.2967(4) 0.0412(5) Uani 1 1 d . . .
C8 C 0.3699(5) 0.42881(13) 0.5118(4) 0.0532(6) Uani 1 1 d . . .
H8A H 0.5137 0.4277 0.4972 0.064 Uiso 1 1 calc R . .
H8B H 0.3558 0.3909 0.6071 0.064 Uiso 1 1 calc R . .
C9 C 0.3030(4) 0.50454(13) 0.5673(4) 0.0449(5) Uani 1 1 d . . .
H9 H 0.2283 0.5027 0.6728 0.054 Uiso 1 1 calc R . .
C10 C 0.4672(4) 0.56704(12) 0.6068(4) 0.0437(5) Uani 1 1 d . . .
C11 C 0.3677(5) 0.63298(13) 0.6829(4) 0.0493(6) Uani 1 1 d . . .
H11A H 0.2153 0.6377 0.5937 0.059 Uiso 1 1 calc R . .
H11B H 0.3714 0.6242 0.8275 0.059 Uiso 1 1 calc R . .
C12 C 0.4853(5) 0.70412(13) 0.6777(4) 0.0489(6) Uani 1 1 d . . .
H12A H 0.6334 0.7016 0.7787 0.059 Uiso 1 1 calc R . .
H12B H 0.4101 0.7432 0.7216 0.059 Uiso 1 1 calc R . .
C13 C 0.7239(4) 0.66391(15) 0.2717(4) 0.0514(6) Uani 1 1 d . . .
H13A H 0.7741 0.6240 0.2167 0.062 Uiso 1 1 calc R . .
H13B H 0.7801 0.7097 0.2628 0.062 Uiso 1 1 calc R . .
C14 C 0.2355(5) 0.41018(15) 0.0999(5) 0.0602(7) Uani 1 1 d . . .
H14A H 0.2689 0.3595 0.1040 0.090 Uiso 1 1 calc R . .
H14B H 0.3603 0.4376 0.0972 0.090 Uiso 1 1 calc R . .
H14C H 0.1128 0.4206 -0.0256 0.090 Uiso 1 1 calc R . .
C15 C -0.0172(4) 0.38847(13) 0.3038(4) 0.0496(6) Uani 1 1 d . . .
H15A H -0.0512 0.4026 0.4294 0.059 Uiso 1 1 calc R . .
H15B H -0.1425 0.4004 0.1795 0.059 Uiso 1 1 calc R . .
C16 C 0.6924(5) 0.54824(17) 0.7662(5) 0.0672(8) Uani 1 1 d . . .
H16A H 0.6774 0.5344 0.8994 0.101 Uiso 1 1 calc R . .
H16B H 0.7867 0.5897 0.7877 0.101 Uiso 1 1 calc R . .
H16C H 0.7545 0.5089 0.7118 0.101 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
N1 C1 1.327(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
O1 C1 1.219(3) . ?
O2 C15 1.418(3) . ?
O2 H3 0.8200 . ?
C1 C2 1.529(3) . ?
C2 C3 1.520(3) . ?
C2 C12 1.531(3) . ?
C2 H2 0.9800 . ?
C3 C13 1.323(3) . ?
C3 C4 1.514(3) . ?
C4 C5 1.548(3) . ?
C4 C10 1.548(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.522(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.555(3) . ?
C6 C7 1.564(3) . ?
C6 H6 0.9800 . ?
C7 C15 1.508(3) . ?
C7 C14 1.522(4) . ?
C7 C8 1.545(3) . ?
C8 C9 1.546(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.532(3) . ?
C9 H9 0.9800 . ?
C10 C16 1.528(4) . ?
C10 C11 1.543(3) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C15 O2 H3 109.5 . . ?
O1 C1 N1 121.4(2) . . ?
O1 C1 C2 123.2(2) . . ?
N1 C1 C2 115.4(2) . . ?
C3 C2 C1 113.65(17) . . ?
C3 C2 C12 111.34(19) . . ?
C1 C2 C12 112.76(19) . . ?
C3 C2 H2 106.1 . . ?
C1 C2 H2 106.1 . . ?
C12 C2 H2 106.1 . . ?
C13 C3 C4 122.4(2) . . ?
C13 C3 C2 119.9(2) . . ?
C4 C3 C2 117.70(18) . . ?
C3 C4 C5 115.28(18) . . ?
C3 C4 C10 113.50(18) . . ?
C5 C4 C10 104.12(18) . . ?
C3 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C10 C4 H4 107.9 . . ?
C6 C5 C4 106.27(17) . . ?
C6 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C5 C6 C9 105.89(17) . . ?
C5 C6 C7 120.10(18) . . ?
C9 C6 C7 89.16(16) . . ?
C5 C6 H6 113.0 . . ?
C9 C6 H6 113.0 . . ?
C7 C6 H6 113.0 . . ?
C15 C7 C14 110.5(2) . . ?
C15 C7 C8 112.3(2) . . ?
C14 C7 C8 116.6(2) . . ?
C15 C7 C6 107.97(18) . . ?
C14 C7 C6 118.49(19) . . ?
C8 C7 C6 89.32(17) . . ?
C7 C8 C9 90.19(18) . . ?
C7 C8 H8A 113.6 . . ?
C9 C8 H8A 113.6 . . ?
C7 C8 H8B 113.6 . . ?
C9 C8 H8B 113.6 . . ?
H8A C8 H8B 110.9 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 C6 107.41(18) . . ?
C8 C9 C6 89.60(18) . . ?
C10 C9 H9 112.7 . . ?
C8 C9 H9 112.7 . . ?
C6 C9 H9 112.7 . . ?
C16 C10 C9 113.2(2) . . ?
C16 C10 C11 111.0(2) . . ?
C9 C10 C11 107.9(2) . . ?
C16 C10 C4 112.4(2) . . ?
C9 C10 C4 102.85(18) . . ?
C11 C10 C4 109.13(18) . . ?
C12 C11 C10 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C2 112.19(19) . . ?
C11 C12 H12A 109.2 . . ?
C2 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C2 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C3 C13 H13A 120.0 . . ?
C3 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C7 111.8(2) . . ?
O2 C15 H15A 109.3 . . ?
C7 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C7 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C3 146.2(2) . . . . ?
N1 C1 C2 C3 -37.0(3) . . . . ?
O1 C1 C2 C12 18.3(3) . . . . ?
N1 C1 C2 C12 -164.9(2) . . . . ?
C1 C2 C3 C13 97.5(2) . . . . ?
C12 C2 C3 C13 -133.8(2) . . . . ?
C1 C2 C3 C4 -83.6(2) . . . . ?
C12 C2 C3 C4 45.0(3) . . . . ?
C13 C3 C4 C5 -107.4(2) . . . . ?
C2 C3 C4 C5 73.8(2) . . . . ?
C13 C3 C4 C10 132.6(2) . . . . ?
C2 C3 C4 C10 -46.2(2) . . . . ?
C3 C4 C5 C6 -156.81(18) . . . . ?
C10 C4 C5 C6 -31.8(2) . . . . ?
C4 C5 C6 C9 13.9(2) . . . . ?
C4 C5 C6 C7 -84.6(2) . . . . ?
C5 C6 C7 C15 -148.7(2) . . . . ?
C9 C6 C7 C15 103.40(19) . . . . ?
C5 C6 C7 C14 -22.1(3) . . . . ?
C9 C6 C7 C14 -130.1(2) . . . . ?
C5 C6 C7 C8 98.1(2) . . . . ?
C9 C6 C7 C8 -9.88(18) . . . . ?
C15 C7 C8 C9 -99.3(2) . . . . ?
C14 C7 C8 C9 131.8(2) . . . . ?
C6 C7 C8 C9 9.93(18) . . . . ?
C7 C8 C9 C10 -119.8(2) . . . . ?
C7 C8 C9 C6 -9.99(18) . . . . ?
C5 C6 C9 C10 9.4(2) . . . . ?
C7 C6 C9 C10 130.51(19) . . . . ?
C5 C6 C9 C8 -111.3(2) . . . . ?
C7 C6 C9 C8 9.87(18) . . . . ?
C8 C9 C10 C16 -50.5(3) . . . . ?
C6 C9 C10 C16 -150.1(2) . . . . ?
C8 C9 C10 C11 -173.70(18) . . . . ?
C6 C9 C10 C11 86.7(2) . . . . ?
C8 C9 C10 C4 71.0(3) . . . . ?
C6 C9 C10 C4 -28.6(2) . . . . ?
C3 C4 C10 C16 -75.1(2) . . . . ?
C5 C4 C10 C16 158.8(2) . . . . ?
C3 C4 C10 C9 162.90(18) . . . . ?
C5 C4 C10 C9 36.8(2) . . . . ?
C3 C4 C10 C11 48.5(3) . . . . ?
C5 C4 C10 C11 -77.7(2) . . . . ?
C16 C10 C11 C12 69.4(3) . . . . ?
C9 C10 C11 C12 -166.08(19) . . . . ?
C4 C10 C11 C12 -55.0(3) . . . . ?
C10 C11 C12 C2 56.4(3) . . . . ?
C3 C2 C12 C11 -48.5(3) . . . . ?
C1 C2 C12 C11 80.6(3) . . . . ?
C14 C7 C15 O2 59.6(3) . . . . ?
C8 C7 C15 O2 -72.5(3) . . . . ?
C6 C7 C15 O2 -169.37(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_150713d
_database_code_depnum_ccdc_archive 'CCDC 1471602'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            CSI-16
_chemical_melting_point          224.8-225.3
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration unk
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_H-M   P2(1)

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

_cell_length_a                   7.3719(4)
_cell_length_b                   11.6158(4)
_cell_length_c                   8.6406(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.209(2)
_cell_angle_gamma                90.00
_cell_volume                     694.35(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1765
_cell_measurement_theta_min      6.4320
_cell_measurement_theta_max      71.5910

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7827
_exptl_absorpt_correction_T_max  0.8504
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2332
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.46
_diffrn_reflns_theta_max         66.19
_reflns_number_total             1549
_reflns_number_gt                1506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0676P)²+0.0894P] 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     SHELXL
_refine_ls_extinction_coef       0.151(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_number_reflns         1549
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
N1 N 0.8575(3) 0.97985(19) 0.3695(3) 0.0365(5) Uani 1 1 d . . .
H1 H 0.9437 1.0237 0.3541 0.044 Uiso 1 1 calc R . .
O1 O 0.5926(3) 1.09005(18) 0.3735(3) 0.0490(5) Uani 1 1 d . . .
O2 O 0.8275(3) 0.5976(2) -0.2487(2) 0.0512(6) Uani 1 1 d . . .
H2 H 0.7096 0.6040 -0.2787 0.077 Uiso 1 1 calc R . .
C1 C 0.6877(4) 1.0024(2) 0.3875(3) 0.0344(5) Uani 1 1 d . . .
C2 C 0.6626(3) 0.8780(2) 0.4349(3) 0.0327(6) Uani 1 1 d . . .
H2A H 0.7017 0.8738 0.5553 0.039 Uiso 1 1 calc R . .
C3 C 0.8456(3) 0.8527(2) 0.3853(3) 0.0301(5) Uani 1 1 d . . .
C4 C 0.7914(3) 0.7893(2) 0.2185(3) 0.0267(5) Uani 1 1 d . . .
C5 C 0.6331(3) 0.6954(2) 0.1915(3) 0.0278(5) Uani 1 1 d . . .
C6 C 0.4450(3) 0.7495(3) 0.1969(3) 0.0386(6) Uani 1 1 d . . .
H6A H 0.3487 0.6895 0.1814 0.046 Uiso 1 1 calc R . .
H6B H 0.3964 0.8037 0.1065 0.046 Uiso 1 1 calc R . .
C7 C 0.4730(3) 0.8122(3) 0.3603(3) 0.0394(6) Uani 1 1 d . . .
H7A H 0.3671 0.8660 0.3425 0.047 Uiso 1 1 calc R . .
H7B H 0.4642 0.7559 0.4403 0.047 Uiso 1 1 calc R . .
C8 C 0.9542(3) 0.7212(2) 0.1859(3) 0.0321(5) Uani 1 1 d . . .
H8A H 1.0298 0.6784 0.2832 0.039 Uiso 1 1 calc R . .
H8B H 1.0394 0.7727 0.1548 0.039 Uiso 1 1 calc R . .
C9 C 0.8484(3) 0.6377(2) 0.0412(3) 0.0328(6) Uani 1 1 d . . .
C10 C 0.6314(3) 0.6655(2) 0.0139(3) 0.0307(5) Uani 1 1 d . . .
H10 H 0.5415 0.6037 -0.0406 0.037 Uiso 1 1 calc R . .
C11 C 0.5822(3) 0.7822(2) -0.0723(3) 0.0375(6) Uani 1 1 d . . .
H11A H 0.4445 0.7976 -0.1072 0.045 Uiso 1 1 calc R . .
H11B H 0.6236 0.7862 -0.1672 0.045 Uiso 1 1 calc R . .
C12 C 0.6983(3) 0.8670(2) 0.0647(3) 0.0350(6) Uani 1 1 d . . .
H12A H 0.6137 0.9240 0.0860 0.042 Uiso 1 1 calc R . .
H12B H 0.7969 0.9062 0.0337 0.042 Uiso 1 1 calc R . .
C13 C 1.0189(4) 0.8041(3) 0.5230(3) 0.0408(6) Uani 1 1 d . . .
H13A H 1.0354 0.8450 0.6235 0.061 Uiso 1 1 calc R . .
H13B H 1.1329 0.8127 0.4943 0.061 Uiso 1 1 calc R . .
H13C H 0.9977 0.7240 0.5380 0.061 Uiso 1 1 calc R . .
C14 C 0.6837(4) 0.5968(2) 0.3162(3) 0.0394(6) Uani 1 1 d . . .
H14A H 0.6018 0.5320 0.2708 0.059 Uiso 1 1 calc R . .
H14B H 0.6648 0.6213 0.4157 0.059 Uiso 1 1 calc R . .
H14C H 0.8164 0.5752 0.3406 0.059 Uiso 1 1 calc R . .
C15 C 0.9140(4) 0.6658(3) -0.1056(3) 0.0416(6) Uani 1 1 d . . .
H15A H 0.8856 0.7461 -0.1348 0.050 Uiso 1 1 calc R . .
H15B H 1.0531 0.6563 -0.0704 0.050 Uiso 1 1 calc R . .
C16 C 0.8966(4) 0.5102(3) 0.0812(4) 0.0463(7) Uani 1 1 d . . .
H16A H 1.0324 0.5021 0.1416 0.069 Uiso 1 1 calc R . .
H16B H 0.8634 0.4670 -0.0195 0.069 Uiso 1 1 calc R . .
H16C H 0.8243 0.4816 0.1466 0.069 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
N1 C1 1.340(3) . ?
N1 C3 1.489(3) . ?
N1 H1 0.8600 . ?
O1 C1 1.218(3) . ?
O2 C15 1.421(3) . ?
O2 H2 0.8200 . ?
C1 C2 1.530(4) . ?
C2 C7 1.527(4) . ?
C2 C3 1.578(3) . ?
C2 H2A 0.9800 . ?
C3 C13 1.521(3) . ?
C3 C4 1.543(3) . ?
C4 C8 1.543(3) . ?
C4 C5 1.555(3) . ?
C4 C12 1.556(3) . ?
C5 C14 1.527(3) . ?
C5 C6 1.538(3) . ?
C5 C10 1.570(3) . ?
C6 C7 1.538(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.562(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C16 1.534(4) . ?
C9 C15 1.541(3) . ?
C9 C10 1.567(3) . ?
C10 C11 1.529(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.550(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N1 C3 95.5(2) . . ?
C1 N1 H1 132.2 . . ?
C3 N1 H1 132.2 . . ?
C15 O2 H2 109.5 . . ?
O1 C1 N1 132.9(3) . . ?
O1 C1 C2 134.2(2) . . ?
N1 C1 C2 92.9(2) . . ?
C7 C2 C1 122.5(2) . . ?
C7 C2 C3 122.4(2) . . ?
C1 C2 C3 84.86(18) . . ?
C7 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
N1 C3 C13 112.3(2) . . ?
N1 C3 C4 113.1(2) . . ?
C13 C3 C4 115.5(2) . . ?
N1 C3 C2 85.56(18) . . ?
C13 C3 C2 115.0(2) . . ?
C4 C3 C2 111.88(17) . . ?
C8 C4 C3 116.64(18) . . ?
C8 C4 C5 101.79(18) . . ?
C3 C4 C5 114.42(17) . . ?
C8 C4 C12 106.41(18) . . ?
C3 C4 C12 114.62(19) . . ?
C5 C4 C12 101.09(17) . . ?
C14 C5 C6 106.75(19) . . ?
C14 C5 C4 115.61(18) . . ?
C6 C5 C4 110.30(19) . . ?
C14 C5 C10 116.19(19) . . ?
C6 C5 C10 114.68(18) . . ?
C4 C5 C10 93.07(16) . . ?
C5 C6 C7 112.6(2) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C2 C7 C6 115.97(19) . . ?
C2 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C2 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C4 C8 C9 105.04(18) . . ?
C4 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C4 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C16 C9 C15 106.0(2) . . ?
C16 C9 C8 114.0(2) . . ?
C15 C9 C8 108.4(2) . . ?
C16 C9 C10 112.2(2) . . ?
C15 C9 C10 115.2(2) . . ?
C8 C9 C10 101.20(18) . . ?
C11 C10 C9 108.35(19) . . ?
C11 C10 C5 101.55(19) . . ?
C9 C10 C5 103.61(17) . . ?
C11 C10 H10 114.0 . . ?
C9 C10 H10 114.0 . . ?
C5 C10 H10 114.0 . . ?
C10 C11 C12 102.47(18) . . ?
C10 C11 H11A 111.3 . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C11 C12 C4 104.3(2) . . ?
C11 C12 H12A 110.9 . . ?
C4 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C4 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C9 115.1(2) . . ?
O2 C15 H15A 108.5 . . ?
C9 C15 H15A 108.5 . . ?
O2 C15 H15B 108.5 . . ?
C9 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C3 N1 C1 O1 -172.3(3) . . . . ?
C3 N1 C1 C2 8.7(2) . . . . ?
O1 C1 C2 C7 47.4(4) . . . . ?
N1 C1 C2 C7 -133.7(2) . . . . ?
O1 C1 C2 C3 172.9(3) . . . . ?
N1 C1 C2 C3 -8.21(19) . . . . ?
C1 N1 C3 C13 -123.7(2) . . . . ?
C1 N1 C3 C4 103.5(2) . . . . ?
C1 N1 C3 C2 -8.5(2) . . . . ?
C7 C2 C3 N1 133.0(2) . . . . ?
C1 C2 C3 N1 7.40(18) . . . . ?
C7 C2 C3 C13 -114.5(3) . . . . ?
C1 C2 C3 C13 120.0(2) . . . . ?
C7 C2 C3 C4 19.9(3) . . . . ?
C1 C2 C3 C4 -105.7(2) . . . . ?
N1 C3 C4 C8 107.1(2) . . . . ?
C13 C3 C4 C8 -24.2(3) . . . . ?
C2 C3 C4 C8 -158.3(2) . . . . ?
N1 C3 C4 C5 -134.3(2) . . . . ?
C13 C3 C4 C5 94.4(2) . . . . ?
C2 C3 C4 C5 -39.7(3) . . . . ?
N1 C3 C4 C12 -18.2(3) . . . . ?
C13 C3 C4 C12 -149.5(2) . . . . ?
C2 C3 C4 C12 76.4(2) . . . . ?
C8 C4 C5 C14 66.0(2) . . . . ?
C3 C4 C5 C14 -60.7(3) . . . . ?
C12 C4 C5 C14 175.53(19) . . . . ?
C8 C4 C5 C6 -172.83(19) . . . . ?
C3 C4 C5 C6 60.5(2) . . . . ?
C12 C4 C5 C6 -63.3(2) . . . . ?
C8 C4 C5 C10 -55.09(19) . . . . ?
C3 C4 C5 C10 178.21(19) . . . . ?
C12 C4 C5 C10 54.48(19) . . . . ?
C14 C5 C6 C7 68.4(3) . . . . ?
C4 C5 C6 C7 -58.0(3) . . . . ?
C10 C5 C6 C7 -161.4(2) . . . . ?
C1 C2 C7 C6 86.8(3) . . . . ?
C3 C2 C7 C6 -19.4(4) . . . . ?
C5 C6 C7 C2 37.9(3) . . . . ?
C3 C4 C8 C9 162.7(2) . . . . ?
C5 C4 C8 C9 37.5(2) . . . . ?
C12 C4 C8 C9 -68.0(2) . . . . ?
C4 C8 C9 C16 -123.2(2) . . . . ?
C4 C8 C9 C15 119.1(2) . . . . ?
C4 C8 C9 C10 -2.5(2) . . . . ?
C16 C9 C10 C11 -163.9(2) . . . . ?
C15 C9 C10 C11 -42.4(3) . . . . ?
C8 C9 C10 C11 74.2(2) . . . . ?
C16 C9 C10 C5 88.8(2) . . . . ?
C15 C9 C10 C5 -149.7(2) . . . . ?
C8 C9 C10 C5 -33.1(2) . . . . ?
C14 C5 C10 C11 -178.48(19) . . . . ?
C6 C5 C10 C11 56.1(2) . . . . ?
C4 C5 C10 C11 -57.90(19) . . . . ?
C14 C5 C10 C9 -66.1(2) . . . . ?
C6 C5 C10 C9 168.5(2) . . . . ?
C4 C5 C10 C9 54.4(2) . . . . ?
C9 C10 C11 C12 -69.9(2) . . . . ?
C5 C10 C11 C12 38.8(2) . . . . ?
C10 C11 C12 C4 -3.5(2) . . . . ?
C8 C4 C12 C11 72.8(2) . . . . ?
C3 C4 C12 C11 -156.78(19) . . . . ?
C5 C4 C12 C11 -33.2(2) . . . . ?
C16 C9 C15 O2 58.2(3) . . . . ?
C8 C9 C15 O2 -179.1(2) . . . . ?
C10 C9 C15 O2 -66.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.19
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_150714e
_database_code_depnum_ccdc_archive 'CCDC 1471598'
_audit_update_record             
;
2016-11-27 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            CSI-30(17)
_chemical_name_systematic        CSI-30(17)
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, y+1/2, -z+'

_cell_length_a                   7.4010(4)
_cell_length_b                   8.9817(4)
_cell_length_c                   11.8039(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.908(5)
_cell_angle_gamma                90
_cell_volume                     777.19(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0170
_cell_measurement_theta_min      6.1600
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.8418
_exptl_absorpt_correction_T_min  0.7818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_preparation       MeOH
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2549
_diffrn_reflns_point_group_measured_fraction_full 0.654
_diffrn_reflns_point_group_measured_fraction_max 0.654
_diffrn_reflns_theta_full        66.179
_diffrn_reflns_theta_max         66.179
_diffrn_reflns_theta_min         3.781
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          -
_reflns_Friedel_coverage         0.224
_reflns_Friedel_fraction_full    0.257
_reflns_Friedel_fraction_max     0.257
_reflns_number_gt                1725
_reflns_number_total             1785
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_coef       0.053(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2015/1 (Sheldrick 2015'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ShelXL
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2a), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C8(H8a,H8b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b),
 C14(H14a,H14b)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.d X=CH2 refined with riding coordinates:
 N1(H1a,H1b), C13(H13a,H13b)
2.e Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0620(3) -0.2803(4) -0.5320(2) 0.0677(8) Uani 1 1 d . . . . .
H1A H 0.0053 -0.2524 -0.4704 0.081 Uiso 1 1 calc R . . . .
H1B H -0.1673 -0.3192 -0.5284 0.081 Uiso 1 1 calc R . . . .
O1 O 0.1443(3) -0.2089(4) -0.6409(2) 0.0736(8) Uani 1 1 d . . . . .
O2 O -0.6660(3) 0.0384(3) -0.5519(2) 0.0714(7) Uani 1 1 d . . . . .
H2 H -0.7208 -0.0358 -0.5786 0.086 Uiso 1 1 calc R . . . .
C1 C -0.0035(3) -0.2633(4) -0.6325(3) 0.0518(7) Uani 1 1 d . . . . .
C2 C -0.1336(4) -0.3176(4) -0.7361(3) 0.0517(7) Uani 1 1 d . . . . .
H2A H -0.1533 -0.4243 -0.7258 0.062 Uiso 1 1 calc R . . . .
C3 C -0.3191(3) -0.2418(3) -0.7465(2) 0.0401(6) Uani 1 1 d . . . . .
C4 C -0.3249(3) -0.0810(3) -0.78217(18) 0.0380(6) Uani 1 1 d . . . . .
C5 C -0.5111(4) -0.0021(3) -0.7820(2) 0.0456(6) Uani 1 1 d . . . . .
H5A H -0.5477 0.0573 -0.8499 0.055 Uiso 1 1 calc R . . . .
H5B H -0.6083 -0.0690 -0.7678 0.055 Uiso 1 1 calc R . . . .
C6 C -0.4338(4) 0.0911(3) -0.6766(2) 0.0455(6) Uani 1 1 d . . . . .
C7 C -0.2380(3) 0.0408(3) -0.69405(19) 0.0400(6) Uani 1 1 d . . . . .
H7 H -0.1674 -0.0013 -0.6251 0.048 Uiso 1 1 calc R . . . .
C8 C -0.1273(4) 0.1458(4) -0.7605(2) 0.0578(8) Uani 1 1 d . . . . .
H8A H 0.0023 0.1264 -0.7419 0.069 Uiso 1 1 calc R . . . .
H8B H -0.1507 0.2490 -0.7429 0.069 Uiso 1 1 calc R . . . .
C9 C -0.1933(5) 0.1117(5) -0.8877(2) 0.0648(9) Uani 1 1 d . . . . .
H9A H -0.3027 0.1680 -0.9146 0.078 Uiso 1 1 calc R . . . .
H9B H -0.0998 0.1366 -0.9346 0.078 Uiso 1 1 calc R . . . .
C10 C -0.2325(4) -0.0545(4) -0.8922(2) 0.0519(7) Uani 1 1 d . . . . .
C11 C -0.0490(4) -0.1375(5) -0.8838(3) 0.0645(9) Uani 1 1 d . . . . .
H11A H -0.0062 -0.1329 -0.9578 0.077 Uiso 1 1 calc R . . . .
H11B H 0.0392 -0.0854 -0.8296 0.077 Uiso 1 1 calc R . . . .
C12 C -0.0535(5) -0.2984(4) -0.8480(3) 0.0676(10) Uani 1 1 d . . . . .
H12A H 0.0694 -0.3382 -0.8386 0.081 Uiso 1 1 calc R . . . .
H12B H -0.1261 -0.3549 -0.9079 0.081 Uiso 1 1 calc R . . . .
C13 C -0.4627(4) -0.3217(4) -0.7317(3) 0.0570(8) Uani 1 1 d . . . . .
H13A H -0.5783 -0.2791 -0.7434 0.068 Uiso 1 1 calc R . . . .
H13B H -0.4488 -0.4209 -0.7095 0.068 Uiso 1 1 calc R . . . .
C14 C -0.4792(4) 0.0257(4) -0.5645(2) 0.0526(7) Uani 1 1 d . . . . .
H14A H -0.4452 -0.0786 -0.5608 0.063 Uiso 1 1 calc R . . . .
H14B H -0.4070 0.0762 -0.5012 0.063 Uiso 1 1 calc R . . . .
C15 C -0.4774(6) 0.2570(4) -0.6827(3) 0.0718(10) Uani 1 1 d . . . . .
H15A H -0.6047 0.2715 -0.6781 0.108 Uiso 1 1 calc GR . . . .
H15B H -0.4490 0.2966 -0.7538 0.108 Uiso 1 1 calc GR . . . .
H15C H -0.4059 0.3073 -0.6202 0.108 Uiso 1 1 calc GR . . . .
C16 C -0.3568(5) -0.1004(6) -1.0015(2) 0.0776(11) Uani 1 1 d . . . . .
H16A H -0.4714 -0.0494 -1.0052 0.116 Uiso 1 1 calc GR . . . .
H16B H -0.3771 -0.2060 -1.0006 0.116 Uiso 1 1 calc GR . . . .
H16C H -0.2996 -0.0747 -1.0670 0.116 Uiso 1 1 calc GR . . . .


_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
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.326(4) . ?
O1 C1 1.214(4) . ?
O2 H2 0.8200 . ?
O2 C14 1.415(3) . ?
C1 C2 1.529(4) . ?
C2 H2A 0.9800 . ?
C2 C3 1.522(4) . ?
C2 C12 1.529(4) . ?
C3 C4 1.503(4) . ?
C3 C13 1.314(4) . ?
C4 C5 1.550(3) . ?
C4 C7 1.584(3) . ?
C4 C10 1.567(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.542(4) . ?
C6 C7 1.559(4) . ?
C6 C14 1.527(4) . ?
C6 C15 1.524(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.545(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(5) . ?
C10 C11 1.541(5) . ?
C10 C16 1.534(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C14 O2 H2 109.5 . . ?
N1 C1 C2 115.6(2) . . ?
O1 C1 N1 121.9(3) . . ?
O1 C1 C2 122.5(3) . . ?
C1 C2 H2A 107.4 . . ?
C1 C2 C12 112.3(3) . . ?
C3 C2 C1 112.6(2) . . ?
C3 C2 H2A 107.4 . . ?
C3 C2 C12 109.4(2) . . ?
C12 C2 H2A 107.4 . . ?
C4 C3 C2 116.3(2) . . ?
C13 C3 C2 118.8(3) . . ?
C13 C3 C4 124.8(3) . . ?
C3 C4 C5 115.5(2) . . ?
C3 C4 C7 119.12(19) . . ?
C3 C4 C10 112.3(2) . . ?
C5 C4 C7 87.95(18) . . ?
C5 C4 C10 114.9(2) . . ?
C10 C4 C7 104.8(2) . . ?
C4 C5 H5A 113.5 . . ?
C4 C5 H5B 113.5 . . ?
H5A C5 H5B 110.8 . . ?
C6 C5 C4 91.03(19) . . ?
C6 C5 H5A 113.5 . . ?
C6 C5 H5B 113.5 . . ?
C5 C6 C7 89.12(19) . . ?
C14 C6 C5 112.9(3) . . ?
C14 C6 C7 108.8(2) . . ?
C15 C6 C5 116.1(2) . . ?
C15 C6 C7 118.1(3) . . ?
C15 C6 C14 110.3(3) . . ?
C4 C7 H7 113.6 . . ?
C6 C7 C4 89.19(18) . . ?
C6 C7 H7 113.6 . . ?
C8 C7 C4 106.63(19) . . ?
C8 C7 C6 117.4(3) . . ?
C8 C7 H7 113.6 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C7 C8 C9 104.8(2) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.2(3) . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C9 C10 C4 102.9(2) . . ?
C9 C10 C11 108.1(3) . . ?
C9 C10 C16 112.5(3) . . ?
C11 C10 C4 110.8(2) . . ?
C16 C10 C4 112.1(2) . . ?
C16 C10 C11 110.2(3) . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.4(3) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C2 C12 H12A 109.2 . . ?
C2 C12 H12B 109.2 . . ?
C11 C12 C2 112.1(3) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C3 C13 H13A 120.0 . . ?
C3 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O2 C14 C6 113.3(2) . . ?
O2 C14 H14A 108.9 . . ?
O2 C14 H14B 108.9 . . ?
C6 C14 H14A 108.9 . . ?
C6 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N1 C1 C2 C3 57.8(4) . . . . ?
N1 C1 C2 C12 -178.2(3) . . . . ?
O1 C1 C2 C3 -122.6(3) . . . . ?
O1 C1 C2 C12 1.4(5) . . . . ?
C1 C2 C3 C4 71.6(3) . . . . ?
C1 C2 C3 C13 -112.9(3) . . . . ?
C1 C2 C12 C11 -72.4(4) . . . . ?
C2 C3 C4 C5 -174.9(2) . . . . ?
C2 C3 C4 C7 -72.2(3) . . . . ?
C2 C3 C4 C10 50.8(3) . . . . ?
C3 C2 C12 C11 53.3(4) . . . . ?
C3 C4 C5 C6 109.1(2) . . . . ?
C3 C4 C7 C6 -105.9(2) . . . . ?
C3 C4 C7 C8 135.6(2) . . . . ?
C3 C4 C10 C9 -160.7(2) . . . . ?
C3 C4 C10 C11 -45.3(3) . . . . ?
C3 C4 C10 C16 78.2(3) . . . . ?
C4 C5 C6 C7 12.6(2) . . . . ?
C4 C5 C6 C14 -97.5(2) . . . . ?
C4 C5 C6 C15 133.8(3) . . . . ?
C4 C7 C8 C9 15.2(3) . . . . ?
C4 C10 C11 C12 48.5(4) . . . . ?
C5 C4 C7 C6 12.28(19) . . . . ?
C5 C4 C7 C8 -106.2(2) . . . . ?
C5 C4 C10 C9 64.7(3) . . . . ?
C5 C4 C10 C11 -179.9(2) . . . . ?
C5 C4 C10 C16 -56.4(4) . . . . ?
C5 C6 C7 C4 -12.34(19) . . . . ?
C5 C6 C7 C8 96.0(2) . . . . ?
C5 C6 C14 O2 -70.4(3) . . . . ?
C6 C7 C8 C9 -82.8(3) . . . . ?
C7 C4 C5 C6 -12.4(2) . . . . ?
C7 C4 C10 C9 -30.0(3) . . . . ?
C7 C4 C10 C11 85.4(3) . . . . ?
C7 C4 C10 C16 -151.1(3) . . . . ?
C7 C6 C14 O2 -167.6(2) . . . . ?
C7 C8 C9 C10 -34.9(3) . . . . ?
C8 C9 C10 C4 40.2(3) . . . . ?
C8 C9 C10 C11 -77.0(3) . . . . ?
C8 C9 C10 C16 161.1(3) . . . . ?
C9 C10 C11 C12 160.6(3) . . . . ?
C10 C4 C5 C6 -117.8(2) . . . . ?
C10 C4 C7 C6 127.5(2) . . . . ?
C10 C4 C7 C8 9.0(3) . . . . ?
C10 C11 C12 C2 -53.8(4) . . . . ?
C12 C2 C3 C4 -54.0(3) . . . . ?
C12 C2 C3 C13 121.6(3) . . . . ?
C13 C3 C4 C5 9.9(3) . . . . ?
C13 C3 C4 C7 112.5(3) . . . . ?
C13 C3 C4 C10 -124.5(3) . . . . ?
C14 C6 C7 C4 101.6(2) . . . . ?
C14 C6 C7 C8 -150.0(2) . . . . ?
C15 C6 C7 C4 -131.7(3) . . . . ?
C15 C6 C7 C8 -23.3(3) . . . . ?
C15 C6 C14 O2 61.3(4) . . . . ?
C16 C10 C11 C12 -76.1(4) . . . . ?

_shelx_SHELXL_version_number     2015/1
_olex2_submission_original_sample_id CSI(17)
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_csi7_0m
_database_code_depnum_ccdc_archive 'CCDC 1471596'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            CSI-7
_chemical_melting_point          260.8-261.1
_chemical_formula_moiety         'C17 H29 N O2'
_chemical_formula_sum            'C17 H29 N O2'
_chemical_formula_weight         279.41
_chemical_absolute_configuration rm

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_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.0528(18)
_cell_length_b                   9.5531(18)
_cell_length_c                   17.179(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1485.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.80
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.55
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_T_max  0.9572
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15761
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.52
_reflns_number_total             4235
_reflns_number_gt                4099
_reflns_threshold_expression     >2sigma(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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0481P)²+0.1851P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_number_reflns         4235
_refine_ls_number_parameters     192
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.53779(8) 0.65223(8) 0.03928(5) 0.02101(16) Uani 1 1 d . . .
O2 O 0.00011(7) 0.52325(7) 0.13782(4) 0.01373(13) Uani 1 1 d . . .
N1 N 0.35632(9) 0.77807(9) -0.01902(5) 0.01675(16) Uani 1 1 d D . .
H@2 H 0.2661(10) 0.7984(16) -0.0224(9) 0.025 Uiso 1 1 d D . .
H@1 H 0.4122(14) 0.8098(15) -0.0556(7) 0.025 Uiso 1 1 d D . .
C1 C 0.23400(11) 0.16619(10) 0.01303(6) 0.01661(17) Uani 1 1 d . . .
H1A H 0.3277 0.1318 -0.0082 0.025 Uiso 1 1 calc R . .
H1B H 0.1930 0.2377 -0.0217 0.025 Uiso 1 1 calc R . .
H1C H 0.1642 0.0882 0.0175 0.025 Uiso 1 1 calc R . .
C2 C 0.26104(10) 0.23061(9) 0.09436(5) 0.01225(16) Uani 1 1 d . . .
C3 C 0.35794(9) 0.36699(9) 0.09101(5) 0.01175(15) Uani 1 1 d . . .
H3 H 0.4232 0.3653 0.0440 0.014 Uiso 1 1 calc R . .
C4 C 0.24297(9) 0.48808(9) 0.08419(5) 0.01035(15) Uani 1 1 d . . .
C5 C 0.29270(9) 0.64339(9) 0.09595(5) 0.01214(16) Uani 1 1 d . . .
H5 H 0.2028 0.7007 0.0848 0.015 Uiso 1 1 calc R . .
C6 C 0.40695(10) 0.69028(9) 0.03579(6) 0.01463(17) Uani 1 1 d . . .
C7 C -0.13658(10) 0.47452(10) 0.16880(5) 0.01595(17) Uani 1 1 d . . .
H7A H -0.1394 0.3721 0.1664 0.024 Uiso 1 1 calc R . .
H7B H -0.2184 0.5131 0.1382 0.024 Uiso 1 1 calc R . .
H7C H -0.1459 0.5049 0.2231 0.024 Uiso 1 1 calc R . .
C8 C 0.13379(9) 0.44225(9) 0.14942(5) 0.01029(15) Uani 1 1 d . . .
C9 C 0.16603(10) 0.48579(10) 0.00359(5) 0.01346(16) Uani 1 1 d . . .
H9A H 0.0920 0.4110 0.0026 0.020 Uiso 1 1 calc R . .
H9B H 0.2398 0.4689 -0.0371 0.020 Uiso 1 1 calc R . .
H9C H 0.1177 0.5761 -0.0057 0.020 Uiso 1 1 calc R . .
C10 C 0.34185(10) 0.68773(10) 0.17783(6) 0.01533(17) Uani 1 1 d . . .
H10A H 0.4413 0.6496 0.1889 0.018 Uiso 1 1 calc R . .
H10B H 0.3472 0.7911 0.1809 0.018 Uiso 1 1 calc R . .
C11 C 0.23156(10) 0.63282(10) 0.23778(5) 0.01517(17) Uani 1 1 d . . .
H11A H 0.1364 0.6825 0.2311 0.018 Uiso 1 1 calc R . .
H11B H 0.2689 0.6538 0.2907 0.018 Uiso 1 1 calc R . .
C12 C 0.20500(10) 0.47417(9) 0.23061(5) 0.01216(16) Uani 1 1 d . . .
C13 C 0.10821(11) 0.42967(10) 0.29991(5) 0.01688(18) Uani 1 1 d . . .
H13A H 0.1671 0.4320 0.3478 0.025 Uiso 1 1 calc R . .
H13B H 0.0714 0.3345 0.2913 0.025 Uiso 1 1 calc R . .
H13C H 0.0245 0.4942 0.3048 0.025 Uiso 1 1 calc R . .
C14 C 0.35446(10) 0.39542(10) 0.23877(5) 0.01498(17) Uani 1 1 d . . .
H14A H 0.4133 0.4429 0.2795 0.018 Uiso 1 1 calc R . .
H14B H 0.3334 0.2995 0.2576 0.018 Uiso 1 1 calc R . .
C15 C 0.45099(10) 0.38380(10) 0.16488(5) 0.01446(17) Uani 1 1 d . . .
H15A H 0.5128 0.4689 0.1601 0.017 Uiso 1 1 calc R . .
H15B H 0.5179 0.3023 0.1701 0.017 Uiso 1 1 calc R . .
C16 C 0.11498(9) 0.28300(9) 0.13394(5) 0.01178(16) Uani 1 1 d . . .
H16A H 0.0294 0.2663 0.0993 0.014 Uiso 1 1 calc R . .
H16B H 0.0981 0.2325 0.1835 0.014 Uiso 1 1 calc R . .
C17 C 0.33173(11) 0.10843(10) 0.13992(6) 0.01663(18) Uani 1 1 d . . .
H17A H 0.2660 0.0270 0.1382 0.025 Uiso 1 1 calc R . .
H17B H 0.3473 0.1366 0.1941 0.025 Uiso 1 1 calc R . .
H17C H 0.4268 0.0841 0.1163 0.025 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2404(12) . ?
O2 C7 1.4252(11) . ?
O2 C8 1.4502(10) . ?
N1 C6 1.3417(13) . ?
N1 H@2 0.842(9) . ?
N1 H@1 0.862(8) . ?
C1 C2 1.5462(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C17 1.5441(13) . ?
C2 C16 1.5689(12) . ?
C2 C3 1.5717(12) . ?
C3 C15 1.5317(12) . ?
C3 C4 1.5606(12) . ?
C3 H3 1.0000 . ?
C4 C9 1.5500(12) . ?
C4 C8 1.5571(12) . ?
C4 C5 1.5636(12) . ?
C5 C6 1.5292(13) . ?
C5 C10 1.5349(13) . ?
C5 H5 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C16 1.5537(12) . ?
C8 C12 1.5665(12) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.5272(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5394(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5381(13) . ?
C12 C14 1.5545(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5451(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
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
C7 O2 C8 119.93(7) . . ?
C6 N1 H@2 121.6(10) . . ?
C6 N1 H@1 122.1(10) . . ?
H@2 N1 H@1 116.0(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C2 C1 102.87(7) . . ?
C17 C2 C16 111.76(7) . . ?
C1 C2 C16 112.66(7) . . ?
C17 C2 C3 114.45(7) . . ?
C1 C2 C3 112.66(7) . . ?
C16 C2 C3 102.82(7) . . ?
C15 C3 C4 110.56(7) . . ?
C15 C3 C2 111.32(7) . . ?
C4 C3 C2 104.18(7) . . ?
C15 C3 H3 110.2 . . ?
C4 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C9 C4 C8 110.71(7) . . ?
C9 C4 C3 110.87(7) . . ?
C8 C4 C3 99.25(6) . . ?
C9 C4 C5 104.97(7) . . ?
C8 C4 C5 110.89(7) . . ?
C3 C4 C5 120.11(7) . . ?
C6 C5 C10 110.03(7) . . ?
C6 C5 C4 112.67(7) . . ?
C10 C5 C4 117.63(7) . . ?
C6 C5 H5 105.1 . . ?
C10 C5 H5 105.1 . . ?
C4 C5 H5 105.1 . . ?
O1 C6 N1 122.91(9) . . ?
O1 C6 C5 121.83(9) . . ?
N1 C6 C5 115.24(8) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C16 114.05(7) . . ?
O2 C8 C4 106.30(7) . . ?
C16 C8 C4 102.81(7) . . ?
O2 C8 C12 111.22(7) . . ?
C16 C8 C12 112.84(7) . . ?
C4 C8 C12 108.96(7) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 109.49(7) . . ?
C11 C10 H10A 109.8 . . ?
C5 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C5 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 112.73(8) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 107.41(7) . . ?
C13 C12 C14 106.99(7) . . ?
C11 C12 C14 109.47(7) . . ?
C13 C12 C8 113.64(7) . . ?
C11 C12 C8 109.10(7) . . ?
C14 C12 C8 110.14(7) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 116.93(7) . . ?
C15 C14 H14A 108.1 . . ?
C12 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
C12 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C3 C15 C14 112.16(7) . . ?
C3 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C3 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C8 C16 C2 107.11(7) . . ?
C8 C16 H16A 110.3 . . ?
C2 C16 H16A 110.3 . . ?
C8 C16 H16B 110.3 . . ?
C2 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C2 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 C2 C3 C15 -32.02(10) . . . . ?
C1 C2 C3 C15 -149.08(8) . . . . ?
C16 C2 C3 C15 89.39(8) . . . . ?
C17 C2 C3 C4 -151.20(7) . . . . ?
C1 C2 C3 C4 91.74(8) . . . . ?
C16 C2 C3 C4 -29.79(8) . . . . ?
C15 C3 C4 C9 170.80(7) . . . . ?
C2 C3 C4 C9 -69.51(8) . . . . ?
C15 C3 C4 C8 -72.73(8) . . . . ?
C2 C3 C4 C8 46.95(8) . . . . ?
C15 C3 C4 C5 48.07(10) . . . . ?
C2 C3 C4 C5 167.76(7) . . . . ?
C9 C4 C5 C6 -63.69(9) . . . . ?
C8 C4 C5 C6 176.71(7) . . . . ?
C3 C4 C5 C6 61.86(10) . . . . ?
C9 C4 C5 C10 166.70(7) . . . . ?
C8 C4 C5 C10 47.10(10) . . . . ?
C3 C4 C5 C10 -67.75(10) . . . . ?
C10 C5 C6 O1 58.19(11) . . . . ?
C4 C5 C6 O1 -75.22(11) . . . . ?
C10 C5 C6 N1 -119.90(9) . . . . ?
C4 C5 C6 N1 106.69(9) . . . . ?
C7 O2 C8 C16 45.54(10) . . . . ?
C7 O2 C8 C4 158.09(7) . . . . ?
C7 O2 C8 C12 -83.45(9) . . . . ?
C9 C4 C8 O2 -48.96(9) . . . . ?
C3 C4 C8 O2 -165.54(7) . . . . ?
C5 C4 C8 O2 67.14(8) . . . . ?
C9 C4 C8 C16 71.17(8) . . . . ?
C3 C4 C8 C16 -45.42(8) . . . . ?
C5 C4 C8 C16 -172.73(7) . . . . ?
C9 C4 C8 C12 -168.90(7) . . . . ?
C3 C4 C8 C12 74.51(8) . . . . ?
C5 C4 C8 C12 -52.80(9) . . . . ?
C6 C5 C10 C11 -176.68(7) . . . . ?
C4 C5 C10 C11 -45.85(10) . . . . ?
C5 C10 C11 C12 53.34(10) . . . . ?
C10 C11 C12 C13 173.06(8) . . . . ?
C10 C11 C12 C14 57.23(10) . . . . ?
C10 C11 C12 C8 -63.35(10) . . . . ?
O2 C8 C12 C13 64.58(9) . . . . ?
C16 C8 C12 C13 -65.04(10) . . . . ?
C4 C8 C12 C13 -178.56(7) . . . . ?
O2 C8 C12 C11 -55.23(9) . . . . ?
C16 C8 C12 C11 175.14(7) . . . . ?
C4 C8 C12 C11 61.62(9) . . . . ?
O2 C8 C12 C14 -175.41(7) . . . . ?
C16 C8 C12 C14 54.97(9) . . . . ?
C4 C8 C12 C14 -58.55(9) . . . . ?
C13 C12 C14 C15 160.94(8) . . . . ?
C11 C12 C14 C15 -82.97(10) . . . . ?
C8 C12 C14 C15 36.98(10) . . . . ?
C4 C3 C15 C14 54.68(10) . . . . ?
C2 C3 C15 C14 -60.61(10) . . . . ?
C12 C14 C15 C3 -35.34(11) . . . . ?
O2 C8 C16 C2 142.68(7) . . . . ?
C4 C8 C16 C2 28.05(8) . . . . ?
C12 C8 C16 C2 -89.16(8) . . . . ?
C17 C2 C16 C8 124.20(8) . . . . ?
C1 C2 C16 C8 -120.56(8) . . . . ?
C3 C2 C16 C8 0.98(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 H@2 O1 0.842(9) 2.140(9) 2.9799(12) 176.2(15) 2_465
N1 H@1 O2 0.862(8) 2.274(10) 3.0761(11) 154.8(13) 2_565

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        30.52
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_150714c
_database_code_depnum_ccdc_archive 'CCDC 1471595'
_audit_update_record             
;
2016-11-27 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            CSI-13(4)
_chemical_name_systematic        CSI-13(4)
_chemical_formula_moiety         'C16 H25 N O, H2 O'
_chemical_formula_sum            'C16 H27 N O2'
_chemical_formula_weight         265.38
_chemical_absolute_configuration unk
_chemical_melting_point          124.0-124.2
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3519(7)
_cell_length_b                   6.7121(7)
_cell_length_c                   18.8242(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.1430(10)
_cell_angle_gamma                90
_cell_volume                     802.00(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.4970
_cell_measurement_theta_min      6.9580
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_correction_T_min  0.7954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_preparation       'in MEOH'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2404
_diffrn_reflns_point_group_measured_fraction_full 0.630
_diffrn_reflns_point_group_measured_fraction_max 0.630
_diffrn_reflns_theta_full        66.169
_diffrn_reflns_theta_max         66.169
_diffrn_reflns_theta_min         4.701
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          -
_reflns_Friedel_coverage         0.162
_reflns_Friedel_fraction_full    0.194
_reflns_Friedel_fraction_max     0.194
_reflns_number_gt                1139
_reflns_number_total             1764
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 98 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1764
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1322
_refine_special_details          'ShelXL 2016'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3857(7) -0.2354(6) -0.9222(2) 0.0662(13) Uani 1 1 d . . . . .
H1A H -0.285823 -0.169034 -0.940844 0.079 Uiso 1 1 calc R . . . .
H1B H -0.489838 -0.173622 -0.904349 0.079 Uiso 1 1 calc R . . . .
O1 O -0.2326(6) -0.5251(5) -0.94623(19) 0.0725(11) Uani 1 1 d . . . . .
O2 O -0.0716(5) -0.9344(6) -0.95618(18) 0.0804(12) Uani 1 1 d . . . . .
H2A H -0.109661 -0.812984 -0.956553 0.096 Uiso 1 1 d R . . . .
H2B H 0.020729 -0.950414 -0.987213 0.096 Uiso 1 1 d R . . . .
C1 C -0.3790(8) -0.4331(8) -0.9212(2) 0.0534(12) Uani 1 1 d . . . . .
C2 C -0.5704(8) -0.5373(7) -0.8900(2) 0.0529(13) Uani 1 1 d . . . . .
H2 H -0.683588 -0.530413 -0.926768 0.064 Uiso 1 1 calc R . . . .
C3 C -0.6535(7) -0.4340(8) -0.8252(2) 0.0503(11) Uani 1 1 d . . . . .
C4 C -0.5429(7) -0.4804(7) -0.7548(2) 0.0517(12) Uani 1 1 d . . . . .
H4 H -0.633355 -0.435005 -0.716962 0.062 Uiso 1 1 calc R . . . .
C5 C -0.3257(7) -0.3811(8) -0.7431(2) 0.0579(14) Uani 1 1 d . . . . .
H5A H -0.249983 -0.381164 -0.786942 0.069 Uiso 1 1 calc R . . . .
H5B H -0.341766 -0.244377 -0.727535 0.069 Uiso 1 1 calc R . . . .
C6 C -0.2070(8) -0.5020(7) -0.6865(2) 0.0590(14) Uani 1 1 d . . . . .
H6 H -0.057833 -0.520750 -0.696250 0.071 Uiso 1 1 calc R . . . .
C7 C -0.2464(9) -0.4592(10) -0.6058(3) 0.0761(16) Uani 1 1 d . . . . .
C8 C -0.3998(10) -0.6391(11) -0.6062(3) 0.0828(19) Uani 1 1 d . . . . .
H8A H -0.365461 -0.736794 -0.569613 0.099 Uiso 1 1 calc R . . . .
H8B H -0.546852 -0.600753 -0.605100 0.099 Uiso 1 1 calc R . . . .
C9 C -0.3301(8) -0.7012(8) -0.6810(3) 0.0632(15) Uani 1 1 d . . . . .
H9 H -0.237802 -0.818269 -0.679929 0.076 Uiso 1 1 calc R . . . .
C10 C -0.4956(8) -0.7067(8) -0.7424(2) 0.0552(13) Uani 1 1 d . . . . .
C11 C -0.3953(8) -0.7908(7) -0.8086(2) 0.0606(14) Uani 1 1 d . . . . .
H11A H -0.259132 -0.728137 -0.813811 0.073 Uiso 1 1 calc R . . . .
H11B H -0.371796 -0.932429 -0.801942 0.073 Uiso 1 1 calc R . . . .
C12 C -0.5287(8) -0.7590(7) -0.8768(3) 0.0602(14) Uani 1 1 d . . . . .
H12A H -0.661857 -0.828437 -0.873249 0.072 Uiso 1 1 calc R . . . .
H12B H -0.456199 -0.814538 -0.916701 0.072 Uiso 1 1 calc R . . . .
C13 C -0.8172(8) -0.3152(8) -0.8293(3) 0.0675(15) Uani 1 1 d . . . . .
H13A H -0.867430 -0.257652 -0.788324 0.081 Uiso 1 1 calc R . . . .
H13B H -0.883172 -0.288496 -0.873218 0.081 Uiso 1 1 calc R . . . .
C14 C -0.3394(11) -0.2588(10) -0.5875(3) 0.099(2) Uani 1 1 d . . . . .
H14A H -0.472264 -0.242191 -0.612758 0.149 Uiso 1 1 calc GR . . . .
H14B H -0.244842 -0.154799 -0.600735 0.149 Uiso 1 1 calc GR . . . .
H14C H -0.359976 -0.252439 -0.537256 0.149 Uiso 1 1 calc GR . . . .
C15 C -0.0459(10) -0.5001(12) -0.5597(3) 0.110(3) Uani 1 1 d . . . . .
H15A H -0.079886 -0.499558 -0.510467 0.165 Uiso 1 1 calc GR . . . .
H15B H 0.056610 -0.398458 -0.568054 0.165 Uiso 1 1 calc GR . . . .
H15C H 0.010552 -0.627736 -0.571909 0.165 Uiso 1 1 calc GR . . . .
C16 C -0.6935(8) -0.8237(9) -0.7240(3) 0.0755(17) Uani 1 1 d . . . . .
H16A H -0.658690 -0.962017 -0.718234 0.113 Uiso 1 1 calc GR . . . .
H16B H -0.798423 -0.809057 -0.761720 0.113 Uiso 1 1 calc GR . . . .
H16C H -0.747513 -0.773123 -0.680600 0.113 Uiso 1 1 calc GR . . . .


_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
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.328(6) . ?
O1 C1 1.225(5) . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8501 . ?
C1 C2 1.538(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.515(6) . ?
C2 C12 1.530(6) . ?
C3 C4 1.509(6) . ?
C3 C13 1.311(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.541(6) . ?
C4 C10 1.564(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(6) . ?
C6 H6 0.9800 . ?
C6 C7 1.574(6) . ?
C6 C9 1.554(7) . ?
C7 C8 1.551(9) . ?
C7 C14 1.514(8) . ?
C7 C15 1.538(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.549(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.534(7) . ?
C10 C11 1.528(6) . ?
C10 C16 1.532(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.527(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A O2 H2B 108.6 . . ?
N1 C1 C2 115.8(5) . . ?
O1 C1 N1 121.5(5) . . ?
O1 C1 C2 122.6(5) . . ?
C1 C2 H2 106.2 . . ?
C3 C2 C1 113.7(4) . . ?
C3 C2 H2 106.2 . . ?
C3 C2 C12 112.2(4) . . ?
C12 C2 C1 111.7(4) . . ?
C12 C2 H2 106.2 . . ?
C4 C3 C2 116.6(4) . . ?
C13 C3 C2 122.0(4) . . ?
C13 C3 C4 121.3(4) . . ?
C3 C4 H4 107.9 . . ?
C3 C4 C5 114.9(4) . . ?
C3 C4 C10 114.3(4) . . ?
C5 C4 H4 107.9 . . ?
C5 C4 C10 103.5(4) . . ?
C10 C4 H4 107.9 . . ?
C4 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C6 C5 C4 106.7(4) . . ?
C6 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
C5 C6 H6 113.2 . . ?
C5 C6 C7 119.2(4) . . ?
C5 C6 C9 105.6(4) . . ?
C7 C6 H6 113.2 . . ?
C9 C6 H6 113.2 . . ?
C9 C6 C7 89.7(4) . . ?
C8 C7 C6 88.6(4) . . ?
C14 C7 C6 117.4(5) . . ?
C14 C7 C8 116.2(5) . . ?
C14 C7 C15 110.6(6) . . ?
C15 C7 C6 110.7(5) . . ?
C15 C7 C8 111.7(5) . . ?
C7 C8 H8A 113.5 . . ?
C7 C8 H8B 113.5 . . ?
H8A C8 H8B 110.8 . . ?
C9 C8 C7 90.7(4) . . ?
C9 C8 H8A 113.5 . . ?
C9 C8 H8B 113.5 . . ?
C6 C9 H9 112.9 . . ?
C8 C9 C6 89.4(4) . . ?
C8 C9 H9 112.9 . . ?
C10 C9 C6 107.7(4) . . ?
C10 C9 C8 118.7(5) . . ?
C10 C9 H9 112.9 . . ?
C9 C10 C4 102.2(4) . . ?
C11 C10 C4 108.7(4) . . ?
C11 C10 C9 109.2(4) . . ?
C11 C10 C16 111.5(4) . . ?
C16 C10 C4 112.1(4) . . ?
C16 C10 C9 112.8(4) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.5(4) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C2 C12 H12A 109.4 . . ?
C2 C12 H12B 109.4 . . ?
C11 C12 C2 111.1(4) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C3 C13 H13A 120.0 . . ?
C3 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N1 C1 C2 C3 -39.9(6) . . . . ?
N1 C1 C2 C12 -168.2(4) . . . . ?
O1 C1 C2 C3 143.0(5) . . . . ?
O1 C1 C2 C12 14.8(6) . . . . ?
C1 C2 C3 C4 -83.0(5) . . . . ?
C1 C2 C3 C13 99.2(6) . . . . ?
C1 C2 C12 C11 78.6(5) . . . . ?
C2 C3 C4 C5 74.8(5) . . . . ?
C2 C3 C4 C10 -44.6(6) . . . . ?
C3 C2 C12 C11 -50.4(6) . . . . ?
C3 C4 C5 C6 -158.6(4) . . . . ?
C3 C4 C10 C9 163.4(4) . . . . ?
C3 C4 C10 C11 48.0(5) . . . . ?
C3 C4 C10 C16 -75.6(5) . . . . ?
C4 C5 C6 C7 -83.3(5) . . . . ?
C4 C5 C6 C9 15.3(5) . . . . ?
C4 C10 C11 C12 -56.0(5) . . . . ?
C5 C4 C10 C9 37.7(5) . . . . ?
C5 C4 C10 C11 -77.6(4) . . . . ?
C5 C4 C10 C16 158.7(4) . . . . ?
C5 C6 C7 C8 98.5(5) . . . . ?
C5 C6 C7 C14 -20.5(8) . . . . ?
C5 C6 C7 C15 -148.7(5) . . . . ?
C5 C6 C9 C8 -111.1(4) . . . . ?
C5 C6 C9 C10 9.0(5) . . . . ?
C6 C7 C8 C9 9.2(4) . . . . ?
C6 C9 C10 C4 -28.9(5) . . . . ?
C6 C9 C10 C11 86.0(5) . . . . ?
C6 C9 C10 C16 -149.5(4) . . . . ?
C7 C6 C9 C8 9.2(4) . . . . ?
C7 C6 C9 C10 129.3(4) . . . . ?
C7 C8 C9 C6 -9.4(4) . . . . ?
C7 C8 C9 C10 -119.3(5) . . . . ?
C8 C9 C10 C4 70.4(5) . . . . ?
C8 C9 C10 C11 -174.6(5) . . . . ?
C8 C9 C10 C16 -50.2(6) . . . . ?
C9 C6 C7 C8 -9.2(4) . . . . ?
C9 C6 C7 C14 -128.3(6) . . . . ?
C9 C6 C7 C15 103.5(5) . . . . ?
C9 C10 C11 C12 -166.7(4) . . . . ?
C10 C4 C5 C6 -33.3(5) . . . . ?
C10 C11 C12 C2 58.7(6) . . . . ?
C12 C2 C3 C4 45.1(6) . . . . ?
C12 C2 C3 C13 -132.8(5) . . . . ?
C13 C3 C4 C5 -107.4(5) . . . . ?
C13 C3 C4 C10 133.2(5) . . . . ?
C14 C7 C8 C9 129.3(5) . . . . ?
C15 C7 C8 C9 -102.5(5) . . . . ?
C16 C10 C11 C12 68.1(6) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_exptl_crystal_mounting_method '25 mg'
_olex2_submission_original_sample_id CSI-13(4)
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150713e
_database_code_depnum_ccdc_archive 'CCDC 1471594'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ?
;
_chemical_name_common            CSI-33
_chemical_melting_point          185.4-185.8
_chemical_formula_moiety         'C16 H25 N O'
_chemical_formula_sum            'C16 H25 N O'
_chemical_formula_weight         247.37
_chemical_absolute_configuration unk

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_H-M   P2(1)2(1)2(1)

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                   8.8646(5)
_cell_length_b                   12.1444(10)
_cell_length_c                   13.9207(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1498.64(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    657
_cell_measurement_theta_min      6.9500
_cell_measurement_theta_max      68.5730

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8126
_exptl_absorpt_correction_T_max  0.8607
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3002
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.83
_diffrn_reflns_theta_max         66.18
_reflns_number_total             2192
_reflns_number_gt                1569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0492P)²+0.0406P] 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     SHELXL
_refine_ls_extinction_coef       0.0127(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_number_reflns         2192
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1239
_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
N1 N 0.0006(3) 0.7130(3) 0.08294(18) 0.0601(8) Uani 1 1 d . . .
H1 H -0.0865 0.7421 0.0732 0.072 Uiso 1 1 calc R . .
O1 O 0.1735(3) 0.7814(3) -0.02910(17) 0.0760(8) Uani 1 1 d . . .
C1 C 0.1340(4) 0.7281(3) 0.0406(2) 0.0572(9) Uani 1 1 d . . .
C2 C 0.2158(4) 0.6552(3) 0.1131(2) 0.0537(9) Uani 1 1 d . . .
H2 H 0.2598 0.5905 0.0817 0.064 Uiso 1 1 calc R . .
C3 C 0.0534(4) 0.6290(3) 0.1526(2) 0.0496(8) Uani 1 1 d . . .
C4 C 0.0182(4) 0.6586(3) 0.2559(2) 0.0468(8) Uani 1 1 d . . .
H4 H 0.0815 0.7209 0.2752 0.056 Uiso 1 1 calc R . .
C5 C -0.1472(4) 0.6824(4) 0.2850(2) 0.0648(11) Uani 1 1 d . . .
H5A H -0.2210 0.6431 0.2466 0.078 Uiso 1 1 calc R . .
H5B H -0.1712 0.7603 0.2884 0.078 Uiso 1 1 calc R . .
C6 C -0.1166(4) 0.6290(4) 0.3843(3) 0.0655(10) Uani 1 1 d . . .
C7 C 0.0207(4) 0.5703(3) 0.3365(2) 0.0542(9) Uani 1 1 d . . .
H7 H -0.0156 0.5009 0.3088 0.065 Uiso 1 1 calc R . .
C8 C 0.1655(5) 0.5457(4) 0.3911(3) 0.0703(11) Uani 1 1 d . . .
H8A H 0.2069 0.6138 0.4161 0.084 Uiso 1 1 calc R . .
H8B H 0.1432 0.4979 0.4450 0.084 Uiso 1 1 calc R . .
C9 C 0.2798(5) 0.4913(4) 0.3274(3) 0.0703(11) Uani 1 1 d . . .
H9 H 0.2824 0.4148 0.3291 0.084 Uiso 1 1 calc R . .
C10 C 0.3769(4) 0.5393(3) 0.2693(3) 0.0637(10) Uani 1 1 d . . .
C11 C 0.3934(4) 0.6622(3) 0.2636(3) 0.0683(11) Uani 1 1 d . . .
H11A H 0.4995 0.6802 0.2702 0.082 Uiso 1 1 calc R . .
H11B H 0.3411 0.6945 0.3180 0.082 Uiso 1 1 calc R . .
C12 C 0.3342(4) 0.7168(4) 0.1715(2) 0.0636(10) Uani 1 1 d . . .
H12A H 0.2922 0.7878 0.1890 0.076 Uiso 1 1 calc R . .
H12B H 0.4198 0.7308 0.1299 0.076 Uiso 1 1 calc R . .
C13 C 0.0015(5) 0.5138(3) 0.1237(2) 0.0733(12) Uani 1 1 d . . .
H13A H -0.1046 0.5065 0.1359 0.110 Uiso 1 1 calc R . .
H13B H 0.0557 0.4599 0.1605 0.110 Uiso 1 1 calc R . .
H13C H 0.0208 0.5025 0.0566 0.110 Uiso 1 1 calc R . .
C14 C -0.2397(5) 0.5551(4) 0.4247(4) 0.1017(18) Uani 1 1 d . . .
H14A H -0.3256 0.5989 0.4419 0.153 Uiso 1 1 calc R . .
H14B H -0.2025 0.5176 0.4806 0.153 Uiso 1 1 calc R . .
H14C H -0.2686 0.5019 0.3770 0.153 Uiso 1 1 calc R . .
C15 C -0.0673(6) 0.7166(4) 0.4587(3) 0.0937(15) Uani 1 1 d . . .
H15A H -0.1517 0.7628 0.4743 0.141 Uiso 1 1 calc R . .
H15B H 0.0122 0.7607 0.4321 0.141 Uiso 1 1 calc R . .
H15C H -0.0319 0.6805 0.5158 0.141 Uiso 1 1 calc R . .
C16 C 0.4807(5) 0.4734(4) 0.2041(3) 0.0931(15) Uani 1 1 d . . .
H16A H 0.4588 0.3964 0.2107 0.140 Uiso 1 1 calc R . .
H16B H 0.5837 0.4868 0.2217 0.140 Uiso 1 1 calc R . .
H16C H 0.4650 0.4954 0.1386 0.140 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
N1 C1 1.334(4) . ?
N1 C3 1.483(4) . ?
N1 H1 0.8600 . ?
O1 C1 1.218(4) . ?
C1 C2 1.526(5) . ?
C2 C12 1.524(5) . ?
C2 C3 1.574(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.514(4) . ?
C3 C13 1.527(5) . ?
C4 C5 1.548(5) . ?
C4 C7 1.553(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.551(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C14 1.521(6) . ?
C6 C15 1.547(6) . ?
C6 C7 1.560(5) . ?
C7 C8 1.521(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.500(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.317(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.502(6) . ?
C10 C16 1.521(5) . ?
C11 C12 1.536(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N1 C3 96.0(3) . . ?
C1 N1 H1 132.0 . . ?
C3 N1 H1 132.0 . . ?
O1 C1 N1 132.8(4) . . ?
O1 C1 C2 134.4(3) . . ?
N1 C1 C2 92.8(3) . . ?
C12 C2 C1 113.3(3) . . ?
C12 C2 C3 122.9(3) . . ?
C1 C2 C3 85.1(2) . . ?
C12 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
C3 C2 H2 111.0 . . ?
N1 C3 C4 113.1(3) . . ?
N1 C3 C13 111.3(3) . . ?
C4 C3 C13 113.9(3) . . ?
N1 C3 C2 85.5(2) . . ?
C4 C3 C2 118.2(3) . . ?
C13 C3 C2 111.7(3) . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 C7 121.2(3) . . ?
C5 C4 C7 87.3(3) . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
C7 C4 H4 109.0 . . ?
C4 C5 C6 89.4(3) . . ?
C4 C5 H5A 113.7 . . ?
C6 C5 H5A 113.7 . . ?
C4 C5 H5B 113.7 . . ?
C6 C5 H5B 113.7 . . ?
H5A C5 H5B 111.0 . . ?
C14 C6 C15 111.2(3) . . ?
C14 C6 C5 116.8(4) . . ?
C15 C6 C5 111.0(3) . . ?
C14 C6 C7 116.6(4) . . ?
C15 C6 C7 112.3(4) . . ?
C5 C6 C7 87.0(2) . . ?
C8 C7 C4 120.6(3) . . ?
C8 C7 C6 122.4(3) . . ?
C4 C7 C6 88.9(3) . . ?
C8 C7 H7 107.7 . . ?
C4 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C9 C8 C7 111.2(3) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 127.6(4) . . ?
C10 C9 H9 116.2 . . ?
C8 C9 H9 116.2 . . ?
C9 C10 C11 122.4(4) . . ?
C9 C10 C16 121.9(4) . . ?
C11 C10 C16 115.6(4) . . ?
C10 C11 C12 116.1(3) . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C2 C12 C11 118.0(3) . . ?
C2 C12 H12A 107.8 . . ?
C11 C12 H12A 107.8 . . ?
C2 C12 H12B 107.8 . . ?
C11 C12 H12B 107.8 . . ?
H12A C12 H12B 107.2 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C3 N1 C1 O1 174.0(4) . . . . ?
C3 N1 C1 C2 -6.7(3) . . . . ?
O1 C1 C2 C12 61.8(5) . . . . ?
N1 C1 C2 C12 -117.4(3) . . . . ?
O1 C1 C2 C3 -174.5(4) . . . . ?
N1 C1 C2 C3 6.3(3) . . . . ?
C1 N1 C3 C4 125.3(3) . . . . ?
C1 N1 C3 C13 -104.9(3) . . . . ?
C1 N1 C3 C2 6.6(3) . . . . ?
C12 C2 C3 N1 108.9(4) . . . . ?
C1 C2 C3 N1 -5.7(2) . . . . ?
C12 C2 C3 C4 -4.9(5) . . . . ?
C1 C2 C3 C4 -119.5(3) . . . . ?
C12 C2 C3 C13 -140.0(3) . . . . ?
C1 C2 C3 C13 105.4(3) . . . . ?
N1 C3 C4 C5 56.1(4) . . . . ?
C13 C3 C4 C5 -72.2(4) . . . . ?
C2 C3 C4 C5 153.7(3) . . . . ?
N1 C3 C4 C7 162.2(3) . . . . ?
C13 C3 C4 C7 33.9(4) . . . . ?
C2 C3 C4 C7 -100.3(4) . . . . ?
C3 C4 C5 C6 145.1(3) . . . . ?
C7 C4 C5 C6 20.4(3) . . . . ?
C4 C5 C6 C14 -138.7(4) . . . . ?
C4 C5 C6 C15 92.4(4) . . . . ?
C4 C5 C6 C7 -20.3(3) . . . . ?
C3 C4 C7 C8 89.2(4) . . . . ?
C5 C4 C7 C8 -147.9(3) . . . . ?
C3 C4 C7 C6 -143.2(3) . . . . ?
C5 C4 C7 C6 -20.3(3) . . . . ?
C14 C6 C7 C8 -95.0(5) . . . . ?
C15 C6 C7 C8 34.9(5) . . . . ?
C5 C6 C7 C8 146.4(4) . . . . ?
C14 C6 C7 C4 138.9(4) . . . . ?
C15 C6 C7 C4 -91.3(3) . . . . ?
C5 C6 C7 C4 20.2(3) . . . . ?
C4 C7 C8 C9 -68.3(5) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
C7 C8 C9 C10 85.2(5) . . . . ?
C8 C9 C10 C11 4.2(6) . . . . ?
C8 C9 C10 C16 -176.3(3) . . . . ?
C9 C10 C11 C12 -108.8(4) . . . . ?
C16 C10 C11 C12 71.7(4) . . . . ?
C1 C2 C12 C11 164.0(3) . . . . ?
C3 C2 C12 C11 64.4(5) . . . . ?
C10 C11 C12 C2 22.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.18
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_mo_csi22_0m
_database_code_depnum_ccdc_archive 'CCDC 1471597'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration unk

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_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.9671(11)
_cell_length_b                   11.2980(12)
_cell_length_c                   12.8986(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1452.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.62
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9531
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15094
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         30.50
_reflns_number_total             4111
_reflns_number_gt                4003
_reflns_threshold_expression     >2sigma(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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0471P)²+0.1830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_number_reflns         4111
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 -0.11933(7) -0.19892(7) 0.57915(5) 0.02296(16) Uani 1 1 d . . .
H1 H -0.1031 -0.2030 0.5153 0.034 Uiso 1 1 calc R . .
O2 O 0.57081(7) 0.22315(7) 0.87184(5) 0.02169(14) Uani 1 1 d . . .
N1 N 0.36370(8) 0.28066(7) 0.79817(6) 0.01579(14) Uani 1 1 d . . .
H1A H 0.3056 0.2998 0.8468 0.019 Uiso 1 1 calc R . .
C1 C 0.00215(9) -0.17709(8) 0.63415(7) 0.01804(17) Uani 1 1 d . . .
H1B H 0.0734 -0.2286 0.6056 0.022 Uiso 1 1 calc R . .
H1C H -0.0109 -0.1991 0.7078 0.022 Uiso 1 1 calc R . .
C2 C 0.04904(8) -0.04847(8) 0.62869(6) 0.01375(15) Uani 1 1 d . . .
C3 C 0.19226(9) -0.03938(7) 0.67784(6) 0.01324(15) Uani 1 1 d . . .
H3 H 0.2206 -0.1122 0.7161 0.016 Uiso 1 1 calc R . .
C4 C 0.22853(9) 0.07627(7) 0.73340(6) 0.01364(15) Uani 1 1 d . . .
H4A H 0.3028 0.0633 0.7831 0.016 Uiso 1 1 calc R . .
H4B H 0.1501 0.1078 0.7716 0.016 Uiso 1 1 calc R . .
C5 C 0.27180(8) 0.16286(7) 0.64667(6) 0.01114(14) Uani 1 1 d . . .
H5 H 0.1882 0.1927 0.6127 0.013 Uiso 1 1 calc R . .
C6 C 0.35288(8) 0.27237(7) 0.68306(6) 0.01260(15) Uani 1 1 d . . .
C7 C 0.49400(9) 0.24849(7) 0.80149(7) 0.01564(16) Uani 1 1 d . . .
C8 C -0.05937(9) 0.03430(9) 0.66899(7) 0.02002(17) Uani 1 1 d . . .
H8A H -0.0741 0.0193 0.7430 0.030 Uiso 1 1 calc R . .
H8B H -0.1429 0.0204 0.6309 0.030 Uiso 1 1 calc R . .
H8C H -0.0309 0.1166 0.6591 0.030 Uiso 1 1 calc R . .
C9 C 0.25390(9) -0.02895(7) 0.56657(6) 0.01294(15) Uani 1 1 d . . .
H9 H 0.3013 -0.1023 0.5434 0.016 Uiso 1 1 calc R . .
C10 C 0.11004(9) -0.01672(8) 0.52101(6) 0.01526(16) Uani 1 1 d . . .
H10A H 0.0895 -0.0754 0.4663 0.018 Uiso 1 1 calc R . .
H10B H 0.0882 0.0644 0.4975 0.018 Uiso 1 1 calc R . .
C11 C 0.34425(8) 0.08136(7) 0.56711(6) 0.01142(14) Uani 1 1 d . . .
C12 C 0.48281(9) 0.04673(8) 0.61080(7) 0.01502(15) Uani 1 1 d . . .
H12A H 0.4704 0.0066 0.6784 0.018 Uiso 1 1 calc R . .
H12B H 0.5260 -0.0102 0.5629 0.018 Uiso 1 1 calc R . .
C13 C 0.57557(9) 0.15353(8) 0.62553(7) 0.01627(16) Uani 1 1 d . . .
H13A H 0.6564 0.1280 0.6641 0.020 Uiso 1 1 calc R . .
H13B H 0.6051 0.1821 0.5566 0.020 Uiso 1 1 calc R . .
C14 C 0.50955(9) 0.25531(7) 0.68361(6) 0.01352(15) Uani 1 1 d . . .
H14 H 0.5542 0.3315 0.6644 0.016 Uiso 1 1 calc R . .
C15 C 0.30389(9) 0.38640(8) 0.63279(7) 0.01751(16) Uani 1 1 d . . .
H15A H 0.3552 0.4535 0.6602 0.026 Uiso 1 1 calc R . .
H15B H 0.2085 0.3975 0.6483 0.026 Uiso 1 1 calc R . .
H15C H 0.3165 0.3816 0.5576 0.026 Uiso 1 1 calc R . .
C16 C 0.35999(9) 0.13598(8) 0.45903(6) 0.01530(16) Uani 1 1 d . . .
H16A H 0.2712 0.1527 0.4299 0.023 Uiso 1 1 calc R . .
H16B H 0.4077 0.0804 0.4138 0.023 Uiso 1 1 calc R . .
H16C H 0.4112 0.2098 0.4643 0.023 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 1.4248(11) . ?
O1 H1 0.8400 . ?
O2 C7 1.2213(12) . ?
N1 C7 1.3492(12) . ?
N1 C6 1.4917(10) . ?
N1 H1A 0.8800 . ?
C1 C2 1.5281(12) . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C2 C8 1.5207(12) . ?
C2 C10 1.5580(11) . ?
C2 C3 1.5653(12) . ?
C3 C4 1.5334(12) . ?
C3 C9 1.5657(11) . ?
C3 H3 1.0000 . ?
C4 C5 1.5474(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5505(11) . ?
C5 C11 1.5564(11) . ?
C5 H5 1.0000 . ?
C6 C15 1.5227(12) . ?
C6 C14 1.5734(12) . ?
C7 C14 1.5302(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.5375(11) . ?
C9 C10 1.5558(12) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.5327(11) . ?
C11 C12 1.5420(12) . ?
C12 C13 1.5320(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5220(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 H1 109.5 . . ?
C7 N1 C6 94.83(7) . . ?
C7 N1 H1A 132.6 . . ?
C6 N1 H1A 132.6 . . ?
O1 C1 C2 113.68(7) . . ?
O1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
O1 C1 H1C 108.8 . . ?
C2 C1 H1C 108.8 . . ?
H1B C1 H1C 107.7 . . ?
C8 C2 C1 110.59(7) . . ?
C8 C2 C10 116.13(7) . . ?
C1 C2 C10 112.30(7) . . ?
C8 C2 C3 117.98(7) . . ?
C1 C2 C3 108.82(7) . . ?
C10 C2 C3 89.43(6) . . ?
C4 C3 C2 117.40(7) . . ?
C4 C3 C9 105.77(6) . . ?
C2 C3 C9 89.51(6) . . ?
C4 C3 H3 113.8 . . ?
C2 C3 H3 113.8 . . ?
C9 C3 H3 113.8 . . ?
C3 C4 C5 105.46(6) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C4 C5 C6 115.53(6) . . ?
C4 C5 C11 103.41(6) . . ?
C6 C5 C11 115.45(7) . . ?
C4 C5 H5 107.3 . . ?
C6 C5 H5 107.3 . . ?
C11 C5 H5 107.3 . . ?
N1 C6 C15 113.19(7) . . ?
N1 C6 C5 112.90(7) . . ?
C15 C6 C5 112.28(7) . . ?
N1 C6 C14 86.07(6) . . ?
C15 C6 C14 115.07(7) . . ?
C5 C6 C14 114.90(7) . . ?
O2 C7 N1 133.64(9) . . ?
O2 C7 C14 133.36(9) . . ?
N1 C7 C14 93.00(7) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C9 C10 118.00(7) . . ?
C11 C9 C3 106.66(6) . . ?
C10 C9 C3 89.50(6) . . ?
C11 C9 H9 113.4 . . ?
C10 C9 H9 113.4 . . ?
C3 C9 H9 113.4 . . ?
C9 C10 C2 90.14(6) . . ?
C9 C10 H10A 113.6 . . ?
C2 C10 H10A 113.6 . . ?
C9 C10 H10B 113.6 . . ?
C2 C10 H10B 113.6 . . ?
H10A C10 H10B 110.9 . . ?
C16 C11 C9 112.47(7) . . ?
C16 C11 C12 110.05(7) . . ?
C9 C11 C12 108.70(7) . . ?
C16 C11 C5 114.14(7) . . ?
C9 C11 C5 102.17(6) . . ?
C12 C11 C5 108.95(6) . . ?
C13 C12 C11 112.71(7) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.28(7) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C7 119.66(7) . . ?
C13 C14 C6 121.29(7) . . ?
C7 C14 C6 84.85(6) . . ?
C13 C14 H14 109.6 . . ?
C7 C14 H14 109.6 . . ?
C6 C14 H14 109.6 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C8 56.88(10) . . . . ?
O1 C1 C2 C10 -74.62(9) . . . . ?
O1 C1 C2 C3 -172.00(7) . . . . ?
C8 C2 C3 C4 -20.96(10) . . . . ?
C1 C2 C3 C4 -147.96(7) . . . . ?
C10 C2 C3 C4 98.61(8) . . . . ?
C8 C2 C3 C9 -128.52(8) . . . . ?
C1 C2 C3 C9 104.48(7) . . . . ?
C10 C2 C3 C9 -8.95(6) . . . . ?
C2 C3 C4 C5 -81.95(8) . . . . ?
C9 C3 C4 C5 15.89(8) . . . . ?
C3 C4 C5 C6 -162.47(7) . . . . ?
C3 C4 C5 C11 -35.35(8) . . . . ?
C7 N1 C6 C15 -124.36(8) . . . . ?
C7 N1 C6 C5 106.68(8) . . . . ?
C7 N1 C6 C14 -8.72(7) . . . . ?
C4 C5 C6 N1 -5.53(10) . . . . ?
C11 C5 C6 N1 -126.32(7) . . . . ?
C4 C5 C6 C15 -134.95(7) . . . . ?
C11 C5 C6 C15 104.25(8) . . . . ?
C4 C5 C6 C14 91.01(8) . . . . ?
C11 C5 C6 C14 -29.78(10) . . . . ?
C6 N1 C7 O2 -170.90(10) . . . . ?
C6 N1 C7 C14 8.96(7) . . . . ?
C4 C3 C9 C11 9.73(9) . . . . ?
C2 C3 C9 C11 128.14(7) . . . . ?
C4 C3 C9 C10 -109.45(7) . . . . ?
C2 C3 C9 C10 8.96(6) . . . . ?
C11 C9 C10 C2 -117.66(7) . . . . ?
C3 C9 C10 C2 -9.00(6) . . . . ?
C8 C2 C10 C9 130.18(7) . . . . ?
C1 C2 C10 C9 -101.16(7) . . . . ?
C3 C2 C10 C9 9.00(6) . . . . ?
C10 C9 C11 C16 -55.31(9) . . . . ?
C3 C9 C11 C16 -153.86(7) . . . . ?
C10 C9 C11 C12 -177.42(7) . . . . ?
C3 C9 C11 C12 84.02(8) . . . . ?
C10 C9 C11 C5 67.51(8) . . . . ?
C3 C9 C11 C5 -31.04(8) . . . . ?
C4 C5 C11 C16 162.34(7) . . . . ?
C6 C5 C11 C16 -70.49(9) . . . . ?
C4 C5 C11 C9 40.67(8) . . . . ?
C6 C5 C11 C9 167.83(7) . . . . ?
C4 C5 C11 C12 -74.22(8) . . . . ?
C6 C5 C11 C12 52.95(9) . . . . ?
C16 C11 C12 C13 62.63(9) . . . . ?
C9 C11 C12 C13 -173.80(7) . . . . ?
C5 C11 C12 C13 -63.22(9) . . . . ?
C11 C12 C13 C14 49.38(10) . . . . ?
C12 C13 C14 C7 77.48(10) . . . . ?
C12 C13 C14 C6 -25.53(11) . . . . ?
O2 C7 C14 C13 48.08(14) . . . . ?
N1 C7 C14 C13 -131.78(8) . . . . ?
O2 C7 C14 C6 171.36(10) . . . . ?
N1 C7 C14 C6 -8.49(6) . . . . ?
N1 C6 C14 C13 129.46(8) . . . . ?
C15 C6 C14 C13 -116.73(9) . . . . ?
C5 C6 C14 C13 16.00(11) . . . . ?
N1 C6 C14 C7 7.69(6) . . . . ?
C15 C6 C14 C7 121.49(7) . . . . ?
C5 C6 C14 C7 -105.77(7) . . . . ?

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
O1 H1 O2 0.84 1.89 2.7311(10) 176.0 4_554
N1 H1A O1 0.88 2.09 2.9138(11) 155.8 3_556

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_150715a
_database_code_depnum_ccdc_archive 'CCDC 1471599'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            CSI15
_chemical_melting_point          212.0-212.2
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_chemical_absolute_configuration unk
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_H-M   P2(1)

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

_cell_length_a                   12.2467(8)
_cell_length_b                   8.0536(4)
_cell_length_c                   29.237(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2990(10)
_cell_angle_gamma                90.00
_cell_volume                     2866.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2419
_cell_measurement_theta_min      3.6340
_cell_measurement_theta_max      68.0320

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_T_max  0.9289
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16603
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.1296
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         66.19
_reflns_number_total             9054
_reflns_number_gt                4844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0141P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.00166(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         9054
_refine_ls_number_parameters     703
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N1 N 0.8587(4) 0.0875(6) 0.91881(16) 0.0455(12) Uani 1 1 d . . .
H1 H 0.9200 0.1197 0.9333 0.055 Uiso 1 1 calc R . .
N2 N 0.9335(3) 0.4558(5) 0.54620(16) 0.0476(12) Uani 1 1 d . . .
H2 H 0.9465 0.3667 0.5315 0.057 Uiso 1 1 calc R . .
N3 N 0.5907(4) 0.7373(6) 0.42645(16) 0.0496(13) Uani 1 1 d . . .
H3 H 0.5353 0.7065 0.4401 0.059 Uiso 1 1 calc R . .
N4 N 0.6014(3) 0.4012(5) 0.03962(15) 0.0451(12) Uani 1 1 d . . .
H4 H 0.5810 0.4924 0.0260 0.054 Uiso 1 1 calc R . .
O1 O 0.8177(3) -0.1248(5) 0.96688(13) 0.0600(11) Uani 1 1 d . . .
O2 O 0.8421(5) 0.6107(5) 0.90092(17) 0.0833(16) Uani 1 1 d . . .
H2A H 0.8351 0.6619 0.9247 0.125 Uiso 1 1 calc R . .
O3 O 1.0158(4) 0.6404(5) 0.50129(15) 0.0622(12) Uani 1 1 d . . .
O4 O 0.6275(4) 0.2021(6) 0.54264(18) 0.0757(15) Uani 1 1 d . . .
H4A H 0.6468 0.1308 0.5252 0.114 Uiso 1 1 calc R . .
O5 O 0.6536(4) 0.9506(5) 0.47461(14) 0.0642(12) Uani 1 1 d . . .
O6 O 0.5957(5) 0.2113(5) 0.40811(18) 0.0936(18) Uani 1 1 d . . .
H6 H 0.6154 0.1555 0.4310 0.140 Uiso 1 1 calc R . .
O7 O 0.4877(3) 0.2229(5) -0.00478(15) 0.0613(12) Uani 1 1 d . . .
O8 O 0.9112(3) 0.6442(5) 0.03739(16) 0.0673(13) Uani 1 1 d . . .
H8 H 0.8893 0.7108 0.0172 0.101 Uiso 1 1 calc R . .
C1 C 0.7930(5) -0.0320(8) 0.9340(2) 0.0465(14) Uani 1 1 d . . .
C2 C 0.6865(5) -0.0318(8) 0.9036(2) 0.0628(18) Uani 1 1 d . . .
H2B H 0.6249 -0.0351 0.9219 0.075 Uiso 1 1 calc R . .
H2C H 0.6819 -0.1267 0.8831 0.075 Uiso 1 1 calc R . .
C3 C 0.6866(5) 0.1333(8) 0.8760(2) 0.0510(15) Uani 1 1 d . . .
C4 C 0.8111(4) 0.1540(7) 0.87432(19) 0.0412(14) Uani 1 1 d . . .
C5 C 0.8387(5) 0.3401(7) 0.8664(2) 0.0477(15) Uani 1 1 d . . .
C6 C 0.8047(6) 0.4410(7) 0.9054(2) 0.0598(18) Uani 1 1 d . . .
H6A H 0.8399 0.3950 0.9343 0.072 Uiso 1 1 calc R . .
C7 C 0.6796(5) 0.4387(8) 0.9066(2) 0.070(2) Uani 1 1 d . . .
H7A H 0.6617 0.4940 0.9343 0.084 Uiso 1 1 calc R . .
H7B H 0.6445 0.4993 0.8804 0.084 Uiso 1 1 calc R . .
C8 C 0.6358(5) 0.2635(8) 0.9058(2) 0.0640(19) Uani 1 1 d . . .
H8A H 0.5577 0.2686 0.8957 0.077 Uiso 1 1 calc R . .
H8B H 0.6435 0.2228 0.9372 0.077 Uiso 1 1 calc R . .
C9 C 0.7763(5) 0.3904(7) 0.8198(2) 0.0563(16) Uani 1 1 d . . .
H9A H 0.8199 0.3563 0.7957 0.068 Uiso 1 1 calc R . .
H9B H 0.7716 0.5106 0.8188 0.068 Uiso 1 1 calc R . .
C10 C 0.6584(5) 0.3191(8) 0.8083(2) 0.0635(19) Uani 1 1 d . . .
H10A H 0.6381 0.3265 0.7754 0.076 Uiso 1 1 calc R . .
H10B H 0.6074 0.3872 0.8232 0.076 Uiso 1 1 calc R . .
C11 C 0.6464(5) 0.1350(8) 0.8237(2) 0.0591(17) Uani 1 1 d . . .
H11 H 0.5704 0.0962 0.8176 0.071 Uiso 1 1 calc R . .
C12 C 0.7277(6) 0.0197(8) 0.8005(2) 0.0611(19) Uani 1 1 d . . .
C13 C 0.8351(5) 0.0399(7) 0.8334(2) 0.0541(17) Uani 1 1 d . . .
H13A H 0.8919 0.0891 0.8171 0.065 Uiso 1 1 calc R . .
H13B H 0.8607 -0.0679 0.8450 0.065 Uiso 1 1 calc R . .
C14 C 0.9625(5) 0.3684(8) 0.8642(2) 0.0659(18) Uani 1 1 d . . .
H14A H 1.0022 0.3410 0.8934 0.099 Uiso 1 1 calc R . .
H14B H 0.9751 0.4828 0.8572 0.099 Uiso 1 1 calc R . .
H14C H 0.9872 0.2991 0.8407 0.099 Uiso 1 1 calc R . .
C15 C 0.6823(6) -0.1592(8) 0.7966(2) 0.084(2) Uani 1 1 d . . .
H15A H 0.6131 -0.1596 0.7776 0.125 Uiso 1 1 calc R . .
H15B H 0.6721 -0.2000 0.8267 0.125 Uiso 1 1 calc R . .
H15C H 0.7333 -0.2293 0.7830 0.125 Uiso 1 1 calc R . .
C16 C 0.7425(7) 0.0703(8) 0.7506(2) 0.090(3) Uani 1 1 d . . .
H16A H 0.7801 0.1748 0.7508 0.134 Uiso 1 1 calc R . .
H16B H 0.6717 0.0803 0.7331 0.134 Uiso 1 1 calc R . .
H16C H 0.7847 -0.0129 0.7369 0.134 Uiso 1 1 calc R . .
C17 C 0.9614(5) 0.6075(7) 0.5329(2) 0.0479(14) Uani 1 1 d . . .
C18 C 0.9150(5) 0.7318(7) 0.5654(2) 0.0550(16) Uani 1 1 d . . .
H18A H 0.8830 0.8270 0.5485 0.066 Uiso 1 1 calc R . .
H18B H 0.9717 0.7699 0.5888 0.066 Uiso 1 1 calc R . .
C19 C 0.8267(5) 0.6311(7) 0.58670(19) 0.0449(14) Uani 1 1 d . . .
C20 C 0.8788(5) 0.4566(7) 0.5881(2) 0.0424(14) Uani 1 1 d . . .
C21 C 0.7892(5) 0.3216(7) 0.5894(2) 0.0455(15) Uani 1 1 d . . .
C22 C 0.7079(5) 0.3380(7) 0.5464(2) 0.0550(17) Uani 1 1 d . . .
H22 H 0.7485 0.3360 0.5193 0.066 Uiso 1 1 calc R . .
C23 C 0.6432(5) 0.4973(8) 0.5461(2) 0.0620(18) Uani 1 1 d . . .
H23A H 0.5964 0.4954 0.5708 0.074 Uiso 1 1 calc R . .
H23B H 0.5966 0.5074 0.5172 0.074 Uiso 1 1 calc R . .
C24 C 0.7217(5) 0.6482(7) 0.5523(2) 0.0576(17) Uani 1 1 d . . .
H24A H 0.6802 0.7420 0.5620 0.069 Uiso 1 1 calc R . .
H24B H 0.7443 0.6755 0.5225 0.069 Uiso 1 1 calc R . .
C25 C 0.9621(5) 0.4620(8) 0.6323(2) 0.0549(16) Uani 1 1 d . . .
H25A H 1.0345 0.4919 0.6246 0.066 Uiso 1 1 calc R . .
H25B H 0.9667 0.3540 0.6471 0.066 Uiso 1 1 calc R . .
C26 C 0.9201(5) 0.5955(8) 0.6656(2) 0.0563(16) Uani 1 1 d . . .
C27 C 0.8113(5) 0.6496(7) 0.6379(2) 0.0524(16) Uani 1 1 d . . .
H27 H 0.7946 0.7652 0.6449 0.063 Uiso 1 1 calc R . .
C28 C 0.7156(5) 0.5358(7) 0.6478(2) 0.0564(17) Uani 1 1 d . . .
H28A H 0.6482 0.5768 0.6312 0.068 Uiso 1 1 calc R . .
H28B H 0.7073 0.5403 0.6804 0.068 Uiso 1 1 calc R . .
C29 C 0.7334(5) 0.3519(7) 0.6338(2) 0.0537(16) Uani 1 1 d . . .
H29A H 0.7774 0.2976 0.6591 0.064 Uiso 1 1 calc R . .
H29B H 0.6624 0.2974 0.6301 0.064 Uiso 1 1 calc R . .
C30 C 0.8393(5) 0.1462(7) 0.5920(2) 0.068(2) Uani 1 1 d . . .
H30A H 0.8729 0.1242 0.5645 0.102 Uiso 1 1 calc R . .
H30B H 0.7825 0.0660 0.5950 0.102 Uiso 1 1 calc R . .
H30C H 0.8936 0.1390 0.6182 0.102 Uiso 1 1 calc R . .
C31 C 0.9097(6) 0.5224(9) 0.7129(2) 0.083(2) Uani 1 1 d . . .
H31A H 0.8618 0.4278 0.7098 0.125 Uiso 1 1 calc R . .
H31B H 0.8799 0.6045 0.7319 0.125 Uiso 1 1 calc R . .
H31C H 0.9809 0.4888 0.7269 0.125 Uiso 1 1 calc R . .
C32 C 1.0009(6) 0.7443(8) 0.6744(2) 0.079(2) Uani 1 1 d . . .
H32A H 1.0726 0.7035 0.6856 0.119 Uiso 1 1 calc R . .
H32B H 0.9752 0.8172 0.6969 0.119 Uiso 1 1 calc R . .
H32C H 1.0048 0.8040 0.6462 0.119 Uiso 1 1 calc R . .
C33 C 0.6637(5) 0.8556(8) 0.4430(2) 0.0491(15) Uani 1 1 d . . .
C34 C 0.7582(5) 0.8513(8) 0.4144(2) 0.0603(17) Uani 1 1 d . . .
H34A H 0.8278 0.8509 0.4338 0.072 Uiso 1 1 calc R . .
H34B H 0.7562 0.9465 0.3940 0.072 Uiso 1 1 calc R . .
C35 C 0.7426(5) 0.6877(8) 0.3864(2) 0.0519(16) Uani 1 1 d . . .
C36 C 0.6171(4) 0.6686(7) 0.3829(2) 0.0442(14) Uani 1 1 d . . .
C37 C 0.5859(5) 0.4845(7) 0.3747(2) 0.0487(15) Uani 1 1 d . . .
C38 C 0.6371(6) 0.3781(8) 0.4147(2) 0.0642(19) Uani 1 1 d . . .
H38 H 0.6157 0.4223 0.4437 0.077 Uiso 1 1 calc R . .
C39 C 0.7614(5) 0.3771(8) 0.4166(2) 0.067(2) Uani 1 1 d . . .
H39A H 0.7828 0.3170 0.3903 0.081 Uiso 1 1 calc R . .
H39B H 0.7923 0.3197 0.4442 0.081 Uiso 1 1 calc R . .
C40 C 0.8080(5) 0.5546(8) 0.4167(2) 0.066(2) Uani 1 1 d . . .
H40A H 0.8811 0.5482 0.4070 0.079 Uiso 1 1 calc R . .
H40B H 0.8160 0.5942 0.4482 0.079 Uiso 1 1 calc R . .
C41 C 0.5760(5) 0.7832(7) 0.3415(2) 0.0499(15) Uani 1 1 d . . .
H41A H 0.5111 0.7356 0.3244 0.060 Uiso 1 1 calc R . .
H41B H 0.5569 0.8918 0.3526 0.060 Uiso 1 1 calc R . .
C42 C 0.6693(6) 0.7994(8) 0.3101(2) 0.0555(17) Uani 1 1 d . . .
C43 C 0.7596(5) 0.6850(8) 0.3343(2) 0.0586(17) Uani 1 1 d . . .
H43 H 0.8332 0.7238 0.3293 0.070 Uiso 1 1 calc R . .
C44 C 0.7409(5) 0.5030(8) 0.3183(2) 0.0640(19) Uani 1 1 d . . .
H44A H 0.7455 0.4969 0.2854 0.077 Uiso 1 1 calc R . .
H44B H 0.7990 0.4343 0.3335 0.077 Uiso 1 1 calc R . .
C45 C 0.6298(5) 0.4333(7) 0.3285(2) 0.0609(18) Uani 1 1 d . . .
H45A H 0.6345 0.3131 0.3279 0.073 Uiso 1 1 calc R . .
H45B H 0.5753 0.4659 0.3035 0.073 Uiso 1 1 calc R . .
C46 C 0.4604(5) 0.4557(8) 0.3702(2) 0.069(2) Uani 1 1 d . . .
H46A H 0.4341 0.4705 0.3997 0.103 Uiso 1 1 calc R . .
H46B H 0.4443 0.3449 0.3594 0.103 Uiso 1 1 calc R . .
H46C H 0.4248 0.5339 0.3487 0.103 Uiso 1 1 calc R . .
C47 C 0.6325(6) 0.7521(8) 0.2596(2) 0.071(2) Uani 1 1 d . . .
H47A H 0.6960 0.7348 0.2437 0.106 Uiso 1 1 calc R . .
H47B H 0.5888 0.8402 0.2450 0.106 Uiso 1 1 calc R . .
H47C H 0.5898 0.6520 0.2588 0.106 Uiso 1 1 calc R . .
C48 C 0.7079(6) 0.9821(8) 0.3061(2) 0.080(2) Uani 1 1 d . . .
H48A H 0.7309 1.0251 0.3363 0.121 Uiso 1 1 calc R . .
H48B H 0.6483 1.0480 0.2918 0.121 Uiso 1 1 calc R . .
H48C H 0.7683 0.9862 0.2878 0.121 Uiso 1 1 calc R . .
C49 C 0.5632(5) 0.2509(7) 0.0261(2) 0.0467(14) Uani 1 1 d . . .
C50 C 0.6270(5) 0.1186(7) 0.0552(2) 0.0579(17) Uani 1 1 d . . .
H50A H 0.6470 0.0269 0.0363 0.069 Uiso 1 1 calc R . .
H50B H 0.5847 0.0764 0.0788 0.069 Uiso 1 1 calc R . .
C51 C 0.7312(4) 0.2142(7) 0.07686(19) 0.0415(14) Uani 1 1 d . . .
C52 C 0.6819(4) 0.3910(7) 0.08047(19) 0.0420(14) Uani 1 1 d . . .
C53 C 0.7741(5) 0.5223(6) 0.0824(2) 0.0415(14) Uani 1 1 d . . .
C54 C 0.8309(5) 0.5106(7) 0.0388(2) 0.0495(15) Uani 1 1 d . . .
H54 H 0.7756 0.5209 0.0120 0.059 Uiso 1 1 calc R . .
C55 C 0.8910(5) 0.3493(8) 0.0356(2) 0.0539(16) Uani 1 1 d . . .
H55A H 0.9523 0.3447 0.0596 0.065 Uiso 1 1 calc R . .
H55B H 0.9201 0.3424 0.0061 0.065 Uiso 1 1 calc R . .
C56 C 0.8147(5) 0.2034(7) 0.0408(2) 0.0531(16) Uani 1 1 d . . .
H56A H 0.8601 0.1062 0.0480 0.064 Uiso 1 1 calc R . .
H56B H 0.7735 0.1838 0.0110 0.064 Uiso 1 1 calc R . .
C57 C 0.6253(5) 0.3805(7) 0.12573(19) 0.0533(16) Uani 1 1 d . . .
H57A H 0.6315 0.4861 0.1418 0.064 Uiso 1 1 calc R . .
H57B H 0.5479 0.3546 0.1186 0.064 Uiso 1 1 calc R . .
C58 C 0.6833(5) 0.2415(8) 0.1566(2) 0.0545(16) Uani 1 1 d . . .
C59 C 0.7752(5) 0.1862(7) 0.12697(19) 0.0483(15) Uani 1 1 d . . .
H59 H 0.7941 0.0691 0.1325 0.058 Uiso 1 1 calc R . .
C60 C 0.8772(5) 0.2978(7) 0.1377(2) 0.0516(16) Uani 1 1 d . . .
H60A H 0.9353 0.2579 0.1205 0.062 Uiso 1 1 calc R . .
H60B H 0.9030 0.2886 0.1702 0.062 Uiso 1 1 calc R . .
C61 C 0.8551(4) 0.4828(7) 0.1259(2) 0.0507(16) Uani 1 1 d . . .
H61A H 0.9250 0.5349 0.1221 0.061 Uiso 1 1 calc R . .
H61B H 0.8271 0.5349 0.1522 0.061 Uiso 1 1 calc R . .
C62 C 0.7275(5) 0.6988(7) 0.0871(2) 0.0600(18) Uani 1 1 d . . .
H62A H 0.6934 0.7063 0.1151 0.090 Uiso 1 1 calc R . .
H62B H 0.6742 0.7217 0.0614 0.090 Uiso 1 1 calc R . .
H62C H 0.7862 0.7783 0.0879 0.090 Uiso 1 1 calc R . .
C63 C 0.6034(5) 0.0941(8) 0.1642(2) 0.078(2) Uani 1 1 d . . .
H63A H 0.5553 0.1259 0.1865 0.117 Uiso 1 1 calc R . .
H63B H 0.6453 -0.0014 0.1752 0.117 Uiso 1 1 calc R . .
H63C H 0.5606 0.0676 0.1357 0.117 Uiso 1 1 calc R . .
C64 C 0.7244(6) 0.3000(8) 0.2049(2) 0.074(2) Uani 1 1 d . . .
H64A H 0.6628 0.3250 0.2214 0.112 Uiso 1 1 calc R . .
H64B H 0.7685 0.3979 0.2031 0.112 Uiso 1 1 calc R . .
H64C H 0.7678 0.2141 0.2207 0.112 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
N1 C1 1.360(7) . ?
N1 C4 1.467(6) . ?
N1 H1 0.8600 . ?
N2 C17 1.338(7) . ?
N2 C20 1.458(6) . ?
N2 H2 0.8600 . ?
N3 C33 1.359(7) . ?
N3 C36 1.456(6) . ?
N3 H3 0.8600 . ?
N4 C49 1.342(6) . ?
N4 C52 1.465(6) . ?
N4 H4 0.8600 . ?
O1 C1 1.229(6) . ?
O2 C6 1.452(7) . ?
O2 H2A 0.8200 . ?
O3 C17 1.227(6) . ?
O4 C22 1.468(7) . ?
O4 H4A 0.8200 . ?
O5 C33 1.217(6) . ?
O6 C38 1.441(7) . ?
O6 H6 0.8200 . ?
O7 C49 1.239(6) . ?
O8 C54 1.461(6) . ?
O8 H8 0.8200 . ?
C1 C2 1.496(7) . ?
C2 C3 1.557(8) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 C8 1.539(8) . ?
C3 C4 1.540(7) . ?
C3 C11 1.553(8) . ?
C4 C5 1.559(7) . ?
C4 C13 1.561(7) . ?
C5 C6 1.495(8) . ?
C5 C14 1.541(7) . ?
C5 C9 1.542(7) . ?
C6 C7 1.537(8) . ?
C6 H6A 0.9800 . ?
C7 C8 1.508(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.556(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.561(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.569(9) . ?
C11 H11 0.9800 . ?
C12 C16 1.543(8) . ?
C12 C15 1.544(8) . ?
C12 C13 1.552(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.530(7) . ?
C18 C19 1.538(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C27 1.538(7) . ?
C19 C20 1.542(7) . ?
C19 C24 1.549(8) . ?
C20 C21 1.549(7) . ?
C20 C25 1.558(7) . ?
C21 C22 1.521(8) . ?
C21 C30 1.538(7) . ?
C21 C29 1.550(7) . ?
C22 C23 1.507(7) . ?
C22 H22 0.9800 . ?
C23 C24 1.548(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.574(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C31 1.521(8) . ?
C26 C27 1.544(8) . ?
C26 C32 1.558(8) . ?
C27 C28 1.539(7) . ?
C27 H27 0.9800 . ?
C28 C29 1.559(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.501(7) . ?
C34 C35 1.551(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.537(7) . ?
C35 C40 1.555(8) . ?
C35 C43 1.560(7) . ?
C36 C37 1.543(7) . ?
C36 C41 1.562(7) . ?
C37 C38 1.528(7) . ?
C37 C46 1.546(7) . ?
C37 C45 1.563(7) . ?
C38 C39 1.518(8) . ?
C38 H38 0.9800 . ?
C39 C40 1.539(8) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.548(8) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C47 1.542(8) . ?
C42 C43 1.549(8) . ?
C42 C48 1.554(8) . ?
C43 C44 1.549(8) . ?
C43 H43 0.9800 . ?
C44 C45 1.531(8) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.524(8) . ?
C50 C51 1.564(7) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C59 1.521(7) . ?
C51 C56 1.550(7) . ?
C51 C52 1.555(7) . ?
C52 C53 1.543(7) . ?
C52 C57 1.563(7) . ?
C53 C54 1.523(8) . ?
C53 C62 1.544(7) . ?
C53 C61 1.557(7) . ?
C54 C55 1.501(7) . ?
C54 H54 0.9800 . ?
C55 C56 1.519(7) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C57 C58 1.559(7) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 C64 1.522(8) . ?
C58 C59 1.558(8) . ?
C58 C63 1.571(7) . ?
C59 C60 1.544(7) . ?
C59 H59 0.9800 . ?
C60 C61 1.546(7) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?

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 N1 C4 110.9(5) . . ?
C1 N1 H1 124.6 . . ?
C4 N1 H1 124.6 . . ?
C17 N2 C20 113.2(5) . . ?
C17 N2 H2 123.4 . . ?
C20 N2 H2 123.4 . . ?
C33 N3 C36 112.1(5) . . ?
C33 N3 H3 123.9 . . ?
C36 N3 H3 123.9 . . ?
C49 N4 C52 111.8(4) . . ?
C49 N4 H4 124.1 . . ?
C52 N4 H4 124.1 . . ?
C6 O2 H2A 109.5 . . ?
C22 O4 H4A 109.5 . . ?
C38 O6 H6 109.5 . . ?
C54 O8 H8 109.5 . . ?
O1 C1 N1 125.6(5) . . ?
O1 C1 C2 126.0(5) . . ?
N1 C1 C2 108.3(5) . . ?
C1 C2 C3 105.0(5) . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2C 110.8 . . ?
C3 C2 H2C 110.8 . . ?
H2B C2 H2C 108.8 . . ?
C8 C3 C4 114.1(5) . . ?
C8 C3 C11 116.6(5) . . ?
C4 C3 C11 100.2(5) . . ?
C8 C3 C2 105.3(5) . . ?
C4 C3 C2 99.6(5) . . ?
C11 C3 C2 120.0(5) . . ?
N1 C4 C3 103.4(4) . . ?
N1 C4 C5 114.3(5) . . ?
C3 C4 C5 109.9(5) . . ?
N1 C4 C13 112.0(4) . . ?
C3 C4 C13 103.3(5) . . ?
C5 C4 C13 113.0(5) . . ?
C6 C5 C14 108.0(5) . . ?
C6 C5 C9 112.2(5) . . ?
C14 C5 C9 108.6(5) . . ?
C6 C5 C4 109.1(5) . . ?
C14 C5 C4 112.2(5) . . ?
C9 C5 C4 106.8(5) . . ?
O2 C6 C5 109.0(5) . . ?
O2 C6 C7 109.8(5) . . ?
C5 C6 C7 112.0(6) . . ?
O2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C8 C7 C6 111.4(5) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C3 118.8(5) . . ?
C7 C8 H8A 107.6 . . ?
C3 C8 H8A 107.6 . . ?
C7 C8 H8B 107.6 . . ?
C3 C8 H8B 107.6 . . ?
H8A C8 H8B 107.0 . . ?
C5 C9 C10 116.9(5) . . ?
C5 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C5 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 113.8(5) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C3 C11 C10 105.2(5) . . ?
C3 C11 C12 105.8(5) . . ?
C10 C11 C12 110.7(5) . . ?
C3 C11 H11 111.6 . . ?
C10 C11 H11 111.6 . . ?
C12 C11 H11 111.6 . . ?
C16 C12 C15 104.8(5) . . ?
C16 C12 C13 112.3(6) . . ?
C15 C12 C13 114.7(5) . . ?
C16 C12 C11 113.5(5) . . ?
C15 C12 C11 110.1(6) . . ?
C13 C12 C11 101.8(5) . . ?
C12 C13 C4 108.6(5) . . ?
C12 C13 H13A 110.0 . . ?
C4 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C4 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N2 126.3(6) . . ?
O3 C17 C18 126.5(6) . . ?
N2 C17 C18 107.1(5) . . ?
C17 C18 C19 103.4(5) . . ?
C17 C18 H18A 111.1 . . ?
C19 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
C19 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C27 C19 C18 120.8(5) . . ?
C27 C19 C20 99.1(4) . . ?
C18 C19 C20 100.6(4) . . ?
C27 C19 C24 116.2(5) . . ?
C18 C19 C24 105.1(5) . . ?
C20 C19 C24 114.2(5) . . ?
N2 C20 C19 102.1(4) . . ?
N2 C20 C21 114.2(5) . . ?
C19 C20 C21 110.4(4) . . ?
N2 C20 C25 112.2(5) . . ?
C19 C20 C25 103.1(5) . . ?
C21 C20 C25 113.6(5) . . ?
C22 C21 C30 110.0(5) . . ?
C22 C21 C20 108.6(5) . . ?
C30 C21 C20 111.5(5) . . ?
C22 C21 C29 111.7(5) . . ?
C30 C21 C29 108.2(5) . . ?
C20 C21 C29 106.8(5) . . ?
O4 C22 C23 106.7(5) . . ?
O4 C22 C21 111.7(5) . . ?
C23 C22 C21 112.0(5) . . ?
O4 C22 H22 108.8 . . ?
C23 C22 H22 108.8 . . ?
C21 C22 H22 108.8 . . ?
C22 C23 C24 110.4(5) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 C19 117.9(5) . . ?
C23 C24 H24A 107.8 . . ?
C19 C24 H24A 107.8 . . ?
C23 C24 H24B 107.8 . . ?
C19 C24 H24B 107.8 . . ?
H24A C24 H24B 107.2 . . ?
C20 C25 C26 107.7(5) . . ?
C20 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 . . ?
C20 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C31 C26 C27 115.6(6) . . ?
C31 C26 C32 105.2(5) . . ?
C27 C26 C32 111.5(5) . . ?
C31 C26 C25 111.3(5) . . ?
C27 C26 C25 101.0(5) . . ?
C32 C26 C25 112.5(5) . . ?
C19 C27 C28 107.7(5) . . ?
C19 C27 C26 107.0(5) . . ?
C28 C27 C26 111.4(5) . . ?
C19 C27 H27 110.3 . . ?
C28 C27 H27 110.3 . . ?
C26 C27 H27 110.3 . . ?
C27 C28 C29 112.6(5) . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C21 C29 C28 117.2(5) . . ?
C21 C29 H29A 108.0 . . ?
C28 C29 H29A 108.0 . . ?
C21 C29 H29B 108.0 . . ?
C28 C29 H29B 108.0 . . ?
H29A C29 H29B 107.2 . . ?
C21 C30 H30A 109.5 . . ?
C21 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C21 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C26 C31 H31A 109.5 . . ?
C26 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C26 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O5 C33 N3 126.4(6) . . ?
O5 C33 C34 125.9(6) . . ?
N3 C33 C34 107.6(5) . . ?
C33 C34 C35 104.8(5) . . ?
C33 C34 H34A 110.8 . . ?
C35 C34 H34A 110.8 . . ?
C33 C34 H34B 110.8 . . ?
C35 C34 H34B 110.8 . . ?
H34A C34 H34B 108.9 . . ?
C36 C35 C34 100.7(5) . . ?
C36 C35 C40 114.7(5) . . ?
C34 C35 C40 105.1(5) . . ?
C36 C35 C43 99.9(5) . . ?
C34 C35 C43 120.3(5) . . ?
C40 C35 C43 115.5(5) . . ?
N3 C36 C35 102.7(4) . . ?
N3 C36 C37 115.2(5) . . ?
C35 C36 C37 109.6(5) . . ?
N3 C36 C41 111.7(4) . . ?
C35 C36 C41 103.2(5) . . ?
C37 C36 C41 113.2(5) . . ?
C38 C37 C36 110.2(5) . . ?
C38 C37 C46 107.5(5) . . ?
C36 C37 C46 112.6(5) . . ?
C38 C37 C45 111.3(5) . . ?
C36 C37 C45 106.6(5) . . ?
C46 C37 C45 108.7(5) . . ?
O6 C38 C39 109.6(5) . . ?
O6 C38 C37 108.1(5) . . ?
C39 C38 C37 110.9(5) . . ?
O6 C38 H38 109.4 . . ?
C39 C38 H38 109.4 . . ?
C37 C38 H38 109.4 . . ?
C38 C39 C40 111.4(5) . . ?
C38 C39 H39A 109.3 . . ?
C40 C39 H39A 109.3 . . ?
C38 C39 H39B 109.3 . . ?
C40 C39 H39B 109.3 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 C35 118.2(5) . . ?
C39 C40 H40A 107.8 . . ?
C35 C40 H40A 107.8 . . ?
C39 C40 H40B 107.8 . . ?
C35 C40 H40B 107.8 . . ?
H40A C40 H40B 107.1 . . ?
C42 C41 C36 108.2(5) . . ?
C42 C41 H41A 110.1 . . ?
C36 C41 H41A 110.1 . . ?
C42 C41 H41B 110.1 . . ?
C36 C41 H41B 110.1 . . ?
H41A C41 H41B 108.4 . . ?
C47 C42 C41 112.9(6) . . ?
C47 C42 C43 114.2(5) . . ?
C41 C42 C43 102.4(5) . . ?
C47 C42 C48 102.8(5) . . ?
C41 C42 C48 112.0(5) . . ?
C43 C42 C48 112.9(6) . . ?
C44 C43 C42 110.5(5) . . ?
C44 C43 C35 106.1(5) . . ?
C42 C43 C35 105.9(5) . . ?
C44 C43 H43 111.4 . . ?
C42 C43 H43 111.4 . . ?
C35 C43 H43 111.4 . . ?
C45 C44 C43 113.2(5) . . ?
C45 C44 H44A 108.9 . . ?
C43 C44 H44A 108.9 . . ?
C45 C44 H44B 108.9 . . ?
C43 C44 H44B 108.9 . . ?
H44A C44 H44B 107.8 . . ?
C44 C45 C37 118.0(5) . . ?
C44 C45 H45A 107.8 . . ?
C37 C45 H45A 107.8 . . ?
C44 C45 H45B 107.8 . . ?
C37 C45 H45B 107.8 . . ?
H45A C45 H45B 107.2 . . ?
C37 C46 H46A 109.5 . . ?
C37 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C37 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C42 C47 H47A 109.5 . . ?
C42 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C42 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C42 C48 H48A 109.5 . . ?
C42 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C42 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O7 C49 N4 125.9(6) . . ?
O7 C49 C50 125.1(5) . . ?
N4 C49 C50 109.0(5) . . ?
C49 C50 C51 103.2(5) . . ?
C49 C50 H50A 111.1 . . ?
C51 C50 H50A 111.1 . . ?
C49 C50 H50B 111.1 . . ?
C51 C50 H50B 111.1 . . ?
H50A C50 H50B 109.1 . . ?
C59 C51 C56 117.2(5) . . ?
C59 C51 C52 99.8(4) . . ?
C56 C51 C52 112.8(5) . . ?
C59 C51 C50 120.3(5) . . ?
C56 C51 C50 105.5(5) . . ?
C52 C51 C50 99.9(4) . . ?
N4 C52 C53 114.6(5) . . ?
N4 C52 C51 103.2(4) . . ?
C53 C52 C51 110.0(4) . . ?
N4 C52 C57 111.8(5) . . ?
C53 C52 C57 113.4(4) . . ?
C51 C52 C57 102.7(4) . . ?
C54 C53 C52 109.0(5) . . ?
C54 C53 C62 109.8(5) . . ?
C52 C53 C62 111.0(5) . . ?
C54 C53 C61 111.3(5) . . ?
C52 C53 C61 106.8(4) . . ?
C62 C53 C61 108.9(5) . . ?
O8 C54 C55 107.4(5) . . ?
O8 C54 C53 110.4(5) . . ?
C55 C54 C53 112.1(5) . . ?
O8 C54 H54 108.9 . . ?
C55 C54 H54 108.9 . . ?
C53 C54 H54 108.9 . . ?
C54 C55 C56 110.6(5) . . ?
C54 C55 H55A 109.5 . . ?
C56 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
C56 C55 H55B 109.5 . . ?
H55A C55 H55B 108.1 . . ?
C55 C56 C51 118.9(5) . . ?
C55 C56 H56A 107.6 . . ?
C51 C56 H56A 107.6 . . ?
C55 C56 H56B 107.6 . . ?
C51 C56 H56B 107.6 . . ?
H56A C56 H56B 107.0 . . ?
C58 C57 C52 108.2(5) . . ?
C58 C57 H57A 110.1 . . ?
C52 C57 H57A 110.1 . . ?
C58 C57 H57B 110.1 . . ?
C52 C57 H57B 110.1 . . ?
H57A C57 H57B 108.4 . . ?
C64 C58 C59 114.8(5) . . ?
C64 C58 C57 113.5(5) . . ?
C59 C58 C57 101.2(5) . . ?
C64 C58 C63 104.5(5) . . ?
C59 C58 C63 111.2(5) . . ?
C57 C58 C63 111.9(5) . . ?
C51 C59 C60 107.6(5) . . ?
C51 C59 C58 107.0(5) . . ?
C60 C59 C58 109.7(5) . . ?
C51 C59 H59 110.8 . . ?
C60 C59 H59 110.8 . . ?
C58 C59 H59 110.8 . . ?
C59 C60 C61 113.4(5) . . ?
C59 C60 H60A 108.9 . . ?
C61 C60 H60A 108.9 . . ?
C59 C60 H60B 108.9 . . ?
C61 C60 H60B 108.9 . . ?
H60A C60 H60B 107.7 . . ?
C60 C61 C53 117.4(5) . . ?
C60 C61 H61A 108.0 . . ?
C53 C61 H61A 108.0 . . ?
C60 C61 H61B 108.0 . . ?
C53 C61 H61B 108.0 . . ?
H61A C61 H61B 107.2 . . ?
C53 C62 H62A 109.5 . . ?
C53 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C53 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C58 C63 H63A 109.5 . . ?
C58 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C58 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C58 C64 H64A 109.5 . . ?
C58 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C58 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 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
C4 N1 C1 O1 169.9(6) . . . . ?
C4 N1 C1 C2 -9.6(7) . . . . ?
O1 C1 C2 C3 166.6(6) . . . . ?
N1 C1 C2 C3 -13.9(7) . . . . ?
C1 C2 C3 C8 -88.6(6) . . . . ?
C1 C2 C3 C4 29.7(6) . . . . ?
C1 C2 C3 C11 137.5(6) . . . . ?
C1 N1 C4 C3 29.3(6) . . . . ?
C1 N1 C4 C5 148.7(5) . . . . ?
C1 N1 C4 C13 -81.3(6) . . . . ?
C8 C3 C4 N1 76.9(6) . . . . ?
C11 C3 C4 N1 -157.8(5) . . . . ?
C2 C3 C4 N1 -34.7(5) . . . . ?
C8 C3 C4 C5 -45.5(7) . . . . ?
C11 C3 C4 C5 79.8(6) . . . . ?
C2 C3 C4 C5 -157.1(5) . . . . ?
C8 C3 C4 C13 -166.3(5) . . . . ?
C11 C3 C4 C13 -41.0(5) . . . . ?
C2 C3 C4 C13 82.1(5) . . . . ?
N1 C4 C5 C6 -55.0(6) . . . . ?
C3 C4 C5 C6 60.6(6) . . . . ?
C13 C4 C5 C6 175.4(5) . . . . ?
N1 C4 C5 C14 64.7(6) . . . . ?
C3 C4 C5 C14 -179.7(5) . . . . ?
C13 C4 C5 C14 -64.9(6) . . . . ?
N1 C4 C5 C9 -176.5(5) . . . . ?
C3 C4 C5 C9 -60.8(6) . . . . ?
C13 C4 C5 C9 54.0(6) . . . . ?
C14 C5 C6 O2 51.0(7) . . . . ?
C9 C5 C6 O2 -68.6(7) . . . . ?
C4 C5 C6 O2 173.3(5) . . . . ?
C14 C5 C6 C7 172.7(5) . . . . ?
C9 C5 C6 C7 53.1(7) . . . . ?
C4 C5 C6 C7 -65.0(7) . . . . ?
O2 C6 C7 C8 173.5(5) . . . . ?
C5 C6 C7 C8 52.2(8) . . . . ?
C6 C7 C8 C3 -37.5(9) . . . . ?
C4 C3 C8 C7 35.9(8) . . . . ?
C11 C3 C8 C7 -80.2(8) . . . . ?
C2 C3 C8 C7 144.0(6) . . . . ?
C6 C5 C9 C10 -80.5(7) . . . . ?
C14 C5 C9 C10 160.1(5) . . . . ?
C4 C5 C9 C10 38.9(7) . . . . ?
C5 C9 C10 C11 -39.2(8) . . . . ?
C8 C3 C11 C10 50.9(7) . . . . ?
C4 C3 C11 C10 -72.7(6) . . . . ?
C2 C3 C11 C10 179.9(5) . . . . ?
C8 C3 C11 C12 168.1(5) . . . . ?
C4 C3 C11 C12 44.5(6) . . . . ?
C2 C3 C11 C12 -62.9(7) . . . . ?
C9 C10 C11 C3 55.5(7) . . . . ?
C9 C10 C11 C12 -58.4(7) . . . . ?
C3 C11 C12 C16 -150.2(6) . . . . ?
C10 C11 C12 C16 -36.7(8) . . . . ?
C3 C11 C12 C15 92.8(6) . . . . ?
C10 C11 C12 C15 -153.8(5) . . . . ?
C3 C11 C12 C13 -29.3(6) . . . . ?
C10 C11 C12 C13 84.2(6) . . . . ?
C16 C12 C13 C4 124.6(5) . . . . ?
C15 C12 C13 C4 -115.9(6) . . . . ?
C11 C12 C13 C4 2.9(6) . . . . ?
N1 C4 C13 C12 134.9(5) . . . . ?
C3 C4 C13 C12 24.3(6) . . . . ?
C5 C4 C13 C12 -94.4(6) . . . . ?
C20 N2 C17 O3 173.7(6) . . . . ?
C20 N2 C17 C18 -5.0(7) . . . . ?
O3 C17 C18 C19 162.6(6) . . . . ?
N2 C17 C18 C19 -18.6(6) . . . . ?
C17 C18 C19 C27 140.2(5) . . . . ?
C17 C18 C19 C20 32.8(6) . . . . ?
C17 C18 C19 C24 -86.0(5) . . . . ?
C17 N2 C20 C19 26.4(6) . . . . ?
C17 N2 C20 C21 145.6(5) . . . . ?
C17 N2 C20 C25 -83.3(6) . . . . ?
C27 C19 C20 N2 -159.1(5) . . . . ?
C18 C19 C20 N2 -35.2(6) . . . . ?
C24 C19 C20 N2 76.8(6) . . . . ?
C27 C19 C20 C21 79.1(5) . . . . ?
C18 C19 C20 C21 -157.1(5) . . . . ?
C24 C19 C20 C21 -45.1(6) . . . . ?
C27 C19 C20 C25 -42.6(5) . . . . ?
C18 C19 C20 C25 81.3(5) . . . . ?
C24 C19 C20 C25 -166.7(5) . . . . ?
N2 C20 C21 C22 -54.3(6) . . . . ?
C19 C20 C21 C22 60.1(6) . . . . ?
C25 C20 C21 C22 175.3(5) . . . . ?
N2 C20 C21 C30 67.1(6) . . . . ?
C19 C20 C21 C30 -178.5(5) . . . . ?
C25 C20 C21 C30 -63.3(6) . . . . ?
N2 C20 C21 C29 -174.9(5) . . . . ?
C19 C20 C21 C29 -60.5(6) . . . . ?
C25 C20 C21 C29 54.7(6) . . . . ?
C30 C21 C22 O4 51.2(6) . . . . ?
C20 C21 C22 O4 173.5(4) . . . . ?
C29 C21 C22 O4 -69.0(6) . . . . ?
C30 C21 C22 C23 170.8(5) . . . . ?
C20 C21 C22 C23 -67.0(6) . . . . ?
C29 C21 C22 C23 50.6(7) . . . . ?
O4 C22 C23 C24 177.3(5) . . . . ?
C21 C22 C23 C24 54.8(7) . . . . ?
C22 C23 C24 C19 -39.4(7) . . . . ?
C27 C19 C24 C23 -78.6(7) . . . . ?
C18 C19 C24 C23 145.1(5) . . . . ?
C20 C19 C24 C23 35.8(7) . . . . ?
N2 C20 C25 C26 134.5(5) . . . . ?
C19 C20 C25 C26 25.4(6) . . . . ?
C21 C20 C25 C26 -94.0(6) . . . . ?
C20 C25 C26 C31 126.0(6) . . . . ?
C20 C25 C26 C27 2.7(6) . . . . ?
C20 C25 C26 C32 -116.2(6) . . . . ?
C18 C19 C27 C28 178.7(5) . . . . ?
C20 C19 C27 C28 -73.1(5) . . . . ?
C24 C19 C27 C28 49.7(7) . . . . ?
C18 C19 C27 C26 -61.5(7) . . . . ?
C20 C19 C27 C26 46.7(6) . . . . ?
C24 C19 C27 C26 169.5(5) . . . . ?
C31 C26 C27 C19 -150.9(5) . . . . ?
C32 C26 C27 C19 89.0(6) . . . . ?
C25 C26 C27 C19 -30.7(6) . . . . ?
C31 C26 C27 C28 -33.5(7) . . . . ?
C32 C26 C27 C28 -153.6(5) . . . . ?
C25 C26 C27 C28 86.7(6) . . . . ?
C19 C27 C28 C29 55.3(7) . . . . ?
C26 C27 C28 C29 -61.7(7) . . . . ?
C22 C21 C29 C28 -80.8(7) . . . . ?
C30 C21 C29 C28 157.9(6) . . . . ?
C20 C21 C29 C28 37.8(7) . . . . ?
C27 C28 C29 C21 -37.2(8) . . . . ?
C36 N3 C33 O5 168.4(6) . . . . ?
C36 N3 C33 C34 -10.2(7) . . . . ?
O5 C33 C34 C35 168.7(6) . . . . ?
N3 C33 C34 C35 -12.7(7) . . . . ?
C33 C34 C35 C36 28.6(6) . . . . ?
C33 C34 C35 C40 -90.8(6) . . . . ?
C33 C34 C35 C43 136.9(5) . . . . ?
C33 N3 C36 C35 28.9(6) . . . . ?
C33 N3 C36 C37 148.0(5) . . . . ?
C33 N3 C36 C41 -81.1(6) . . . . ?
C34 C35 C36 N3 -33.7(6) . . . . ?
C40 C35 C36 N3 78.5(6) . . . . ?
C43 C35 C36 N3 -157.4(4) . . . . ?
C34 C35 C36 C37 -156.7(5) . . . . ?
C40 C35 C36 C37 -44.5(7) . . . . ?
C43 C35 C36 C37 79.7(6) . . . . ?
C34 C35 C36 C41 82.5(5) . . . . ?
C40 C35 C36 C41 -165.3(5) . . . . ?
C43 C35 C36 C41 -41.2(6) . . . . ?
N3 C36 C37 C38 -54.6(7) . . . . ?
C35 C36 C37 C38 60.6(7) . . . . ?
C41 C36 C37 C38 175.2(5) . . . . ?
N3 C36 C37 C46 65.5(6) . . . . ?
C35 C36 C37 C46 -179.3(5) . . . . ?
C41 C36 C37 C46 -64.8(6) . . . . ?
N3 C36 C37 C45 -175.5(5) . . . . ?
C35 C36 C37 C45 -60.2(6) . . . . ?
C41 C36 C37 C45 54.3(6) . . . . ?
C36 C37 C38 O6 173.6(5) . . . . ?
C46 C37 C38 O6 50.5(7) . . . . ?
C45 C37 C38 O6 -68.4(7) . . . . ?
C36 C37 C38 C39 -66.2(7) . . . . ?
C46 C37 C38 C39 170.7(5) . . . . ?
C45 C37 C38 C39 51.9(7) . . . . ?
O6 C38 C39 C40 171.8(5) . . . . ?
C37 C38 C39 C40 52.5(7) . . . . ?
C38 C39 C40 C35 -37.7(8) . . . . ?
C36 C35 C40 C39 34.7(8) . . . . ?
C34 C35 C40 C39 144.2(6) . . . . ?
C43 C35 C40 C39 -80.7(7) . . . . ?
N3 C36 C41 C42 134.7(5) . . . . ?
C35 C36 C41 C42 25.0(6) . . . . ?
C37 C36 C41 C42 -93.4(6) . . . . ?
C36 C41 C42 C47 125.6(5) . . . . ?
C36 C41 C42 C43 2.4(6) . . . . ?
C36 C41 C42 C48 -118.9(6) . . . . ?
C47 C42 C43 C44 -36.8(8) . . . . ?
C41 C42 C43 C44 85.6(6) . . . . ?
C48 C42 C43 C44 -153.7(5) . . . . ?
C47 C42 C43 C35 -151.3(5) . . . . ?
C41 C42 C43 C35 -28.8(6) . . . . ?
C48 C42 C43 C35 91.8(6) . . . . ?
C36 C35 C43 C44 -73.0(6) . . . . ?
C34 C35 C43 C44 178.3(5) . . . . ?
C40 C35 C43 C44 50.6(7) . . . . ?
C36 C35 C43 C42 44.5(6) . . . . ?
C34 C35 C43 C42 -64.2(7) . . . . ?
C40 C35 C43 C42 168.0(5) . . . . ?
C42 C43 C44 C45 -59.6(7) . . . . ?
C35 C43 C44 C45 54.7(7) . . . . ?
C43 C44 C45 C37 -37.7(8) . . . . ?
C38 C37 C45 C44 -82.1(7) . . . . ?
C36 C37 C45 C44 38.1(7) . . . . ?
C46 C37 C45 C44 159.7(5) . . . . ?
C52 N4 C49 O7 173.3(6) . . . . ?
C52 N4 C49 C50 -6.2(7) . . . . ?
O7 C49 C50 C51 163.5(6) . . . . ?
N4 C49 C50 C51 -17.0(7) . . . . ?
C49 C50 C51 C59 138.7(5) . . . . ?
C49 C50 C51 C56 -86.0(5) . . . . ?
C49 C50 C51 C52 31.1(6) . . . . ?
C49 N4 C52 C53 146.5(5) . . . . ?
C49 N4 C52 C51 27.0(6) . . . . ?
C49 N4 C52 C57 -82.7(6) . . . . ?
C59 C51 C52 N4 -158.0(4) . . . . ?
C56 C51 C52 N4 76.9(5) . . . . ?
C50 C51 C52 N4 -34.7(5) . . . . ?
C59 C51 C52 C53 79.3(5) . . . . ?
C56 C51 C52 C53 -45.8(6) . . . . ?
C50 C51 C52 C53 -157.4(5) . . . . ?
C59 C51 C52 C57 -41.7(5) . . . . ?
C56 C51 C52 C57 -166.8(5) . . . . ?
C50 C51 C52 C57 81.6(5) . . . . ?
N4 C52 C53 C54 -55.5(6) . . . . ?
C51 C52 C53 C54 60.2(6) . . . . ?
C57 C52 C53 C54 174.5(5) . . . . ?
N4 C52 C53 C62 65.6(6) . . . . ?
C51 C52 C53 C62 -178.7(5) . . . . ?
C57 C52 C53 C62 -64.4(6) . . . . ?
N4 C52 C53 C61 -175.8(5) . . . . ?
C51 C52 C53 C61 -60.1(6) . . . . ?
C57 C52 C53 C61 54.2(6) . . . . ?
C52 C53 C54 O8 174.3(4) . . . . ?
C62 C53 C54 O8 52.5(6) . . . . ?
C61 C53 C54 O8 -68.2(6) . . . . ?
C52 C53 C54 C55 -66.0(6) . . . . ?
C62 C53 C54 C55 172.2(5) . . . . ?
C61 C53 C54 C55 51.5(6) . . . . ?
O8 C54 C55 C56 175.3(5) . . . . ?
C53 C54 C55 C56 53.9(6) . . . . ?
C54 C55 C56 C51 -40.3(7) . . . . ?
C59 C51 C56 C55 -77.6(7) . . . . ?
C52 C51 C56 C55 37.4(7) . . . . ?
C50 C51 C56 C55 145.5(5) . . . . ?
N4 C52 C57 C58 134.6(5) . . . . ?
C53 C52 C57 C58 -94.0(6) . . . . ?
C51 C52 C57 C58 24.6(6) . . . . ?
C52 C57 C58 C64 126.0(6) . . . . ?
C52 C57 C58 C59 2.5(6) . . . . ?
C52 C57 C58 C63 -116.0(6) . . . . ?
C56 C51 C59 C60 49.8(6) . . . . ?
C52 C51 C59 C60 -72.2(5) . . . . ?
C50 C51 C59 C60 -179.9(5) . . . . ?
C56 C51 C59 C58 167.7(5) . . . . ?
C52 C51 C59 C58 45.7(5) . . . . ?
C50 C51 C59 C58 -62.0(7) . . . . ?
C64 C58 C59 C51 -152.7(5) . . . . ?
C57 C58 C59 C51 -30.1(6) . . . . ?
C63 C58 C59 C51 88.9(6) . . . . ?
C64 C58 C59 C60 -36.2(7) . . . . ?
C57 C58 C59 C60 86.4(5) . . . . ?
C63 C58 C59 C60 -154.6(5) . . . . ?
C51 C59 C60 C61 54.0(7) . . . . ?
C58 C59 C60 C61 -62.1(6) . . . . ?
C59 C60 C61 C53 -36.0(8) . . . . ?
C54 C53 C61 C60 -81.4(6) . . . . ?
C52 C53 C61 C60 37.4(7) . . . . ?
C62 C53 C61 C60 157.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        66.19
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
