# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_mp5
_database_code_depnum_ccdc_archive 'CCDC 1022612'
_audit_update_record             
;
2014-09-02 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2013-08-11
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   9.2888(2)
_cell_length_b                   6.04300(10)
_cell_length_c                   27.8317(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.26(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4995
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.3558
_cell_measurement_theta_min      3.1731
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87996
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7248
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.561
_diffrn_reflns_theta_min         3.176
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -115.00  -78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7051 -141.0000  178.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00   -7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7051   57.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega -126.00  -97.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00    3.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000   30.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega -114.00  -80.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega -126.00  -79.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega  113.00  176.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
  8 omega   26.00   51.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   62.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   93.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   91.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   95.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   87.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 14 omega   48.00   90.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   77.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   47.00   90.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 17 omega  119.00  144.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   37.00  112.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 19 omega   66.00  139.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -30.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0938253000
_diffrn_orient_matrix_UB_12      0.0488481000
_diffrn_orient_matrix_UB_13      0.0488354000
_diffrn_orient_matrix_UB_21      0.1603572000
_diffrn_orient_matrix_UB_22      -0.1029469000
_diffrn_orient_matrix_UB_23      0.0259850000
_diffrn_orient_matrix_UB_31      0.1746960000
_diffrn_orient_matrix_UB_32      0.1203628000
_diffrn_orient_matrix_UB_33      0.0023671000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3023
_reflns_number_total             3120
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).

Flack parameter (From Shelx 2013/4)
Flack x =   0.203(298) by hole-in-one fit to all intensities
            0.015(132) from 1357 selected quotients (Parsons' method)

Hooft y parameter (From Olex2)          0.07(12)

;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.044
_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)+(0.0465P)²+0.2270P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0833
_refine_special_details          
;
 The NH was located in a difference map and allowed to refine freely but given 
a thermal parameter Uiso equivalent to 1.5 times Uequiv of the parent Nitrogen.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.0343(2) 0.8788(3) 0.12837(7) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.0722 0.9541 0.1555 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0686(2) 0.9821(3) 0.09977(8) 0.0267(4) Uani 1 1 d . . . . .
H2 H -0.1002 1.1273 0.1075 0.032 Uiso 1 1 calc R U . . .
C3 C -0.1250(2) 0.8742(4) 0.06007(8) 0.0300(5) Uani 1 1 d . . . . .
H3 H -0.1974 0.9430 0.0411 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0749(2) 0.6648(4) 0.04821(7) 0.0294(4) Uani 1 1 d . . . . .
H4 H -0.1112 0.5921 0.0205 0.035 Uiso 1 1 calc R U . . .
C5 C 0.0278(2) 0.5610(3) 0.07660(7) 0.0248(4) Uani 1 1 d . . . . .
H5 H 0.0614 0.4177 0.0681 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0822(2) 0.6661(3) 0.11763(6) 0.0210(4) Uani 1 1 d . . . . .
C7 C 0.1847(2) 0.5485(4) 0.15115(7) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.2643 0.6496 0.1599 0.031 Uiso 1 1 calc R U . . .
H7B H 0.2267 0.4188 0.1346 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1070(2) 0.4719(3) 0.19683(7) 0.0203(4) Uani 1 1 d . . . . .
H8A H 0.0608 0.6013 0.2123 0.024 Uiso 1 1 calc R U . . .
H8B H 0.0302 0.3662 0.1879 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2078(2) 0.3614(3) 0.23296(6) 0.0188(4) Uani 1 1 d . . . . .
H9 H 0.2915 0.4627 0.2381 0.023 Uiso 1 1 calc R U . . .
N9 N 0.26364(17) 0.1529(3) 0.21389(6) 0.0212(3) Uani 1 1 d . . . . .
H9A H 0.313(3) 0.176(5) 0.1858(10) 0.032 Uiso 1 1 d . U . . .
C10 C 0.13259(19) 0.3291(3) 0.28169(7) 0.0194(4) Uani 1 1 d . . . . .
O10 O 0.05142(16) 0.4735(2) 0.29693(5) 0.0264(3) Uani 1 1 d . . . . .
N11 N 0.16514(16) 0.1454(3) 0.30680(6) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.2577(2) -0.0345(3) 0.28963(7) 0.0216(4) Uani 1 1 d . . . . .
H12A H 0.1971 -0.1579 0.2778 0.026 Uiso 1 1 calc R U . . .
H12B H 0.3171 -0.0905 0.3166 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3547(2) 0.0444(3) 0.24969(7) 0.0225(4) Uani 1 1 d . . . . .
H13A H 0.4269 0.1498 0.2624 0.027 Uiso 1 1 calc R U . . .
H13B H 0.4061 -0.0824 0.2351 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1061(2) 0.1148(3) 0.35524(7) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.0661 -0.0364 0.3581 0.027 Uiso 1 1 calc R U . . .
H14B H 0.0267 0.2214 0.3605 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2208(2) 0.1488(3) 0.39329(7) 0.0223(4) Uani 1 1 d . . . . .
C16 C 0.2598(2) -0.0207(3) 0.42410(7) 0.0252(4) Uani 1 1 d . . . . .
H16 H 0.2145 -0.1611 0.4214 0.030 Uiso 1 1 calc R U . . .
C17 C 0.3647(2) 0.0128(4) 0.45903(7) 0.0291(5) Uani 1 1 d . . . . .
H17 H 0.3903 -0.1043 0.4801 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4318(2) 0.2161(4) 0.46304(8) 0.0308(5) Uani 1 1 d . . . . .
H18 H 0.5026 0.2394 0.4872 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3955(3) 0.3864(4) 0.43172(9) 0.0343(5) Uani 1 1 d . . . . .
H19 H 0.4421 0.5258 0.4342 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2905(2) 0.3522(4) 0.39674(8) 0.0306(5) Uani 1 1 d . . . . .
H20 H 0.2663 0.4682 0.3752 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.391(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C6 C7 1.510(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.528(3) . ?
C9 H9 1.0000 . ?
C9 N9 1.462(2) . ?
C9 C10 1.538(3) . ?
N9 H9A 0.92(3) . ?
N9 C13 1.462(2) . ?
C10 O10 1.229(2) . ?
C10 N11 1.346(3) . ?
N11 C12 1.466(2) . ?
N11 C14 1.467(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(3) . ?
C15 C16 1.384(3) . ?
C15 C20 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.73(19) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.30(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.43(19) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.56(19) . . ?
C1 C6 C7 120.21(18) . . ?
C5 C6 C7 121.15(19) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 110.97(15) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.93(15) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C10 110.94(15) . . ?
N9 C9 C8 110.80(15) . . ?
N9 C9 H9 107.7 . . ?
N9 C9 C10 111.82(15) . . ?
C10 C9 H9 107.7 . . ?
C9 N9 H9A 111.0(18) . . ?
C9 N9 C13 110.13(15) . . ?
C13 N9 H9A 111.0(18) . . ?
O10 C10 C9 119.53(17) . . ?
O10 C10 N11 122.98(18) . . ?
N11 C10 C9 117.42(16) . . ?
C10 N11 C12 125.03(16) . . ?
C10 N11 C14 119.80(16) . . ?
C12 N11 C14 115.17(15) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
N11 C12 C13 110.86(15) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
N9 C13 C12 107.37(15) . . ?
N9 C13 H13A 110.2 . . ?
N9 C13 H13B 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N11 C14 H14A 109.4 . . ?
N11 C14 H14B 109.4 . . ?
N11 C14 C15 111.22(15) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C16 C15 C14 121.10(18) . . ?
C16 C15 C20 119.27(18) . . ?
C20 C15 C14 119.62(17) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.3(2) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?


_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-2
####################################################################### 
# 
# 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_mp6
_database_code_depnum_ccdc_archive 'CCDC 1022613'
_audit_update_record             
;
2014-09-02 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2013-09-14
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H20 N2 O'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   27.3686(6)
_cell_length_b                   6.32664(13)
_cell_length_c                   8.74746(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1514.63(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.4240
_cell_measurement_theta_min      4.8410
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78987
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4385
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         3.230
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.7542
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5282   38.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega -112.00  -15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5282  -57.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00    0.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -55.00   -2.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   70.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega   50.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  9 omega   50.00   77.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   76.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   62.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   60.0000 70
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0496463000
_diffrn_orient_matrix_UB_12      0.0523605000
_diffrn_orient_matrix_UB_13      0.0737583000
_diffrn_orient_matrix_UB_21      0.0263509000
_diffrn_orient_matrix_UB_22      -0.0712999000
_diffrn_orient_matrix_UB_23      -0.1468433000
_diffrn_orient_matrix_UB_31      -0.0032222000
_diffrn_orient_matrix_UB_32      0.2268999000
_diffrn_orient_matrix_UB_33      -0.0632127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_full    0.568
_reflns_Friedel_fraction_max     0.583
_reflns_number_gt                2143
_reflns_number_total             2162
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+0.3028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H2 of C2, H1 of C1, H3 of C3, H4 of C4, H5 of C5, H9 of
  C9, H15 of C15, H16 of C16, H17 of C17, H18 of C18, H19 of C19
 At 1.5 times of:
  H9A of C19
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.70670(8) 0.3445(4) 0.4709(3) 0.0389(6) Uani 1 1 d . . . . .
H1 H 0.7144 0.2044 0.5017 0.047 Uiso 1 1 calc R U . . .
C2 C 0.73326(9) 0.4363(5) 0.3542(4) 0.0505(7) Uani 1 1 d . . . . .
H2 H 0.7588 0.3595 0.3060 0.061 Uiso 1 1 calc R U . . .
C3 C 0.72272(9) 0.6389(5) 0.3077(4) 0.0562(8) Uani 1 1 d . . . . .
H3 H 0.7408 0.7027 0.2273 0.067 Uiso 1 1 calc R U . . .
C4 C 0.68576(11) 0.7482(4) 0.3786(4) 0.0554(8) Uani 1 1 d . . . . .
H4 H 0.6782 0.8878 0.3464 0.066 Uiso 1 1 calc R U . . .
C5 C 0.65940(9) 0.6570(4) 0.4967(4) 0.0449(6) Uani 1 1 d . . . . .
H5 H 0.6344 0.7356 0.5460 0.054 Uiso 1 1 calc R U . . .
C6 C 0.66934(7) 0.4502(4) 0.5439(3) 0.0324(5) Uani 1 1 d . . . . .
C7 C 0.63892(8) 0.3440(4) 0.6645(3) 0.0402(6) Uani 1 1 d . . . . .
H7A H 0.6341 0.4424 0.7511 0.048 Uiso 1 1 calc R U . . .
H7B H 0.6565 0.2182 0.7033 0.048 Uiso 1 1 calc R U . . .
C8 C 0.58920(7) 0.2763(4) 0.6021(3) 0.0322(5) Uani 1 1 d . . . . .
H8A H 0.5942 0.1670 0.5226 0.039 Uiso 1 1 calc R U . . .
H8B H 0.5733 0.3995 0.5529 0.039 Uiso 1 1 calc R U . . .
C9 C 0.55505(8) 0.1883(3) 0.7255(3) 0.0297(5) Uani 1 1 d . . . . .
H9 H 0.5724 0.0660 0.7737 0.036 Uiso 1 1 calc R U . . .
N9 N 0.54643(6) 0.3421(3) 0.8462(2) 0.0308(4) Uani 1 1 d . . . . .
C10 C 0.50943(7) 0.0989(3) 0.6473(3) 0.0281(5) Uani 1 1 d . . . . .
O10 O 0.51302(5) -0.0568(3) 0.5643(2) 0.0403(4) Uani 1 1 d . . . . .
N11 N 0.46634(6) 0.2004(3) 0.6692(2) 0.0259(4) Uani 1 1 d . . . . .
C12 C 0.46003(8) 0.3802(3) 0.7746(3) 0.0328(5) Uani 1 1 d . . . . .
H12A H 0.4469 0.3287 0.8732 0.039 Uiso 1 1 calc R U . . .
H12B H 0.4362 0.4813 0.7309 0.039 Uiso 1 1 calc R U . . .
C13 C 0.50823(8) 0.4915(4) 0.8017(3) 0.0324(5) Uani 1 1 d . . . . .
H13A H 0.5182 0.5658 0.7071 0.039 Uiso 1 1 calc R U . . .
H13B H 0.5041 0.5986 0.8832 0.039 Uiso 1 1 calc R U . . .
C14 C 0.42152(7) 0.1104(3) 0.6134(3) 0.0278(5) Uani 1 1 d . . . . .
C15 C 0.40654(8) -0.0857(3) 0.6668(3) 0.0368(5) Uani 1 1 d . . . . .
H15 H 0.4266 -0.1630 0.7356 0.044 Uiso 1 1 calc R U . . .
C16 C 0.36242(10) -0.1677(4) 0.6192(4) 0.0502(8) Uani 1 1 d . . . . .
H16 H 0.3522 -0.3030 0.6540 0.060 Uiso 1 1 calc R U . . .
C17 C 0.33311(9) -0.0534(5) 0.5212(4) 0.0538(8) Uani 1 1 d . . . . .
H17 H 0.3026 -0.1097 0.4894 0.065 Uiso 1 1 calc R U . . .
C18 C 0.34789(9) 0.1432(5) 0.4688(3) 0.0471(7) Uani 1 1 d . . . . .
H18 H 0.3274 0.2216 0.4020 0.057 Uiso 1 1 calc R U . . .
C19 C 0.39273(8) 0.2257(4) 0.5138(3) 0.0338(5) Uani 1 1 d . . . . .
H19 H 0.4034 0.3590 0.4767 0.041 Uiso 1 1 calc R U . . .
H9A H 0.5367(11) 0.272(5) 0.934(4) 0.051 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.381(4) . ?
C1 C6 1.379(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(4) . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.533(3) . ?
C9 H9 1.0000 . ?
C9 N9 1.455(3) . ?
C9 C10 1.532(3) . ?
N9 C13 1.462(3) . ?
N9 H9A 0.93(4) . ?
C10 O10 1.228(3) . ?
C10 N11 1.356(3) . ?
N11 C12 1.475(3) . ?
N11 C14 1.438(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.514(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.388(3) . ?
C14 C19 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C6 C1 C2 121.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 121.3(2) . . ?
C5 C6 C7 121.2(2) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.6(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 113.14(19) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9 106.8 . . ?
N9 C9 C8 111.52(18) . . ?
N9 C9 H9 106.8 . . ?
N9 C9 C10 116.01(17) . . ?
C10 C9 C8 108.42(19) . . ?
C10 C9 H9 106.8 . . ?
C9 N9 C13 110.81(18) . . ?
C9 N9 H9A 109(2) . . ?
C13 N9 H9A 109.0(19) . . ?
O10 C10 C9 119.66(18) . . ?
O10 C10 N11 122.20(19) . . ?
N11 C10 C9 118.11(18) . . ?
C10 N11 C12 123.73(17) . . ?
C10 N11 C14 120.43(16) . . ?
C14 N11 C12 114.70(15) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
N11 C12 C13 110.75(18) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
N9 C13 C12 111.34(18) . . ?
N9 C13 H13A 109.4 . . ?
N9 C13 H13B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 N11 119.5(2) . . ?
C19 C14 N11 119.42(18) . . ?
C19 C14 C15 121.0(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 118.9(2) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O10 0.93(4) 2.24(3) 3.090(3) 153(3) 2_655


_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mp8
_database_code_depnum_ccdc_archive 'CCDC 1022614'
_audit_update_record             
;
2014-09-02 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.3351(3)
_cell_length_b                   10.0384(5)
_cell_length_c                   15.6306(9)
_cell_angle_alpha                106.562(5)
_cell_angle_beta                 98.033(5)
_cell_angle_gamma                95.518(4)
_cell_volume                     786.30(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      76.6620
_cell_measurement_theta_min      4.6260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49608
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.310
_diffrn_reflns_theta_min         2.996
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0420707000
_diffrn_orient_matrix_UB_12      -0.1411879000
_diffrn_orient_matrix_UB_13      -0.0759417000
_diffrn_orient_matrix_UB_21      -0.0463965000
_diffrn_orient_matrix_UB_22      -0.0784063000
_diffrn_orient_matrix_UB_23      0.0691983000
_diffrn_orient_matrix_UB_31      -0.2879291000
_diffrn_orient_matrix_UB_32      0.0095410000
_diffrn_orient_matrix_UB_33      -0.0187805000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2979
_reflns_number_total             3220
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0662P)²+0.1517P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
 The NH was located in a difference map and allowed to refine 
freely but given a thermal parameter Uiso 1.5 times the Uequiv 
of the parent nitrogen.
The ring of the phenylethyl chain was modeled as disordered over
two positions by rotation about the C6-C7 bond (C3 and C6 belonged
to both parts)
The occupancies refined to 47:53 minor:major. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H9 of C9, H21 of C21, H5 of C5, H2A of C2A, H2 of C2,
  H5A of C5A, H4 of C4, H20 of C20, H17 of C17, H18 of C18, H1A of C1A, H19 of
  C19, H4A of C4A, H1 of C1
 At 1.5 times of:
  H11 of C21
2. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(H3B)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(H5A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(H3A)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C1A(H1A), C2A(H2A), C3(H3A), C3(H3B), C4(H4), C5(H5),
 C4A(H4A), C5A(H5A), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.5404(7) 0.2354(3) 0.08712(19) 0.0449(8) Uani 0.478(3) 1 d . . P A 1
H1 H 0.4945 0.1964 0.1325 0.054 Uiso 0.478(3) 1 calc R . P A 1
C2 C 0.5203(7) 0.1481(3) -0.0011(2) 0.0482(9) Uani 0.478(3) 1 d . . P A 1
H2 H 0.4677 0.0502 -0.0141 0.058 Uiso 0.478(3) 1 calc R . P A 1
C1A C 0.3985(5) 0.2909(3) 0.07153(17) 0.0378(6) Uani 0.522(3) 1 d . . P A 2
H1A H 0.2635 0.2934 0.1054 0.045 Uiso 0.522(3) 1 calc R . P A 2
C2A C 0.3614(6) 0.1994(3) -0.01679(18) 0.0458(7) Uani 0.522(3) 1 d . . P A 2
H2A H 0.2031 0.1404 -0.0433 0.055 Uiso 0.522(3) 1 calc R . P A 2
C3 C 0.5719(3) 0.19710(16) -0.06693(9) 0.0483(4) Uani 1 1 d . . . . .
H3A H 0.5483 0.1365 -0.1274 0.058 Uiso 0.478(3) 1 calc R . P A 1
H3B H 0.5515 0.1374 -0.1275 0.058 Uiso 0.522(3) 1 calc R . P A 2
C4 C 0.6649(7) 0.3444(4) -0.0462(2) 0.0487(8) Uani 0.478(3) 1 d . . P A 1
H4 H 0.7131 0.3814 -0.0921 0.058 Uiso 0.478(3) 1 calc R . P A 1
C5 C 0.6829(6) 0.4316(3) 0.04197(19) 0.0421(7) Uani 0.478(3) 1 d . . P A 1
H5 H 0.7350 0.5297 0.0557 0.050 Uiso 0.478(3) 1 calc R . P A 1
C4A C 0.7874(7) 0.2770(4) -0.0285(2) 0.0572(10) Uani 0.522(3) 1 d . . P A 2
H4A H 0.9251 0.2729 -0.0613 0.069 Uiso 0.522(3) 1 calc R . P A 2
C5A C 0.8232(6) 0.3687(4) 0.0594(2) 0.0505(8) Uani 0.522(3) 1 d . . P A 2
H5A H 0.9834 0.4262 0.0852 0.061 Uiso 0.522(3) 1 calc R . P A 2
C6 C 0.6254(2) 0.37684(13) 0.11014(8) 0.0321(3) Uani 1 1 d . . . . .
C7 C 0.6636(2) 0.47393(12) 0.20640(8) 0.0326(3) Uani 1 1 d . . . . .
H7A H 0.5064 0.4613 0.2319 0.039 Uiso 1 1 calc R . . . .
H7B H 0.6931 0.5726 0.2059 0.039 Uiso 1 1 calc R . . . .
C8 C 0.8904(2) 0.44522(11) 0.26685(7) 0.0280(2) Uani 1 1 d . . . . .
H8A H 1.0398 0.4424 0.2356 0.034 Uiso 1 1 calc R . . . .
H8B H 0.8480 0.3513 0.2741 0.034 Uiso 1 1 calc R . . . .
C9 C 0.9668(2) 0.55297(11) 0.36128(7) 0.0253(2) Uani 1 1 d . . . . .
H9 H 1.1329 0.5329 0.3897 0.030 Uiso 1 1 calc R . . . .
C10 C 0.7699(2) 0.53450(11) 0.42122(7) 0.0263(2) Uani 1 1 d . . . . .
O10 O 0.65500(17) 0.41626(8) 0.41071(6) 0.0351(2) Uani 1 1 d . . . . .
N11 N 0.73464(18) 0.64644(10) 0.48656(6) 0.0276(2) Uani 1 1 d . . . . .
C12 C 0.8555(2) 0.78994(11) 0.50218(7) 0.0277(2) Uani 1 1 d . . . . .
H12A H 0.9149 0.8354 0.5680 0.033 Uiso 1 1 calc R . . . .
H12B H 0.7290 0.8443 0.4805 0.033 Uiso 1 1 calc R . . . .
C13 C 1.0799(2) 0.79109(11) 0.45309(7) 0.0269(2) Uani 1 1 d . . . . .
H13A H 1.1367 0.8881 0.4535 0.032 Uiso 1 1 calc R . . . .
H13B H 1.2241 0.7583 0.4847 0.032 Uiso 1 1 calc R . . . .
N14 N 1.00728(17) 0.69959(9) 0.35939(6) 0.0248(2) Uani 1 1 d . . . . .
C15 C 1.2091(2) 0.72093(11) 0.30729(8) 0.0276(2) Uani 1 1 d . . . . .
H15A H 1.1711 0.6488 0.2471 0.033 Uiso 1 1 calc R . . . .
H15B H 1.3749 0.7088 0.3393 0.033 Uiso 1 1 calc R . . . .
C16 C 1.2305(2) 0.86547(11) 0.29470(7) 0.0264(2) Uani 1 1 d . . . . .
C17 C 1.4557(2) 0.95959(12) 0.32832(7) 0.0288(2) Uani 1 1 d . . . . .
H17 H 1.5976 0.9337 0.3607 0.035 Uiso 1 1 calc R . . . .
C18 C 1.4757(2) 1.09148(12) 0.31501(8) 0.0326(3) Uani 1 1 d . . . . .
H18 H 1.6300 1.1552 0.3387 0.039 Uiso 1 1 calc R . . . .
C19 C 1.2709(2) 1.12926(12) 0.26738(8) 0.0346(3) Uani 1 1 d . . . . .
H19 H 1.2837 1.2193 0.2586 0.041 Uiso 1 1 calc R . . . .
C20 C 1.0465(2) 1.03574(13) 0.23234(8) 0.0350(3) Uani 1 1 d . . . . .
H20 H 0.9066 1.0611 0.1986 0.042 Uiso 1 1 calc R . . . .
C21 C 1.0264(2) 0.90459(12) 0.24656(8) 0.0316(3) Uani 1 1 d . . . . .
H21 H 0.8715 0.8413 0.2231 0.038 Uiso 1 1 calc R . . . .
H11 H 0.616(3) 0.6296(17) 0.5207(12) 0.047 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.391(4) . ?
C1 C6 1.375(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.310(4) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.398(4) . ?
C1A C6 1.368(3) . ?
C2A H2A 0.9500 . ?
C2A C3 1.455(3) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C3 C4 1.442(4) . ?
C3 C4A 1.297(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.394(4) . ?
C5A H5A 0.9500 . ?
C5A C6 1.401(3) . ?
C6 C7 1.5150(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5307(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5335(14) . ?
C9 H9 1.0000 . ?
C9 C10 1.5335(15) . ?
C9 N14 1.4763(13) . ?
C10 O10 1.2379(13) . ?
C10 N11 1.3347(15) . ?
N11 C12 1.4586(13) . ?
N11 H11 0.917(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5102(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N14 1.4644(13) . ?
N14 C15 1.4724(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5147(14) . ?
C16 C17 1.3911(16) . ?
C16 C21 1.3885(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3942(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3803(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3861(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3930(17) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C6 C1 C2 121.4(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C2A C1A H1A 119.3 . . ?
C6 C1A H1A 119.3 . . ?
C6 C1A C2A 121.3(2) . . ?
C1A C2A H2A 120.9 . . ?
C1A C2A C3 118.2(2) . . ?
C3 C2A H2A 120.9 . . ?
C2 C3 H3A 120.5 . . ?
C2 C3 C4 118.99(19) . . ?
C2A C3 H3B 120.2 . . ?
C4 C3 H3A 120.5 . . ?
C4A C3 C2A 119.64(18) . . ?
C4A C3 H3B 120.2 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C3 C4A H4A 119.0 . . ?
C3 C4A C5A 122.0(3) . . ?
C5A C4A H4A 119.0 . . ?
C4A C5A H5A 119.6 . . ?
C4A C5A C6 120.7(2) . . ?
C6 C5A H5A 119.6 . . ?
C1 C6 C5 118.08(19) . . ?
C1 C6 C7 122.94(15) . . ?
C1A C6 C5A 118.14(18) . . ?
C1A C6 C7 120.62(14) . . ?
C5 C6 C7 118.97(15) . . ?
C5A C6 C7 121.20(15) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.74(9) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C7 C8 C9 114.88(9) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C10 110.50(9) . . ?
C10 C9 H9 107.3 . . ?
N14 C9 C8 113.52(9) . . ?
N14 C9 H9 107.3 . . ?
N14 C9 C10 110.76(8) . . ?
O10 C10 C9 119.81(10) . . ?
O10 C10 N11 121.36(10) . . ?
N11 C10 C9 118.76(9) . . ?
C10 N11 C12 125.12(9) . . ?
C10 N11 H11 115.3(11) . . ?
C12 N11 H11 119.4(11) . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
N11 C12 C13 110.66(9) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N14 C13 C12 110.19(8) . . ?
N14 C13 H13A 109.6 . . ?
N14 C13 H13B 109.6 . . ?
C13 N14 C9 108.03(8) . . ?
C13 N14 C15 109.92(8) . . ?
C15 N14 C9 111.25(8) . . ?
N14 C15 H15A 109.2 . . ?
N14 C15 H15B 109.2 . . ?
N14 C15 C16 111.93(9) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C17 C16 C15 121.05(10) . . ?
C21 C16 C15 120.15(10) . . ?
C21 C16 C17 118.76(10) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.75(11) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.88(11) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.99(11) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.98(11) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.63(11) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O10 0.917(19) 2.009(19) 2.9246(12) 176.7(16) 2_666

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
C1 C2 C3 C2A -74.6(4) . . . . ?
C1 C2 C3 C4 3.3(5) . . . . ?
C1 C2 C3 C4A 47.0(4) . . . . ?
C1 C6 C7 C8 69.6(2) . . . . ?
C2 C1 C6 C1A 81.8(4) . . . . ?
C2 C1 C6 C5 2.2(4) . . . . ?
C2 C1 C6 C5A -41.2(4) . . . . ?
C2 C1 C6 C7 -176.6(3) . . . . ?
C2 C3 C4 C5 -3.7(4) . . . . ?
C2 C3 C4A C5A -45.5(4) . . . . ?
C1A C2A C3 C2 75.6(3) . . . . ?
C1A C2A C3 C4 -43.3(3) . . . . ?
C1A C2A C3 C4A 1.2(4) . . . . ?
C1A C6 C7 C8 121.70(18) . . . . ?
C2A C1A C6 C1 -71.9(3) . . . . ?
C2A C1A C6 C5 45.0(3) . . . . ?
C2A C1A C6 C5A -1.4(4) . . . . ?
C2A C1A C6 C7 -179.2(2) . . . . ?
C2A C3 C4 C5 41.4(4) . . . . ?
C2A C3 C4A C5A -1.6(5) . . . . ?
C3 C4 C5 C6 3.4(5) . . . . ?
C3 C4A C5A C6 0.5(6) . . . . ?
C4 C3 C4A C5A 75.3(4) . . . . ?
C4 C5 C6 C1 -2.7(4) . . . . ?
C4 C5 C6 C1A -47.1(4) . . . . ?
C4 C5 C6 C5A 69.5(3) . . . . ?
C4 C5 C6 C7 176.2(3) . . . . ?
C5 C6 C7 C8 -109.1(2) . . . . ?
C4A C3 C4 C5 -78.5(3) . . . . ?
C4A C5A C6 C1 42.3(4) . . . . ?
C4A C5A C6 C1A 1.0(4) . . . . ?
C4A C5A C6 C5 -79.7(4) . . . . ?
C4A C5A C6 C7 178.8(3) . . . . ?
C5A C6 C7 C8 -56.0(2) . . . . ?
C6 C1 C2 C3 -2.6(5) . . . . ?
C6 C1A C2A C3 0.4(4) . . . . ?
C6 C7 C8 C9 171.24(9) . . . . ?
C7 C8 C9 C10 73.14(11) . . . . ?
C7 C8 C9 N14 -51.98(13) . . . . ?
C8 C9 C10 O10 31.86(14) . . . . ?
C8 C9 C10 N11 -151.01(10) . . . . ?
C8 C9 N14 C13 -179.74(8) . . . . ?
C8 C9 N14 C15 -59.02(11) . . . . ?
C9 C10 N11 C12 4.87(16) . . . . ?
C9 N14 C15 C16 172.88(9) . . . . ?
C10 C9 N14 C13 55.28(11) . . . . ?
C10 C9 N14 C15 176.00(8) . . . . ?
C10 N11 C12 C13 -16.00(15) . . . . ?
O10 C10 N11 C12 -178.05(10) . . . . ?
N11 C12 C13 N14 47.42(12) . . . . ?
C12 C13 N14 C9 -68.88(11) . . . . ?
C12 C13 N14 C15 169.57(9) . . . . ?
C13 N14 C15 C16 -67.52(11) . . . . ?
N14 C9 C10 O10 158.53(10) . . . . ?
N14 C9 C10 N11 -24.33(13) . . . . ?
N14 C15 C16 C17 119.28(11) . . . . ?
N14 C15 C16 C21 -62.76(13) . . . . ?
C15 C16 C17 C18 178.79(10) . . . . ?
C15 C16 C21 C20 -178.15(10) . . . . ?
C16 C17 C18 C19 -0.50(17) . . . . ?
C17 C16 C21 C20 -0.14(17) . . . . ?
C17 C18 C19 C20 -0.46(18) . . . . ?
C18 C19 C20 C21 1.11(18) . . . . ?
C19 C20 C21 C16 -0.81(18) . . . . ?
C21 C16 C17 C18 0.79(16) . . . . ?

