# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1823137'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N O2'
_chemical_formula_weight         339.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.8428(4)
_cell_length_b                   12.3190(8)
_cell_length_c                   21.3880(12)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1802.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1250
_cell_measurement_theta_min      4.1350
_cell_measurement_theta_max      70.1460

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.428
_exptl_crystal_size_min          0.369
_exptl_absorpt_coefficient_mu    0.616
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            4335
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.134
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             2874
_reflns_number_gt                2521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.418
_reflns_Friedel_fraction_max     0.562
_reflns_Friedel_fraction_full    0.606

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
'Sheldrick GM (2015) Acta Crystallogr A 71:3--8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0650P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 1.1091(3) 0.77526(18) 0.50488(8) 0.0581(5) Uani 1 1 d . . . . .
C14 C 0.9115(4) 0.7769(2) 0.62397(11) 0.0410(6) Uani 1 1 d . . . . .
O2 O 1.0731(4) 0.60005(19) 0.49436(9) 0.0667(6) Uani 1 1 d . . . . .
C9 C 0.8117(4) 0.8736(2) 0.72297(11) 0.0401(6) Uani 1 1 d . . . . .
C3 C 0.5076(4) 0.8668(2) 0.90425(12) 0.0473(6) Uani 1 1 d . . . . .
C13 C 1.0653(4) 0.8636(2) 0.60881(11) 0.0460(6) Uani 1 1 d . . . . .
C15 C 0.9649(5) 0.6705(2) 0.59190(12) 0.0513(7) Uani 1 1 d . . . . .
H15A H 1.0583 0.6327 0.6181 0.062 Uiso 1 1 calc R U . . .
H15B H 0.8482 0.6260 0.5898 0.062 Uiso 1 1 calc R U . . .
N1 N 0.4172(4) 0.8703(2) 0.95964(10) 0.0578(6) Uani 1 1 d . . . . .
C10 C 0.7624(4) 0.8652(2) 0.79419(11) 0.0413(6) Uani 1 1 d . . . . .
C7 C 0.7173(4) 0.6780(2) 0.70644(12) 0.0476(6) Uani 1 1 d . . . . .
H7A H 0.6066 0.6915 0.6792 0.057 Uiso 1 1 calc R U . . .
H7B H 0.7702 0.6073 0.6958 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5179(4) 0.7726(2) 0.86781(11) 0.0445(6) Uani 1 1 d . . . . .
C5 C 0.6114(5) 0.7748(2) 0.80376(11) 0.0482(6) Uani 1 1 d . . . . .
H5 H 0.5028 0.8026 0.7785 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8728(4) 0.7641(2) 0.69449(11) 0.0400(5) Uani 1 1 d . . . . .
C1 C 0.6631(5) 0.9708(2) 0.81549(12) 0.0529(7) Uani 1 1 d . . . . .
H1A H 0.7514 1.0310 0.8082 0.063 Uiso 1 1 calc R U . . .
H1B H 0.5472 0.9826 0.7903 0.063 Uiso 1 1 calc R U . . .
C16 C 1.0497(4) 0.6785(3) 0.52684(13) 0.0524(7) Uani 1 1 d . . . . .
C12 C 0.9967(5) 0.9705(2) 0.63664(13) 0.0589(8) Uani 1 1 d . . . . .
H12A H 0.8766 0.9926 0.6162 0.071 Uiso 1 1 calc R U . . .
H12B H 1.0943 1.0259 0.6287 0.071 Uiso 1 1 calc R U . . .
C17 C 1.0676(5) 0.8754(2) 0.53763(12) 0.0530(7) Uani 1 1 d . . . . .
H17A H 0.9414 0.9025 0.5240 0.064 Uiso 1 1 calc R U . . .
H17B H 1.1652 0.9290 0.5262 0.064 Uiso 1 1 calc R U . . .
C22 C 0.4343(5) 0.6795(3) 0.89252(13) 0.0605(8) Uani 1 1 d . . . . .
H22 H 0.4406 0.6146 0.8704 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3341(5) 0.7802(3) 0.98098(14) 0.0646(8) Uani 1 1 d . . . . .
H20 H 0.2675 0.7832 1.0188 0.077 Uiso 1 1 calc R U . . .
C11 C 0.9610(5) 0.9623(2) 0.70726(13) 0.0574(8) Uani 1 1 d . . . . .
H11A H 1.0834 0.9464 0.7282 0.069 Uiso 1 1 calc R U . . .
H11B H 0.9139 1.0316 0.7227 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3419(5) 0.6828(3) 0.94980(15) 0.0700(10) Uani 1 1 d . . . . .
H21 H 0.2862 0.6206 0.9669 0.084 Uiso 1 1 calc R U . . .
C6 C 0.6474(6) 0.6758(3) 0.77356(15) 0.0726(11) Uani 1 1 d . . . . .
H6A H 0.5277 0.6337 0.7749 0.087 Uiso 1 1 calc R U . . .
H6B H 0.7439 0.6367 0.7980 0.087 Uiso 1 1 calc R U . . .
C19 C 0.9452(5) 0.8444(3) 0.83356(12) 0.0581(8) Uani 1 1 d . . . . .
H19A H 1.0377 0.9019 0.8269 0.087 Uiso 1 1 calc R U . . .
H19B H 0.9101 0.8419 0.8770 0.087 Uiso 1 1 calc R U . . .
H19C H 1.0027 0.7764 0.8215 0.087 Uiso 1 1 calc R U . . .
C2 C 0.6048(5) 0.9698(2) 0.88433(12) 0.0571(8) Uani 1 1 d . . . . .
H2A H 0.7208 0.9808 0.9096 0.069 Uiso 1 1 calc R U . . .
H2B H 0.5168 1.0300 0.8922 0.069 Uiso 1 1 calc R U . . .
C18 C 1.2717(4) 0.8336(3) 0.63132(14) 0.0647(9) Uani 1 1 d . . . . .
H18A H 1.3103 0.7659 0.6129 0.097 Uiso 1 1 calc R U . . .
H18B H 1.3618 0.8894 0.6191 0.097 Uiso 1 1 calc R U . . .
H18C H 1.2717 0.8269 0.6760 0.097 Uiso 1 1 calc R U . . .
H8 H 0.987(4) 0.741(2) 0.7143(13) 0.051(8) Uiso 1 1 d . . . . .
H9 H 0.687(4) 0.890(2) 0.7009(12) 0.046(7) Uiso 1 1 d . . . . .
H14 H 0.787(4) 0.801(2) 0.6034(13) 0.051(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.344(4) . ?
O1 C17 1.447(4) . ?
C14 C15 1.523(4) . ?
C14 C13 1.534(4) . ?
C14 C8 1.539(3) . ?
C14 H14 1.00(3) . ?
O2 C16 1.201(3) . ?
C9 C11 1.533(4) . ?
C9 C8 1.539(3) . ?
C9 C10 1.564(3) . ?
C9 H9 0.99(3) . ?
C3 N1 1.337(3) . ?
C3 C4 1.399(4) . ?
C3 C2 1.495(4) . ?
C13 C12 1.520(4) . ?
C13 C17 1.529(3) . ?
C13 C18 1.537(4) . ?
C15 C16 1.511(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N1 C20 1.328(4) . ?
C10 C19 1.529(4) . ?
C10 C5 1.533(4) . ?
C10 C1 1.537(4) . ?
C7 C6 1.514(4) . ?
C7 C8 1.524(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 C22 1.386(4) . ?
C4 C5 1.512(3) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9800 . ?
C8 H8 0.93(3) . ?
C1 C2 1.526(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C11 1.533(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C22 C21 1.379(4) . ?
C22 H22 0.9300 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C21 H21 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C16 O1 C17 121.9(2) . . ?
C15 C14 C13 109.8(2) . . ?
C15 C14 C8 113.2(2) . . ?
C13 C14 C8 113.4(2) . . ?
C15 C14 H14 104.9(16) . . ?
C13 C14 H14 106.7(16) . . ?
C8 C14 H14 108.2(16) . . ?
C11 C9 C8 110.9(2) . . ?
C11 C9 C10 113.9(2) . . ?
C8 C9 C10 112.7(2) . . ?
C11 C9 H9 108.8(16) . . ?
C8 C9 H9 102.9(16) . . ?
C10 C9 H9 106.9(16) . . ?
N1 C3 C4 122.9(3) . . ?
N1 C3 C2 115.5(2) . . ?
C4 C3 C2 121.5(2) . . ?
C12 C13 C17 108.1(2) . . ?
C12 C13 C14 108.0(2) . . ?
C17 C13 C14 106.5(2) . . ?
C12 C13 C18 111.7(3) . . ?
C17 C13 C18 109.0(2) . . ?
C14 C13 C18 113.4(2) . . ?
C16 C15 C14 116.8(2) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C20 N1 C3 118.4(3) . . ?
C19 C10 C5 110.9(2) . . ?
C19 C10 C1 109.9(2) . . ?
C5 C10 C1 106.1(2) . . ?
C19 C10 C9 111.8(2) . . ?
C5 C10 C9 108.9(2) . . ?
C1 C10 C9 109.1(2) . . ?
C6 C7 C8 113.1(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C22 C4 C3 116.9(2) . . ?
C22 C4 C5 122.3(2) . . ?
C3 C4 C5 120.8(2) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 C10 116.9(3) . . ?
C4 C5 C10 114.8(2) . . ?
C6 C5 H5 100.6 . . ?
C4 C5 H5 100.6 . . ?
C10 C5 H5 100.6 . . ?
C7 C8 C9 110.7(2) . . ?
C7 C8 C14 110.8(2) . . ?
C9 C8 C14 110.2(2) . . ?
C7 C8 H8 107.2(18) . . ?
C9 C8 H8 108.3(18) . . ?
C14 C8 H8 109.4(17) . . ?
C2 C1 C10 113.3(2) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
O2 C16 O1 118.1(2) . . ?
O2 C16 C15 122.1(3) . . ?
O1 C16 C15 119.7(3) . . ?
C13 C12 C11 112.2(2) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O1 C17 C13 113.7(2) . . ?
O1 C17 H17A 108.8 . . ?
C13 C17 H17A 108.8 . . ?
O1 C17 H17B 108.8 . . ?
C13 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C21 C22 C4 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C4 C22 H22 119.9 . . ?
N1 C20 C21 123.2(3) . . ?
N1 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C9 C11 C12 111.7(2) . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6A 107.7 . . ?
C7 C6 H6A 107.7 . . ?
C5 C6 H6B 107.7 . . ?
C7 C6 H6B 107.7 . . ?
H6A C6 H6B 107.1 . . ?
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 . . ?
C3 C2 C1 113.5(2) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C15 C14 C13 C12 174.8(2) . . . . ?
C8 C14 C13 C12 -57.4(3) . . . . ?
C15 C14 C13 C17 59.0(3) . . . . ?
C8 C14 C13 C17 -173.3(2) . . . . ?
C15 C14 C13 C18 -60.9(3) . . . . ?
C8 C14 C13 C18 66.9(3) . . . . ?
C13 C14 C15 C16 -38.6(3) . . . . ?
C8 C14 C15 C16 -166.4(2) . . . . ?
C4 C3 N1 C20 0.2(5) . . . . ?
C2 C3 N1 C20 -177.6(3) . . . . ?
C11 C9 C10 C19 -57.5(3) . . . . ?
C8 C9 C10 C19 69.9(3) . . . . ?
C11 C9 C10 C5 179.6(2) . . . . ?
C8 C9 C10 C5 -53.0(3) . . . . ?
C11 C9 C10 C1 64.2(3) . . . . ?
C8 C9 C10 C1 -168.3(2) . . . . ?
N1 C3 C4 C22 -2.0(4) . . . . ?
C2 C3 C4 C22 175.6(3) . . . . ?
N1 C3 C4 C5 176.3(3) . . . . ?
C2 C3 C4 C5 -6.1(4) . . . . ?
C22 C4 C5 C6 -12.2(5) . . . . ?
C3 C4 C5 C6 169.6(3) . . . . ?
C22 C4 C5 C10 -156.9(3) . . . . ?
C3 C4 C5 C10 24.9(4) . . . . ?
C19 C10 C5 C6 -76.4(3) . . . . ?
C1 C10 C5 C6 164.4(3) . . . . ?
C9 C10 C5 C6 47.0(4) . . . . ?
C19 C10 C5 C4 68.9(3) . . . . ?
C1 C10 C5 C4 -50.3(3) . . . . ?
C9 C10 C5 C4 -167.7(2) . . . . ?
C6 C7 C8 C9 -47.1(3) . . . . ?
C6 C7 C8 C14 -169.8(3) . . . . ?
C11 C9 C8 C7 -176.2(2) . . . . ?
C10 C9 C8 C7 54.8(3) . . . . ?
C11 C9 C8 C14 -53.2(3) . . . . ?
C10 C9 C8 C14 177.8(2) . . . . ?
C15 C14 C8 C7 -54.7(3) . . . . ?
C13 C14 C8 C7 179.3(2) . . . . ?
C15 C14 C8 C9 -177.6(2) . . . . ?
C13 C14 C8 C9 56.4(3) . . . . ?
C19 C10 C1 C2 -58.3(3) . . . . ?
C5 C10 C1 C2 61.6(3) . . . . ?
C9 C10 C1 C2 178.7(3) . . . . ?
C17 O1 C16 O2 173.1(3) . . . . ?
C17 O1 C16 C15 -9.6(4) . . . . ?
C14 C15 C16 O2 -170.2(3) . . . . ?
C14 C15 C16 O1 12.6(4) . . . . ?
C17 C13 C12 C11 171.8(3) . . . . ?
C14 C13 C12 C11 57.0(3) . . . . ?
C18 C13 C12 C11 -68.3(3) . . . . ?
C16 O1 C17 C13 33.6(4) . . . . ?
C12 C13 C17 O1 -173.4(2) . . . . ?
C14 C13 C17 O1 -57.5(3) . . . . ?
C18 C13 C17 O1 65.1(3) . . . . ?
C3 C4 C22 C21 1.6(5) . . . . ?
C5 C4 C22 C21 -176.7(3) . . . . ?
C3 N1 C20 C21 2.1(5) . . . . ?
C8 C9 C11 C12 54.3(3) . . . . ?
C10 C9 C11 C12 -177.4(2) . . . . ?
C13 C12 C11 C9 -57.3(4) . . . . ?
N1 C20 C21 C22 -2.4(6) . . . . ?
C4 C22 C21 C20 0.5(5) . . . . ?
C4 C5 C6 C7 172.5(3) . . . . ?
C10 C5 C6 C7 -43.5(5) . . . . ?
C8 C7 C6 C5 42.8(5) . . . . ?
N1 C3 C2 C1 -166.3(3) . . . . ?
C4 C3 C2 C1 15.9(4) . . . . ?
C10 C1 C2 C3 -45.1(4) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1823138'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H36 N2 O2'
_chemical_formula_weight         432.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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                   11.4355(16)
_cell_length_b                   7.2184(7)
_cell_length_c                   14.3262(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.092(10)
_cell_angle_gamma                90
_cell_volume                     1181.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1160
_cell_measurement_theta_min      3.8649
_cell_measurement_theta_max      72.4953

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.211
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            4375
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.868
_diffrn_reflns_theta_max         72.649
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_point_group_measured_fraction_full 0.685
_reflns_number_total             3096
_reflns_number_gt                2615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.254
_reflns_Friedel_fraction_max     0.293
_reflns_Friedel_fraction_full    0.316

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    
'Sheldrick GM (2015) Acta Crystallogr A 71:3--8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0739P)²+0.0648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3096
_refine_ls_number_parameters     319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
O1 O 0.4188(3) 0.5618(5) -0.29018(17) 0.0590(8) Uani 1 1 d . . . . .
O1W O 0.2529(4) -0.1574(6) -0.3422(3) 0.0789(10) Uani 1 1 d . . . . .
N1 N -0.0022(3) 0.2129(6) 0.3734(2) 0.0632(9) Uani 1 1 d . . . . .
C8 C 0.2870(3) 0.2124(5) -0.0154(2) 0.0402(7) Uani 1 1 d . . . . .
C5 C 0.1468(3) 0.1199(5) 0.1461(2) 0.0478(8) Uani 1 1 d . . . . .
C17 C 0.3596(3) 0.4026(6) -0.2550(2) 0.0463(8) Uani 1 1 d . . . . .
C14 C 0.3095(3) 0.2283(5) -0.1197(2) 0.0418(7) Uani 1 1 d . . . . .
C13 C 0.3222(3) 0.4305(5) -0.1520(2) 0.0419(8) Uani 1 1 d . . . . .
C9 C 0.1798(3) 0.3290(5) 0.0099(2) 0.0386(7) Uani 1 1 d . . . . .
C21 C 0.2950(3) 0.3235(6) -0.4219(2) 0.0483(9) Uani 1 1 d . . . . .
C22 C 0.3090(4) 0.4708(7) -0.4827(2) 0.0624(11) Uani 1 1 d . . . . .
H22 H 0.2889 0.5903 -0.4652 0.075 Uiso 1 1 calc R U . . .
C10 C 0.1597(3) 0.3244(5) 0.1168(2) 0.0386(7) Uani 1 1 d . . . . .
C20 C 0.2566(3) 0.3560(6) -0.3235(2) 0.0454(8) Uani 1 1 d . . . . .
H20A H 0.2172 0.2459 -0.3018 0.055 Uiso 1 1 calc R U . . .
H20B H 0.2007 0.4573 -0.3238 0.055 Uiso 1 1 calc R U . . .
C1 C 0.0454(3) 0.4219(6) 0.1378(2) 0.0491(8) Uani 1 1 d . . . . .
H1A H -0.0176 0.3653 0.1007 0.059 Uiso 1 1 calc R U . . .
H1B H 0.0508 0.5506 0.1189 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2670(3) 0.0110(5) 0.0134(2) 0.0479(9) Uani 1 1 d . . . . .
H7A H 0.2038 -0.0410 -0.0252 0.057 Uiso 1 1 calc R U . . .
H7B H 0.3372 -0.0603 0.0028 0.057 Uiso 1 1 calc R U . . .
C19 C 0.2620(3) 0.4165(6) 0.1723(2) 0.0510(9) Uani 1 1 d . . . . .
H19A H 0.2653 0.5456 0.1566 0.077 Uiso 1 1 calc R U . . .
H19B H 0.3341 0.3577 0.1569 0.077 Uiso 1 1 calc R U . . .
H19C H 0.2503 0.4034 0.2380 0.077 Uiso 1 1 calc R U . . .
N2 N 0.3203(3) 0.1508(5) -0.4460(2) 0.0622(10) Uani 1 1 d . . . . .
C4 C 0.1090(3) 0.0974(5) 0.2461(2) 0.0467(8) Uani 1 1 d . . . . .
C11 C 0.1806(3) 0.5261(5) -0.0307(2) 0.0474(8) Uani 1 1 d . . . . .
H11A H 0.1049 0.5828 -0.0221 0.057 Uiso 1 1 calc R U . . .
H11B H 0.2388 0.5992 0.0037 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2074(3) 0.5307(6) -0.1350(2) 0.0478(8) Uani 1 1 d . . . . .
H12A H 0.1442 0.4717 -0.1709 0.057 Uiso 1 1 calc R U . . .
H12B H 0.2129 0.6583 -0.1557 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0409(3) 0.2314(6) 0.2873(2) 0.0522(9) Uani 1 1 d . . . . .
C16 C 0.4477(3) 0.2417(7) -0.2453(2) 0.0550(10) Uani 1 1 d . . . . .
H16A H 0.4418 0.1625 -0.3000 0.066 Uiso 1 1 calc R U . . .
H16B H 0.5269 0.2894 -0.2394 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2368(5) -0.0048(6) 0.1156(3) 0.0670(13) Uani 1 1 d . . . . .
C26 C 0.1348(4) -0.0617(6) 0.2983(3) 0.0606(11) Uani 1 1 d . . . . .
H26 H 0.1804 -0.1550 0.2736 0.073 Uiso 1 1 calc R U . . .
C18 C 0.4232(3) 0.5320(7) -0.0994(2) 0.0585(10) Uani 1 1 d . . . . .
H18A H 0.4259 0.6584 -0.1200 0.088 Uiso 1 1 calc R U . . .
H18B H 0.4959 0.4721 -0.1119 0.088 Uiso 1 1 calc R U . . .
H18C H 0.4107 0.5288 -0.0335 0.088 Uiso 1 1 calc R U . . .
C15 C 0.4178(4) 0.1314(7) -0.1573(2) 0.0583(10) Uani 1 1 d . . . . .
H15A H 0.4006 0.0033 -0.1728 0.070 Uiso 1 1 calc R U . . .
H15B H 0.4823 0.1349 -0.1115 0.070 Uiso 1 1 calc R U . . .
C28 C 0.0243(4) 0.0567(8) 0.4208(3) 0.0705(13) Uani 1 1 d . . . . .
H28 H -0.0056 0.0415 0.4798 0.085 Uiso 1 1 calc R U . . .
C25 C 0.3633(4) 0.1225(8) -0.5306(3) 0.0746(14) Uani 1 1 d . . . . .
H25 H 0.3825 0.0020 -0.5473 0.089 Uiso 1 1 calc R U . . .
C27 C 0.0922(4) -0.0796(7) 0.3868(3) 0.0706(13) Uani 1 1 d . . . . .
H27 H 0.1100 -0.1839 0.4227 0.085 Uiso 1 1 calc R U . . .
C2 C 0.0150(4) 0.4143(6) 0.2411(3) 0.0611(11) Uani 1 1 d . . . . .
H2A H 0.0586 0.5103 0.2746 0.073 Uiso 1 1 calc R U . . .
H2B H -0.0676 0.4414 0.2462 0.073 Uiso 1 1 calc R U . . .
C23 C 0.3532(5) 0.4381(8) -0.5694(3) 0.0756(14) Uani 1 1 d . . . . .
H23 H 0.3641 0.5354 -0.6107 0.091 Uiso 1 1 calc R U . . .
C24 C 0.3807(4) 0.2610(9) -0.5938(3) 0.0750(15) Uani 1 1 d . . . . .
H24 H 0.4105 0.2352 -0.6520 0.090 Uiso 1 1 calc R U . . .
H8 H 0.354(3) 0.261(6) 0.021(2) 0.042(9) Uiso 1 1 d . . . . .
H9 H 0.115(3) 0.266(6) -0.020(3) 0.056(11) Uiso 1 1 d . . . . .
H14 H 0.231(3) 0.190(6) -0.155(2) 0.058(12) Uiso 1 1 d . . . . .
H1W H 0.277(5) -0.053(9) -0.375(4) 0.10(2) Uiso 1 1 d . . . . .
H2W H 0.178(8) -0.196(17) -0.362(6) 0.21(4) Uiso 1 1 d . . . . .
H6 H 0.223(4) -0.126(8) 0.129(3) 0.067(13) Uiso 1 1 d . . . . .
H1 H 0.374(7) 0.681(13) -0.299(5) 0.16(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.435(5) . ?
O1 H1 1.01(9) . ?
O1W H1W 0.94(7) . ?
O1W H2W 0.93(10) . ?
N1 C28 1.344(6) . ?
N1 C3 1.352(4) . ?
C8 C7 1.530(5) . ?
C8 C14 1.530(4) . ?
C8 C9 1.541(4) . ?
C8 H8 0.98(3) . ?
C5 C6 1.447(6) . ?
C5 C4 1.520(4) . ?
C5 C10 1.543(5) . ?
C17 C16 1.540(6) . ?
C17 C20 1.543(5) . ?
C17 C13 1.564(4) . ?
C14 C15 1.537(5) . ?
C14 C13 1.539(5) . ?
C14 H14 1.05(4) . ?
C13 C12 1.527(5) . ?
C13 C18 1.541(5) . ?
C9 C11 1.537(5) . ?
C9 C10 1.556(4) . ?
C9 H9 0.96(4) . ?
C21 N2 1.328(6) . ?
C21 C22 1.387(6) . ?
C21 C20 1.511(4) . ?
C22 C23 1.377(5) . ?
C22 H22 0.9300 . ?
C10 C1 1.524(5) . ?
C10 C19 1.542(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C1 C2 1.534(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 C6 1.520(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 C25 1.341(5) . ?
C4 C3 1.387(5) . ?
C4 C26 1.396(6) . ?
C11 C12 1.537(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 C2 1.502(6) . ?
C16 C15 1.540(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 H6 0.91(5) . ?
C26 C27 1.381(5) . ?
C26 H26 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C28 C27 1.355(7) . ?
C28 H28 0.9300 . ?
C25 C24 1.369(8) . ?
C25 H25 0.9300 . ?
C27 H27 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C23 C24 1.365(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C17 O1 H1 119(4) . . ?
H1W O1W H2W 112(7) . . ?
C28 N1 C3 117.4(4) . . ?
C7 C8 C14 111.5(3) . . ?
C7 C8 C9 109.1(3) . . ?
C14 C8 C9 110.6(3) . . ?
C7 C8 H8 109(2) . . ?
C14 C8 H8 109.8(19) . . ?
C9 C8 H8 107(2) . . ?
C6 C5 C4 116.6(3) . . ?
C6 C5 C10 115.8(3) . . ?
C4 C5 C10 113.1(3) . . ?
O1 C17 C16 108.7(3) . . ?
O1 C17 C20 108.0(3) . . ?
C16 C17 C20 112.0(3) . . ?
O1 C17 C13 112.2(3) . . ?
C16 C17 C13 102.3(3) . . ?
C20 C17 C13 113.5(3) . . ?
C8 C14 C15 118.3(3) . . ?
C8 C14 C13 112.7(3) . . ?
C15 C14 C13 103.9(3) . . ?
C8 C14 H14 106.5(19) . . ?
C15 C14 H14 113(2) . . ?
C13 C14 H14 101(2) . . ?
C12 C13 C14 108.1(3) . . ?
C12 C13 C18 109.3(3) . . ?
C14 C13 C18 112.4(3) . . ?
C12 C13 C17 118.5(3) . . ?
C14 C13 C17 101.1(3) . . ?
C18 C13 C17 107.2(3) . . ?
C11 C9 C8 113.6(3) . . ?
C11 C9 C10 113.3(3) . . ?
C8 C9 C10 111.5(3) . . ?
C11 C9 H9 107(3) . . ?
C8 C9 H9 104(2) . . ?
C10 C9 H9 107(2) . . ?
N2 C21 C22 121.7(3) . . ?
N2 C21 C20 117.5(3) . . ?
C22 C21 C20 120.7(4) . . ?
C23 C22 C21 119.3(4) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C1 C10 C19 109.8(3) . . ?
C1 C10 C5 107.3(3) . . ?
C19 C10 C5 110.5(3) . . ?
C1 C10 C9 110.0(2) . . ?
C19 C10 C9 111.2(3) . . ?
C5 C10 C9 107.9(3) . . ?
C21 C20 C17 112.7(3) . . ?
C21 C20 H20A 109.0 . . ?
C17 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C17 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C10 C1 C2 113.6(3) . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C6 C7 C8 111.9(3) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
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 . . ?
C21 N2 C25 117.9(4) . . ?
C3 C4 C26 117.2(3) . . ?
C3 C4 C5 120.6(3) . . ?
C26 C4 C5 122.1(3) . . ?
C12 C11 C9 113.1(3) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 110.3(3) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
N1 C3 C4 123.3(4) . . ?
N1 C3 C2 114.6(4) . . ?
C4 C3 C2 122.0(3) . . ?
C15 C16 C17 107.4(3) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C5 C6 C7 115.7(3) . . ?
C5 C6 H6 114(3) . . ?
C7 C6 H6 109(3) . . ?
C27 C26 C4 119.6(4) . . ?
C27 C26 H26 120.2 . . ?
C4 C26 H26 120.2 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C15 C16 104.9(3) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.8 . . ?
N1 C28 C27 123.4(3) . . ?
N1 C28 H28 118.3 . . ?
C27 C28 H28 118.3 . . ?
N2 C25 C24 123.6(5) . . ?
N2 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
C28 C27 C26 119.2(4) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C3 C2 C1 114.1(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C24 C23 C22 119.1(5) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 118.3(4) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?

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 C8 C14 C15 -62.3(5) . . . . ?
C9 C8 C14 C15 176.1(3) . . . . ?
C7 C8 C14 C13 176.4(3) . . . . ?
C9 C8 C14 C13 54.8(4) . . . . ?
C8 C14 C13 C12 -61.7(3) . . . . ?
C15 C14 C13 C12 169.1(3) . . . . ?
C8 C14 C13 C18 59.0(4) . . . . ?
C15 C14 C13 C18 -70.2(3) . . . . ?
C8 C14 C13 C17 173.1(2) . . . . ?
C15 C14 C13 C17 43.9(3) . . . . ?
O1 C17 C13 C12 84.1(4) . . . . ?
C16 C17 C13 C12 -159.7(3) . . . . ?
C20 C17 C13 C12 -38.8(5) . . . . ?
O1 C17 C13 C14 -158.1(3) . . . . ?
C16 C17 C13 C14 -41.8(3) . . . . ?
C20 C17 C13 C14 79.0(4) . . . . ?
O1 C17 C13 C18 -40.2(4) . . . . ?
C16 C17 C13 C18 76.1(4) . . . . ?
C20 C17 C13 C18 -163.0(3) . . . . ?
C7 C8 C9 C11 -170.1(3) . . . . ?
C14 C8 C9 C11 -47.1(4) . . . . ?
C7 C8 C9 C10 60.4(4) . . . . ?
C14 C8 C9 C10 -176.6(3) . . . . ?
N2 C21 C22 C23 -1.7(6) . . . . ?
C20 C21 C22 C23 174.8(4) . . . . ?
C6 C5 C10 C1 168.6(3) . . . . ?
C4 C5 C10 C1 -53.0(4) . . . . ?
C6 C5 C10 C19 -71.7(4) . . . . ?
C4 C5 C10 C19 66.7(4) . . . . ?
C6 C5 C10 C9 50.0(4) . . . . ?
C4 C5 C10 C9 -171.6(3) . . . . ?
C11 C9 C10 C1 56.9(4) . . . . ?
C8 C9 C10 C1 -173.4(3) . . . . ?
C11 C9 C10 C19 -65.0(4) . . . . ?
C8 C9 C10 C19 64.6(4) . . . . ?
C11 C9 C10 C5 173.7(3) . . . . ?
C8 C9 C10 C5 -56.7(4) . . . . ?
N2 C21 C20 C17 91.6(4) . . . . ?
C22 C21 C20 C17 -85.1(4) . . . . ?
O1 C17 C20 C21 56.8(4) . . . . ?
C16 C17 C20 C21 -62.9(4) . . . . ?
C13 C17 C20 C21 -178.1(3) . . . . ?
C19 C10 C1 C2 -60.6(4) . . . . ?
C5 C10 C1 C2 59.6(4) . . . . ?
C9 C10 C1 C2 176.7(3) . . . . ?
C14 C8 C7 C6 -176.3(3) . . . . ?
C9 C8 C7 C6 -53.8(4) . . . . ?
C22 C21 N2 C25 1.8(6) . . . . ?
C20 C21 N2 C25 -174.8(3) . . . . ?
C6 C5 C4 C3 167.4(4) . . . . ?
C10 C5 C4 C3 29.3(5) . . . . ?
C6 C5 C4 C26 -16.5(6) . . . . ?
C10 C5 C4 C26 -154.6(4) . . . . ?
C8 C9 C11 C12 48.2(4) . . . . ?
C10 C9 C11 C12 176.7(3) . . . . ?
C14 C13 C12 C11 60.1(4) . . . . ?
C18 C13 C12 C11 -62.6(4) . . . . ?
C17 C13 C12 C11 174.2(3) . . . . ?
C9 C11 C12 C13 -54.8(4) . . . . ?
C28 N1 C3 C4 0.8(6) . . . . ?
C28 N1 C3 C2 -175.9(4) . . . . ?
C26 C4 C3 N1 -1.2(6) . . . . ?
C5 C4 C3 N1 175.1(3) . . . . ?
C26 C4 C3 C2 175.3(4) . . . . ?
C5 C4 C3 C2 -8.4(6) . . . . ?
O1 C17 C16 C15 143.6(3) . . . . ?
C20 C17 C16 C15 -97.1(4) . . . . ?
C13 C17 C16 C15 24.8(4) . . . . ?
C4 C5 C6 C7 175.8(4) . . . . ?
C10 C5 C6 C7 -47.3(5) . . . . ?
C8 C7 C6 C5 48.4(5) . . . . ?
C3 C4 C26 C27 0.2(6) . . . . ?
C5 C4 C26 C27 -176.0(4) . . . . ?
C8 C14 C15 C16 -154.3(3) . . . . ?
C13 C14 C15 C16 -28.6(4) . . . . ?
C17 C16 C15 C14 1.9(4) . . . . ?
C3 N1 C28 C27 0.7(7) . . . . ?
C21 N2 C25 C24 -1.1(7) . . . . ?
N1 C28 C27 C26 -1.7(8) . . . . ?
C4 C26 C27 C28 1.1(7) . . . . ?
N1 C3 C2 C1 -170.0(3) . . . . ?
C4 C3 C2 C1 13.3(6) . . . . ?
C10 C1 C2 C3 -40.1(5) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C22 C23 C24 C25 -0.1(7) . . . . ?
N2 C25 C24 C23 0.3(7) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1823139'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H32 N2'
_chemical_formula_weight         396.55

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.8675(2)
_cell_length_b                   12.2525(4)
_cell_length_c                   23.0556(8)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2222.47(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2225
_cell_measurement_theta_min      4.1010
_cell_measurement_theta_max      72.3040

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.165
_exptl_absorpt_coefficient_mu    0.519
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            5374
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.834
_diffrn_reflns_theta_max         66.996
_diffrn_reflns_theta_full        66.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.836
_reflns_number_total             3316
_reflns_number_gt                2995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.457
_reflns_Friedel_fraction_max     0.619
_reflns_Friedel_fraction_full    0.619

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    
'Sheldrick GM (2015) Acta Crystallogr A 71:3--8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1029P)²+0.2927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3316
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.0842(4) 0.7606(3) 0.16044(14) 0.0613(8) Uani 1 1 d . . . . .
C9 C 0.4014(4) 1.0190(2) -0.01632(14) 0.0425(7) Uani 1 1 d . . . . .
C10 C 0.3064(4) 0.9303(3) 0.01833(15) 0.0444(7) Uani 1 1 d . . . . .
C7 C 0.1325(5) 1.1290(3) -0.02763(17) 0.0552(8) Uani 1 1 d . . . . .
H7A H 0.0543 1.1592 -0.0559 0.066 Uiso 1 1 calc R U . . .
H7B H 0.1711 1.1883 -0.0030 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2838(4) 1.0804(3) -0.05901(14) 0.0461(7) Uani 1 1 d . . . . .
C22 C 0.9914(4) 1.3001(3) -0.22968(15) 0.0467(7) Uani 1 1 d . . . . .
H22 H 1.0294 1.2282 -0.2291 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6070(5) 1.2251(3) -0.15317(14) 0.0476(8) Uani 1 1 d . . . . .
C1 C 0.4195(4) 0.8878(3) 0.06789(16) 0.0501(8) Uani 1 1 d . . . . .
H1A H 0.5234 0.8583 0.0515 0.060 Uiso 1 1 calc R U . . .
H1B H 0.4503 0.9484 0.0928 0.060 Uiso 1 1 calc R U . . .
C3 C 0.1511(4) 0.8246(3) 0.11937(16) 0.0498(8) Uani 1 1 d . . . . .
C27 C -0.1774(5) 0.8555(3) 0.14962(16) 0.0581(9) Uani 1 1 d . . . . .
H27 H -0.2899 0.8646 0.1610 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5410(4) 1.1224(3) -0.12372(15) 0.0466(7) Uani 1 1 d . . . . .
C20 C 0.7686(5) 1.2395(3) -0.16820(15) 0.0492(8) Uani 1 1 d . . . . .
C2 C 0.3339(4) 0.8001(3) 0.10430(18) 0.0570(9) Uani 1 1 d . . . . .
H2A H 0.3383 0.7315 0.0833 0.068 Uiso 1 1 calc R U . . .
H2B H 0.3977 0.7908 0.1400 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1480(4) 0.9834(3) 0.04803(16) 0.0504(8) Uani 1 1 d . . . . .
C26 C -0.0779(5) 0.7778(4) 0.17474(17) 0.0641(10) Uani 1 1 d . . . . .
H26 H -0.1256 0.7343 0.2035 0.077 Uiso 1 1 calc R U . . .
C12 C 0.6582(4) 1.0651(3) -0.08105(16) 0.0505(8) Uani 1 1 d . . . . .
H12A H 0.7049 1.1182 -0.0542 0.061 Uiso 1 1 calc R U . . .
H12B H 0.7520 1.0321 -0.1020 0.061 Uiso 1 1 calc R U . . .
C28 C -0.1078(4) 0.9203(3) 0.10717(15) 0.0525(8) Uani 1 1 d . . . . .
H28 H -0.1743 0.9731 0.0891 0.063 Uiso 1 1 calc R U . . .
C15 C 0.3033(5) 1.2443(3) -0.13342(17) 0.0572(9) Uani 1 1 d . . . . .
H15A H 0.2325 1.2976 -0.1138 0.069 Uiso 1 1 calc R U . . .
H15B H 0.2344 1.2040 -0.1609 0.069 Uiso 1 1 calc R U . . .
C19 C 0.2508(5) 0.8346(3) -0.02085(17) 0.0573(9) Uani 1 1 d . . . . .
H19A H 0.3482 0.7912 -0.0307 0.086 Uiso 1 1 calc R U . . .
H19B H 0.2002 0.8628 -0.0556 0.086 Uiso 1 1 calc R U . . .
H19C H 0.1695 0.7904 -0.0006 0.086 Uiso 1 1 calc R U . . .
C21 C 0.8493(4) 1.3291(3) -0.20110(14) 0.0467(7) Uani 1 1 d . . . . .
C14 C 0.3884(4) 1.1679(3) -0.09015(15) 0.0455(7) Uani 1 1 d . . . . .
C16 C 0.4557(5) 1.2999(3) -0.16388(18) 0.0613(10) Uani 1 1 d . . . . .
H16A H 0.4342 1.3075 -0.2051 0.074 Uiso 1 1 calc R U . . .
H16B H 0.4762 1.3717 -0.1476 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5633(4) 0.9767(3) -0.04695(16) 0.0504(8) Uani 1 1 d . . . . .
H11A H 0.6393 0.9463 -0.0181 0.060 Uiso 1 1 calc R U . . .
H11B H 0.5319 0.9184 -0.0733 0.060 Uiso 1 1 calc R U . . .
C6 C 0.0390(5) 1.0453(3) 0.0094(2) 0.0701(12) Uani 1 1 d . . . . .
N2 N 0.7893(5) 1.4352(3) -0.20224(17) 0.0754(10) Uani 1 1 d . . . . .
C25 C 0.8800(6) 1.5137(3) -0.23258(19) 0.0666(10) Uani 1 1 d . . . . .
H25 H 0.8421 1.5856 -0.2337 0.080 Uiso 1 1 calc R U . . .
C4 C 0.0616(4) 0.9073(3) 0.09092(14) 0.0462(7) Uani 1 1 d . . . . .
C18 C 0.4897(6) 1.0433(3) -0.17311(17) 0.0618(10) Uani 1 1 d . . . . .
H18A H 0.5901 1.0137 -0.1907 0.093 Uiso 1 1 calc R U . . .
H18B H 0.4249 1.0822 -0.2017 0.093 Uiso 1 1 calc R U . . .
H18C H 0.4221 0.9851 -0.1575 0.093 Uiso 1 1 calc R U . . .
C23 C 1.0759(6) 1.3758(4) -0.2586(2) 0.0712(11) Uani 1 1 d . . . . .
H23 H 1.1738 1.3556 -0.2785 0.085 Uiso 1 1 calc R U . . .
C24 C 1.0249(6) 1.4842(4) -0.26062(19) 0.0697(11) Uani 1 1 d . . . . .
H24 H 1.0886 1.5357 -0.2808 0.084 Uiso 1 1 calc R U . . .
H14 H 0.442(4) 1.208(2) -0.0603(14) 0.035(8) Uiso 1 1 d . . . . .
H9 H 0.444(5) 1.078(3) 0.0146(17) 0.058(10) Uiso 1 1 d . . . . .
H20 H 0.843(5) 1.180(3) -0.1587(18) 0.064(11) Uiso 1 1 d . . . . .
H6 H -0.059(5) 1.082(3) 0.0345(15) 0.052(10) Uiso 1 1 d . . . . .
H8 H 0.236(5) 1.019(3) -0.0883(15) 0.059(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C26 1.334(5) . ?
N1 C3 1.337(5) . ?
C9 C10 1.542(4) . ?
C9 C11 1.545(4) . ?
C9 C8 1.547(5) . ?
C9 H9 1.07(4) . ?
C10 C1 1.539(5) . ?
C10 C19 1.543(5) . ?
C10 C5 1.564(4) . ?
C7 C8 1.515(5) . ?
C7 C6 1.524(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.531(4) . ?
C8 H8 1.08(4) . ?
C22 C23 1.322(5) . ?
C22 C21 1.346(5) . ?
C22 H22 0.9300 . ?
C17 C20 1.329(5) . ?
C17 C13 1.521(5) . ?
C17 C16 1.523(5) . ?
C1 C2 1.521(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.397(5) . ?
C3 C2 1.510(5) . ?
C27 C26 1.362(6) . ?
C27 C28 1.373(5) . ?
C27 H27 0.9300 . ?
C13 C12 1.520(5) . ?
C13 C14 1.533(5) . ?
C13 C18 1.549(5) . ?
C20 C21 1.477(5) . ?
C20 H20 0.96(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.450(5) . ?
C5 C4 1.520(5) . ?
C26 H26 0.9300 . ?
C12 C11 1.533(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C28 C4 1.394(5) . ?
C28 H28 0.9300 . ?
C15 C14 1.523(5) . ?
C15 C16 1.547(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 N2 1.384(5) . ?
C14 H14 0.94(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6 1.06(4) . ?
N2 C25 1.386(5) . ?
C25 C24 1.360(6) . ?
C25 H25 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C23 C24 1.388(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C26 N1 C3 117.3(4) . . ?
C10 C9 C11 113.6(3) . . ?
C10 C9 C8 112.5(3) . . ?
C11 C9 C8 111.4(3) . . ?
C10 C9 H9 106(2) . . ?
C11 C9 H9 106(2) . . ?
C8 C9 H9 106(2) . . ?
C1 C10 C9 110.0(3) . . ?
C1 C10 C19 109.9(3) . . ?
C9 C10 C19 111.7(3) . . ?
C1 C10 C5 106.1(3) . . ?
C9 C10 C5 108.7(3) . . ?
C19 C10 C5 110.3(3) . . ?
C8 C7 C6 112.5(3) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C14 111.8(3) . . ?
C7 C8 C9 111.0(3) . . ?
C14 C8 C9 108.5(3) . . ?
C7 C8 H8 107(2) . . ?
C14 C8 H8 112.6(19) . . ?
C9 C8 H8 105(2) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C20 C17 C13 123.6(3) . . ?
C20 C17 C16 128.7(3) . . ?
C13 C17 C16 107.6(3) . . ?
C2 C1 C10 113.1(3) . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C10 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C3 C4 124.0(3) . . ?
N1 C3 C2 114.9(3) . . ?
C4 C3 C2 121.1(3) . . ?
C26 C27 C28 118.5(4) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
C12 C13 C17 117.6(3) . . ?
C12 C13 C14 108.4(3) . . ?
C17 C13 C14 101.1(3) . . ?
C12 C13 C18 110.2(3) . . ?
C17 C13 C18 106.2(3) . . ?
C14 C13 C18 113.2(3) . . ?
C17 C20 C21 130.1(3) . . ?
C17 C20 H20 115(2) . . ?
C21 C20 H20 115(2) . . ?
C3 C2 C1 114.1(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 C10 114.8(3) . . ?
C4 C5 C10 112.7(3) . . ?
N1 C26 C27 123.7(4) . . ?
N1 C26 H26 118.1 . . ?
C27 C26 H26 118.1 . . ?
C13 C12 C11 111.3(3) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C27 C28 C4 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C4 C28 H28 119.8 . . ?
C14 C15 C16 103.1(3) . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
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 . . ?
C22 C21 N2 121.5(3) . . ?
C22 C21 C20 114.3(3) . . ?
N2 C21 C20 124.1(3) . . ?
C15 C14 C8 120.1(3) . . ?
C15 C14 C13 103.7(3) . . ?
C8 C14 C13 113.8(3) . . ?
C15 C14 H14 110.6(18) . . ?
C8 C14 H14 105.1(18) . . ?
C13 C14 H14 102(2) . . ?
C17 C16 C15 105.5(3) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C12 C11 C9 113.5(3) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C6 C7 114.3(3) . . ?
C5 C6 H6 108.3(19) . . ?
C7 C6 H6 112.0(18) . . ?
C21 N2 C25 119.1(4) . . ?
C24 C25 N2 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
N2 C25 H25 120.4 . . ?
C28 C4 C3 116.0(3) . . ?
C28 C4 C5 122.2(3) . . ?
C3 C4 C5 121.7(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C23 C24 122.9(4) . . ?
C22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C25 C24 C23 118.7(4) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?

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
C11 C9 C10 C1 63.2(4) . . . . ?
C8 C9 C10 C1 -169.0(3) . . . . ?
C11 C9 C10 C19 -59.2(4) . . . . ?
C8 C9 C10 C19 68.6(3) . . . . ?
C11 C9 C10 C5 179.0(3) . . . . ?
C8 C9 C10 C5 -53.3(3) . . . . ?
C6 C7 C8 C14 -173.2(3) . . . . ?
C6 C7 C8 C9 -51.9(4) . . . . ?
C10 C9 C8 C7 55.5(4) . . . . ?
C11 C9 C8 C7 -175.6(3) . . . . ?
C10 C9 C8 C14 178.7(3) . . . . ?
C11 C9 C8 C14 -52.4(3) . . . . ?
C9 C10 C1 C2 179.8(3) . . . . ?
C19 C10 C1 C2 -56.8(4) . . . . ?
C5 C10 C1 C2 62.4(3) . . . . ?
C26 N1 C3 C4 -0.1(6) . . . . ?
C26 N1 C3 C2 -179.0(4) . . . . ?
C20 C17 C13 C12 34.8(5) . . . . ?
C16 C17 C13 C12 -148.1(3) . . . . ?
C20 C17 C13 C14 152.6(3) . . . . ?
C16 C17 C13 C14 -30.3(3) . . . . ?
C20 C17 C13 C18 -89.1(4) . . . . ?
C16 C17 C13 C18 88.1(3) . . . . ?
C13 C17 C20 C21 174.2(3) . . . . ?
C16 C17 C20 C21 -2.3(6) . . . . ?
N1 C3 C2 C1 -167.2(3) . . . . ?
C4 C3 C2 C1 13.9(5) . . . . ?
C10 C1 C2 C3 -43.6(4) . . . . ?
C1 C10 C5 C6 169.8(3) . . . . ?
C9 C10 C5 C6 51.6(4) . . . . ?
C19 C10 C5 C6 -71.2(4) . . . . ?
C1 C10 C5 C4 -52.5(3) . . . . ?
C9 C10 C5 C4 -170.8(3) . . . . ?
C19 C10 C5 C4 66.4(4) . . . . ?
C3 N1 C26 C27 0.6(6) . . . . ?
C28 C27 C26 N1 -0.1(6) . . . . ?
C17 C13 C12 C11 169.5(3) . . . . ?
C14 C13 C12 C11 55.6(4) . . . . ?
C18 C13 C12 C11 -68.7(4) . . . . ?
C26 C27 C28 C4 -0.9(5) . . . . ?
C23 C22 C21 N2 1.1(5) . . . . ?
C23 C22 C21 C20 -177.6(4) . . . . ?
C17 C20 C21 C22 -153.1(4) . . . . ?
C17 C20 C21 N2 28.4(6) . . . . ?
C16 C15 C14 C8 -167.9(3) . . . . ?
C16 C15 C14 C13 -39.5(4) . . . . ?
C7 C8 C14 C15 -55.0(4) . . . . ?
C9 C8 C14 C15 -177.7(3) . . . . ?
C7 C8 C14 C13 -178.7(3) . . . . ?
C9 C8 C14 C13 58.6(3) . . . . ?
C12 C13 C14 C15 167.4(3) . . . . ?
C17 C13 C14 C15 43.1(3) . . . . ?
C18 C13 C14 C15 -70.0(4) . . . . ?
C12 C13 C14 C8 -60.4(4) . . . . ?
C17 C13 C14 C8 175.3(3) . . . . ?
C18 C13 C14 C8 62.2(4) . . . . ?
C20 C17 C16 C15 -176.5(4) . . . . ?
C13 C17 C16 C15 6.5(4) . . . . ?
C14 C15 C16 C17 20.2(4) . . . . ?
C13 C12 C11 C9 -53.9(4) . . . . ?
C10 C9 C11 C12 -179.6(3) . . . . ?
C8 C9 C11 C12 52.1(4) . . . . ?
C4 C5 C6 C7 173.5(3) . . . . ?
C10 C5 C6 C7 -50.8(5) . . . . ?
C8 C7 C6 C5 50.7(5) . . . . ?
C22 C21 N2 C25 -1.4(6) . . . . ?
C20 C21 N2 C25 177.1(3) . . . . ?
C21 N2 C25 C24 0.3(6) . . . . ?
C27 C28 C4 C3 1.2(5) . . . . ?
C27 C28 C4 C5 -174.5(3) . . . . ?
N1 C3 C4 C28 -0.7(5) . . . . ?
C2 C3 C4 C28 178.1(3) . . . . ?
N1 C3 C4 C5 175.1(3) . . . . ?
C2 C3 C4 C5 -6.1(5) . . . . ?
C6 C5 C4 C28 -21.1(5) . . . . ?
C10 C5 C4 C28 -157.6(3) . . . . ?
C6 C5 C4 C3 163.4(4) . . . . ?
C10 C5 C4 C3 26.9(4) . . . . ?
C21 C22 C23 C24 0.3(7) . . . . ?
N2 C25 C24 C23 1.0(6) . . . . ?
C22 C23 C24 C25 -1.3(7) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.045

