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

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

data_1dh444
_database_code_depnum_ccdc_archive 'CCDC 1524381'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N2 O, C2 H6 O'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.4563(5)
_cell_length_b                   18.7494(8)
_cell_length_c                   9.4799(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.253(3)
_cell_angle_gamma                90
_cell_volume                     2036.23(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9820
_cell_measurement_theta_min      4.1620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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_F_000             800
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30771
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.075
_diffrn_reflns_theta_min         3.531
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -84.00  -53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  153.0000    1.4328 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  -99.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00  -55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  153.0000  -76.6376 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   38.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega  -18.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   57.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -99.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega  -71.00   73.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348    0.0000  -30.0000 144

#__ type_ start__ end____ width___ exp.time_
  8 omega    0.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348 -113.0000 -165.1299 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0290749000
_diffrn_orient_matrix_UB_12      -0.0278650000
_diffrn_orient_matrix_UB_13      -0.0362471000
_diffrn_orient_matrix_UB_21      0.0539447000
_diffrn_orient_matrix_UB_22      0.0180011000
_diffrn_orient_matrix_UB_23      0.0092896000
_diffrn_orient_matrix_UB_31      0.0088427000
_diffrn_orient_matrix_UB_32      -0.0181852000
_diffrn_orient_matrix_UB_33      0.0647909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3545
_reflns_number_total             4900
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.033
_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)+(0.0685P)²+1.0141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_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
O1 O 0.58309(18) 0.63031(12) 1.28302(16) 0.0858(6) Uani 1 1 d . . . . .
N1 N 0.59125(14) 0.65934(9) 1.04916(16) 0.0451(4) Uani 1 1 d . . . . .
N2 N 0.51119(14) 0.59962(9) 0.68898(16) 0.0447(4) Uani 1 1 d . . . . .
H2 H 0.5662 0.5767 0.6474 0.054 Uiso 1 1 calc R . . . .
C1 C 0.62229(16) 0.62532(9) 0.91571(18) 0.0396(4) Uani 1 1 d . . . . .
C2 C 0.51638(16) 0.62815(9) 0.82268(18) 0.0404(4) Uani 1 1 d . . . . .
C3 C 0.40249(16) 0.61428(10) 0.6336(2) 0.0442(4) Uani 1 1 d . . . . .
C4 C 0.3576(2) 0.59844(12) 0.5005(2) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.4016 0.5741 0.4339 0.068 Uiso 1 1 calc R . . . .
C5 C 0.2454(2) 0.62033(13) 0.4719(3) 0.0656(6) Uani 1 1 d . . . . .
H5 H 0.2128 0.6109 0.3838 0.079 Uiso 1 1 calc R . . . .
C6 C 0.1794(2) 0.65644(13) 0.5725(3) 0.0648(6) Uani 1 1 d . . . . .
H6 H 0.1036 0.6702 0.5501 0.078 Uiso 1 1 calc R . . . .
C7 C 0.22353(18) 0.67211(12) 0.7033(3) 0.0569(5) Uani 1 1 d . . . . .
H7 H 0.1784 0.6962 0.7693 0.068 Uiso 1 1 calc R . . . .
C8 C 0.33806(16) 0.65124(10) 0.7360(2) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.41312(16) 0.66010(10) 0.85620(19) 0.0420(4) Uani 1 1 d . . . . .
C10 C 0.39559(18) 0.70088(11) 0.9905(2) 0.0524(5) Uani 1 1 d . . . . .
H10A H 0.3535 0.6717 1.0578 0.063 Uiso 1 1 calc R . . . .
H10B H 0.3500 0.7435 0.9719 0.063 Uiso 1 1 calc R . . . .
C11 C 0.51447(19) 0.72133(11) 1.0510(2) 0.0534(5) Uani 1 1 d . . . . .
H11A H 0.5483 0.7594 0.9953 0.064 Uiso 1 1 calc R . . . .
H11B H 0.5056 0.7383 1.1470 0.064 Uiso 1 1 calc R . . . .
C12 C 0.60482(18) 0.61450(13) 1.1591(2) 0.0555(5) Uani 1 1 d . . . . .
C13 C 0.64676(19) 0.54665(12) 1.1020(2) 0.0562(5) Uani 1 1 d . . . . .
H13 H 0.6654 0.5067 1.1558 0.067 Uiso 1 1 calc R . . . .
C14 C 0.65428(16) 0.55034(10) 0.9640(2) 0.0456(4) Uani 1 1 d . . . . .
C15 C 0.6881(2) 0.49342(12) 0.8626(3) 0.0650(6) Uani 1 1 d . . . . .
H15A H 0.6205 0.4782 0.8105 0.097 Uiso 1 1 calc GR . . . .
H15B H 0.7202 0.4536 0.9134 0.097 Uiso 1 1 calc GR . . . .
H15C H 0.7454 0.5117 0.7985 0.097 Uiso 1 1 calc GR . . . .
C16 C 0.72704(17) 0.66445(11) 0.8468(2) 0.0473(5) Uani 1 1 d . . . . .
H16A H 0.7433 0.6423 0.7564 0.057 Uiso 1 1 calc R . . . .
H16B H 0.7050 0.7136 0.8289 0.057 Uiso 1 1 calc R . . . .
C17 C 0.83691(17) 0.66379(11) 0.9344(2) 0.0484(5) Uani 1 1 d . . . . .
C18 C 0.8515(2) 0.70997(14) 1.0467(3) 0.0648(6) Uani 1 1 d . . . . .
H18 H 0.7928 0.7425 1.0677 0.078 Uiso 1 1 calc R . . . .
C19 C 0.9517(3) 0.70870(18) 1.1284(3) 0.0847(9) Uani 1 1 d . . . . .
H19 H 0.9597 0.7400 1.2040 0.102 Uiso 1 1 calc R . . . .
C20 C 1.0389(3) 0.6615(2) 1.0981(3) 0.0890(9) Uani 1 1 d . . . . .
H20 H 1.1061 0.6605 1.1535 0.107 Uiso 1 1 calc R . . . .
C21 C 1.0275(2) 0.61597(18) 0.9869(3) 0.0845(8) Uani 1 1 d . . . . .
H21 H 1.0873 0.5843 0.9657 0.101 Uiso 1 1 calc R . . . .
C22 C 0.9266(2) 0.61682(14) 0.9053(3) 0.0660(6) Uani 1 1 d . . . . .
H22 H 0.9193 0.5853 0.8300 0.079 Uiso 1 1 calc R . . . .
O2 O 0.71278(17) 0.58412(14) 0.50513(18) 0.0915(7) Uani 1 1 d . . . . .
H2A H 0.6811 0.5944 0.4301 0.137 Uiso 1 1 calc GR . . . .
C23 C 0.8351(4) 0.5781(3) 0.4845(4) 0.1419(18) Uani 1 1 d . . . . .
H23A H 0.8671 0.6258 0.4939 0.170 Uiso 1 1 calc R . . . .
H23B H 0.8654 0.5506 0.5632 0.170 Uiso 1 1 calc R . . . .
C24 C 0.8820(4) 0.5497(3) 0.3658(4) 0.1361(16) Uani 1 1 d . . . . .
H24A H 0.8482 0.5036 0.3486 0.204 Uiso 1 1 calc GR . . . .
H24B H 0.9649 0.5449 0.3778 0.204 Uiso 1 1 calc GR . . . .
H24C H 0.8660 0.5804 0.2871 0.204 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.238(3) . ?
N1 C1 1.462(2) . ?
N1 C11 1.458(3) . ?
N1 C12 1.348(3) . ?
N2 H2 0.8600 . ?
N2 C2 1.377(2) . ?
N2 C3 1.377(2) . ?
C1 C2 1.498(2) . ?
C1 C14 1.523(3) . ?
C1 C16 1.553(3) . ?
C2 C9 1.365(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.405(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.403(3) . ?
C8 C9 1.434(3) . ?
C9 C10 1.499(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.525(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.464(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.314(3) . ?
C14 C15 1.488(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.505(3) . ?
C17 C18 1.382(3) . ?
C17 C22 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9300 . ?
O2 H2A 0.8200 . ?
O2 C23 1.420(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.358(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C11 N1 C1 120.49(15) . . ?
C12 N1 C1 111.67(16) . . ?
C12 N1 C11 123.76(17) . . ?
C2 N2 H2 126.0 . . ?
C2 N2 C3 107.98(15) . . ?
C3 N2 H2 126.0 . . ?
N1 C1 C2 107.13(14) . . ?
N1 C1 C14 101.65(14) . . ?
N1 C1 C16 110.44(15) . . ?
C2 C1 C14 113.76(15) . . ?
C2 C1 C16 111.15(15) . . ?
C14 C1 C16 112.16(15) . . ?
N2 C2 C1 124.05(16) . . ?
C9 C2 N2 110.54(16) . . ?
C9 C2 C1 125.39(16) . . ?
N2 C3 C4 129.25(19) . . ?
N2 C3 C8 108.18(16) . . ?
C4 C3 C8 122.56(19) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 C9 106.92(16) . . ?
C7 C8 C3 118.59(19) . . ?
C7 C8 C9 134.47(19) . . ?
C2 C9 C8 106.35(16) . . ?
C2 C9 C10 122.76(17) . . ?
C8 C9 C10 130.66(17) . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C9 C10 C11 108.98(16) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
N1 C11 C10 109.44(16) . . ?
N1 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O1 C12 N1 124.2(2) . . ?
O1 C12 C13 128.8(2) . . ?
N1 C12 C13 107.04(17) . . ?
C12 C13 H13 124.9 . . ?
C14 C13 C12 110.21(18) . . ?
C14 C13 H13 124.9 . . ?
C13 C14 C1 109.34(18) . . ?
C13 C14 C15 128.6(2) . . ?
C15 C14 C1 122.07(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16A 108.7 . . ?
C1 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C1 114.16(15) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 C22 117.8(2) . . ?
C22 C17 C16 121.0(2) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.9(3) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C23 O2 H2A 109.5 . . ?
O2 C23 H23A 106.7 . . ?
O2 C23 H23B 106.7 . . ?
H23A C23 H23B 106.6 . . ?
C24 C23 O2 122.6(4) . . ?
C24 C23 H23A 106.7 . . ?
C24 C23 H23B 106.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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_idh502
_database_code_depnum_ccdc_archive 'CCDC 1524380'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H24 N2 O)'
_chemical_formula_sum            'C40 H48 N4 O2'
_chemical_formula_weight         616.82
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7853(6)
_cell_length_b                   15.0292(8)
_cell_length_c                   19.3138(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.062(6)
_cell_angle_gamma                90
_cell_volume                     3547.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5324
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3640
_cell_measurement_theta_min      4.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.040
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   31.00   69.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629 -160.0000  -96.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   51.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -99.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   43.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   38.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   15.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -38.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   35.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -57.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   19.0000   30.0000 121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0141888000
_diffrn_orient_matrix_UB_12      0.0069509000
_diffrn_orient_matrix_UB_13      0.0379498000
_diffrn_orient_matrix_UB_21      0.0086361000
_diffrn_orient_matrix_UB_22      -0.0463668000
_diffrn_orient_matrix_UB_23      0.0058139000
_diffrn_orient_matrix_UB_31      0.0556014000
_diffrn_orient_matrix_UB_32      0.0054439000
_diffrn_orient_matrix_UB_33      0.0011641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4579
_reflns_number_total             8219
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    ?
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8219
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.029
_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)+(0.0488P)²+1.9298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1756
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C233
 1.54 with sigma of 0.005
 C22-C233
 1.54 with sigma of 0.005
 C22-C23
 1.54 with sigma of 0.005
 C24-C23
 1.54 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C233)
4. Others
 Sof(H22C)=Sof(H22D)=Sof(H24C)=Sof(H24D)=Sof(C233)=Sof(H23C)=Sof(H23D)=1-FVAR(1)
 Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H24A)=Sof(H24B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B), C0AA(H0AA,H0AB), C22(H22A,H22B), C22(H22C,H22D), C23(H23A,
 H23B), C24(H24A,H24B), C24(H24C,H24D), C37(H37A,H37B), C38(H38A,H38B),
 C233(H23C,H23D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), N3(H3), C27(H27),
 C28(H28), C29(H29), C30(H30), C34(H34)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C36(H36A,H36B,H36C), C39(H39A,H39B,
 H39C)
;
_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
O1 O -0.04960(15) 0.43849(15) 0.40985(12) 0.0808(7) Uani 1 1 d . . . . .
N1 N 0.24830(15) 0.57000(13) 0.55419(11) 0.0481(5) Uani 1 1 d . . . . .
H1 H 0.1866 0.5549 0.5600 0.058 Uiso 1 1 calc R . . . .
N2 N 0.12405(15) 0.48250(13) 0.41681(11) 0.0477(5) Uani 1 1 d . . . . .
C1 C 0.18554(19) 0.56550(16) 0.41713(13) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.2451(2) 0.56303(19) 0.35799(14) 0.0622(7) Uani 1 1 d . . . . .
H2A H 0.2733 0.5034 0.3562 0.075 Uiso 1 1 calc R . . . .
H2B H 0.1919 0.5746 0.3115 0.075 Uiso 1 1 calc R . . . .
C3 C 0.3390(2) 0.6288(2) 0.36836(17) 0.0791(9) Uani 1 1 d . . . . .
H3A H 0.3714 0.6216 0.3292 0.095 Uiso 1 1 calc R . . . .
H3B H 0.3103 0.6889 0.3658 0.095 Uiso 1 1 calc R . . . .
C4 C 0.4265(2) 0.6168(2) 0.43956(15) 0.0639(7) Uani 1 1 d . . . . .
H4A H 0.4714 0.5658 0.4367 0.077 Uiso 1 1 calc R . . . .
H4B H 0.4732 0.6690 0.4496 0.077 Uiso 1 1 calc R . . . .
C5 C 0.37570(18) 0.60327(16) 0.49957(13) 0.0469(6) Uani 1 1 d . . . . .
C6 C 0.42359(18) 0.61043(15) 0.57595(14) 0.0474(6) Uani 1 1 d . . . . .
C7 C 0.5274(2) 0.63369(19) 0.62071(16) 0.0626(7) Uani 1 1 d . . . . .
H7 H 0.5829 0.6483 0.6006 0.075 Uiso 1 1 calc R . . . .
C8 C 0.5468(2) 0.6348(2) 0.69402(17) 0.0737(9) Uani 1 1 d . . . . .
H8 H 0.6158 0.6506 0.7236 0.088 Uiso 1 1 calc R . . . .
C9 C 0.4654(2) 0.6128(2) 0.72532(16) 0.0695(8) Uani 1 1 d . . . . .
H9 H 0.4807 0.6141 0.7754 0.083 Uiso 1 1 calc R . . . .
C10 C 0.3619(2) 0.58913(18) 0.68307(14) 0.0585(7) Uani 1 1 d . . . . .
H10 H 0.3074 0.5739 0.7039 0.070 Uiso 1 1 calc R . . . .
C11 C 0.34230(18) 0.58883(15) 0.60864(13) 0.0460(6) Uani 1 1 d . . . . .
C12 C 0.26958(18) 0.57945(15) 0.48876(13) 0.0431(5) Uani 1 1 d . . . . .
C13 C 0.0941(2) 0.63370(18) 0.40343(15) 0.0601(7) Uani 1 1 d . . . . .
C14 C 0.0008(2) 0.5930(2) 0.39808(16) 0.0697(8) Uani 1 1 d . . . . .
H14 H -0.0665 0.6215 0.3890 0.084 Uiso 1 1 calc R . . . .
C15 C 0.0169(2) 0.49695(19) 0.40830(14) 0.0567(7) Uani 1 1 d . . . . .
C16 C 0.1146(3) 0.7310(2) 0.3978(2) 0.0964(11) Uani 1 1 d . . . . .
H16A H 0.1775 0.7483 0.4365 0.145 Uiso 1 1 calc GR . . . .
H16B H 0.0519 0.7640 0.4012 0.145 Uiso 1 1 calc GR . . . .
H16C H 0.1273 0.7431 0.3522 0.145 Uiso 1 1 calc GR . . . .
C17 C 0.1741(2) 0.39589(16) 0.43814(13) 0.0506(6) Uani 1 1 d . . . . .
H17A H 0.1415 0.3694 0.4727 0.061 Uiso 1 1 calc R . . . .
H17B H 0.2514 0.4045 0.4626 0.061 Uiso 1 1 calc R . . . .
C18 C 0.1626(2) 0.33165(17) 0.37627(14) 0.0563(7) Uani 1 1 d . . . . .
H18A H 0.0857 0.3260 0.3496 0.068 Uiso 1 1 calc R . . . .
H18B H 0.2001 0.3558 0.3435 0.068 Uiso 1 1 calc R . . . .
C19 C 0.2080(2) 0.24058(17) 0.40062(17) 0.0679(8) Uani 1 1 d . . . . .
H19A H 0.1673 0.2150 0.4309 0.081 Uiso 1 1 calc R . . . .
H19B H 0.2835 0.2467 0.4300 0.081 Uiso 1 1 calc R . . . .
C20 C 0.2034(3) 0.1772(2) 0.3388(2) 0.1020(12) Uani 1 1 d . . . . .
H20A H 0.2448 0.2013 0.3091 0.153 Uiso 1 1 calc GR . . . .
H20B H 0.1287 0.1692 0.3103 0.153 Uiso 1 1 calc GR . . . .
H20C H 0.2338 0.1208 0.3580 0.153 Uiso 1 1 calc GR . . . .
O2 O 0.99362(14) -0.06976(14) 0.41413(11) 0.0686(6) Uani 1 1 d . . . . .
N3 N 0.77567(15) 0.06317(14) 0.52101(11) 0.0513(5) Uani 1 1 d . . . . .
H3 H 0.8433 0.0474 0.5350 0.062 Uiso 1 1 calc R . . . .
N4 N 0.81683(14) -0.02278(12) 0.39339(11) 0.0459(5) Uani 1 1 d . . . . .
C0AA C 0.7750(2) -0.10718(16) 0.41041(14) 0.0509(6) Uani 1 1 d . . . . .
H0AA H 0.7119 -0.0955 0.4272 0.061 Uiso 1 1 calc R . . . .
H0AB H 0.8306 -0.1344 0.4501 0.061 Uiso 1 1 calc R . . . .
C21 C 0.75672(18) 0.06228(16) 0.38708(14) 0.0483(6) Uani 1 1 d . . . . .
C22 C 0.6590(2) 0.0639(2) 0.31749(15) 0.0677(8) Uani 1 1 d D . . . .
H22A H 0.6863 0.0765 0.2767 0.081 Uiso 0.889(5) 1 calc R . P A 1
H22B H 0.6262 0.0052 0.3101 0.081 Uiso 0.889(5) 1 calc R . P A 1
H22C H 0.6610 0.1204 0.2937 0.081 Uiso 0.111(5) 1 calc R . P A 2
H22D H 0.6714 0.0179 0.2856 0.081 Uiso 0.111(5) 1 calc R . P A 2
C23 C 0.5702(3) 0.1318(2) 0.31777(18) 0.0752(11) Uani 0.889(5) 1 d D . P A 1
H23A H 0.6013 0.1911 0.3219 0.090 Uiso 0.889(5) 1 calc R . P A 1
H23B H 0.5126 0.1284 0.2721 0.090 Uiso 0.889(5) 1 calc R . P A 1
C24 C 0.5215(2) 0.1164(2) 0.37936(15) 0.0680(8) Uani 1 1 d D . . . .
H24A H 0.4797 0.1682 0.3852 0.082 Uiso 0.889(5) 1 calc R . P A 1
H24B H 0.4722 0.0658 0.3682 0.082 Uiso 0.889(5) 1 calc R . P A 1
H24C H 0.5240 0.1775 0.3639 0.082 Uiso 0.111(5) 1 calc R . P A 2
H24D H 0.4503 0.1053 0.3859 0.082 Uiso 0.111(5) 1 calc R . P A 2
C25 C 0.60981(18) 0.09936(16) 0.44781(15) 0.0503(6) Uani 1 1 d . . . . .
C26 C 0.60681(18) 0.10342(16) 0.52115(15) 0.0514(6) Uani 1 1 d . . . . .
C27 C 0.5263(2) 0.12511(19) 0.55438(18) 0.0677(8) Uani 1 1 d . . . . .
H27 H 0.4560 0.1402 0.5265 0.081 Uiso 1 1 calc R . . . .
C28 C 0.5525(3) 0.1238(2) 0.6282(2) 0.0776(9) Uani 1 1 d . . . . .
H28 H 0.4996 0.1391 0.6505 0.093 Uiso 1 1 calc R . . . .
C29 C 0.6565(3) 0.0999(2) 0.67076(18) 0.0747(9) Uani 1 1 d . . . . .
H29 H 0.6716 0.0990 0.7209 0.090 Uiso 1 1 calc R . . . .
C30 C 0.7378(2) 0.07758(18) 0.64020(15) 0.0623(7) Uani 1 1 d . . . . .
H30 H 0.8073 0.0613 0.6686 0.075 Uiso 1 1 calc R . . . .
C31 C 0.71161(19) 0.08036(16) 0.56544(14) 0.0496(6) Uani 1 1 d . . . . .
C32 C 0.71347(18) 0.07545(15) 0.45031(14) 0.0463(6) Uani 1 1 d . . . . .
C33 C 0.8471(2) 0.12876(18) 0.38767(15) 0.0596(7) Uani 1 1 d . . . . .
C34 C 0.9399(2) 0.08571(19) 0.39510(16) 0.0649(8) Uani 1 1 d . . . . .
H34 H 1.0059 0.1125 0.3961 0.078 Uiso 1 1 calc R . . . .
C35 C 0.92436(19) -0.00980(18) 0.40157(14) 0.0515(6) Uani 1 1 d . . . . .
C36 C 0.8278(3) 0.22672(19) 0.3830(2) 0.0925(11) Uani 1 1 d . . . . .
H36A H 0.7854 0.2421 0.3347 0.139 Uiso 1 1 calc GR . . . .
H36B H 0.8968 0.2572 0.3948 0.139 Uiso 1 1 calc GR . . . .
H36C H 0.7889 0.2439 0.4165 0.139 Uiso 1 1 calc GR . . . .
C37 C 0.7423(2) -0.17301(17) 0.34917(14) 0.0572(7) Uani 1 1 d . . . . .
H37A H 0.8038 -0.1838 0.3305 0.069 Uiso 1 1 calc R . . . .
H37B H 0.6831 -0.1484 0.3103 0.069 Uiso 1 1 calc R . . . .
C38 C 0.7054(3) -0.26105(18) 0.37454(18) 0.0723(8) Uani 1 1 d . . . . .
H38A H 0.7677 -0.2880 0.4096 0.087 Uiso 1 1 calc R . . . .
H38B H 0.6510 -0.2483 0.3991 0.087 Uiso 1 1 calc R . . . .
C39 C 0.6586(4) -0.3268(2) 0.3158(2) 0.1227(15) Uani 1 1 d . . . . .
H39A H 0.5935 -0.3028 0.2826 0.184 Uiso 1 1 calc GR . . . .
H39B H 0.6410 -0.3808 0.3365 0.184 Uiso 1 1 calc GR . . . .
H39C H 0.7112 -0.3393 0.2904 0.184 Uiso 1 1 calc GR . . . .
C233 C 0.5429(9) 0.0515(14) 0.3229(11) 0.0752(11) Uani 0.111(5) 1 d D . P A 2
H23C H 0.5335 -0.0092 0.3369 0.090 Uiso 0.111(5) 1 calc R . P A 2
H23D H 0.4904 0.0624 0.2760 0.090 Uiso 0.111(5) 1 calc R . P A 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
O1 C15 1.229(3) . ?
N1 H1 0.8600 . ?
N1 C11 1.374(3) . ?
N1 C12 1.376(3) . ?
N2 C1 1.474(3) . ?
N2 C15 1.349(3) . ?
N2 C17 1.456(3) . ?
C1 C2 1.548(3) . ?
C1 C12 1.497(3) . ?
C1 C13 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.507(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.499(3) . ?
C5 C6 1.426(3) . ?
C5 C12 1.359(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.403(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C13 C14 1.318(4) . ?
C13 C16 1.495(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.463(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.509(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.507(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.515(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 C35 1.237(3) . ?
N3 H3 0.8600 . ?
N3 C31 1.373(3) . ?
N3 C32 1.376(3) . ?
N4 C0AA 1.451(3) . ?
N4 C21 1.478(3) . ?
N4 C35 1.351(3) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C0AA C37 1.504(3) . ?
C21 C22 1.544(4) . ?
C21 C32 1.494(3) . ?
C21 C33 1.525(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C22 H22D 0.9700 . ?
C22 C23 1.527(3) . ?
C22 C233 1.529(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.514(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C24 C25 1.487(4) . ?
C24 C233 1.546(5) . ?
C25 C26 1.430(4) . ?
C25 C32 1.360(3) . ?
C26 C27 1.402(3) . ?
C26 C31 1.405(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.367(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.389(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.384(4) . ?
C33 C34 1.322(4) . ?
C33 C36 1.491(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.460(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.532(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.492(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C233 H23C 0.9700 . ?
C233 H23D 0.9700 . ?

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
C11 N1 H1 125.8 . . ?
C11 N1 C12 108.50(18) . . ?
C12 N1 H1 125.8 . . ?
C15 N2 C1 112.7(2) . . ?
C15 N2 C17 121.7(2) . . ?
C17 N2 C1 124.46(18) . . ?
N2 C1 C2 110.72(19) . . ?
N2 C1 C12 111.09(19) . . ?
N2 C1 C13 100.84(19) . . ?
C12 C1 C2 108.09(19) . . ?
C12 C1 C13 111.9(2) . . ?
C13 C1 C2 114.1(2) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 C1 115.3(2) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.8(2) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C6 C5 C4 129.6(2) . . ?
C12 C5 C4 123.8(2) . . ?
C12 C5 C6 106.6(2) . . ?
C7 C6 C5 134.4(2) . . ?
C7 C6 C11 118.2(2) . . ?
C11 C6 C5 107.3(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 121.2 . . ?
C9 C10 C11 117.7(2) . . ?
C11 C10 H10 121.2 . . ?
N1 C11 C6 107.5(2) . . ?
N1 C11 C10 130.3(2) . . ?
C10 C11 C6 122.3(2) . . ?
N1 C12 C1 123.56(19) . . ?
C5 C12 N1 110.1(2) . . ?
C5 C12 C1 126.3(2) . . ?
C14 C13 C1 109.5(2) . . ?
C14 C13 C16 128.5(3) . . ?
C16 C13 C1 122.0(3) . . ?
C13 C14 H14 124.5 . . ?
C13 C14 C15 111.0(2) . . ?
C15 C14 H14 124.5 . . ?
O1 C15 N2 124.5(3) . . ?
O1 C15 C14 129.6(2) . . ?
N2 C15 C14 105.9(2) . . ?
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 . . ?
N2 C17 H17A 108.6 . . ?
N2 C17 H17B 108.6 . . ?
N2 C17 C18 114.5(2) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.2(2) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C18 C19 C20 113.8(3) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C31 N3 H3 125.7 . . ?
C31 N3 C32 108.53(19) . . ?
C32 N3 H3 125.7 . . ?
C0AA N4 C21 123.90(17) . . ?
C35 N4 C0AA 122.0(2) . . ?
C35 N4 C21 111.79(19) . . ?
N4 C0AA H0AA 108.4 . . ?
N4 C0AA H0AB 108.4 . . ?
N4 C0AA C37 115.7(2) . . ?
H0AA C0AA H0AB 107.4 . . ?
C37 C0AA H0AA 108.4 . . ?
C37 C0AA H0AB 108.4 . . ?
N4 C21 C22 110.7(2) . . ?
N4 C21 C32 110.8(2) . . ?
N4 C21 C33 101.04(18) . . ?
C32 C21 C22 108.08(19) . . ?
C32 C21 C33 111.6(2) . . ?
C33 C21 C22 114.5(2) . . ?
C21 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C21 C22 H22C 107.4 . . ?
C21 C22 H22D 107.4 . . ?
H22A C22 H22B 107.5 . . ?
H22C C22 H22D 107.0 . . ?
C23 C22 C21 114.8(2) . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C233 C22 C21 119.5(9) . . ?
C233 C22 H22C 107.4 . . ?
C233 C22 H22D 107.4 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22 112.2(3) . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C23 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
H24C C24 H24D 108.7 . . ?
C25 C24 C23 110.1(2) . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C25 C24 H24C 110.6 . . ?
C25 C24 H24D 110.6 . . ?
C25 C24 C233 105.9(9) . . ?
C233 C24 H24C 110.6 . . ?
C233 C24 H24D 110.6 . . ?
C26 C25 C24 129.7(2) . . ?
C32 C25 C24 123.7(2) . . ?
C32 C25 C26 106.6(2) . . ?
C27 C26 C25 134.5(3) . . ?
C27 C26 C31 118.4(3) . . ?
C31 C26 C25 107.1(2) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.1(3) . . ?
C28 C27 H27 120.4 . . ?
C27 C28 H28 119.3 . . ?
C27 C28 C29 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 121.4 . . ?
C29 C30 C31 117.2(3) . . ?
C31 C30 H30 121.4 . . ?
N3 C31 C26 107.6(2) . . ?
N3 C31 C30 129.8(2) . . ?
C30 C31 C26 122.6(2) . . ?
N3 C32 C21 123.26(19) . . ?
C25 C32 N3 110.1(2) . . ?
C25 C32 C21 126.6(2) . . ?
C34 C33 C21 109.5(2) . . ?
C34 C33 C36 128.1(3) . . ?
C36 C33 C21 122.4(3) . . ?
C33 C34 H34 124.7 . . ?
C33 C34 C35 110.5(2) . . ?
C35 C34 H34 124.7 . . ?
O2 C35 N4 124.3(2) . . ?
O2 C35 C34 128.8(2) . . ?
N4 C35 C34 106.9(2) . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C0AA C37 H37A 109.5 . . ?
C0AA C37 H37B 109.5 . . ?
C0AA C37 C38 110.9(2) . . ?
H37A C37 H37B 108.0 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C37 C38 H38A 108.5 . . ?
C37 C38 H38B 108.5 . . ?
H38A C38 H38B 107.5 . . ?
C39 C38 C37 114.9(3) . . ?
C39 C38 H38A 108.5 . . ?
C39 C38 H38B 108.5 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C22 C233 C24 110.3(4) . . ?
C22 C233 H23C 109.6 . . ?
C22 C233 H23D 109.6 . . ?
C24 C233 H23C 109.6 . . ?
C24 C233 H23D 109.6 . . ?
H23C C233 H23D 108.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
