# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_d8v17030
_database_code_depnum_ccdc_archive 'CCDC 1569086'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_audit_creation_date             2017-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H23 N O2'
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.36
_chemical_absolute_configuration rmad
_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 0.0033 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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.1907(5)
_cell_length_b                   24.8299(16)
_cell_length_c                   7.3077(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1486.20(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2388
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      28.143
_cell_measurement_theta_min      2.619
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.2474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1825 before and 0.0981 after correction. The Ratio of minimum to maximum transmission is 0.3317. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.1128
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6521
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.500
_diffrn_ambient_temperature      301.83
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                1942
_reflns_number_total             2769
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0859
_refine_ls_restrained_S_all      1.027
_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)+(0.1197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C11 \\sim O1' \\sim O1: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
C15 \\sim O2' \\sim O2: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
3. Others
 Fixed Sof: O1(0.5) O2(0.5) O1'(0.5) O2'(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C)
;
_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 0.2247(5) 0.78192(15) 0.6575(6) 0.0351(10) Uani 1 1 d . . . . .
C1 C 0.1269(7) 0.7368(2) 0.9394(8) 0.0471(15) Uani 1 1 d . . . . .
H1A H 0.182044 0.763956 1.009454 0.071 Uiso 1 1 calc GR . . . .
H1B H 0.141346 0.702370 0.997133 0.071 Uiso 1 1 calc GR . . . .
H1C H 0.012638 0.745102 0.932880 0.071 Uiso 1 1 calc GR . . . .
C2 C 0.1968(6) 0.7350(2) 0.7502(8) 0.0383(13) Uani 1 1 d . . . . .
C3 C 0.2334(6) 0.6864(2) 0.6699(8) 0.0376(12) Uani 1 1 d . . . . .
H3 H 0.214558 0.655038 0.735984 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2983(6) 0.68211(19) 0.4917(7) 0.0352(12) Uani 1 1 d . . . . .
C5 C 0.3380(7) 0.7324(2) 0.4120(8) 0.0424(13) Uani 1 1 d . . . . .
H5 H 0.392189 0.732726 0.300129 0.051 Uiso 1 1 calc R . . . .
C6 C 0.2999(7) 0.7806(2) 0.4930(8) 0.0395(13) Uani 1 1 d . . . . .
C7 C 0.3386(9) 0.8325(2) 0.3956(10) 0.0575(17) Uani 1 1 d . . . . .
H7A H 0.240139 0.847443 0.345625 0.086 Uiso 1 1 calc GR . . . .
H7B H 0.414705 0.825590 0.298462 0.086 Uiso 1 1 calc GR . . . .
H7C H 0.385731 0.857568 0.480562 0.086 Uiso 1 1 calc GR . . . .
C8 C 0.1673(7) 0.83472(19) 0.7368(9) 0.0436(13) Uani 1 1 d . . . . .
H8A H 0.135788 0.858528 0.637610 0.052 Uiso 1 1 calc R . . . .
H8B H 0.071310 0.828279 0.811432 0.052 Uiso 1 1 calc R . . . .
C9 C 0.2954(8) 0.8622(2) 0.8517(9) 0.0494(15) Uani 1 1 d . . . . .
H9A H 0.393401 0.866515 0.781106 0.074 Uiso 1 1 calc GR . . . .
H9B H 0.318235 0.840665 0.957763 0.074 Uiso 1 1 calc GR . . . .
H9C H 0.256246 0.896906 0.889389 0.074 Uiso 1 1 calc GR . . . .
C10 C 0.3190(7) 0.63060(19) 0.3972(8) 0.0375(13) Uani 1 1 d . . . . .
C11 C 0.3971(6) 0.6281(2) 0.2227(9) 0.0426(14) Uani 1 1 d . U . . .
C12 C 0.3960(7) 0.5754(2) 0.1140(9) 0.0462(14) Uani 1 1 d . . . . .
H12A H 0.392832 0.584035 -0.015379 0.055 Uiso 1 1 calc R . . . .
H12B H 0.497387 0.556474 0.137431 0.055 Uiso 1 1 calc R . . . .
C13 C 0.2551(7) 0.53800(19) 0.1572(8) 0.0390(13) Uani 1 1 d . . . . .
C14 C 0.2568(7) 0.5301(2) 0.3626(8) 0.0452(15) Uani 1 1 d . . . . .
H14A H 0.354766 0.510389 0.395444 0.054 Uiso 1 1 calc R . . . .
H14B H 0.163842 0.508066 0.396398 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2515(8) 0.5819(2) 0.4739(8) 0.0548(17) Uani 1 1 d . U . . .
C16 C 0.2765(9) 0.4843(2) 0.0574(11) 0.0603(18) Uani 1 1 d . . . . .
H16A H 0.278067 0.490398 -0.072245 0.090 Uiso 1 1 calc GR . . . .
H16B H 0.187411 0.460774 0.087644 0.090 Uiso 1 1 calc GR . . . .
H16C H 0.377483 0.467918 0.094398 0.090 Uiso 1 1 calc GR . . . .
C17 C 0.0937(8) 0.5628(3) 0.0961(10) 0.0585(18) Uani 1 1 d . . . . .
H17A H 0.080789 0.597555 0.152088 0.088 Uiso 1 1 calc GR . . . .
H17B H 0.005160 0.539846 0.132410 0.088 Uiso 1 1 calc GR . . . .
H17C H 0.093418 0.566730 -0.034595 0.088 Uiso 1 1 calc GR . . . .
O1 O 0.4962(18) 0.6634(10) 0.171(3) 0.049(4) Uani 0.5 1 d . U P A 1
O2 O 0.1493(14) 0.5810(5) 0.6100(15) 0.053(3) Uani 0.5 1 d . U P B 1
O1' O 0.4453(19) 0.6675(9) 0.129(3) 0.050(4) Uani 0.5 1 d . U P A 2
O2' O 0.2358(18) 0.5750(6) 0.6429(18) 0.070(3) Uani 0.5 1 d . U P B 2


_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 C2 1.367(6) . ?
N1 C6 1.351(7) . ?
N1 C8 1.509(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.496(8) . ?
C2 C3 1.375(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(8) . ?
C4 C5 1.415(7) . ?
C4 C10 1.463(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(7) . ?
C6 C7 1.505(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.507(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.428(8) . ?
C10 C15 1.444(8) . ?
C11 C12 1.530(7) . ?
C11 O1 1.25(2) . ?
C11 O1' 1.26(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.514(7) . ?
C13 C14 1.514(9) . ?
C13 C16 1.530(7) . ?
C13 C17 1.526(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.521(8) . ?
C15 O2 1.300(13) . ?
C15 O2' 1.253(14) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 N1 C8 119.8(5) . . ?
C6 N1 C2 119.8(4) . . ?
C6 N1 C8 120.3(4) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 119.8(5) . . ?
N1 C2 C3 120.0(5) . . ?
C3 C2 C1 120.2(5) . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 122.9(5) . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C5 113.5(5) . . ?
C3 C4 C10 123.1(5) . . ?
C5 C4 C10 123.4(5) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 C4 122.7(5) . . ?
C6 C5 H5 118.6 . . ?
N1 C6 C5 120.5(5) . . ?
N1 C6 C7 119.8(5) . . ?
C5 C6 C7 119.7(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 N1 112.9(4) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C4 120.7(4) . . ?
C11 C10 C15 118.8(5) . . ?
C15 C10 C4 120.4(5) . . ?
C10 C11 C12 119.9(4) . . ?
O1 C11 C10 121.9(11) . . ?
O1 C11 C12 116.5(11) . . ?
O1' C11 C10 126.4(11) . . ?
O1' C11 C12 112.6(11) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 114.9(4) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 C16 110.4(5) . . ?
C12 C13 C17 110.6(5) . . ?
C14 C13 C12 106.2(5) . . ?
C14 C13 C16 111.0(5) . . ?
C14 C13 C17 110.5(5) . . ?
C17 C13 C16 108.2(5) . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C13 C14 C15 114.9(4) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C10 C15 C14 119.3(5) . . ?
O2 C15 C10 123.8(8) . . ?
O2 C15 C14 114.5(7) . . ?
O2' C15 C10 122.4(9) . . ?
O2' C15 C14 114.5(8) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C3 H3 O2 0.93 2.12 2.741(14) 122.8 .
C3 H3 O2' 0.93 2.11 2.775(16) 127.5 .
C5 H5 O1 0.93 2.14 2.78(2) 124.7 .
C5 H5 O1' 0.93 2.09 2.76(2) 128.1 .

_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_cd17306
_database_code_depnum_ccdc_archive 'CCDC 1569090'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O2'
_chemical_formula_weight         349.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   17.439(3)
_cell_length_b                   12.082(2)
_cell_length_c                   9.2298(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.491(4)
_cell_angle_gamma                90
_cell_volume                     1941.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2484
_cell_measurement_theta_min      4.680
_cell_measurement_theta_max      52.981

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10438
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3412
_reflns_number_gt                2511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.2842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3412
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.41646(7) 0.57454(11) 0.12232(15) 0.0403(4) Uani 1 1 d . . . . .
O1 O 0.69113(8) 0.70285(12) 0.05045(16) 0.0695(4) Uani 1 1 d . . . . .
O2 O 0.66041(7) 0.43373(11) 0.40412(16) 0.0638(4) Uani 1 1 d . . . . .
C1 C 0.70683(10) 0.66100(15) 0.1703(2) 0.0461(4) Uani 1 1 d . . . . .
C2 C 0.78296(11) 0.69117(18) 0.2472(2) 0.0637(6) Uani 1 1 d . . . . .
H2A H 0.7742 0.7484 0.3180 0.076 Uiso 1 1 calc R U . . .
H2B H 0.8160 0.7221 0.1767 0.076 Uiso 1 1 calc R U . . .
C3 C 0.82462(10) 0.59599(17) 0.3237(2) 0.0541(5) Uani 1 1 d . . . . .
C4 C 0.76841(10) 0.54821(16) 0.4252(2) 0.0498(5) Uani 1 1 d . . . . .
H4A H 0.7913 0.4829 0.4710 0.060 Uiso 1 1 calc R U . . .
H4B H 0.7608 0.6019 0.5011 0.060 Uiso 1 1 calc R U . . .
C5 C 0.69097(9) 0.51681(14) 0.35602(18) 0.0413(4) Uani 1 1 d . . . . .
C6 C 0.65669(9) 0.58549(13) 0.24149(17) 0.0367(4) Uani 1 1 d . . . . .
C7 C 0.57625(9) 0.57892(12) 0.19819(17) 0.0352(4) Uani 1 1 d . . . . .
C8 C 0.52421(9) 0.50866(13) 0.26532(18) 0.0389(4) Uani 1 1 d . . . . .
H8 H 0.5434 0.4621 0.3392 0.047 Uiso 1 1 calc R U . . .
C9 C 0.44762(9) 0.50546(13) 0.22772(18) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.46331(9) 0.64579(13) 0.05416(18) 0.0404(4) Uani 1 1 d . . . . .
C11 C 0.54027(9) 0.64630(13) 0.08933(17) 0.0396(4) Uani 1 1 d . . . . .
H11 H 0.5709 0.6938 0.0386 0.048 Uiso 1 1 calc R U . . .
C12 C 0.33286(9) 0.57373(15) 0.0859(2) 0.0486(5) Uani 1 1 d . . . . .
H12A H 0.3136 0.4989 0.0948 0.058 Uiso 1 1 calc R U . . .
H12B H 0.3231 0.5968 -0.0142 0.058 Uiso 1 1 calc R U . . .
C13 C 0.28991(10) 0.64988(16) 0.1838(2) 0.0535(5) Uani 1 1 d . . . . .
H13A H 0.2989 0.6264 0.2839 0.064 Uiso 1 1 calc R U . . .
H13B H 0.3092 0.7248 0.1757 0.064 Uiso 1 1 calc R U . . .
C14 C 0.20509(10) 0.64831(16) 0.1431(2) 0.0510(5) Uani 1 1 d . . . . .
C15 C 0.15781(12) 0.5682(2) 0.1938(2) 0.0707(6) Uani 1 1 d . . . . .
H15 H 0.1782 0.5134 0.2555 0.085 Uiso 1 1 calc R U . . .
C16 C 0.07954(14) 0.5682(3) 0.1537(3) 0.0856(8) Uani 1 1 d . . . . .
H16 H 0.0478 0.5141 0.1894 0.103 Uiso 1 1 calc R U . . .
C17 C 0.04978(13) 0.6474(3) 0.0627(3) 0.0896(8) Uani 1 1 d . . . . .
H17 H -0.0027 0.6482 0.0374 0.108 Uiso 1 1 calc R U . . .
C18 C 0.09568(14) 0.7247(2) 0.0088(4) 0.0957(9) Uani 1 1 d . . . . .
H18 H 0.0751 0.7776 -0.0557 0.115 Uiso 1 1 calc R U . . .
C19 C 0.17277(12) 0.72587(18) 0.0484(3) 0.0753(7) Uani 1 1 d . . . . .
H19 H 0.2038 0.7800 0.0107 0.090 Uiso 1 1 calc R U . . .
C20 C 0.84721(12) 0.5082(2) 0.2166(3) 0.0832(8) Uani 1 1 d . . . . .
H20A H 0.8018 0.4782 0.1673 0.125 Uiso 1 1 calc R U . . .
H20B H 0.8750 0.4502 0.2677 0.125 Uiso 1 1 calc R U . . .
H20C H 0.8791 0.5408 0.1469 0.125 Uiso 1 1 calc R U . . .
C21 C 0.89656(12) 0.6376(2) 0.4090(3) 0.0842(8) Uani 1 1 d . . . . .
H21A H 0.9214 0.5769 0.4599 0.126 Uiso 1 1 calc R U . . .
H21B H 0.8825 0.6926 0.4776 0.126 Uiso 1 1 calc R U . . .
H21C H 0.9311 0.6695 0.3434 0.126 Uiso 1 1 calc R U . . .
C22 C 0.42950(11) 0.72178(15) -0.0604(2) 0.0555(5) Uani 1 1 d . . . . .
H22A H 0.4695 0.7663 -0.0975 0.083 Uiso 1 1 calc R U . . .
H22B H 0.3921 0.7689 -0.0194 0.083 Uiso 1 1 calc R U . . .
H22C H 0.4052 0.6790 -0.1378 0.083 Uiso 1 1 calc R U . . .
C23 C 0.39690(11) 0.42378(16) 0.2966(2) 0.0591(5) Uani 1 1 d . . . . .
H23A H 0.3765 0.3727 0.2245 0.089 Uiso 1 1 calc R U . . .
H23B H 0.3554 0.4621 0.3385 0.089 Uiso 1 1 calc R U . . .
H23C H 0.4261 0.3840 0.3711 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.366(2) . ?
N1 C9 1.369(2) . ?
N1 C12 1.476(2) . ?
O1 C1 1.232(2) . ?
O2 C5 1.232(2) . ?
C1 C6 1.449(2) . ?
C1 C2 1.511(3) . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.511(2) . ?
C3 C20 1.518(3) . ?
C3 C21 1.526(3) . ?
C4 C5 1.507(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.445(2) . ?
C6 C7 1.437(2) . ?
C7 C11 1.410(2) . ?
C7 C8 1.413(2) . ?
C8 C9 1.360(2) . ?
C8 H8 0.9300 . ?
C9 C23 1.493(2) . ?
C10 C11 1.361(2) . ?
C10 C22 1.494(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.519(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.504(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.372(3) . ?
C14 C19 1.378(3) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.345(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C10 N1 C9 119.26(13) . . ?
C10 N1 C12 120.61(14) . . ?
C9 N1 C12 120.12(14) . . ?
O1 C1 C6 123.96(16) . . ?
O1 C1 C2 117.61(16) . . ?
C6 C1 C2 118.43(16) . . ?
C1 C2 C3 114.78(16) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 105.58(15) . . ?
C2 C3 C20 111.32(17) . . ?
C4 C3 C20 109.92(17) . . ?
C2 C3 C21 110.32(19) . . ?
C4 C3 C21 110.48(16) . . ?
C20 C3 C21 109.19(16) . . ?
C5 C4 C3 115.61(15) . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
O2 C5 C6 124.26(15) . . ?
O2 C5 C4 116.67(15) . . ?
C6 C5 C4 119.06(15) . . ?
C7 C6 C5 121.68(14) . . ?
C7 C6 C1 120.97(14) . . ?
C5 C6 C1 117.35(14) . . ?
C11 C7 C8 112.92(14) . . ?
C11 C7 C6 123.40(14) . . ?
C8 C7 C6 123.60(14) . . ?
C9 C8 C7 123.52(15) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 N1 120.34(15) . . ?
C8 C9 C23 120.55(16) . . ?
N1 C9 C23 119.07(15) . . ?
C11 C10 N1 120.10(15) . . ?
C11 C10 C22 120.45(16) . . ?
N1 C10 C22 119.45(15) . . ?
C10 C11 C7 123.82(15) . . ?
C10 C11 H11 118.1 . . ?
C7 C11 H11 118.1 . . ?
N1 C12 C13 112.11(13) . . ?
N1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 110.90(14) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C19 117.70(18) . . ?
C15 C14 C13 121.72(19) . . ?
C19 C14 C13 120.53(19) . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 C23 H23A 109.5 . . ?
C9 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C9 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -139.46(18) . . . . ?
C6 C1 C2 C3 40.8(2) . . . . ?
C1 C2 C3 C4 -55.3(2) . . . . ?
C1 C2 C3 C20 64.0(2) . . . . ?
C1 C2 C3 C21 -174.66(16) . . . . ?
C2 C3 C4 C5 53.6(2) . . . . ?
C20 C3 C4 C5 -66.5(2) . . . . ?
C21 C3 C4 C5 172.90(17) . . . . ?
C3 C4 C5 O2 144.01(17) . . . . ?
C3 C4 C5 C6 -37.2(2) . . . . ?
O2 C5 C6 C7 15.7(3) . . . . ?
C4 C5 C6 C7 -162.94(15) . . . . ?
O2 C5 C6 C1 -163.63(16) . . . . ?
C4 C5 C6 C1 17.7(2) . . . . ?
O1 C1 C6 C7 -18.6(3) . . . . ?
C2 C1 C6 C7 161.13(16) . . . . ?
O1 C1 C6 C5 160.82(17) . . . . ?
C2 C1 C6 C5 -19.5(2) . . . . ?
C5 C6 C7 C11 178.46(14) . . . . ?
C1 C6 C7 C11 -2.2(2) . . . . ?
C5 C6 C7 C8 2.0(2) . . . . ?
C1 C6 C7 C8 -178.66(15) . . . . ?
C11 C7 C8 C9 0.7(2) . . . . ?
C6 C7 C8 C9 177.52(15) . . . . ?
C7 C8 C9 N1 -1.7(2) . . . . ?
C7 C8 C9 C23 175.90(16) . . . . ?
C10 N1 C9 C8 0.8(2) . . . . ?
C12 N1 C9 C8 -177.65(14) . . . . ?
C10 N1 C9 C23 -176.92(15) . . . . ?
C12 N1 C9 C23 4.7(2) . . . . ?
C9 N1 C10 C11 1.2(2) . . . . ?
C12 N1 C10 C11 179.58(14) . . . . ?
C9 N1 C10 C22 -179.66(14) . . . . ?
C12 N1 C10 C22 -1.3(2) . . . . ?
N1 C10 C11 C7 -2.3(2) . . . . ?
C22 C10 C11 C7 178.57(15) . . . . ?
C8 C7 C11 C10 1.3(2) . . . . ?
C6 C7 C11 C10 -175.52(15) . . . . ?
C10 N1 C12 C13 -92.24(19) . . . . ?
C9 N1 C12 C13 86.16(19) . . . . ?
N1 C12 C13 C14 179.37(15) . . . . ?
C12 C13 C14 C15 84.0(2) . . . . ?
C12 C13 C14 C19 -93.6(2) . . . . ?
C19 C14 C15 C16 -2.0(3) . . . . ?
C13 C14 C15 C16 -179.62(19) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 C14 0.3(4) . . . . ?
C15 C14 C19 C18 1.5(3) . . . . ?
C13 C14 C19 C18 179.2(2) . . . . ?

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
C22 H22B O2 0.96 2.46 3.372(2) 158.4 2_655
C11 H11 O1 0.93 2.10 2.763(2) 127.5 .
C8 H8 O2 0.93 2.12 2.780(2) 127.0 .
C8 H8 O2 0.93 2.12 2.780(2) 127.0 .
C11 H11 O1 0.93 2.10 2.763(2) 127.5 .
C22 H22B O2 0.96 2.46 3.372(2) 158.4 2_655

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd17307
_database_code_depnum_ccdc_archive 'CCDC 1569087'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H58 N2 O8'
_chemical_formula_weight         742.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   19.4307(19)
_cell_length_b                   17.6059(16)
_cell_length_c                   11.8488(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.348(2)
_cell_angle_gamma                90
_cell_volume                     4052.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2218
_cell_measurement_theta_min      4.608
_cell_measurement_theta_max      39.919

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22198
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.048
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             7122
_reflns_number_gt                4385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0928P)²+1.0972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7122
_refine_ls_number_parameters     495
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1990
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.03056(13) 0.39461(13) 0.9938(2) 0.0495(6) Uani 1 1 d . . . . .
N2 N 0.47438(12) 0.62244(13) 0.9513(2) 0.0467(6) Uani 1 1 d . . . . .
O1 O 0.18722(12) 0.61997(13) 1.03053(19) 0.0675(7) Uani 1 1 d . . . . .
O2 O 0.15215(12) 0.51841(13) 0.66522(19) 0.0679(7) Uani 1 1 d . . . . .
O3 O 0.33049(14) 0.39271(13) 1.05618(19) 0.0732(7) Uani 1 1 d . . . . .
O4 O 0.33953(13) 0.45799(13) 0.67112(18) 0.0685(7) Uani 1 1 d . . . . .
O5 O 0.33618(18) 0.46746(18) 0.2632(2) 0.1140(11) Uani 1 1 d D . . . .
H5A H 0.3232 0.4314 0.2006 0.137 Uiso 1 1 d DR U . . .
H5B H 0.3285 0.4414 0.3299 0.137 Uiso 1 1 d DR U . . .
O6 O 0.2899(2) 0.41580(19) 0.4604(3) 0.1278(12) Uani 1 1 d D . . . .
H6A H 0.2547 0.4597 0.4758 0.153 Uiso 1 1 d DR U . . .
H6B H 0.2962 0.4225 0.5373 0.153 Uiso 1 1 d DR U . . .
O7 O 0.2348(2) 0.5764(2) 0.2581(3) 0.1529(16) Uani 1 1 d D . . . .
H7A H 0.2467 0.5335 0.2363 0.183 Uiso 1 1 d DR U . . .
H7B H 0.2087 0.5884 0.1906 0.183 Uiso 1 1 d DR U . . .
O8 O 0.1722(2) 0.5002(2) 0.4333(3) 0.1418(14) Uani 1 1 d D . . . .
H8A H 0.1776 0.5399 0.4884 0.170 Uiso 1 1 d DR U . . .
H8B H 0.2041 0.5450 0.3976 0.170 Uiso 1 1 d DR U . . .
C1 C 0.20092(15) 0.61155(16) 0.9291(3) 0.0491(8) Uani 1 1 d . . . . .
C2 C 0.25409(16) 0.66447(18) 0.8819(3) 0.0568(8) Uani 1 1 d . . . . .
H2A H 0.2985 0.6392 0.8848 0.068 Uiso 1 1 calc R U . . .
H2B H 0.2574 0.7090 0.9298 0.068 Uiso 1 1 calc R U . . .
C3 C 0.23913(15) 0.68999(17) 0.7615(3) 0.0504(8) Uani 1 1 d . . . . .
C4 C 0.22934(17) 0.61900(17) 0.6916(3) 0.0575(8) Uani 1 1 d . . . . .
H4A H 0.2138 0.6339 0.6164 0.069 Uiso 1 1 calc R U . . .
H4B H 0.2738 0.5946 0.6844 0.069 Uiso 1 1 calc R U . . .
C5 C 0.17945(15) 0.56118(16) 0.7360(3) 0.0478(7) Uani 1 1 d . . . . .
C6 C 0.16781(14) 0.55648(15) 0.8558(2) 0.0442(7) Uani 1 1 d . . . . .
C7 C 0.12180(15) 0.50022(15) 0.9016(2) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.07362(15) 0.45903(16) 0.8360(3) 0.0482(7) Uani 1 1 d . . . . .
H8 H 0.0723 0.4668 0.7583 0.058 Uiso 1 1 calc R U . . .
C9 C 0.02899(16) 0.40857(17) 0.8801(3) 0.0499(8) Uani 1 1 d . . . . .
C10 C 0.07806(16) 0.42981(16) 1.0622(3) 0.0497(8) Uani 1 1 d . . . . .
C11 C 0.12200(16) 0.48110(16) 1.0172(3) 0.0498(8) Uani 1 1 d . . . . .
H11 H 0.1539 0.5048 1.0652 0.060 Uiso 1 1 calc R U . . .
C12 C -0.01823(16) 0.33884(17) 1.0408(3) 0.0567(8) Uani 1 1 d . . . . .
H12A H -0.0634 0.3471 1.0065 0.068 Uiso 1 1 calc R U . . .
H12B H -0.0217 0.3476 1.1213 0.068 Uiso 1 1 calc R U . . .
C13 C 0.00273(16) 0.25755(16) 1.0216(3) 0.0495(8) Uani 1 1 d . . . . .
C14 C 0.07021(17) 0.23412(18) 1.0274(3) 0.0646(10) Uani 1 1 d . . . . .
H14 H 0.1047 0.2697 1.0415 0.077 Uiso 1 1 calc R U . . .
C15 C 0.0878(2) 0.1595(2) 1.0128(3) 0.0790(11) Uani 1 1 d . . . . .
H15 H 0.1336 0.1446 1.0190 0.095 Uiso 1 1 calc R U . . .
C16 C 0.0374(3) 0.1069(2) 0.9891(3) 0.0810(12) Uani 1 1 d . . . . .
H16 H 0.0489 0.0562 0.9779 0.097 Uiso 1 1 calc R U . . .
C17 C -0.0296(2) 0.1297(2) 0.9821(4) 0.0841(12) Uani 1 1 d . . . . .
H17 H -0.0640 0.0944 0.9654 0.101 Uiso 1 1 calc R U . . .
C18 C -0.04668(19) 0.2043(2) 0.9994(3) 0.0667(10) Uani 1 1 d . . . . .
H18 H -0.0927 0.2188 0.9961 0.080 Uiso 1 1 calc R U . . .
C19 C 0.08058(19) 0.41318(19) 1.1866(3) 0.0690(10) Uani 1 1 d . . . . .
H19A H 0.1181 0.4406 1.2216 0.103 Uiso 1 1 calc R U . . .
H19B H 0.0872 0.3597 1.1982 0.103 Uiso 1 1 calc R U . . .
H19C H 0.0381 0.4286 1.2194 0.103 Uiso 1 1 calc R U . . .
C20 C -0.02300(19) 0.3690(2) 0.8075(3) 0.0737(11) Uani 1 1 d . . . . .
H20A H -0.0186 0.3854 0.7307 0.110 Uiso 1 1 calc R U . . .
H20B H -0.0683 0.3810 0.8328 0.110 Uiso 1 1 calc R U . . .
H20C H -0.0157 0.3152 0.8121 0.110 Uiso 1 1 calc R U . . .
C21 C 0.17394(16) 0.73865(18) 0.7564(3) 0.0652(9) Uani 1 1 d . . . . .
H21A H 0.1353 0.7086 0.7786 0.098 Uiso 1 1 calc R U . . .
H21B H 0.1663 0.7568 0.6808 0.098 Uiso 1 1 calc R U . . .
H21C H 0.1793 0.7811 0.8068 0.098 Uiso 1 1 calc R U . . .
C22 C 0.29955(17) 0.7368(2) 0.7181(3) 0.0729(10) Uani 1 1 d . . . . .
H22A H 0.3055 0.7814 0.7640 0.109 Uiso 1 1 calc R U . . .
H22B H 0.2902 0.7516 0.6413 0.109 Uiso 1 1 calc R U . . .
H22C H 0.3408 0.7068 0.7220 0.109 Uiso 1 1 calc R U . . .
C23 C 0.31240(16) 0.38919(16) 0.9551(3) 0.0501(8) Uani 1 1 d . . . . .
C24 C 0.26109(18) 0.32774(18) 0.9252(3) 0.0626(9) Uani 1 1 d . . . . .
H24A H 0.2151 0.3483 0.9332 0.075 Uiso 1 1 calc R U . . .
H24B H 0.2666 0.2868 0.9795 0.075 Uiso 1 1 calc R U . . .
C25 C 0.26633(16) 0.29475(16) 0.8082(3) 0.0504(8) Uani 1 1 d . . . . .
C26 C 0.26480(17) 0.36213(17) 0.7277(3) 0.0569(8) Uani 1 1 d . . . . .
H26A H 0.2715 0.3436 0.6516 0.068 Uiso 1 1 calc R U . . .
H26B H 0.2195 0.3853 0.7294 0.068 Uiso 1 1 calc R U . . .
C27 C 0.31801(15) 0.42223(16) 0.7535(3) 0.0469(7) Uani 1 1 d . . . . .
C28 C 0.33947(15) 0.43802(15) 0.8688(2) 0.0431(7) Uani 1 1 d . . . . .
C29 C 0.38527(15) 0.50010(15) 0.8963(2) 0.0430(7) Uani 1 1 d . . . . .
C30 C 0.42264(15) 0.54069(15) 0.8156(2) 0.0457(7) Uani 1 1 d . . . . .
H30 H 0.4177 0.5265 0.7403 0.055 Uiso 1 1 calc R U . . .
C31 C 0.46563(15) 0.59957(16) 0.8416(2) 0.0469(7) Uani 1 1 d . . . . .
C32 C 0.43806(17) 0.58650(16) 1.0334(3) 0.0517(8) Uani 1 1 d . . . . .
C33 C 0.39573(17) 0.52762(16) 1.0070(2) 0.0517(8) Uani 1 1 d . . . . .
H33 H 0.3723 0.5041 1.0650 0.062 Uiso 1 1 calc R U . . .
C34 C 0.52122(16) 0.68582(18) 0.9794(3) 0.0568(8) Uani 1 1 d . . . . .
H34A H 0.5612 0.6821 0.9323 0.068 Uiso 1 1 calc R U . . .
H34B H 0.5370 0.6803 1.0572 0.068 Uiso 1 1 calc R U . . .
C35 C 0.49023(16) 0.76341(17) 0.9646(2) 0.0488(8) Uani 1 1 d . . . . .
C36 C 0.53329(19) 0.8246(2) 0.9479(3) 0.0639(10) Uani 1 1 d . . . . .
H36 H 0.5805 0.8170 0.9430 0.077 Uiso 1 1 calc R U . . .
C37 C 0.5063(3) 0.8970(2) 0.9384(3) 0.0784(12) Uani 1 1 d . . . . .
H37 H 0.5356 0.9379 0.9270 0.094 Uiso 1 1 calc R U . . .
C38 C 0.4377(3) 0.9092(2) 0.9456(3) 0.0782(12) Uani 1 1 d . . . . .
H38 H 0.4202 0.9582 0.9400 0.094 Uiso 1 1 calc R U . . .
C39 C 0.3945(2) 0.8495(2) 0.9611(3) 0.0710(10) Uani 1 1 d . . . . .
H39 H 0.3474 0.8577 0.9653 0.085 Uiso 1 1 calc R U . . .
C40 C 0.42062(17) 0.77682(18) 0.9704(3) 0.0593(9) Uani 1 1 d . . . . .
H40 H 0.3907 0.7363 0.9808 0.071 Uiso 1 1 calc R U . . .
C41 C 0.4464(2) 0.6130(2) 1.1543(3) 0.0715(10) Uani 1 1 d . . . . .
H41A H 0.4139 0.5870 1.2002 0.107 Uiso 1 1 calc R U . . .
H41B H 0.4383 0.6667 1.1579 0.107 Uiso 1 1 calc R U . . .
H41C H 0.4923 0.6021 1.1814 0.107 Uiso 1 1 calc R U . . .
C42 C 0.50456(19) 0.6394(2) 0.7525(3) 0.0709(10) Uani 1 1 d . . . . .
H42A H 0.4998 0.6933 0.7617 0.106 Uiso 1 1 calc R U . . .
H42B H 0.4866 0.6249 0.6795 0.106 Uiso 1 1 calc R U . . .
H42C H 0.5523 0.6258 0.7587 0.106 Uiso 1 1 calc R U . . .
C43 C 0.20572(19) 0.2422(2) 0.7812(3) 0.0793(11) Uani 1 1 d . . . . .
H43A H 0.2067 0.1999 0.8324 0.119 Uiso 1 1 calc R U . . .
H43B H 0.2089 0.2239 0.7052 0.119 Uiso 1 1 calc R U . . .
H43C H 0.1634 0.2696 0.7890 0.119 Uiso 1 1 calc R U . . .
C44 C 0.33289(17) 0.25058(18) 0.7950(3) 0.0654(9) Uani 1 1 d . . . . .
H44A H 0.3714 0.2840 0.8069 0.098 Uiso 1 1 calc R U . . .
H44B H 0.3342 0.2296 0.7203 0.098 Uiso 1 1 calc R U . . .
H44C H 0.3350 0.2102 0.8494 0.098 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag



N1 C10 1.363(4) . ?
N1 C9 1.369(4) . ?
N1 C12 1.483(4) . ?
N2 C31 1.367(4) . ?
N2 C32 1.370(4) . ?
N2 C34 1.473(4) . ?
O1 C1 1.246(4) . ?
O2 C5 1.237(4) . ?
O3 C23 1.242(4) . ?
O4 C27 1.243(3) . ?
O5 H5A 1.0041 . ?
O5 H5B 0.9293 . ?
O6 H6A 1.0506 . ?
O6 H6B 0.9239 . ?
O7 H7A 0.8325 . ?
O7 H7B 0.9604 . ?
O8 H8A 0.9600 . ?
O8 H8B 1.0946 . ?
C1 C6 1.442(4) . ?
C1 C2 1.508(4) . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(4) . ?
C3 C21 1.529(4) . ?
C3 C22 1.533(4) . ?
C4 C5 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.445(4) . ?
C6 C7 1.448(4) . ?
C7 C8 1.404(4) . ?
C7 C11 1.411(4) . ?
C8 C9 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C20 1.485(4) . ?
C10 C11 1.360(4) . ?
C10 C19 1.502(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.507(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.363(4) . ?
C13 C14 1.375(4) . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C28 1.445(4) . ?
C23 C24 1.508(4) . ?
C24 C25 1.509(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C44 1.520(4) . ?
C25 C26 1.522(4) . ?
C25 C43 1.526(4) . ?
C26 C27 1.506(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.445(4) . ?
C28 C29 1.442(4) . ?
C29 C33 1.408(4) . ?
C29 C30 1.409(4) . ?
C30 C31 1.362(4) . ?
C30 H30 0.9300 . ?
C31 C42 1.490(4) . ?
C32 C33 1.355(4) . ?
C32 C41 1.511(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.501(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C40 1.376(4) . ?
C35 C36 1.381(4) . ?
C36 C37 1.382(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.355(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.359(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.380(5) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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
C10 N1 C9 120.2(3) . . ?
C10 N1 C12 120.5(3) . . ?
C9 N1 C12 119.3(3) . . ?
C31 N2 C32 119.0(3) . . ?
C31 N2 C34 120.0(3) . . ?
C32 N2 C34 121.0(3) . . ?
H7A O5 H5A 92.6 . . ?
H7A O5 H5B 104.6 . . ?
H5A O5 H5B 105.9 . . ?
H6A O6 H6B 78.9 . . ?
H8B O7 H7A 96.0 . . ?
H8B O7 H7B 129.3 . . ?
H7A O7 H7B 95.0 . . ?
H6A O8 H8A 90.9 . . ?
H6A O8 H8B 83.4 . . ?
H8A O8 H8B 71.6 . . ?
O1 C1 C6 123.9(3) . . ?
O1 C1 C2 116.6(3) . . ?
C6 C1 C2 119.5(3) . . ?
C1 C2 C3 114.4(3) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 106.8(3) . . ?
C4 C3 C21 110.4(3) . . ?
C2 C3 C21 110.1(3) . . ?
C4 C3 C22 110.4(3) . . ?
C2 C3 C22 110.1(3) . . ?
C21 C3 C22 109.0(3) . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
O2 C5 C6 123.8(3) . . ?
O2 C5 C4 116.3(3) . . ?
C6 C5 C4 119.9(3) . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C7 121.3(3) . . ?
C8 C7 C11 113.6(3) . . ?
C8 C7 C6 123.8(3) . . ?
C11 C7 C6 122.6(3) . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C8 C9 N1 119.9(3) . . ?
C8 C9 C20 121.1(3) . . ?
N1 C9 C20 119.0(3) . . ?
C11 C10 N1 119.4(3) . . ?
C11 C10 C19 120.5(3) . . ?
N1 C10 C19 120.0(3) . . ?
C10 C11 C7 123.5(3) . . ?
C10 C11 H11 118.3 . . ?
C7 C11 H11 118.3 . . ?
N1 C12 C13 113.3(2) . . ?
N1 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N1 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C12 119.4(3) . . ?
C14 C13 C12 122.6(3) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.3(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 121.1(4) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C28 123.6(3) . . ?
O3 C23 C24 115.7(3) . . ?
C28 C23 C24 120.7(3) . . ?
C23 C24 C25 115.7(3) . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
C24 C25 C44 111.6(3) . . ?
C24 C25 C26 106.0(3) . . ?
C44 C25 C26 109.8(3) . . ?
C24 C25 C43 110.9(3) . . ?
C44 C25 C43 108.8(3) . . ?
C26 C25 C43 109.7(3) . . ?
C27 C26 C25 114.6(3) . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
O4 C27 C28 123.4(3) . . ?
O4 C27 C26 116.0(3) . . ?
C28 C27 C26 120.6(3) . . ?
C29 C28 C23 121.6(3) . . ?
C29 C28 C27 121.5(3) . . ?
C23 C28 C27 116.9(3) . . ?
C33 C29 C30 113.1(3) . . ?
C33 C29 C28 123.1(3) . . ?
C30 C29 C28 123.8(3) . . ?
C31 C30 C29 123.7(3) . . ?
C31 C30 H30 118.1 . . ?
C29 C30 H30 118.1 . . ?
C30 C31 N2 120.1(3) . . ?
C30 C31 C42 121.1(3) . . ?
N2 C31 C42 118.8(3) . . ?
C33 C32 N2 120.6(3) . . ?
C33 C32 C41 120.4(3) . . ?
N2 C32 C41 119.0(3) . . ?
C32 C33 C29 123.5(3) . . ?
C32 C33 H33 118.3 . . ?
C29 C33 H33 118.3 . . ?
N2 C34 C35 114.8(3) . . ?
N2 C34 H34A 108.6 . . ?
C35 C34 H34A 108.6 . . ?
N2 C34 H34B 108.6 . . ?
C35 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C40 C35 C36 118.2(3) . . ?
C40 C35 C34 122.8(3) . . ?
C36 C35 C34 118.9(3) . . ?
C35 C36 C37 120.1(4) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.9(4) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C39 119.8(4) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C38 C39 C40 120.1(4) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C35 C40 C39 121.0(3) . . ?
C35 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C32 C41 H41A 109.5 . . ?
C32 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C32 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C31 C42 H42A 109.5 . . ?
C31 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C31 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C25 C43 H43A 109.5 . . ?
C25 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C25 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C25 C44 H44A 109.5 . . ?
C25 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C25 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 -142.5(3) . . . . ?
C6 C1 C2 C3 35.8(4) . . . . ?
C1 C2 C3 C4 -54.5(3) . . . . ?
C1 C2 C3 C21 65.5(3) . . . . ?
C1 C2 C3 C22 -174.4(3) . . . . ?
C2 C3 C4 C5 50.6(4) . . . . ?
C21 C3 C4 C5 -69.1(4) . . . . ?
C22 C3 C4 C5 170.3(3) . . . . ?
C3 C4 C5 O2 154.7(3) . . . . ?
C3 C4 C5 C6 -27.4(4) . . . . ?
O1 C1 C6 C5 169.4(3) . . . . ?
C2 C1 C6 C5 -8.8(4) . . . . ?
O1 C1 C6 C7 -8.0(5) . . . . ?
C2 C1 C6 C7 173.8(3) . . . . ?
O2 C5 C6 C1 -177.8(3) . . . . ?
C4 C5 C6 C1 4.5(4) . . . . ?
O2 C5 C6 C7 -0.5(5) . . . . ?
C4 C5 C6 C7 -178.2(3) . . . . ?
C1 C6 C7 C8 161.7(3) . . . . ?
C5 C6 C7 C8 -15.5(4) . . . . ?
C1 C6 C7 C11 -19.0(4) . . . . ?
C5 C6 C7 C11 163.7(3) . . . . ?
C11 C7 C8 C9 3.3(4) . . . . ?
C6 C7 C8 C9 -177.4(3) . . . . ?
C7 C8 C9 N1 -1.4(4) . . . . ?
C7 C8 C9 C20 177.3(3) . . . . ?
C10 N1 C9 C8 -1.7(4) . . . . ?
C12 N1 C9 C8 -179.5(3) . . . . ?
C10 N1 C9 C20 179.6(3) . . . . ?
C12 N1 C9 C20 1.8(4) . . . . ?
C9 N1 C10 C11 2.6(4) . . . . ?
C12 N1 C10 C11 -179.6(3) . . . . ?
C9 N1 C10 C19 -178.8(3) . . . . ?
C12 N1 C10 C19 -1.0(4) . . . . ?
N1 C10 C11 C7 -0.4(4) . . . . ?
C19 C10 C11 C7 -179.1(3) . . . . ?
C8 C7 C11 C10 -2.4(4) . . . . ?
C6 C7 C11 C10 178.3(3) . . . . ?
C10 N1 C12 C13 -100.2(3) . . . . ?
C9 N1 C12 C13 77.6(4) . . . . ?
N1 C12 C13 C18 -143.5(3) . . . . ?
N1 C12 C13 C14 37.7(4) . . . . ?
C18 C13 C14 C15 -0.8(5) . . . . ?
C12 C13 C14 C15 178.1(3) . . . . ?
C13 C14 C15 C16 1.7(6) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C14 C13 C18 C17 -0.8(5) . . . . ?
C12 C13 C18 C17 -179.6(3) . . . . ?
C16 C17 C18 C13 1.4(6) . . . . ?
O3 C23 C24 C25 -148.7(3) . . . . ?
C28 C23 C24 C25 29.2(4) . . . . ?
C23 C24 C25 C44 67.0(4) . . . . ?
C23 C24 C25 C26 -52.4(4) . . . . ?
C23 C24 C25 C43 -171.5(3) . . . . ?
C24 C25 C26 C27 54.2(3) . . . . ?
C44 C25 C26 C27 -66.4(3) . . . . ?
C43 C25 C26 C27 174.0(3) . . . . ?
C25 C26 C27 O4 149.3(3) . . . . ?
C25 C26 C27 C28 -33.1(4) . . . . ?
O3 C23 C28 C29 -6.1(4) . . . . ?
C24 C23 C28 C29 176.1(3) . . . . ?
O3 C23 C28 C27 174.4(3) . . . . ?
C24 C23 C28 C27 -3.3(4) . . . . ?
O4 C27 C28 C29 3.4(4) . . . . ?
C26 C27 C28 C29 -173.9(3) . . . . ?
O4 C27 C28 C23 -177.1(3) . . . . ?
C26 C27 C28 C23 5.5(4) . . . . ?
C23 C28 C29 C33 -13.5(4) . . . . ?
C27 C28 C29 C33 165.9(3) . . . . ?
C23 C28 C29 C30 168.2(3) . . . . ?
C27 C28 C29 C30 -12.4(4) . . . . ?
C33 C29 C30 C31 1.3(4) . . . . ?
C28 C29 C30 C31 179.7(3) . . . . ?
C29 C30 C31 N2 -0.1(4) . . . . ?
C29 C30 C31 C42 179.0(3) . . . . ?
C32 N2 C31 C30 -1.6(4) . . . . ?
C34 N2 C31 C30 179.6(3) . . . . ?
C32 N2 C31 C42 179.3(3) . . . . ?
C34 N2 C31 C42 0.4(4) . . . . ?
C31 N2 C32 C33 2.0(4) . . . . ?
C34 N2 C32 C33 -179.2(3) . . . . ?
C31 N2 C32 C41 -178.5(3) . . . . ?
C34 N2 C32 C41 0.3(4) . . . . ?
N2 C32 C33 C29 -0.8(5) . . . . ?
C41 C32 C33 C29 179.7(3) . . . . ?
C30 C29 C33 C32 -0.8(4) . . . . ?
C28 C29 C33 C32 -179.2(3) . . . . ?
C31 N2 C34 C35 83.2(3) . . . . ?
C32 N2 C34 C35 -95.6(3) . . . . ?
N2 C34 C35 C40 25.5(4) . . . . ?
N2 C34 C35 C36 -156.5(3) . . . . ?
C40 C35 C36 C37 0.5(5) . . . . ?
C34 C35 C36 C37 -177.5(3) . . . . ?
C35 C36 C37 C38 0.2(5) . . . . ?
C36 C37 C38 C39 -0.8(6) . . . . ?
C37 C38 C39 C40 0.6(6) . . . . ?
C36 C35 C40 C39 -0.7(5) . . . . ?
C34 C35 C40 C39 177.3(3) . . . . ?
C38 C39 C40 C35 0.1(5) . . . . ?

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
C8 H8 O2 0.93 2.13 2.768(4) 124.8 .
C11 H11 O1 0.93 2.17 2.757(4) 120.1 .
C12 H12A O1 0.97 2.50 3.449(4) 164.9 3_567
C26 H26A O6 0.97 2.63 3.351(4) 131.4 .
C30 H30 O4 0.93 2.09 2.744(4) 126.1 .
C33 H33 O3 0.93 2.13 2.761(4) 124.5 .
C33 H33 O5 0.93 2.55 3.441(4) 160.7 1_556
C34 H34A O3 0.97 2.48 3.232(4) 133.9 3_667
O6 H6A O8 1.05 1.82 2.740(6) 144.6 .
O7 H7B O1 0.96 2.01 2.932(4) 160.2 1_554
O6 H6A O8 1.05 1.82 2.740(6) 144.6 .

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd17331
_database_code_depnum_ccdc_archive 'CCDC 1569089'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O2'
_chemical_formula_weight         349.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.7838(11)
_cell_length_b                   11.793(2)
_cell_length_c                   12.664(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.498(4)
_cell_angle_gamma                90
_cell_volume                     980.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1716
_cell_measurement_theta_min      4.793
_cell_measurement_theta_max      46.780

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5676
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             3466
_reflns_number_gt                2854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_fraction_full    0.895

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.8(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3466
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5052(5) 0.7895(3) 0.5311(3) 0.0431(8) Uani 1 1 d . . . . .
O1 O 0.0081(5) 0.5277(4) 0.6481(2) 0.0801(11) Uani 1 1 d . . . . .
O2 O 0.4160(11) 0.7606(6) 0.9171(3) 0.169(4) Uani 1 1 d . . . . .
C1 C 0.0669(7) 0.5685(4) 0.7394(3) 0.0576(11) Uani 1 1 d . . . . .
C2 C -0.0381(9) 0.5256(6) 0.8247(4) 0.0814(15) Uani 1 1 d . . . . .
H2A H -0.1674 0.5648 0.8137 0.098 Uiso 1 1 calc R U . . .
H2B H -0.0679 0.4458 0.8108 0.098 Uiso 1 1 calc R U . . .
C3 C 0.0726(8) 0.5383(4) 0.9415(3) 0.0644(12) Uani 1 1 d . . . . .
C4 C 0.1520(12) 0.6567(6) 0.9585(5) 0.098(2) Uani 1 1 d . . . . .
H4A H 0.2355 0.6634 1.0325 0.118 Uiso 1 1 calc R U . . .
H4B H 0.0376 0.7080 0.9511 0.118 Uiso 1 1 calc R U . . .
C5 C 0.2774(12) 0.6945(6) 0.8803(4) 0.092(2) Uani 1 1 d . . . . .
C6 C 0.2231(7) 0.6554(4) 0.7696(3) 0.0533(10) Uani 1 1 d . . . . .
C7 C 0.3179(6) 0.7016(3) 0.6903(3) 0.0454(9) Uani 1 1 d . . . . .
C8 C 0.5045(6) 0.7609(3) 0.7161(3) 0.0501(10) Uani 1 1 d . . . . .
H8 H 0.5683 0.7728 0.7892 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5961(6) 0.8015(3) 0.6401(3) 0.0490(9) Uani 1 1 d . . . . .
C10 C 0.7949(7) 0.8635(5) 0.6759(4) 0.0716(14) Uani 1 1 d . . . . .
H10A H 0.8271 0.8747 0.7535 0.107 Uiso 1 1 calc R U . . .
H10B H 0.7842 0.9358 0.6401 0.107 Uiso 1 1 calc R U . . .
H10C H 0.9006 0.8198 0.6572 0.107 Uiso 1 1 calc R U . . .
C11 C 0.2280(5) 0.6972(3) 0.5770(3) 0.0420(8) Uani 1 1 d . . . . .
H11 H 0.1010 0.6630 0.5536 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3157(5) 0.7400(3) 0.4997(3) 0.0408(8) Uani 1 1 d . . . . .
C13 C 0.1991(6) 0.7360(4) 0.3824(3) 0.0555(10) Uani 1 1 d . . . . .
H13A H 0.0800 0.6897 0.3753 0.083 Uiso 1 1 calc R U . . .
H13B H 0.2835 0.7043 0.3393 0.083 Uiso 1 1 calc R U . . .
H13C H 0.1589 0.8114 0.3574 0.083 Uiso 1 1 calc R U . . .
C14 C 0.6167(6) 0.8261(3) 0.4467(4) 0.0512(10) Uani 1 1 d . . . . .
H14 H 0.7547 0.8453 0.4886 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5297(9) 0.9349(4) 0.3928(6) 0.0891(18) Uani 1 1 d . . . . .
H15A H 0.6216 0.9667 0.3542 0.134 Uiso 1 1 calc R U . . .
H15B H 0.5109 0.9875 0.4473 0.134 Uiso 1 1 calc R U . . .
H15C H 0.4009 0.9199 0.3425 0.134 Uiso 1 1 calc R U . . .
C16 C 0.6430(5) 0.7285(3) 0.3753(3) 0.0434(8) Uani 1 1 d . . . . .
C17 C 0.6234(7) 0.7420(4) 0.2643(4) 0.0623(11) Uani 1 1 d . . . . .
H17 H 0.5875 0.8122 0.2316 0.075 Uiso 1 1 calc R U . . .
C18 C 0.6573(9) 0.6510(6) 0.2024(4) 0.0819(17) Uani 1 1 d . . . . .
H18 H 0.6453 0.6614 0.1282 0.098 Uiso 1 1 calc R U . . .
C19 C 0.7079(8) 0.5465(5) 0.2468(5) 0.0774(15) Uani 1 1 d . . . . .
H19 H 0.7266 0.4855 0.2037 0.093 Uiso 1 1 calc R U . . .
C20 C 0.7307(6) 0.5338(4) 0.3575(4) 0.0602(11) Uani 1 1 d . . . . .
H20 H 0.7668 0.4633 0.3895 0.072 Uiso 1 1 calc R U . . .
C21 C 0.7012(5) 0.6229(3) 0.4216(3) 0.0442(9) Uani 1 1 d . . . . .
H21 H 0.7203 0.6127 0.4963 0.053 Uiso 1 1 calc R U . . .
C22 C 0.2535(12) 0.4566(7) 0.9684(6) 0.112(2) Uani 1 1 d . . . . .
H22A H 0.3464 0.4752 0.9250 0.168 Uiso 1 1 calc R U . . .
H22B H 0.2057 0.3803 0.9529 0.168 Uiso 1 1 calc R U . . .
H22C H 0.3219 0.4631 1.0443 0.168 Uiso 1 1 calc R U . . .
C23 C -0.0599(13) 0.5085(8) 1.0159(6) 0.120(3) Uani 1 1 d . . . . .
H23A H 0.0081 0.5288 1.0894 0.180 Uiso 1 1 calc R U . . .
H23B H -0.0865 0.4285 1.0121 0.180 Uiso 1 1 calc R U . . .
H23C H -0.1861 0.5492 0.9940 0.180 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.370(5) . ?
N1 C12 1.377(5) . ?
N1 C14 1.519(5) . ?
O1 C1 1.223(5) . ?
O2 C5 1.221(7) . ?
C1 C6 1.455(6) . ?
C1 C2 1.522(6) . ?
C2 C3 1.489(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.492(9) . ?
C3 C23 1.498(7) . ?
C3 C22 1.530(8) . ?
C4 C5 1.525(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.433(7) . ?
C6 C7 1.429(6) . ?
C7 C8 1.411(5) . ?
C7 C11 1.413(5) . ?
C8 C9 1.357(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.501(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.499(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C16 1.502(6) . ?
C14 C15 1.503(7) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.388(5) . ?
C16 C21 1.391(5) . ?
C17 C18 1.382(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C9 N1 C12 119.1(3) . . ?
C9 N1 C14 120.1(3) . . ?
C12 N1 C14 120.7(3) . . ?
O1 C1 C6 124.7(4) . . ?
O1 C1 C2 116.1(4) . . ?
C6 C1 C2 119.1(4) . . ?
C3 C2 C1 117.5(4) . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C2 C3 C4 108.1(4) . . ?
C2 C3 C23 111.6(5) . . ?
C4 C3 C23 112.3(6) . . ?
C2 C3 C22 109.6(5) . . ?
C4 C3 C22 108.4(6) . . ?
C23 C3 C22 106.6(6) . . ?
C3 C4 C5 114.8(5) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
O2 C5 C6 124.3(5) . . ?
O2 C5 C4 116.2(5) . . ?
C6 C5 C4 119.5(5) . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 C1 120.6(4) . . ?
C5 C6 C1 118.4(4) . . ?
C8 C7 C11 112.7(3) . . ?
C8 C7 C6 124.2(4) . . ?
C11 C7 C6 123.0(4) . . ?
C9 C8 C7 123.7(4) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 N1 120.5(3) . . ?
C8 C9 C10 119.6(4) . . ?
N1 C9 C10 119.9(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 124.1(3) . . ?
C12 C11 H11 117.9 . . ?
C7 C11 H11 117.9 . . ?
C11 C12 N1 119.6(3) . . ?
C11 C12 C13 118.8(3) . . ?
N1 C12 C13 121.5(3) . . ?
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 . . ?
C16 C14 C15 118.2(4) . . ?
C16 C14 N1 111.2(3) . . ?
C15 C14 N1 110.7(3) . . ?
C16 C14 H14 105.2 . . ?
C15 C14 H14 105.2 . . ?
N1 C14 H14 105.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.4(4) . . ?
C17 C16 C14 121.8(4) . . ?
C21 C16 C14 119.7(3) . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 121.9(5) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 118.0(5) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C16 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 158.1(5) . . . . ?
C6 C1 C2 C3 -23.5(8) . . . . ?
C1 C2 C3 C4 47.6(7) . . . . ?
C1 C2 C3 C23 171.6(6) . . . . ?
C1 C2 C3 C22 -70.5(7) . . . . ?
C2 C3 C4 C5 -52.8(7) . . . . ?
C23 C3 C4 C5 -176.4(6) . . . . ?
C22 C3 C4 C5 66.0(7) . . . . ?
C3 C4 C5 O2 -147.0(7) . . . . ?
C3 C4 C5 C6 35.4(9) . . . . ?
O2 C5 C6 C7 -6.5(10) . . . . ?
C4 C5 C6 C7 170.9(5) . . . . ?
O2 C5 C6 C1 174.3(7) . . . . ?
C4 C5 C6 C1 -8.2(9) . . . . ?
O1 C1 C6 C7 1.3(7) . . . . ?
C2 C1 C6 C7 -177.0(5) . . . . ?
O1 C1 C6 C5 -179.5(6) . . . . ?
C2 C1 C6 C5 2.2(7) . . . . ?
C5 C6 C7 C8 19.1(7) . . . . ?
C1 C6 C7 C8 -161.7(4) . . . . ?
C5 C6 C7 C11 -157.6(5) . . . . ?
C1 C6 C7 C11 21.6(6) . . . . ?
C11 C7 C8 C9 -5.0(5) . . . . ?
C6 C7 C8 C9 178.0(4) . . . . ?
C7 C8 C9 N1 2.2(6) . . . . ?
C7 C8 C9 C10 -179.9(4) . . . . ?
C12 N1 C9 C8 2.7(5) . . . . ?
C14 N1 C9 C8 -174.7(4) . . . . ?
C12 N1 C9 C10 -175.2(4) . . . . ?
C14 N1 C9 C10 7.4(5) . . . . ?
C8 C7 C11 C12 3.3(5) . . . . ?
C6 C7 C11 C12 -179.6(4) . . . . ?
C7 C11 C12 N1 1.1(6) . . . . ?
C7 C11 C12 C13 -176.5(4) . . . . ?
C9 N1 C12 C11 -4.3(5) . . . . ?
C14 N1 C12 C11 173.1(3) . . . . ?
C9 N1 C12 C13 173.2(4) . . . . ?
C14 N1 C12 C13 -9.3(5) . . . . ?
C9 N1 C14 C16 120.8(4) . . . . ?
C12 N1 C14 C16 -56.6(5) . . . . ?
C9 N1 C14 C15 -105.6(5) . . . . ?
C12 N1 C14 C15 77.0(5) . . . . ?
C15 C14 C16 C17 11.4(6) . . . . ?
N1 C14 C16 C17 141.1(4) . . . . ?
C15 C14 C16 C21 -172.8(4) . . . . ?
N1 C14 C16 C21 -43.1(5) . . . . ?
C21 C16 C17 C18 1.4(6) . . . . ?
C14 C16 C17 C18 177.3(4) . . . . ?
C16 C17 C18 C19 0.8(8) . . . . ?
C17 C18 C19 C20 -1.8(8) . . . . ?
C18 C19 C20 C21 0.7(7) . . . . ?
C19 C20 C21 C16 1.4(6) . . . . ?
C17 C16 C21 C20 -2.4(5) . . . . ?
C14 C16 C21 C20 -178.4(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
C15 H15A O1 0.96 2.62 3.481(7) 149.3 2_656
C11 H11 O1 0.93 2.18 2.776(5) 121.0 .
C8 H8 O2 0.93 2.13 2.758(6) 123.6 .
C8 H8 O2 0.93 2.13 2.758(6) 123.6 .
C11 H11 O1 0.93 2.18 2.776(5) 121.0 .
C15 H15A O1 0.96 2.62 3.481(7) 149.3 2_656

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v17061_0m
_database_code_depnum_ccdc_archive 'CCDC 1569088'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6562(3)
_cell_length_b                   9.3060(3)
_cell_length_c                   12.0490(4)
_cell_angle_alpha                83.1427(10)
_cell_angle_beta                 77.2334(10)
_cell_angle_gamma                75.0473(11)
_cell_volume                     912.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      4.540
_cell_measurement_theta_max      54.750

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23873
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3190
_reflns_number_gt                2648
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1241P)²+0.5287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2333
_refine_ls_wR_factor_gt          0.2184
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3254(2) 0.6579(2) 0.47077(18) 0.0492(6) Uani 1 1 d . . . . .
O1 O 0.7647(3) 0.7874(5) 0.6238(2) 0.1216(13) Uani 1 1 d . . . . .
O2 O 0.3187(3) 0.6901(4) 0.8962(2) 0.1148(12) Uani 1 1 d . . . . .
C1 C 0.6780(4) 0.7862(4) 0.7194(2) 0.0683(8) Uani 1 1 d . . . . .
C2 C 0.7398(6) 0.8308(4) 0.8145(3) 0.0894(12) Uani 1 1 d . . . . .
H2A H 0.6835 0.9328 0.8306 0.107 Uiso 1 1 calc R U . . .
H2B H 0.8551 0.8273 0.7894 0.107 Uiso 1 1 calc R U . . .
C3 C 0.7158(4) 0.7311(3) 0.9237(2) 0.0653(8) Uani 1 1 d . . . . .
C4 C 0.5399(5) 0.7269(5) 0.9561(3) 0.0900(11) Uani 1 1 d . . . . .
H4A H 0.4803 0.8172 0.9936 0.108 Uiso 1 1 calc R U . . .
H4B H 0.5308 0.6438 1.0119 0.108 Uiso 1 1 calc R U . . .
C5 C 0.4557(4) 0.7130(4) 0.8626(3) 0.0731(9) Uani 1 1 d . . . . .
C6 C 0.5276(3) 0.7383(3) 0.7435(2) 0.0504(6) Uani 1 1 d . . . . .
C7 C 0.4557(3) 0.7147(2) 0.6528(2) 0.0455(6) Uani 1 1 d . . . . .
C8 C 0.3305(3) 0.6368(3) 0.6685(2) 0.0513(7) Uani 1 1 d . . . . .
H8 H 0.2880 0.6043 0.7422 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2696(3) 0.6075(3) 0.5808(2) 0.0522(7) Uani 1 1 d . . . . .
C10 C 0.1422(3) 0.5189(4) 0.6029(3) 0.0701(8) Uani 1 1 d . . . . .
H10A H 0.1177 0.4903 0.6829 0.105 Uiso 1 1 calc R U . . .
H10B H 0.1824 0.4312 0.5606 0.105 Uiso 1 1 calc R U . . .
H10C H 0.0451 0.5785 0.5795 0.105 Uiso 1 1 calc R U . . .
C11 C 0.5039(3) 0.7663(3) 0.5382(2) 0.0485(6) Uani 1 1 d . . . . .
H11 H 0.5830 0.8212 0.5217 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4411(3) 0.7402(3) 0.4509(2) 0.0494(6) Uani 1 1 d . . . . .
C13 C 0.4980(4) 0.7975(4) 0.3318(2) 0.0692(8) Uani 1 1 d . . . . .
H13A H 0.5789 0.8516 0.3310 0.104 Uiso 1 1 calc R U . . .
H13B H 0.4072 0.8626 0.3037 0.104 Uiso 1 1 calc R U . . .
H13C H 0.5444 0.7153 0.2841 0.104 Uiso 1 1 calc R U . . .
C14 C 0.2648(3) 0.6239(3) 0.3735(2) 0.0557(7) Uani 1 1 d . . . . .
H14A H 0.2151 0.5400 0.3969 0.067 Uiso 1 1 calc R U . . .
H14B H 0.3570 0.5940 0.3118 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1420(3) 0.7522(3) 0.3292(2) 0.0492(6) Uani 1 1 d . . . . .
C16 C 0.1496(4) 0.7769(3) 0.2125(2) 0.0606(7) Uani 1 1 d . . . . .
H16 H 0.2332 0.7180 0.1628 0.073 Uiso 1 1 calc R U . . .
C17 C 0.0343(4) 0.8880(4) 0.1696(3) 0.0739(9) Uani 1 1 d . . . . .
H17 H 0.0404 0.9034 0.0912 0.089 Uiso 1 1 calc R U . . .
C18 C -0.0891(4) 0.9759(4) 0.2416(3) 0.0780(10) Uani 1 1 d . . . . .
H18 H -0.1672 1.0504 0.2126 0.094 Uiso 1 1 calc R U . . .
C19 C -0.0964(4) 0.9532(3) 0.3561(3) 0.0716(9) Uani 1 1 d . . . . .
H19 H -0.1799 1.0134 0.4050 0.086 Uiso 1 1 calc R U . . .
C20 C 0.0177(3) 0.8428(3) 0.4011(3) 0.0585(7) Uani 1 1 d . . . . .
H20 H 0.0109 0.8293 0.4796 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8227(5) 0.5761(5) 0.8976(4) 0.0958(12) Uani 1 1 d . . . . .
H21A H 0.8045 0.5080 0.9628 0.144 Uiso 1 1 calc R U . . .
H21B H 0.9354 0.5799 0.8800 0.144 Uiso 1 1 calc R U . . .
H21C H 0.7955 0.5429 0.8335 0.144 Uiso 1 1 calc R U . . .
C22 C 0.7739(7) 0.7851(6) 1.0178(4) 0.1177(16) Uani 1 1 d . . . . .
H22A H 0.7085 0.8827 1.0362 0.176 Uiso 1 1 calc R U . . .
H22B H 0.8860 0.7892 0.9924 0.176 Uiso 1 1 calc R U . . .
H22C H 0.7640 0.7175 1.0843 0.176 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.376(3) . ?
N1 C9 1.377(3) . ?
N1 C14 1.481(3) . ?
O1 C1 1.228(4) . ?
O2 C5 1.230(4) . ?
C1 C6 1.442(4) . ?
C1 C2 1.507(4) . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.496(5) . ?
C3 C22 1.519(4) . ?
C3 C21 1.526(5) . ?
C4 C5 1.504(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.450(4) . ?
C6 C7 1.436(4) . ?
C7 C11 1.415(3) . ?
C7 C8 1.420(3) . ?
C8 C9 1.363(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.501(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.358(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.492(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.384(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C12 N1 C9 119.1(2) . . ?
C12 N1 C14 119.4(2) . . ?
C9 N1 C14 121.4(2) . . ?
O1 C1 C6 123.0(3) . . ?
O1 C1 C2 116.8(3) . . ?
C6 C1 C2 120.1(3) . . ?
C1 C2 C3 113.2(3) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C22 112.4(3) . . ?
C4 C3 C2 108.5(3) . . ?
C22 C3 C2 110.8(3) . . ?
C4 C3 C21 110.5(3) . . ?
C22 C3 C21 107.6(3) . . ?
C2 C3 C21 107.0(3) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4B 107.9 . . ?
C5 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
O2 C5 C6 123.9(3) . . ?
O2 C5 C4 114.6(3) . . ?
C6 C5 C4 121.3(3) . . ?
C7 C6 C1 120.8(2) . . ?
C7 C6 C5 122.3(2) . . ?
C1 C6 C5 116.9(2) . . ?
C11 C7 C8 113.3(2) . . ?
C11 C7 C6 123.0(2) . . ?
C8 C7 C6 123.7(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C8 C9 N1 120.3(2) . . ?
C8 C9 C10 120.4(3) . . ?
N1 C9 C10 119.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 123.6(2) . . ?
C12 C11 H11 118.2 . . ?
C7 C11 H11 118.2 . . ?
C11 C12 N1 120.3(2) . . ?
C11 C12 C13 120.8(2) . . ?
N1 C12 C13 118.9(2) . . ?
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 . . ?
N1 C14 C15 114.3(2) . . ?
N1 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N1 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 118.5(2) . . ?
C20 C15 C14 122.3(2) . . ?
C16 C15 C14 119.1(2) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -137.3(4) . . . . ?
C6 C1 C2 C3 39.8(5) . . . . ?
C1 C2 C3 C4 -53.8(4) . . . . ?
C1 C2 C3 C22 -177.7(4) . . . . ?
C1 C2 C3 C21 65.3(4) . . . . ?
C22 C3 C4 C5 165.1(4) . . . . ?
C2 C3 C4 C5 42.2(5) . . . . ?
C21 C3 C4 C5 -74.7(4) . . . . ?
C3 C4 C5 O2 170.8(4) . . . . ?
C3 C4 C5 C6 -14.5(5) . . . . ?
O1 C1 C6 C7 -11.4(5) . . . . ?
C2 C1 C6 C7 171.6(3) . . . . ?
O1 C1 C6 C5 167.4(4) . . . . ?
C2 C1 C6 C5 -9.6(4) . . . . ?
O2 C5 C6 C7 -10.6(5) . . . . ?
C4 C5 C6 C7 175.2(3) . . . . ?
O2 C5 C6 C1 170.6(4) . . . . ?
C4 C5 C6 C1 -3.7(5) . . . . ?
C1 C6 C7 C11 -14.3(4) . . . . ?
C5 C6 C7 C11 166.9(3) . . . . ?
C1 C6 C7 C8 165.3(2) . . . . ?
C5 C6 C7 C8 -13.5(4) . . . . ?
C11 C7 C8 C9 3.5(3) . . . . ?
C6 C7 C8 C9 -176.1(2) . . . . ?
C7 C8 C9 N1 -2.1(4) . . . . ?
C7 C8 C9 C10 177.4(2) . . . . ?
C12 N1 C9 C8 -1.1(3) . . . . ?
C14 N1 C9 C8 178.2(2) . . . . ?
C12 N1 C9 C10 179.4(2) . . . . ?
C14 N1 C9 C10 -1.3(3) . . . . ?
C8 C7 C11 C12 -2.1(3) . . . . ?
C6 C7 C11 C12 177.6(2) . . . . ?
C7 C11 C12 N1 -0.9(4) . . . . ?
C7 C11 C12 C13 -179.8(2) . . . . ?
C9 N1 C12 C11 2.5(3) . . . . ?
C14 N1 C12 C11 -176.8(2) . . . . ?
C9 N1 C12 C13 -178.6(2) . . . . ?
C14 N1 C12 C13 2.1(3) . . . . ?
C12 N1 C14 C15 -77.7(3) . . . . ?
C9 N1 C14 C15 103.0(3) . . . . ?
N1 C14 C15 C20 -42.3(3) . . . . ?
N1 C14 C15 C16 140.3(2) . . . . ?
C20 C15 C16 C17 -0.9(4) . . . . ?
C14 C15 C16 C17 176.6(2) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C15 -0.3(5) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C14 C15 C20 C19 -176.4(2) . . . . ?

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
C11 H11 O1 0.93 2.14 2.739(3) 120.9 .
C8 H8 O2 0.93 2.20 2.821(4) 123.6 .
C8 H8 O2 0.93 2.20 2.821(4) 123.6 .
C11 H11 O1 0.93 2.14 2.739(3) 120.9 .

_refine_diff_density_max         0.818
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

