# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_6a-trans
_database_code_depnum_ccdc_archive 'CCDC 1028121'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.2930(2)
_cell_length_b                   6.84225(8)
_cell_length_c                   22.5979(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.8593(9)
_cell_angle_gamma                90
_cell_volume                     3137.36(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19431
_cell_measurement_temperature    99.94(17)
_cell_measurement_theta_max      74.3680
_cell_measurement_theta_min      3.8850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3784
_exptl_crystal_size_mid          0.1863
_exptl_crystal_size_min          0.0972
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28439
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.508
_diffrn_reflns_theta_min         3.913
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.94(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0288037000
_diffrn_orient_matrix_UB_12      0.0322593000
_diffrn_orient_matrix_UB_13      -0.0626884000
_diffrn_orient_matrix_UB_21      -0.0683974000
_diffrn_orient_matrix_UB_22      0.0377116000
_diffrn_orient_matrix_UB_23      0.0263798000
_diffrn_orient_matrix_UB_31      0.0159725000
_diffrn_orient_matrix_UB_32      0.2196698000
_diffrn_orient_matrix_UB_33      0.0046757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2999
_reflns_number_total             3181
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.294
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1396
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14'-C13' = C18'-C13'
 1.39 with sigma of 0.02
3. Rigid bond restraints
 C13', C13, C14', C14, C15, C15', C16, C16', C17, C17', C18, C18'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C13 \\sim C13': within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(C13') = Uanis(C13)
5. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C13')=Sof(C14')=Sof(H14')=Sof(C15')=Sof(H15')=
 Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17')=Sof(C18')=Sof(H18')=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=
 Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C4(H4A,H4B)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18')
6.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 0.38473(4) 0.81235(12) 0.33103(3) 0.0202(2) Uani 1 1 d . . . . .
H1AA H 0.3604 0.9378 0.3311 0.024 Uiso 0.541(11) 1 calc R . P A 1
H1AB H 0.3902 0.7715 0.2894 0.024 Uiso 0.541(11) 1 calc R . P A 1
H1BC H 0.3844 0.7807 0.2883 0.024 Uiso 0.459(11) 1 calc R . P A 2
H1BD H 0.3631 0.9410 0.3358 0.024 Uiso 0.459(11) 1 calc R . P A 2
C2 C 0.31312(4) 0.70556(12) 0.41166(3) 0.0170(2) Uani 1 1 d . . . . .
C3 C 0.29118(4) 0.51368(13) 0.44040(4) 0.0183(2) Uani 1 1 d . . . . .
C4 C 0.29934(4) 0.36774(13) 0.38990(4) 0.0206(2) Uani 1 1 d . . . . .
H4A H 0.2582 0.3568 0.3661 0.025 Uiso 1 1 calc R . . . .
H4B H 0.3113 0.2369 0.4054 0.025 Uiso 1 1 calc R . . . .
C5 C 0.35554(4) 0.45335(12) 0.35266(4) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.3989 0.4118 0.3701 0.023 Uiso 1 1 calc R . . . .
C6 C 0.33643(5) 0.47102(14) 0.49337(4) 0.0240(2) Uani 1 1 d . . . . .
H6A H 0.3821 0.4628 0.4802 0.036 Uiso 1 1 calc GR . . . .
H6B H 0.3237 0.3467 0.5114 0.036 Uiso 1 1 calc GR . . . .
H6C H 0.3325 0.5762 0.5225 0.036 Uiso 1 1 calc GR . . . .
C7 C 0.35239(4) 0.39692(12) 0.28803(4) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.40059(4) 0.27555(13) 0.26492(4) 0.0224(2) Uani 1 1 d . . . . .
H8 H 0.4365 0.2349 0.2894 0.027 Uiso 1 1 calc R . . . .
C9 C 0.39671(5) 0.21301(14) 0.20628(4) 0.0264(2) Uani 1 1 d . . . . .
H9 H 0.4293 0.1276 0.1912 0.032 Uiso 1 1 calc R . . . .
C10 C 0.34508(5) 0.27572(14) 0.16988(4) 0.0257(2) Uani 1 1 d . . . . .
H10 H 0.3421 0.2328 0.1300 0.031 Uiso 1 1 calc R . . . .
C11 C 0.29768(4) 0.40199(13) 0.19232(4) 0.0240(2) Uani 1 1 d . . . . .
H11 H 0.2630 0.4479 0.1673 0.029 Uiso 1 1 calc R . . . .
C12 C 0.30098(4) 0.46102(13) 0.25114(4) 0.0217(2) Uani 1 1 d . . . . .
H12 H 0.2681 0.5454 0.2663 0.026 Uiso 1 1 calc R . . . .
C13 C 0.4547(7) 0.843(3) 0.3610(6) 0.0167(11) Uani 0.541(11) 1 d . U P A 1
C14 C 0.4619(3) 0.9889(8) 0.4028(2) 0.0154(7) Uani 0.541(11) 1 d . U P A 1
H14 H 0.4255 1.0688 0.4131 0.019 Uiso 0.541(11) 1 calc R . P A 1
C15 C 0.5229(2) 1.0164(7) 0.42901(18) 0.0262(8) Uani 0.541(11) 1 d . U P A 1
H15 H 0.5290 1.1208 0.4563 0.031 Uiso 0.541(11) 1 calc R . P A 1
C16 C 0.5756(2) 0.8951(8) 0.4165(3) 0.0337(10) Uani 0.541(11) 1 d . U P A 1
H16 H 0.6172 0.9152 0.4353 0.040 Uiso 0.541(11) 1 calc R . P A 1
C17 C 0.56708(17) 0.7470(6) 0.3768(3) 0.0385(10) Uani 0.541(11) 1 d . U P A 1
H17 H 0.6029 0.6629 0.3682 0.046 Uiso 0.541(11) 1 calc R . P A 1
C18 C 0.5061(2) 0.7181(6) 0.3489(3) 0.0329(9) Uani 0.541(11) 1 d . U P A 1
H18 H 0.5001 0.6133 0.3218 0.039 Uiso 0.541(11) 1 calc R . P A 1
C13' C 0.4514(8) 0.826(3) 0.3517(7) 0.0167(11) Uani 0.459(11) 1 d D U P A 2
C14' C 0.4711(4) 0.9412(12) 0.3987(4) 0.0290(13) Uani 0.459(11) 1 d D U P A 2
H14' H 0.4388 1.0202 0.4171 0.035 Uiso 0.459(11) 1 calc R . P A 2
C15' C 0.5363(3) 0.9490(13) 0.4214(2) 0.0375(13) Uani 0.459(11) 1 d . U P A 2
H15' H 0.5470 1.0280 0.4547 0.045 Uiso 0.459(11) 1 calc R . P A 2
C16' C 0.5829(3) 0.8415(10) 0.3946(3) 0.0368(13) Uani 0.459(11) 1 d . U P A 2
H16' H 0.6273 0.8465 0.4084 0.044 Uiso 0.459(11) 1 calc R . P A 2
C17' C 0.56612(16) 0.7241(6) 0.3470(4) 0.0364(12) Uani 0.459(11) 1 d . U P A 2
H17' H 0.5990 0.6477 0.3284 0.044 Uiso 0.459(11) 1 calc R . P A 2
C18' C 0.5022(2) 0.7174(6) 0.3263(3) 0.0240(9) Uani 0.459(11) 1 d D U P A 2
H18' H 0.4920 0.6355 0.2935 0.029 Uiso 0.459(11) 1 calc R . P A 2
N1 N 0.34656(3) 0.66434(10) 0.36230(3) 0.0179(2) Uani 1 1 d . . . . .
O1 O 0.30312(3) 0.87188(9) 0.43072(3) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.22432(3) 0.52237(9) 0.45678(3) 0.0217(2) Uani 1 1 d . . . . .
H2 H 0.2214(8) 0.566(3) 0.4971(8) 0.060(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C13 1.577(13) . ?
C1 C13' 1.427(16) . ?
C1 N1 1.4631(10) . ?
C2 C3 1.5337(11) . ?
C2 N1 1.3444(10) . ?
C2 O1 1.2346(10) . ?
C3 C4 1.5272(11) . ?
C3 C6 1.5258(11) . ?
C3 O2 1.4130(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5429(11) . ?
C5 H5 1.0000 . ?
C5 C7 1.5111(11) . ?
C5 N1 1.4716(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3909(12) . ?
C7 C12 1.3964(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.3936(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.3902(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3940(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.3898(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(10) . ?
C13 C18 1.377(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.361(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(6) . ?
C18 H18 0.9500 . ?
C13' C14' 1.378(12) . ?
C13' C18' 1.401(16) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.413(10) . ?
C15' H15' 0.9500 . ?
C15' C16' 1.349(7) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.381(6) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.372(6) . ?
C18' H18' 0.9500 . ?
O2 H2 0.960(18) . ?

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
H1AA C1 H1AB 108.0 . . ?
H1BC C1 H1BD 107.8 . . ?
C13 C1 H1AA 109.4 . . ?
C13 C1 H1AB 109.4 . . ?
C13' C1 H1BC 108.9 . . ?
C13' C1 H1BD 108.9 . . ?
C13' C1 N1 113.2(10) . . ?
N1 C1 H1AA 109.4 . . ?
N1 C1 H1AB 109.4 . . ?
N1 C1 H1BC 108.9 . . ?
N1 C1 H1BD 108.9 . . ?
N1 C1 C13 111.3(7) . . ?
N1 C2 C3 108.97(7) . . ?
O1 C2 C3 126.23(7) . . ?
O1 C2 N1 124.78(8) . . ?
C4 C3 C2 102.00(6) . . ?
C6 C3 C2 108.72(7) . . ?
C6 C3 C4 112.98(7) . . ?
O2 C3 C2 111.15(7) . . ?
O2 C3 C4 109.79(6) . . ?
O2 C3 C6 111.80(7) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.39(6) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 H5 109.3 . . ?
C7 C5 C4 114.16(7) . . ?
C7 C5 H5 109.3 . . ?
N1 C5 C4 101.40(6) . . ?
N1 C5 H5 109.3 . . ?
N1 C5 C7 112.96(7) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.72(7) . . ?
C8 C7 C12 119.12(8) . . ?
C12 C7 C5 121.15(7) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.68(8) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.95(8) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.60(8) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.29(8) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.30(8) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C1 118.2(10) . . ?
C18 C13 C1 120.9(8) . . ?
C18 C13 C14 120.7(9) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.5(7) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.5(6) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C14' C13' C1 123.5(12) . . ?
C14' C13' C18' 114.4(11) . . ?
C18' C13' C1 122.1(9) . . ?
C13' C14' H14' 118.0 . . ?
C13' C14' C15' 124.1(8) . . ?
C15' C14' H14' 118.0 . . ?
C14' C15' H15' 120.8 . . ?
C16' C15' C14' 118.4(5) . . ?
C16' C15' H15' 120.8 . . ?
C15' C16' H16' 120.0 . . ?
C15' C16' C17' 120.1(4) . . ?
C17' C16' H16' 120.0 . . ?
C16' C17' H17' 119.8 . . ?
C18' C17' C16' 120.3(4) . . ?
C18' C17' H17' 119.8 . . ?
C13' C18' H18' 118.6 . . ?
C17' C18' C13' 122.7(6) . . ?
C17' C18' H18' 118.6 . . ?
C1 N1 C5 122.68(7) . . ?
C2 N1 C1 122.20(7) . . ?
C2 N1 C5 113.18(7) . . ?
C3 O2 H2 109.5(10) . . ?

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
O2 H2 O1 0.960(18) 1.766(18) 2.7091(8) 166.7(16) 7_566

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 C13 C14 C15 -179.8(9) . . . . ?
C1 C13 C18 C17 -179.0(9) . . . . ?
C1 C13' C14' C15' 176.8(13) . . . . ?
C1 C13' C18' C17' -177.7(12) . . . . ?
C2 C3 C4 C5 28.93(8) . . . . ?
C3 C2 N1 C1 -168.02(7) . . . . ?
C3 C2 N1 C5 -3.46(9) . . . . ?
C3 C4 C5 C7 -152.52(7) . . . . ?
C3 C4 C5 N1 -30.75(8) . . . . ?
C4 C5 C7 C8 -112.63(9) . . . . ?
C4 C5 C7 C12 65.93(10) . . . . ?
C4 C5 N1 C1 -173.82(7) . . . . ?
C4 C5 N1 C2 21.71(8) . . . . ?
C5 C7 C8 C9 176.48(8) . . . . ?
C5 C7 C12 C11 -177.74(8) . . . . ?
C6 C3 C4 C5 -87.58(8) . . . . ?
C7 C5 N1 C1 -51.22(10) . . . . ?
C7 C5 N1 C2 144.31(7) . . . . ?
C7 C8 C9 C10 1.51(14) . . . . ?
C8 C7 C12 C11 0.84(13) . . . . ?
C8 C9 C10 C11 0.39(14) . . . . ?
C9 C10 C11 C12 -1.66(13) . . . . ?
C10 C11 C12 C7 1.05(13) . . . . ?
C12 C7 C8 C9 -2.12(13) . . . . ?
C13 C1 C13' C14' -10(11) . . . . ?
C13 C1 C13' C18' 168(15) . . . . ?
C13 C1 N1 C2 81.6(5) . . . . ?
C13 C1 N1 C5 -81.5(5) . . . . ?
C13 C14 C15 C16 -3.2(12) . . . . ?
C14 C13 C18 C17 -4(2) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C13 1.0(11) . . . . ?
C18 C13 C14 C15 5(2) . . . . ?
C13' C1 C13 C14 160(14) . . . . ?
C13' C1 C13 C18 -24(12) . . . . ?
C13' C1 N1 C2 89.5(6) . . . . ?
C13' C1 N1 C5 -73.6(6) . . . . ?
C13' C14' C15' C16' 1.8(16) . . . . ?
C14' C13' C18' C17' 0(2) . . . . ?
C14' C15' C16' C17' -1.4(8) . . . . ?
C15' C16' C17' C18' 0.6(6) . . . . ?
C16' C17' C18' C13' -0.1(13) . . . . ?
C18' C13' C14' C15' -1(2) . . . . ?
N1 C1 C13 C14 -93.6(14) . . . . ?
N1 C1 C13 C18 82.1(14) . . . . ?
N1 C1 C13' C14' -87(2) . . . . ?
N1 C1 C13' C18' 91.4(18) . . . . ?
N1 C2 C3 C4 -16.59(8) . . . . ?
N1 C2 C3 C6 102.98(8) . . . . ?
N1 C2 C3 O2 -133.55(7) . . . . ?
N1 C5 C7 C8 132.20(8) . . . . ?
N1 C5 C7 C12 -49.24(10) . . . . ?
O1 C2 C3 C4 164.59(8) . . . . ?
O1 C2 C3 C6 -75.84(10) . . . . ?
O1 C2 C3 O2 47.63(11) . . . . ?
O1 C2 N1 C1 10.83(12) . . . . ?
O1 C2 N1 C5 175.38(7) . . . . ?
O2 C3 C4 C5 146.87(7) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 -15 0.0821 -1.0126 -0.0024 -14.9878 0.9687 -0.3262 -0.0868
-8 0 -11 0.0598 -8.0038 -0.0020 -10.9841 0.9191 0.2576 -0.1796
3 -4 -3 0.1864 2.9978 -3.9945 -2.9969 -0.0273 -0.4347 -0.8436
-13 0 4 0.0666 -12.9866 0.0002 4.0094 0.1227 0.9940 -0.1886
13 0 -4 0.0501 12.9866 -0.0002 -4.0094 -0.1227 -0.9940 0.1886
12 0 5 0.0374 11.9954 0.0012 4.9848 -0.6580 -0.6889 0.2152
-12 0 -5 0.0598 -11.9954 -0.0012 -4.9848 0.6580 0.6889 -0.2152
-2 -4 4 0.1674 -1.9922 -3.9936 4.0026 -0.3224 0.0912 -0.8904
3 4 5 0.1441 2.9995 3.9950 4.9897 -0.2703 0.0771 0.9488
1 0 15 0.0821 1.0126 0.0024 14.9878 -0.9687 0.3262 0.0868
####################################################################### 
# 
# 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_6a-cis
_database_code_depnum_ccdc_archive 'CCDC 1028122'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 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      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                   7.63367(18)
_cell_length_b                   29.2305(5)
_cell_length_c                   6.84862(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.295(2)
_cell_angle_gamma                90
_cell_volume                     1493.12(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6054
_cell_measurement_temperature    99.94(19)
_cell_measurement_theta_max      74.3290
_cell_measurement_theta_min      6.0460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.4724
_exptl_crystal_size_mid          0.1559
_exptl_crystal_size_min          0.0887
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10140
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.481
_diffrn_reflns_theta_min         5.933
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.94(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0804290000
_diffrn_orient_matrix_UB_12      -0.0482402000
_diffrn_orient_matrix_UB_13      -0.0039450000
_diffrn_orient_matrix_UB_21      -0.1898694000
_diffrn_orient_matrix_UB_22      -0.0206859000
_diffrn_orient_matrix_UB_23      -0.0417683000
_diffrn_orient_matrix_UB_31      -0.0110958000
_diffrn_orient_matrix_UB_32      0.0046773000
_diffrn_orient_matrix_UB_33      -0.2264570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2578
_reflns_number_total             2899
_reflns_odcompleteness_completeness 97.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.046
_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)+(0.0417P)²+0.5070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 0.11279(16) 0.61519(4) 0.39315(17) 0.0209(3) Uani 1 1 d . . . . .
H1A H 0.0091 0.6331 0.4168 0.025 Uiso 1 1 calc R . . . .
H1B H 0.0763 0.5997 0.2622 0.025 Uiso 1 1 calc R . . . .
C2 C 0.23410(15) 0.53989(4) 0.51951(17) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.31298(15) 0.51822(4) 0.72353(17) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.22254(16) 0.54550(4) 0.86309(17) 0.0203(3) Uani 1 1 d . . . . .
H4A H 0.3008 0.5477 0.9981 0.024 Uiso 1 1 calc R . . . .
H4B H 0.1074 0.5313 0.8742 0.024 Uiso 1 1 calc R . . . .
C5 C 0.19163(15) 0.59294(4) 0.76433(16) 0.0186(2) Uani 1 1 d . . . . .
H5 H 0.3046 0.6112 0.8017 0.022 Uiso 1 1 calc R . . . .
C6 C 0.28499(17) 0.46696(4) 0.72625(18) 0.0228(3) Uani 1 1 d . . . . .
H6A H 0.1563 0.4603 0.6968 0.034 Uiso 1 1 calc GR . . . .
H6B H 0.3402 0.4549 0.8585 0.034 Uiso 1 1 calc GR . . . .
H6C H 0.3404 0.4525 0.6251 0.034 Uiso 1 1 calc GR . . . .
C7 C 0.03867(16) 0.62027(4) 0.81330(16) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.06889(17) 0.66470(4) 0.88632(18) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.1857 0.6775 0.9058 0.028 Uiso 1 1 calc R . . . .
C9 C -0.07077(19) 0.69051(4) 0.9310(2) 0.0285(3) Uani 1 1 d . . . . .
H9 H -0.0488 0.7207 0.9819 0.034 Uiso 1 1 calc R . . . .
C10 C -0.24142(18) 0.67224(4) 0.9012(2) 0.0286(3) Uani 1 1 d . . . . .
H10 H -0.3373 0.6900 0.9295 0.034 Uiso 1 1 calc R . . . .
C11 C -0.27238(17) 0.62783(4) 0.82979(19) 0.0268(3) Uani 1 1 d . . . . .
H11 H -0.3893 0.6151 0.8108 0.032 Uiso 1 1 calc R . . . .
C12 C -0.13364(16) 0.60201(4) 0.78621(18) 0.0224(3) Uani 1 1 d . . . . .
H12 H -0.1559 0.5717 0.7375 0.027 Uiso 1 1 calc R . . . .
C13 C 0.26699(16) 0.64727(4) 0.38744(16) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.41663(17) 0.63093(4) 0.32413(18) 0.0241(3) Uani 1 1 d . . . . .
H14 H 0.4195 0.6000 0.2828 0.029 Uiso 1 1 calc R . . . .
C15 C 0.56164(19) 0.65915(5) 0.3205(2) 0.0297(3) Uani 1 1 d . . . . .
H15 H 0.6635 0.6475 0.2781 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5579(2) 0.70451(5) 0.3789(2) 0.0346(3) Uani 1 1 d . . . . .
H16 H 0.6569 0.7240 0.3758 0.042 Uiso 1 1 calc R . . . .
C17 C 0.4099(2) 0.72123(5) 0.4417(2) 0.0364(3) Uani 1 1 d . . . . .
H17 H 0.4071 0.7523 0.4816 0.044 Uiso 1 1 calc R . . . .
C18 C 0.2648(2) 0.69278(4) 0.4466(2) 0.0293(3) Uani 1 1 d . . . . .
H18 H 0.1637 0.7045 0.4906 0.035 Uiso 1 1 calc R . . . .
N1 N 0.16178(13) 0.58069(3) 0.55056(14) 0.0181(2) Uani 1 1 d . . . . .
O1 O 0.24301(11) 0.52392(3) 0.35488(12) 0.0226(2) Uani 1 1 d . . . . .
O2 O 0.49889(11) 0.53067(3) 0.76807(12) 0.0216(2) Uani 1 1 d . . . . .
H2 H 0.564(3) 0.5113(6) 0.707(3) 0.048(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.5120(17) . ?
C1 N1 1.4653(14) . ?
C2 C3 1.5355(15) . ?
C2 N1 1.3500(15) . ?
C2 O1 1.2354(14) . ?
C3 C4 1.5190(16) . ?
C3 C6 1.5142(15) . ?
C3 O2 1.4336(14) . ?
C4 C5 1.5387(16) . ?
C5 C7 1.5103(16) . ?
C5 N1 1.4769(14) . ?
C7 C8 1.3933(16) . ?
C7 C12 1.3948(17) . ?
C8 C9 1.3921(18) . ?
C9 C10 1.382(2) . ?
C10 C11 1.3896(19) . ?
C11 C12 1.3838(18) . ?
C13 C14 1.3898(18) . ?
C13 C18 1.3919(17) . ?
C14 C15 1.3849(18) . ?
C15 C16 1.387(2) . ?
C16 C17 1.381(2) . ?
C17 C18 1.391(2) . ?

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
N1 C1 C13 111.57(9) . . ?
N1 C2 C3 108.38(9) . . ?
O1 C2 C3 125.98(10) . . ?
O1 C2 N1 125.54(10) . . ?
C4 C3 C2 102.32(9) . . ?
C6 C3 C2 112.98(9) . . ?
C6 C3 C4 115.31(10) . . ?
O2 C3 C2 105.52(9) . . ?
O2 C3 C4 107.14(9) . . ?
O2 C3 C6 112.61(9) . . ?
C3 C4 C5 104.13(9) . . ?
C7 C5 C4 115.63(10) . . ?
N1 C5 C4 101.20(9) . . ?
N1 C5 C7 112.64(9) . . ?
C8 C7 C5 119.74(11) . . ?
C8 C7 C12 118.93(11) . . ?
C12 C7 C5 121.32(10) . . ?
C9 C8 C7 120.53(12) . . ?
C10 C9 C8 120.01(12) . . ?
C9 C10 C11 119.80(12) . . ?
C12 C11 C10 120.32(12) . . ?
C11 C12 C7 120.40(11) . . ?
C14 C13 C1 119.41(11) . . ?
C14 C13 C18 118.74(12) . . ?
C18 C13 C1 121.84(12) . . ?
C15 C14 C13 120.94(12) . . ?
C14 C15 C16 119.91(13) . . ?
C17 C16 C15 119.75(13) . . ?
C16 C17 C18 120.30(13) . . ?
C17 C18 C13 120.35(13) . . ?
C1 N1 C5 121.59(9) . . ?
C2 N1 C1 122.75(10) . . ?
C2 N1 C5 112.85(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.91(2) 1.92(2) 2.8007(12) 162.4(17) 3_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 C13 C14 C15 -178.82(11) . . . . ?
C1 C13 C18 C17 179.26(12) . . . . ?
C2 C3 C4 C5 -30.36(11) . . . . ?
C3 C2 N1 C1 165.28(10) . . . . ?
C3 C2 N1 C5 4.03(13) . . . . ?
C3 C4 C5 C7 154.38(9) . . . . ?
C3 C4 C5 N1 32.35(11) . . . . ?
C4 C5 C7 C8 126.85(11) . . . . ?
C4 C5 C7 C12 -53.41(14) . . . . ?
C4 C5 N1 C1 175.47(10) . . . . ?
C4 C5 N1 C2 -23.05(12) . . . . ?
C5 C7 C8 C9 179.56(11) . . . . ?
C5 C7 C12 C11 -179.23(11) . . . . ?
C6 C3 C4 C5 -153.40(9) . . . . ?
C7 C5 N1 C1 51.39(14) . . . . ?
C7 C5 N1 C2 -147.12(10) . . . . ?
C7 C8 C9 C10 -0.59(19) . . . . ?
C8 C7 C12 C11 0.51(18) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 -0.73(19) . . . . ?
C10 C11 C12 C7 -0.06(19) . . . . ?
C12 C7 C8 C9 -0.18(18) . . . . ?
C13 C1 N1 C2 -89.87(13) . . . . ?
C13 C1 N1 C5 69.77(13) . . . . ?
C13 C14 C15 C16 -0.59(19) . . . . ?
C14 C13 C18 C17 0.16(18) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C18 C13 C14 C15 0.30(18) . . . . ?
N1 C1 C13 C14 69.37(13) . . . . ?
N1 C1 C13 C18 -109.72(12) . . . . ?
N1 C2 C3 C4 17.10(12) . . . . ?
N1 C2 C3 C6 141.70(11) . . . . ?
N1 C2 C3 O2 -94.85(11) . . . . ?
N1 C5 C7 C8 -117.46(11) . . . . ?
N1 C5 C7 C12 62.28(14) . . . . ?
O1 C2 C3 C4 -166.27(11) . . . . ?
O1 C2 C3 C6 -41.66(16) . . . . ?
O1 C2 C3 O2 81.78(14) . . . . ?
O1 C2 N1 C1 -11.37(18) . . . . ?
O1 C2 N1 C5 -172.61(11) . . . . ?
O2 C3 C4 C5 80.37(10) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 18 0 0.0444 1.0016 18.0001 0.0008 -0.7878 -0.5625 0.0729
-3 15 0 0.0559 -3.0024 15.0099 0.0078 -0.9656 0.2593 0.1018
3 -15 0 0.0559 3.0024 -15.0099 -0.0078 0.9656 -0.2593 -0.1018
-4 -10 0 0.0672 -4.0042 -9.9912 0.0059 0.1599 0.9667 -0.0036
4 10 0 0.0524 4.0042 9.9912 -0.0059 -0.1599 -0.9667 0.0036
-1 2 4 0.2283 -1.0001 2.0000 3.9997 -0.1927 -0.0185 -0.8853
1 -2 -4 0.2283 1.0001 -2.0000 -3.9997 0.1927 0.0185 0.8853
-1 -18 0 0.0444 -1.0016 -18.0001 -0.0008 0.7878 0.5625 -0.0729
####################################################################### 
# 
# 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_6d-trans
_database_code_depnum_ccdc_archive 'CCDC 1028123'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H21NO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4972(2)
_cell_length_b                   14.1613(2)
_cell_length_c                   17.5538(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3106.62(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9208
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2860
_cell_measurement_theta_min      3.9910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3033
_exptl_crystal_size_mid          0.1817
_exptl_crystal_size_min          0.1602
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15485
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         5.039
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   25.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega -122.00  -94.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00  -10.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  125.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega -119.00  -86.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   98.00  145.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  119.0000 -166.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   26.00  109.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00   87.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   83.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00  100.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 10 omega  106.00  172.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   71.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   98.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.0607  -57.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 14 omega -117.00  -92.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00  178.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000 -180.0000 117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0362913000
_diffrn_orient_matrix_UB_12      0.0938024000
_diffrn_orient_matrix_UB_13      0.0363134000
_diffrn_orient_matrix_UB_21      0.0853571000
_diffrn_orient_matrix_UB_22      -0.0534065000
_diffrn_orient_matrix_UB_23      0.0464629000
_diffrn_orient_matrix_UB_31      0.0810496000
_diffrn_orient_matrix_UB_32      0.0143286000
_diffrn_orient_matrix_UB_33      -0.0649829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2826
_reflns_number_total             3132
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.050
_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)+(0.0430P)²+1.2120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C19(H19A,H19B,H19C)
;
_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 0.23346(9) 0.50205(8) 0.46037(7) 0.0221(2) Uani 1 1 d . . . . .
H1A H 0.2299 0.5715 0.4543 0.027 Uiso 1 1 calc R . . . .
H1B H 0.2434 0.4885 0.5153 0.027 Uiso 1 1 calc R . . . .
C2 C 0.41009(9) 0.42453(8) 0.45274(7) 0.0204(2) Uani 1 1 d . . . . .
C3 C 0.48546(9) 0.38620(8) 0.39098(6) 0.0217(2) Uani 1 1 d . . . . .
C4 C 0.44958(9) 0.44045(9) 0.32024(7) 0.0240(3) Uani 1 1 d . . . . .
H4A H 0.4572 0.4009 0.2740 0.029 Uiso 1 1 calc R . . . .
H4B H 0.4926 0.4986 0.3137 0.029 Uiso 1 1 calc R . . . .
C5 C 0.33103(9) 0.46493(8) 0.33469(6) 0.0217(2) Uani 1 1 d . . . . .
H5 H 0.2845 0.4129 0.3150 0.026 Uiso 1 1 calc R . . . .
C6 C 0.46912(10) 0.28023(8) 0.38198(7) 0.0272(3) Uani 1 1 d . . . . .
H6A H 0.5222 0.2551 0.3462 0.041 Uiso 1 1 calc GR . . . .
H6B H 0.3970 0.2680 0.3623 0.041 Uiso 1 1 calc GR . . . .
H6C H 0.4776 0.2493 0.4316 0.041 Uiso 1 1 calc GR . . . .
C7 C 0.29904(9) 0.55706(9) 0.29804(7) 0.0227(2) Uani 1 1 d . . . . .
C8 C 0.22510(10) 0.55794(10) 0.23871(7) 0.0281(3) Uani 1 1 d . . . . .
H8 H 0.1896 0.5013 0.2246 0.034 Uiso 1 1 calc R . . . .
C9 C 0.20305(11) 0.64119(11) 0.20006(8) 0.0350(3) Uani 1 1 d . . . . .
H9 H 0.1530 0.6414 0.1594 0.042 Uiso 1 1 calc R . . . .
C10 C 0.25417(12) 0.72391(10) 0.22092(8) 0.0367(3) Uani 1 1 d . . . . .
H10 H 0.2398 0.7807 0.1940 0.044 Uiso 1 1 calc R . . . .
C11 C 0.32635(11) 0.72434(9) 0.28106(8) 0.0318(3) Uani 1 1 d . . . . .
H11 H 0.3605 0.7814 0.2958 0.038 Uiso 1 1 calc R . . . .
C12 C 0.34839(10) 0.64099(9) 0.31947(7) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.3976 0.6412 0.3607 0.031 Uiso 1 1 calc R . . . .
C13 C 0.12841(9) 0.45996(9) 0.43484(6) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.10308(10) 0.36500(9) 0.44729(7) 0.0280(3) Uani 1 1 d . . . . .
C15 C 0.00061(11) 0.33350(11) 0.42619(8) 0.0366(3) Uani 1 1 d . . . . .
H15 H -0.0179 0.2690 0.4332 0.044 Uiso 1 1 calc R . . . .
C16 C -0.07350(11) 0.39505(12) 0.39536(8) 0.0413(4) Uani 1 1 d . . . . .
H16 H -0.1430 0.3727 0.3829 0.050 Uiso 1 1 calc R . . . .
C17 C -0.04802(11) 0.48854(12) 0.38248(8) 0.0392(4) Uani 1 1 d . . . . .
H17 H -0.0991 0.5304 0.3608 0.047 Uiso 1 1 calc R . . . .
C18 C 0.05311(10) 0.52028(10) 0.40173(7) 0.0301(3) Uani 1 1 d . . . . .
H18 H 0.0717 0.5843 0.3923 0.036 Uiso 1 1 calc R . . . .
C19 C 0.18118(12) 0.29831(9) 0.48346(8) 0.0349(3) Uani 1 1 d . . . . .
H19A H 0.2405 0.2865 0.4482 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.1451 0.2386 0.4952 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.2089 0.3263 0.5305 0.052 Uiso 1 1 calc GR . . . .
N1 N 0.32647(8) 0.46667(7) 0.41871(5) 0.0205(2) Uani 1 1 d . . . . .
O1 O 0.42346(7) 0.41645(6) 0.52222(4) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.59460(6) 0.40192(6) 0.40994(5) 0.0247(2) Uani 1 1 d . . . . .
H2 H 0.5960(15) 0.4623(14) 0.4282(11) 0.054(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C13 1.5098(16) . ?
C1 N1 1.4618(14) . ?
C2 C3 1.5354(16) . ?
C2 N1 1.3436(15) . ?
C2 O1 1.2362(14) . ?
C3 C4 1.5273(16) . ?
C3 C6 1.5228(16) . ?
C3 O2 1.4215(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5426(16) . ?
C5 H5 1.0000 . ?
C5 C7 1.5086(16) . ?
C5 N1 1.4762(14) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3924(17) . ?
C7 C12 1.3908(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3878(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3870(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3987(17) . ?
C13 C18 1.3976(18) . ?
C14 C15 1.4058(19) . ?
C14 C19 1.4992(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3833(19) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.914(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 107.6 . . ?
C13 C1 H1A 108.7 . . ?
C13 C1 H1B 108.7 . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C13 114.05(9) . . ?
N1 C2 C3 108.67(10) . . ?
O1 C2 C3 125.52(10) . . ?
O1 C2 N1 125.80(11) . . ?
C4 C3 C2 102.48(9) . . ?
C6 C3 C2 109.83(10) . . ?
C6 C3 C4 111.84(10) . . ?
O2 C3 C2 111.59(9) . . ?
O2 C3 C4 113.16(10) . . ?
O2 C3 C6 107.89(9) . . ?
C3 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C3 C4 C5 105.15(9) . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C4 C5 H5 109.6 . . ?
C7 C5 C4 112.26(10) . . ?
C7 C5 H5 109.6 . . ?
N1 C5 C4 101.83(9) . . ?
N1 C5 H5 109.6 . . ?
N1 C5 C7 113.66(9) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 120.17(11) . . ?
C12 C7 C5 120.41(10) . . ?
C12 C7 C8 119.27(11) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.33(12) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.88(12) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.32(13) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.66(13) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.51(12) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C1 122.00(11) . . ?
C18 C13 C1 117.88(11) . . ?
C18 C13 C14 120.02(12) . . ?
C13 C14 C15 118.04(13) . . ?
C13 C14 C19 121.63(11) . . ?
C15 C14 C19 120.31(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.89(14) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.97(13) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.84(14) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.21(13) . . ?
C17 C18 H18 119.4 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C5 122.43(9) . . ?
C2 N1 C1 123.24(9) . . ?
C2 N1 C5 114.01(9) . . ?
C3 O2 H2 104.3(12) . . ?

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
O2 H2 O1 0.914(19) 1.94(2) 2.8435(12) 169.6(17) 5_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 C13 C14 C15 175.79(11) . . . . ?
C1 C13 C14 C19 -2.99(18) . . . . ?
C1 C13 C18 C17 -174.80(11) . . . . ?
C2 C3 C4 C5 -26.79(11) . . . . ?
C3 C2 N1 C1 173.20(9) . . . . ?
C3 C2 N1 C5 -0.45(13) . . . . ?
C3 C4 C5 C7 148.34(10) . . . . ?
C3 C4 C5 N1 26.42(11) . . . . ?
C4 C5 C7 C8 114.05(12) . . . . ?
C4 C5 C7 C12 -61.47(14) . . . . ?
C4 C5 N1 C1 169.78(10) . . . . ?
C4 C5 N1 C2 -16.52(12) . . . . ?
C5 C7 C8 C9 -173.87(11) . . . . ?
C5 C7 C12 C11 173.99(11) . . . . ?
C6 C3 C4 C5 90.80(11) . . . . ?
C7 C5 N1 C1 48.82(14) . . . . ?
C7 C5 N1 C2 -137.47(10) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C7 C12 C11 -1.57(18) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C10 C11 C12 C7 0.21(19) . . . . ?
C12 C7 C8 C9 1.71(18) . . . . ?
C13 C1 N1 C2 -122.42(12) . . . . ?
C13 C1 N1 C5 50.70(14) . . . . ?
C13 C14 C15 C16 -1.18(18) . . . . ?
C14 C13 C18 C17 1.65(18) . . . . ?
C14 C15 C16 C17 1.8(2) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C13 -1.05(19) . . . . ?
C18 C13 C14 C15 -0.52(17) . . . . ?
C18 C13 C14 C19 -179.30(11) . . . . ?
C19 C14 C15 C16 177.61(12) . . . . ?
N1 C1 C13 C14 68.22(14) . . . . ?
N1 C1 C13 C18 -115.40(12) . . . . ?
N1 C2 C3 C4 17.44(12) . . . . ?
N1 C2 C3 C6 -101.57(11) . . . . ?
N1 C2 C3 O2 138.83(10) . . . . ?
N1 C5 C7 C8 -131.04(11) . . . . ?
N1 C5 C7 C12 53.44(14) . . . . ?
O1 C2 C3 C4 -163.67(11) . . . . ?
O1 C2 C3 C6 77.33(14) . . . . ?
O1 C2 C3 O2 -42.28(15) . . . . ?
O1 C2 N1 C1 -5.70(17) . . . . ?
O1 C2 N1 C5 -179.35(11) . . . . ?
O2 C3 C4 C5 -147.10(10) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 9 1 0.0726 0.9895 8.9955 1.0142 0.9165 -0.3488 0.1432
-1 -9 -1 0.0876 -0.9895 -8.9955 -1.0142 -0.9165 0.3488 -0.1432
5 -1 -9 0.1460 5.0108 -0.9915 -9.0024 -0.2381 0.0624 0.9769
-5 -6 6 0.1037 -5.0003 -6.0038 5.9909 -0.5271 0.1722 -0.8806
-5 -3 8 0.1332 -5.0055 -3.0058 7.9960 -0.1732 0.1048 -0.9684
4 8 -3 0.1062 3.9949 8.0009 -2.9873 0.7870 -0.2251 0.6326
8 0 3 0.0608 7.9973 0.0133 3.0045 0.4006 0.8215 0.4531
-5 1 -9 0.0557 -4.9919 0.9907 -9.0038 -0.4152 -0.8973 0.1947
-1 -1 11 0.1420 -1.0106 -1.0005 11.0018 0.2690 0.4783 -0.8112
-8 -1 3 0.1132 -8.0026 -1.0123 2.9960 -0.2766 -0.4898 -0.8578
-1 -5 10 0.1206 -1.0053 -4.9978 9.9955 -0.1423 0.6455 -0.8026
1 5 -10 0.1213 1.0053 4.9978 -9.9955 0.1423 -0.6455 0.8026
-7 5 -2 0.1130 -7.0036 4.9850 -1.9963 0.1409 -0.9568 -0.3665
6 4 5 0.0775 5.9909 4.0073 5.0103 0.7753 0.5301 0.2174
7 4 1 0.0783 6.9951 4.0088 1.0094 0.6666 0.4299 0.5588

_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_6e-cis
_database_code_depnum_ccdc_archive 'CCDC 1028124'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18NO3
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.86998(8)
_cell_length_b                   15.21957(20)
_cell_length_c                   27.0563(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2828.95(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11195
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3340
_cell_measurement_theta_min      3.2220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.2277
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.1111
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15654
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.468
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1809656000
_diffrn_orient_matrix_UB_12      -0.0372672000
_diffrn_orient_matrix_UB_13      0.0262972000
_diffrn_orient_matrix_UB_21      0.1311419000
_diffrn_orient_matrix_UB_22      0.0614955000
_diffrn_orient_matrix_UB_23      -0.0306197000
_diffrn_orient_matrix_UB_31      -0.0186162000
_diffrn_orient_matrix_UB_32      0.0712196000
_diffrn_orient_matrix_UB_33      0.0401685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                5249
_reflns_number_total             5473
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.057
_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)+(0.0310P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C105(H105)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C101(H10A,H10B), C104(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C108(H108), C109(H109), C110(H110), C112(H112), C113(H113), C114(H114),
 C115(H115), C116(H116)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C106(H10E,H10F,H10G)
;
_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 -0.0147(2) 0.84906(11) 0.09626(7) 0.0214(4) Uani 1 1 d . . . . .
H1A H -0.1317 0.8252 0.0797 0.026 Uiso 1 1 calc R . . . .
H1B H 0.0248 0.9028 0.0782 0.026 Uiso 1 1 calc R . . . .
C2 C 0.1121(2) 0.69973(12) 0.08085(6) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.3076(2) 0.65095(11) 0.08490(7) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.4533(3) 0.72627(11) 0.08427(7) 0.0233(4) Uani 1 1 d . . . . .
H4A H 0.4930 0.7404 0.0500 0.028 Uiso 1 1 calc R . . . .
H4B H 0.5707 0.7112 0.1037 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3446(2) 0.80367(12) 0.10776(7) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.3550 0.7996 0.1446 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3353(3) 0.58312(12) 0.04466(7) 0.0251(4) Uani 1 1 d . . . . .
H6A H 0.2360 0.5373 0.0479 0.038 Uiso 1 1 calc GR . . . .
H6B H 0.4649 0.5568 0.0477 0.038 Uiso 1 1 calc GR . . . .
H6C H 0.3231 0.6114 0.0123 0.038 Uiso 1 1 calc GR . . . .
C7 C 0.4095(2) 0.89258(12) 0.09132(7) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.4749(3) 0.95825(12) 0.12050(8) 0.0282(4) Uani 1 1 d . . . . .
H8 H 0.4872 0.9547 0.1554 0.034 Uiso 1 1 calc R . . . .
C9 C 0.4827(3) 1.00848(13) 0.04481(8) 0.0309(4) Uani 1 1 d . . . . .
H9 H 0.5009 1.0466 0.0174 0.037 Uiso 1 1 calc R . . . .
C10 C 0.4157(3) 0.92586(13) 0.04159(7) 0.0274(4) Uani 1 1 d . . . . .
H10 H 0.3797 0.8954 0.0123 0.033 Uiso 1 1 calc R . . . .
C11 C -0.0680(2) 0.87401(12) 0.14858(7) 0.0216(4) Uani 1 1 d . . . . .
C12 C -0.1605(3) 0.81382(13) 0.17953(7) 0.0264(4) Uani 1 1 d . . . . .
H12 H -0.1805 0.7551 0.1688 0.032 Uiso 1 1 calc R . . . .
C13 C -0.2235(3) 0.83971(16) 0.22611(8) 0.0355(5) Uani 1 1 d . . . . .
H13 H -0.2869 0.7986 0.2471 0.043 Uiso 1 1 calc R . . . .
C14 C -0.1943(3) 0.92536(17) 0.24214(8) 0.0394(5) Uani 1 1 d . . . . .
H14 H -0.2397 0.9432 0.2738 0.047 Uiso 1 1 calc R . . . .
C15 C -0.0989(3) 0.98456(15) 0.21190(8) 0.0372(5) Uani 1 1 d . . . . .
H15 H -0.0772 1.0430 0.2229 0.045 Uiso 1 1 calc R . . . .
C16 C -0.0347(3) 0.95867(13) 0.16552(7) 0.0275(4) Uani 1 1 d . . . . .
H16 H 0.0327 0.9994 0.1451 0.033 Uiso 1 1 calc R . . . .
N1 N 0.1418(2) 0.78457(9) 0.09260(6) 0.0199(3) Uani 1 1 d . . . . .
O1 O -0.04671(18) 0.66667(8) 0.07052(5) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.31297(19) 0.61243(8) 0.13307(5) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.248(4) 0.5629(19) 0.1325(11) 0.055(8) Uiso 1 1 d . . . . .
O3 O 0.5211(2) 1.03050(9) 0.09282(6) 0.0336(3) Uani 1 1 d . . . . .
C101 C 0.0734(2) 0.26655(11) 0.14373(7) 0.0214(4) Uani 1 1 d . . . . .
H10A H 0.0408 0.2229 0.1696 0.026 Uiso 1 1 calc R . . . .
H10B H 0.2036 0.2908 0.1515 0.026 Uiso 1 1 calc R . . . .
C102 C -0.0201(2) 0.42262(11) 0.14062(7) 0.0198(3) Uani 1 1 d . . . . .
C103 C -0.2045(2) 0.47930(11) 0.13908(7) 0.0212(4) Uani 1 1 d . . . . .
C104 C -0.3650(2) 0.41425(12) 0.15293(8) 0.0250(4) Uani 1 1 d . . . . .
H10C H -0.4812 0.4235 0.1319 0.030 Uiso 1 1 calc R . . . .
H10D H -0.4031 0.4220 0.1880 0.030 Uiso 1 1 calc R . . . .
C105 C -0.2810(2) 0.32138(11) 0.14457(7) 0.0207(4) Uani 1 1 d . . . . .
H105 H -0.3207 0.2994 0.1112 0.025 Uiso 1 1 calc R . . . .
C106 C -0.1938(3) 0.55804(12) 0.17326(7) 0.0251(4) Uani 1 1 d . . . . .
H10E H -0.1793 0.5379 0.2075 0.038 Uiso 1 1 calc GR . . . .
H10F H -0.3134 0.5927 0.1702 0.038 Uiso 1 1 calc GR . . . .
H10G H -0.0816 0.5945 0.1642 0.038 Uiso 1 1 calc GR . . . .
C107 C -0.3389(2) 0.25611(12) 0.18330(7) 0.0218(4) Uani 1 1 d . . . . .
C108 C -0.4561(3) 0.18556(12) 0.17736(7) 0.0257(4) Uani 1 1 d . . . . .
H108 H -0.5146 0.1689 0.1470 0.031 Uiso 1 1 calc R . . . .
C109 C -0.3692(3) 0.18554(14) 0.25513(7) 0.0305(4) Uani 1 1 d . . . . .
H109 H -0.3563 0.1689 0.2888 0.037 Uiso 1 1 calc R . . . .
C110 C -0.2820(3) 0.25576(13) 0.23437(7) 0.0270(4) Uani 1 1 d . . . . .
H110 H -0.1993 0.2969 0.2504 0.032 Uiso 1 1 calc R . . . .
C111 C 0.0817(2) 0.22081(11) 0.09422(7) 0.0200(3) Uani 1 1 d . . . . .
C112 C 0.2081(3) 0.25038(12) 0.05748(7) 0.0245(4) Uani 1 1 d . . . . .
H112 H 0.2872 0.3005 0.0634 0.029 Uiso 1 1 calc R . . . .
C113 C 0.2194(3) 0.20710(13) 0.01230(7) 0.0273(4) Uani 1 1 d . . . . .
H113 H 0.3056 0.2278 -0.0125 0.033 Uiso 1 1 calc R . . . .
C114 C 0.1047(3) 0.13366(12) 0.00346(7) 0.0266(4) Uani 1 1 d . . . . .
H114 H 0.1138 0.1034 -0.0272 0.032 Uiso 1 1 calc R . . . .
C115 C -0.0234(3) 0.10468(12) 0.03960(7) 0.0260(4) Uani 1 1 d . . . . .
H115 H -0.1034 0.0549 0.0335 0.031 Uiso 1 1 calc R . . . .
C116 C -0.0352(3) 0.14797(11) 0.08462(7) 0.0232(4) Uani 1 1 d . . . . .
H116 H -0.1236 0.1278 0.1091 0.028 Uiso 1 1 calc R . . . .
N101 N -0.0696(2) 0.33772(10) 0.14526(6) 0.0198(3) Uani 1 1 d . . . . .
O101 O 0.14843(17) 0.44991(8) 0.13626(5) 0.0236(3) Uani 1 1 d . . . . .
O102 O -0.22881(19) 0.50504(9) 0.08862(5) 0.0242(3) Uani 1 1 d . . . . .
H102 H -0.162(4) 0.5504(19) 0.0830(10) 0.051(8) Uiso 1 1 d . . . . .
O103 O -0.4791(2) 0.14143(9) 0.22086(5) 0.0310(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.511(2) . ?
C1 N1 1.459(2) . ?
C2 C3 1.539(2) . ?
C2 N1 1.345(2) . ?
C2 O1 1.233(2) . ?
C3 C4 1.522(2) . ?
C3 C6 1.512(2) . ?
C3 O2 1.430(2) . ?
C4 C5 1.533(2) . ?
C5 C7 1.492(2) . ?
C5 N1 1.481(2) . ?
C7 C8 1.351(3) . ?
C7 C10 1.438(3) . ?
C8 O3 1.368(2) . ?
C9 C10 1.342(3) . ?
C9 O3 1.367(3) . ?
C11 C12 1.395(3) . ?
C11 C16 1.387(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.387(3) . ?
C101 C111 1.511(2) . ?
C101 N101 1.463(2) . ?
C102 C103 1.533(2) . ?
C102 N101 1.342(2) . ?
C102 O101 1.236(2) . ?
C103 C104 1.528(2) . ?
C103 C106 1.516(2) . ?
C103 O102 1.430(2) . ?
C104 C105 1.543(2) . ?
C105 C107 1.498(2) . ?
C105 N101 1.473(2) . ?
C107 C108 1.352(3) . ?
C107 C110 1.436(3) . ?
C108 O103 1.364(2) . ?
C109 C110 1.348(3) . ?
C109 O103 1.371(3) . ?
C111 C112 1.395(3) . ?
C111 C116 1.393(2) . ?
C112 C113 1.391(3) . ?
C113 C114 1.388(3) . ?
C114 C115 1.387(3) . ?
C115 C116 1.387(3) . ?

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
N1 C1 C11 114.29(14) . . ?
N1 C2 C3 108.29(14) . . ?
O1 C2 C3 126.24(15) . . ?
O1 C2 N1 125.41(16) . . ?
C4 C3 C2 102.11(13) . . ?
C6 C3 C2 112.84(14) . . ?
C6 C3 C4 115.03(15) . . ?
O2 C3 C2 106.58(13) . . ?
O2 C3 C4 107.58(14) . . ?
O2 C3 C6 111.91(14) . . ?
C3 C4 C5 104.71(14) . . ?
C7 C5 C4 115.33(15) . . ?
N1 C5 C4 101.11(13) . . ?
N1 C5 C7 112.12(15) . . ?
C8 C7 C5 126.60(18) . . ?
C8 C7 C10 106.04(17) . . ?
C10 C7 C5 127.36(17) . . ?
C7 C8 O3 110.62(18) . . ?
C10 C9 O3 110.95(18) . . ?
C9 C10 C7 106.23(18) . . ?
C12 C11 C1 120.54(16) . . ?
C16 C11 C1 120.23(17) . . ?
C16 C11 C12 119.14(18) . . ?
C13 C12 C11 120.03(19) . . ?
C14 C13 C12 120.3(2) . . ?
C15 C14 C13 119.7(2) . . ?
C14 C15 C16 120.1(2) . . ?
C11 C16 C15 120.7(2) . . ?
C1 N1 C5 122.83(14) . . ?
C2 N1 C1 123.36(14) . . ?
C2 N1 C5 113.36(14) . . ?
C9 O3 C8 106.16(15) . . ?
N101 C101 C111 113.06(14) . . ?
N101 C102 C103 109.57(14) . . ?
O101 C102 C103 125.62(16) . . ?
O101 C102 N101 124.75(16) . . ?
C104 C103 C102 102.98(13) . . ?
C106 C103 C102 112.83(15) . . ?
C106 C103 C104 113.44(16) . . ?
O102 C103 C102 106.06(14) . . ?
O102 C103 C104 109.11(15) . . ?
O102 C103 C106 111.82(14) . . ?
C103 C104 C105 106.72(13) . . ?
C107 C105 C104 113.93(15) . . ?
N101 C105 C104 102.24(13) . . ?
N101 C105 C107 111.40(14) . . ?
C108 C107 C105 127.01(17) . . ?
C108 C107 C110 105.88(17) . . ?
C110 C107 C105 127.11(17) . . ?
C107 C108 O103 110.95(17) . . ?
C110 C109 O103 110.54(17) . . ?
C109 C110 C107 106.45(18) . . ?
C112 C111 C101 120.45(16) . . ?
C116 C111 C101 120.69(16) . . ?
C116 C111 C112 118.86(17) . . ?
C113 C112 C111 120.55(17) . . ?
C114 C113 C112 120.08(17) . . ?
C115 C114 C113 119.63(18) . . ?
C116 C115 C114 120.32(17) . . ?
C115 C116 C111 120.54(17) . . ?
C101 N101 C105 122.45(14) . . ?
C102 N101 C101 122.69(14) . . ?
C102 N101 C105 114.27(14) . . ?
C108 O103 C109 106.17(15) . . ?

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
O2 H2 O101 0.88(3) 1.85(3) 2.7209(18) 170(3) .
O102 H102 O1 0.84(3) 1.97(3) 2.8029(18) 171(3) .

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 C11 C12 C13 -174.59(16) . . . . ?
C1 C11 C16 C15 174.16(17) . . . . ?
C2 C3 C4 C5 29.88(17) . . . . ?
C3 C2 N1 C1 -175.31(15) . . . . ?
C3 C2 N1 C5 -2.8(2) . . . . ?
C3 C4 C5 C7 -152.31(15) . . . . ?
C3 C4 C5 N1 -31.15(17) . . . . ?
C4 C5 C7 C8 -122.9(2) . . . . ?
C4 C5 C7 C10 57.0(2) . . . . ?
C4 C5 N1 C1 -165.92(15) . . . . ?
C4 C5 N1 C2 21.52(19) . . . . ?
C5 C7 C8 O3 -179.85(16) . . . . ?
C5 C7 C10 C9 179.69(17) . . . . ?
C6 C3 C4 C5 152.46(15) . . . . ?
C7 C5 N1 C1 -42.5(2) . . . . ?
C7 C5 N1 C2 144.91(16) . . . . ?
C7 C8 O3 C9 0.0(2) . . . . ?
C8 C7 C10 C9 -0.4(2) . . . . ?
C10 C7 C8 O3 0.2(2) . . . . ?
C10 C9 O3 C8 -0.3(2) . . . . ?
C11 C1 N1 C2 105.2(2) . . . . ?
C11 C1 N1 C5 -66.6(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C11 C16 C15 -2.4(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
C16 C11 C12 C13 2.0(3) . . . . ?
N1 C1 C11 C12 -69.6(2) . . . . ?
N1 C1 C11 C16 113.91(18) . . . . ?
N1 C2 C3 C4 -17.37(18) . . . . ?
N1 C2 C3 C6 -141.43(16) . . . . ?
N1 C2 C3 O2 95.34(16) . . . . ?
N1 C5 C7 C8 122.1(2) . . . . ?
N1 C5 C7 C10 -58.0(2) . . . . ?
O1 C2 C3 C4 165.19(18) . . . . ?
O1 C2 C3 C6 41.1(2) . . . . ?
O1 C2 C3 O2 -82.1(2) . . . . ?
O1 C2 N1 C1 2.2(3) . . . . ?
O1 C2 N1 C5 174.67(16) . . . . ?
O2 C3 C4 C5 -82.09(16) . . . . ?
O3 C9 C10 C7 0.4(2) . . . . ?
C101 C111 C112 C113 178.45(16) . . . . ?
C101 C111 C116 C115 -178.25(16) . . . . ?
C102 C103 C104 C105 -18.53(19) . . . . ?
C103 C102 N101 C101 174.85(15) . . . . ?
C103 C102 N101 C105 3.5(2) . . . . ?
C103 C104 C105 C107 140.57(16) . . . . ?
C103 C104 C105 N101 20.26(19) . . . . ?
C104 C105 C107 C108 112.4(2) . . . . ?
C104 C105 C107 C110 -67.3(2) . . . . ?
C104 C105 N101 C101 173.59(15) . . . . ?
C104 C105 N101 C102 -15.0(2) . . . . ?
C105 C107 C108 O103 -179.09(16) . . . . ?
C105 C107 C110 C109 179.66(17) . . . . ?
C106 C103 C104 C105 -140.80(16) . . . . ?
C107 C105 N101 C101 51.5(2) . . . . ?
C107 C105 N101 C102 -137.06(16) . . . . ?
C107 C108 O103 C109 -1.0(2) . . . . ?
C108 C107 C110 C109 -0.1(2) . . . . ?
C110 C107 C108 O103 0.7(2) . . . . ?
C110 C109 O103 C108 0.9(2) . . . . ?
C111 C101 N101 C102 -100.39(19) . . . . ?
C111 C101 N101 C105 70.3(2) . . . . ?
C111 C112 C113 C114 -0.2(3) . . . . ?
C112 C111 C116 C115 1.2(3) . . . . ?
C112 C113 C114 C115 1.1(3) . . . . ?
C113 C114 C115 C116 -0.9(3) . . . . ?
C114 C115 C116 C111 -0.2(3) . . . . ?
C116 C111 C112 C113 -1.0(3) . . . . ?
N101 C101 C111 C112 90.06(19) . . . . ?
N101 C101 C111 C116 -90.54(19) . . . . ?
N101 C102 C103 C104 9.81(19) . . . . ?
N101 C102 C103 C106 132.50(16) . . . . ?
N101 C102 C103 O102 -104.77(16) . . . . ?
N101 C105 C107 C108 -132.58(19) . . . . ?
N101 C105 C107 C110 47.7(2) . . . . ?
O101 C102 C103 C104 -172.93(19) . . . . ?
O101 C102 C103 C106 -50.2(2) . . . . ?
O101 C102 C103 O102 72.5(2) . . . . ?
O101 C102 N101 C101 -2.4(3) . . . . ?
O101 C102 N101 C105 -173.81(17) . . . . ?
O102 C103 C104 C105 93.82(16) . . . . ?
O103 C109 C110 C107 -0.5(2) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 6 -14 0.0516 -0.0001 6.0097 -13.9974 -0.5921 0.7981 -0.1342
0 -6 14 0.0596 0.0001 -6.0097 13.9974 0.5921 -0.7981 0.1342
0 5 16 0.0948 0.0025 4.9915 15.9947 0.2350 -0.1825 0.9979
0 7 12 0.1066 0.0025 6.9943 11.9953 0.0552 0.0632 0.9799
1 -10 -1 0.0709 0.9975 -10.0016 -0.9975 0.5270 -0.4537 -0.7709
4 0 -6 0.0617 3.9980 0.0035 -5.9974 0.5657 0.7082 -0.3151
1 7 12 0.0926 1.0022 6.9943 11.9956 0.2361 0.1942 0.9613
1 -6 -13 0.1080 0.9972 -5.9935 -12.9950 0.0621 0.1601 -0.9674
-3 -6 -6 0.0768 -3.0007 -5.9976 -5.9979 -0.4772 -0.5787 -0.6122
-3 4 11 0.1174 -2.9971 3.9944 10.9955 -0.4021 -0.4841 0.7819
-4 -3 2 0.0885 -3.9990 -3.0017 1.9991 -0.5592 -0.7702 -0.0590
0 -9 7 0.0478 -0.0011 -9.0061 6.9999 0.5195 -0.7683 -0.3602
-1 5 -14 0.0566 -1.0000 5.0095 -13.9974 -0.7357 0.6055 -0.1869
####################################################################### 
# 
# 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_6h-cis
_database_code_depnum_ccdc_archive 'CCDC 1028125'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT112_Trans-6h            
;
PROBLEM: ADDSYM Detects Additional (Pseudo) Symm. Elem...          Y Check 
RESPONSE: This is a pseudo symmetry element with only 91 % of the structure
fitting it (the OMe group does not fit). The data have been carefully 
checked and we are certain that the space group is correct.
;


_audit_creation_date             2014-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 N O3'
_chemical_formula_sum            'C19 H21 N O3'
_chemical_formula_weight         311.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H21NO2
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                   6.98428(14)
_cell_length_b                   15.3845(4)
_cell_length_c                   16.6168(4)
_cell_angle_alpha                110.497(2)
_cell_angle_beta                 97.0023(18)
_cell_angle_gamma                102.2736(19)
_cell_volume                     1596.16(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15928
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3190
_cell_measurement_theta_min      3.1310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3203
_exptl_crystal_size_mid          0.0911
_exptl_crystal_size_min          0.0389
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.566
_diffrn_reflns_theta_min         2.907
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2261811000
_diffrn_orient_matrix_UB_12      0.0372701000
_diffrn_orient_matrix_UB_13      0.0416153000
_diffrn_orient_matrix_UB_21      -0.0413255000
_diffrn_orient_matrix_UB_22      0.0748161000
_diffrn_orient_matrix_UB_23      0.0810787000
_diffrn_orient_matrix_UB_31      -0.0234224000
_diffrn_orient_matrix_UB_32      -0.0733085000
_diffrn_orient_matrix_UB_33      0.0443106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5244
_reflns_number_total             6446
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.271
_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)+(0.0300P)²+2.7940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1611
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C105(H105)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C101(H10A,H10B), C104(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C108(H108), C109(H109), C110(H110), C111(H111), C112(H112),
 C114(H114), C115(H115), C117(H117), C118(H118)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C19(H19A,H19B,H19C), C106(H10E,H10F,H10G), C119(H11A,H11B,
 H11C)
;
_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 0.4738(4) 0.34387(18) -0.21821(16) 0.0170(5) Uani 1 1 d . . . . .
H1A H 0.6178 0.3768 -0.1920 0.020 Uiso 1 1 calc R . . . .
H1B H 0.4249 0.3761 -0.2555 0.020 Uiso 1 1 calc R . . . .
C2 C 0.4388(4) 0.35057(17) -0.07031(16) 0.0154(5) Uani 1 1 d . . . . .
C3 C 0.2656(4) 0.33056(17) -0.02480(16) 0.0157(5) Uani 1 1 d . . . . .
C4 C 0.1012(4) 0.35685(18) -0.07286(16) 0.0173(5) Uani 1 1 d . . . . .
H4A H 0.1114 0.4265 -0.0449 0.021 Uiso 1 1 calc R . . . .
H4B H -0.0335 0.3191 -0.0737 0.021 Uiso 1 1 calc R . . . .
C5 C 0.1409(3) 0.33061(18) -0.16605(16) 0.0153(5) Uani 1 1 d . . . . .
H5 H 0.0828 0.2596 -0.1998 0.018 Uiso 1 1 calc R . . . .
C6 C 0.3198(4) 0.38339(19) 0.07401(16) 0.0202(5) Uani 1 1 d . . . . .
H6A H 0.3637 0.4531 0.0888 0.030 Uiso 1 1 calc GR . . . .
H6B H 0.4286 0.3630 0.0987 0.030 Uiso 1 1 calc GR . . . .
H6C H 0.2022 0.3684 0.0985 0.030 Uiso 1 1 calc GR . . . .
C7 C 0.0622(3) 0.38381(18) -0.21839(16) 0.0153(5) Uani 1 1 d . . . . .
C8 C -0.0693(4) 0.33115(18) -0.29960(16) 0.0178(5) Uani 1 1 d . . . . .
H8 H -0.1086 0.2626 -0.3215 0.021 Uiso 1 1 calc R . . . .
C9 C -0.1438(4) 0.37809(19) -0.34905(17) 0.0206(5) Uani 1 1 d . . . . .
H9 H -0.2352 0.3416 -0.4040 0.025 Uiso 1 1 calc R . . . .
C10 C -0.0849(4) 0.47814(19) -0.31835(17) 0.0203(5) Uani 1 1 d . . . . .
H10 H -0.1328 0.5102 -0.3527 0.024 Uiso 1 1 calc R . . . .
C11 C 0.0450(4) 0.53091(19) -0.23681(18) 0.0211(5) Uani 1 1 d . . . . .
H11 H 0.0844 0.5994 -0.2151 0.025 Uiso 1 1 calc R . . . .
C12 C 0.1174(4) 0.48436(18) -0.18695(17) 0.0187(5) Uani 1 1 d . . . . .
H12 H 0.2051 0.5211 -0.1311 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4496(4) 0.23911(18) -0.27479(16) 0.0166(5) Uani 1 1 d . . . . .
C14 C 0.5524(4) 0.18623(18) -0.24160(17) 0.0176(5) Uani 1 1 d . . . . .
H14 H 0.6408 0.2176 -0.1854 0.021 Uiso 1 1 calc R . . . .
C15 C 0.5285(4) 0.08939(19) -0.28861(17) 0.0188(5) Uani 1 1 d . . . . .
H15 H 0.5976 0.0543 -0.2644 0.023 Uiso 1 1 calc R . . . .
C16 C 0.4021(4) 0.04323(18) -0.37195(17) 0.0185(5) Uani 1 1 d . . . . .
C17 C 0.3011(4) 0.09447(19) -0.40727(17) 0.0199(5) Uani 1 1 d . . . . .
H17 H 0.2165 0.0635 -0.4643 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3251(4) 0.19230(19) -0.35804(17) 0.0191(5) Uani 1 1 d . . . . .
H18 H 0.2550 0.2273 -0.3820 0.023 Uiso 1 1 calc R . . . .
C19 C 0.2497(4) -0.1060(2) -0.49460(18) 0.0265(6) Uani 1 1 d . . . . .
H19A H 0.1148 -0.1017 -0.4865 0.040 Uiso 1 1 calc GR . . . .
H19B H 0.2515 -0.1737 -0.5158 0.040 Uiso 1 1 calc GR . . . .
H19C H 0.2864 -0.0790 -0.5378 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.3624(3) 0.35293(15) -0.14784(13) 0.0150(4) Uani 1 1 d . . . . .
O1 O 0.6165(3) 0.35740(13) -0.04294(12) 0.0196(4) Uani 1 1 d . . . . .
O2 O 0.2049(3) 0.22787(13) -0.05150(12) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.285(5) 0.210(3) -0.020(2) 0.037(10) Uiso 1 1 d . . . . .
O3 O 0.3895(3) -0.05301(13) -0.41295(12) 0.0250(4) Uani 1 1 d . . . . .
C101 C 0.5238(4) 0.15207(18) 0.22295(16) 0.0177(5) Uani 1 1 d . . . . .
H10A H 0.5530 0.1091 0.2525 0.021 Uiso 1 1 calc R . . . .
H10B H 0.3792 0.1291 0.1949 0.021 Uiso 1 1 calc R . . . .
C102 C 0.5715(4) 0.15151(17) 0.07803(16) 0.0160(5) Uani 1 1 d . . . . .
C103 C 0.7481(4) 0.17087(18) 0.03423(16) 0.0162(5) Uani 1 1 d . . . . .
C104 C 0.9124(4) 0.14751(19) 0.08528(16) 0.0178(5) Uani 1 1 d . . . . .
H10C H 1.0464 0.1879 0.0888 0.021 Uiso 1 1 calc R . . . .
H10D H 0.9088 0.0786 0.0573 0.021 Uiso 1 1 calc R . . . .
C105 C 0.8637(3) 0.17075(18) 0.17682(16) 0.0160(5) Uani 1 1 d . . . . .
H105 H 0.9199 0.2415 0.2124 0.019 Uiso 1 1 calc R . . . .
C106 C 0.6975(4) 0.11422(19) -0.06405(17) 0.0213(5) Uani 1 1 d . . . . .
H10E H 0.6615 0.0450 -0.0763 0.032 Uiso 1 1 calc GR . . . .
H10F H 0.8141 0.1307 -0.0886 0.032 Uiso 1 1 calc GR . . . .
H10G H 0.5841 0.1302 -0.0909 0.032 Uiso 1 1 calc GR . . . .
C107 C 0.9396(4) 0.11533(18) 0.22724(16) 0.0158(5) Uani 1 1 d . . . . .
C108 C 1.0790(4) 0.16510(19) 0.30687(17) 0.0187(5) Uani 1 1 d . . . . .
H108 H 1.1241 0.2336 0.3296 0.022 Uiso 1 1 calc R . . . .
C109 C 1.1526(4) 0.1152(2) 0.35333(17) 0.0223(6) Uani 1 1 d . . . . .
H109 H 1.2494 0.1494 0.4070 0.027 Uiso 1 1 calc R . . . .
C110 C 1.0844(4) 0.0155(2) 0.32119(18) 0.0224(6) Uani 1 1 d . . . . .
H110 H 1.1317 -0.0186 0.3536 0.027 Uiso 1 1 calc R . . . .
C111 C 0.9467(4) -0.0348(2) 0.24153(18) 0.0228(6) Uani 1 1 d . . . . .
H111 H 0.9012 -0.1032 0.2192 0.027 Uiso 1 1 calc R . . . .
C112 C 0.8757(4) 0.01494(19) 0.19453(17) 0.0194(5) Uani 1 1 d . . . . .
H112 H 0.7830 -0.0197 0.1397 0.023 Uiso 1 1 calc R . . . .
C113 C 0.5709(4) 0.25389(19) 0.29052(16) 0.0175(5) Uani 1 1 d . . . . .
C114 C 0.4864(4) 0.32142(19) 0.27355(17) 0.0190(5) Uani 1 1 d . . . . .
H114 H 0.3920 0.3020 0.2200 0.023 Uiso 1 1 calc R . . . .
C115 C 0.5367(4) 0.41673(19) 0.33310(17) 0.0202(5) Uani 1 1 d . . . . .
H115 H 0.4767 0.4618 0.3206 0.024 Uiso 1 1 calc R . . . .
C116 C 0.6761(4) 0.44541(19) 0.41127(17) 0.0200(5) Uani 1 1 d . . . . .
C117 C 0.7623(4) 0.3788(2) 0.42933(17) 0.0223(6) Uani 1 1 d . . . . .
H117 H 0.8582 0.3985 0.4825 0.027 Uiso 1 1 calc R . . . .
C118 C 0.7082(4) 0.2840(2) 0.36979(17) 0.0205(5) Uani 1 1 d . . . . .
H118 H 0.7655 0.2386 0.3831 0.025 Uiso 1 1 calc R . . . .
C119 C 0.6757(5) 0.6102(2) 0.4545(2) 0.0321(7) Uani 1 1 d . . . . .
H11A H 0.7167 0.6121 0.4007 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.7374 0.6728 0.5032 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.5293 0.5960 0.4456 0.048 Uiso 1 1 calc GR . . . .
N101 N 0.6424(3) 0.14721(15) 0.15525(13) 0.0155(4) Uani 1 1 d . . . . .
O101 O 0.3953(3) 0.14586(13) 0.04953(12) 0.0216(4) Uani 1 1 d . . . . .
O102 O 0.8062(3) 0.27304(13) 0.05722(12) 0.0193(4) Uani 1 1 d . . . . .
H102 H 0.725(6) 0.288(3) 0.025(2) 0.038(10) Uiso 1 1 d . . . . .
O103 O 0.7390(3) 0.53713(14) 0.47484(12) 0.0266(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C13 1.515(3) . ?
C1 N1 1.465(3) . ?
C2 C3 1.535(3) . ?
C2 N1 1.349(3) . ?
C2 O1 1.238(3) . ?
C3 C4 1.523(3) . ?
C3 C6 1.511(3) . ?
C3 O2 1.432(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.534(3) . ?
C5 H5 1.0000 . ?
C5 C7 1.517(3) . ?
C5 N1 1.480(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.392(3) . ?
C7 C12 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(3) . ?
C13 C18 1.390(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(4) . ?
C16 C17 1.387(3) . ?
C16 O3 1.374(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 O3 1.422(3) . ?
O2 H2 0.87(4) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C101 C113 1.511(3) . ?
C101 N101 1.467(3) . ?
C102 C103 1.534(3) . ?
C102 N101 1.347(3) . ?
C102 O101 1.237(3) . ?
C103 C104 1.522(3) . ?
C103 C106 1.511(3) . ?
C103 O102 1.432(3) . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C104 C105 1.534(3) . ?
C105 H105 1.0000 . ?
C105 C107 1.515(3) . ?
C105 N101 1.478(3) . ?
C106 H10E 0.9800 . ?
C106 H10F 0.9800 . ?
C106 H10G 0.9800 . ?
C107 C108 1.395(3) . ?
C107 C112 1.393(4) . ?
C108 H108 0.9500 . ?
C108 C109 1.392(4) . ?
C109 H109 0.9500 . ?
C109 C110 1.385(4) . ?
C110 H110 0.9500 . ?
C110 C111 1.390(4) . ?
C111 H111 0.9500 . ?
C111 C112 1.388(4) . ?
C112 H112 0.9500 . ?
C113 C114 1.390(3) . ?
C113 C118 1.395(4) . ?
C114 H114 0.9500 . ?
C114 C115 1.390(4) . ?
C115 H115 0.9500 . ?
C115 C116 1.392(4) . ?
C116 C117 1.391(4) . ?
C116 O103 1.371(3) . ?
C117 H117 0.9500 . ?
C117 C118 1.384(4) . ?
C118 H118 0.9500 . ?
C119 H11A 0.9800 . ?
C119 H11B 0.9800 . ?
C119 H11C 0.9800 . ?
C119 O103 1.418(3) . ?
O102 H102 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.0 . . ?
C13 C1 H1A 109.3 . . ?
C13 C1 H1B 109.3 . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C13 111.5(2) . . ?
N1 C2 C3 108.5(2) . . ?
O1 C2 C3 125.7(2) . . ?
O1 C2 N1 125.7(2) . . ?
C4 C3 C2 101.95(19) . . ?
C6 C3 C2 113.8(2) . . ?
C6 C3 C4 115.5(2) . . ?
O2 C3 C2 105.11(19) . . ?
O2 C3 C4 106.78(19) . . ?
O2 C3 C6 112.6(2) . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C3 C4 C5 103.60(19) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C4 C5 H5 108.9 . . ?
C7 C5 C4 115.8(2) . . ?
C7 C5 H5 108.9 . . ?
N1 C5 C4 101.32(18) . . ?
N1 C5 H5 108.9 . . ?
N1 C5 C7 112.5(2) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.3(2) . . ?
C8 C7 C12 119.1(2) . . ?
C12 C7 C5 121.6(2) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C1 119.0(2) . . ?
C18 C13 C1 122.7(2) . . ?
C18 C13 C14 118.2(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.1(2) . . ?
O3 C16 C15 114.9(2) . . ?
O3 C16 C17 125.0(2) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 121.2(2) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
C1 N1 C5 121.66(19) . . ?
C2 N1 C1 122.6(2) . . ?
C2 N1 C5 112.4(2) . . ?
C3 O2 H2 110(2) . . ?
C16 O3 C19 117.4(2) . . ?
H10A C101 H10B 108.0 . . ?
C113 C101 H10A 109.4 . . ?
C113 C101 H10B 109.4 . . ?
N101 C101 H10A 109.4 . . ?
N101 C101 H10B 109.4 . . ?
N101 C101 C113 111.2(2) . . ?
N101 C102 C103 108.5(2) . . ?
O101 C102 C103 125.8(2) . . ?
O101 C102 N101 125.6(2) . . ?
C104 C103 C102 102.52(19) . . ?
C106 C103 C102 113.0(2) . . ?
C106 C103 C104 115.0(2) . . ?
O102 C103 C102 105.64(19) . . ?
O102 C103 C104 107.1(2) . . ?
O102 C103 C106 112.6(2) . . ?
C103 C104 H10C 110.9 . . ?
C103 C104 H10D 110.9 . . ?
C103 C104 C105 104.03(19) . . ?
H10C C104 H10D 109.0 . . ?
C105 C104 H10C 110.9 . . ?
C105 C104 H10D 110.9 . . ?
C104 C105 H105 109.1 . . ?
C107 C105 C104 114.8(2) . . ?
C107 C105 H105 109.1 . . ?
N101 C105 C104 101.49(19) . . ?
N101 C105 H105 109.1 . . ?
N101 C105 C107 112.9(2) . . ?
C103 C106 H10E 109.5 . . ?
C103 C106 H10F 109.5 . . ?
C103 C106 H10G 109.5 . . ?
H10E C106 H10F 109.5 . . ?
H10E C106 H10G 109.5 . . ?
H10F C106 H10G 109.5 . . ?
C108 C107 C105 119.7(2) . . ?
C112 C107 C105 121.1(2) . . ?
C112 C107 C108 119.1(2) . . ?
C107 C108 H108 119.8 . . ?
C109 C108 C107 120.5(2) . . ?
C109 C108 H108 119.8 . . ?
C108 C109 H109 120.1 . . ?
C110 C109 C108 119.9(2) . . ?
C110 C109 H109 120.1 . . ?
C109 C110 H110 120.0 . . ?
C109 C110 C111 120.1(2) . . ?
C111 C110 H110 120.0 . . ?
C110 C111 H111 120.0 . . ?
C112 C111 C110 120.0(3) . . ?
C112 C111 H111 120.0 . . ?
C107 C112 H112 119.8 . . ?
C111 C112 C107 120.4(2) . . ?
C111 C112 H112 119.8 . . ?
C114 C113 C101 120.9(2) . . ?
C114 C113 C118 118.2(2) . . ?
C118 C113 C101 120.8(2) . . ?
C113 C114 H114 119.2 . . ?
C113 C114 C115 121.5(2) . . ?
C115 C114 H114 119.2 . . ?
C114 C115 H115 120.4 . . ?
C114 C115 C116 119.2(2) . . ?
C116 C115 H115 120.4 . . ?
C117 C116 C115 120.0(2) . . ?
O103 C116 C115 124.8(2) . . ?
O103 C116 C117 115.2(2) . . ?
C116 C117 H117 120.0 . . ?
C118 C117 C116 119.9(2) . . ?
C118 C117 H117 120.0 . . ?
C113 C118 H118 119.5 . . ?
C117 C118 C113 121.1(2) . . ?
C117 C118 H118 119.5 . . ?
H11A C119 H11B 109.5 . . ?
H11A C119 H11C 109.5 . . ?
H11B C119 H11C 109.5 . . ?
O103 C119 H11A 109.5 . . ?
O103 C119 H11B 109.5 . . ?
O103 C119 H11C 109.5 . . ?
C101 N101 C105 121.69(19) . . ?
C102 N101 C101 122.6(2) . . ?
C102 N101 C105 112.6(2) . . ?
C103 O102 H102 110(2) . . ?
C116 O103 C119 117.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O101 0.87(4) 1.95(4) 2.798(3) 164(3) .
O102 H102 O1 0.85(4) 1.99(4) 2.814(3) 161(3) .

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 C13 C14 C15 176.9(2) . . . . ?
C1 C13 C18 C17 -177.8(2) . . . . ?
C2 C3 C4 C5 32.1(2) . . . . ?
C3 C2 N1 C1 -162.8(2) . . . . ?
C3 C2 N1 C5 -3.2(3) . . . . ?
C3 C4 C5 C7 -155.8(2) . . . . ?
C3 C4 C5 N1 -33.8(2) . . . . ?
C4 C5 C7 C8 -123.2(2) . . . . ?
C4 C5 C7 C12 56.4(3) . . . . ?
C4 C5 N1 C1 -176.7(2) . . . . ?
C4 C5 N1 C2 23.5(2) . . . . ?
C5 C7 C8 C9 -180.0(2) . . . . ?
C5 C7 C12 C11 179.2(2) . . . . ?
C6 C3 C4 C5 156.0(2) . . . . ?
C7 C5 N1 C1 -52.4(3) . . . . ?
C7 C5 N1 C2 147.8(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -1.7(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C12 C7 C8 C9 0.4(4) . . . . ?
C13 C1 N1 C2 84.8(3) . . . . ?
C13 C1 N1 C5 -72.9(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 O3 179.9(2) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C15 C16 O3 C19 174.6(2) . . . . ?
C16 C17 C18 C13 0.6(4) . . . . ?
C17 C16 O3 C19 -5.5(4) . . . . ?
C18 C13 C14 C15 -1.6(4) . . . . ?
N1 C1 C13 C14 -74.8(3) . . . . ?
N1 C1 C13 C18 103.7(3) . . . . ?
N1 C2 C3 C4 -18.7(2) . . . . ?
N1 C2 C3 C6 -143.7(2) . . . . ?
N1 C2 C3 O2 92.6(2) . . . . ?
N1 C5 C7 C8 120.9(2) . . . . ?
N1 C5 C7 C12 -59.5(3) . . . . ?
O1 C2 C3 C4 165.4(2) . . . . ?
O1 C2 C3 C6 40.3(3) . . . . ?
O1 C2 C3 O2 -83.4(3) . . . . ?
O1 C2 N1 C1 13.2(4) . . . . ?
O1 C2 N1 C5 172.8(2) . . . . ?
O2 C3 C4 C5 -77.9(2) . . . . ?
O3 C16 C17 C18 179.2(2) . . . . ?
C101 C113 C114 C115 -176.4(2) . . . . ?
C101 C113 C118 C117 175.5(2) . . . . ?
C102 C103 C104 C105 -29.4(2) . . . . ?
C103 C102 N101 C101 165.5(2) . . . . ?
C103 C102 N101 C105 5.2(3) . . . . ?
C103 C104 C105 C107 154.1(2) . . . . ?
C103 C104 C105 N101 32.0(2) . . . . ?
C104 C105 C107 C108 118.0(3) . . . . ?
C104 C105 C107 C112 -60.6(3) . . . . ?
C104 C105 N101 C101 175.8(2) . . . . ?
C104 C105 N101 C102 -23.7(3) . . . . ?
C105 C107 C108 C109 -179.0(2) . . . . ?
C105 C107 C112 C111 180.0(2) . . . . ?
C106 C103 C104 C105 -152.5(2) . . . . ?
C107 C105 N101 C101 52.5(3) . . . . ?
C107 C105 N101 C102 -147.0(2) . . . . ?
C107 C108 C109 C110 -1.2(4) . . . . ?
C108 C107 C112 C111 1.4(4) . . . . ?
C108 C109 C110 C111 1.7(4) . . . . ?
C109 C110 C111 C112 -0.7(4) . . . . ?
C110 C111 C112 C107 -0.9(4) . . . . ?
C112 C107 C108 C109 -0.4(4) . . . . ?
C113 C101 N101 C102 -95.3(3) . . . . ?
C113 C101 N101 C105 63.3(3) . . . . ?
C113 C114 C115 C116 0.5(4) . . . . ?
C114 C113 C118 C117 -1.3(4) . . . . ?
C114 C115 C116 C117 -0.4(4) . . . . ?
C114 C115 C116 O103 179.6(2) . . . . ?
C115 C116 C117 C118 -0.5(4) . . . . ?
C115 C116 O103 C119 -8.1(4) . . . . ?
C116 C117 C118 C113 1.3(4) . . . . ?
C117 C116 O103 C119 172.0(3) . . . . ?
C118 C113 C114 C115 0.3(4) . . . . ?
N101 C101 C113 C114 79.9(3) . . . . ?
N101 C101 C113 C118 -96.8(3) . . . . ?
N101 C102 C103 C104 15.8(3) . . . . ?
N101 C102 C103 C106 140.2(2) . . . . ?
N101 C102 C103 O102 -96.2(2) . . . . ?
N101 C105 C107 C108 -126.3(2) . . . . ?
N101 C105 C107 C112 55.1(3) . . . . ?
O101 C102 C103 C104 -167.7(2) . . . . ?
O101 C102 C103 C106 -43.2(3) . . . . ?
O101 C102 C103 O102 80.3(3) . . . . ?
O101 C102 N101 C101 -11.0(4) . . . . ?
O101 C102 N101 C105 -171.4(2) . . . . ?
O102 C103 C104 C105 81.5(2) . . . . ?
O103 C116 C117 C118 179.5(2) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 0 5 0.0368 -3.9999 0.0160 4.9760 -0.6970 0.5699 0.3130
4 0 -5 0.0368 3.9999 -0.0160 -4.9760 0.6970 -0.5699 -0.3130
-2 -6 8 0.0865 -2.0029 -5.9874 7.9943 -0.3435 0.2830 0.8401
2 6 -8 0.0865 2.0029 5.9874 -7.9943 0.3435 -0.2830 -0.8401
0 0 10 0.0147 -0.0063 0.0091 10.0043 0.4152 0.8121 0.4428
0 0 -10 0.0242 0.0063 -0.0091 -10.0043 -0.4152 -0.8121 -0.4428
0 -4 -8 0.0526 0.0054 -4.0076 -8.0007 -0.4811 -0.9487 -0.0609
0 -3 11 0.0395 -0.0067 -2.9902 11.0067 0.3451 0.6690 0.7071
-4 7 -4 0.1285 -3.9948 7.0083 -4.0325 -0.8102 0.3625 -0.5989
####################################################################### 
# 
# 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_6p-cis
_database_code_depnum_ccdc_archive 'CCDC 1028126'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT112_Trans-6p            
;
PROBLEM: ADDSYM Detects Additional (Pseudo) Symm. Elem...          Y Check 
RESPONSE: This is a pseudo symmetry element with only 84 % of the structure
fitting it (the OMe group does not fit). The data have been carefully 
checked and we are certain that the space group is correct.
;

_audit_creation_date             2014-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H20 N2 O3'
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                   6.8071(3)
_cell_length_b                   15.0202(7)
_cell_length_c                   15.8559(8)
_cell_angle_alpha                90.798(4)
_cell_angle_beta                 101.156(4)
_cell_angle_gamma                100.035(4)
_cell_volume                     1564.30(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.2830
_cell_measurement_theta_min      4.2050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2231
_exptl_crystal_size_mid          0.1164
_exptl_crystal_size_min          0.0297
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11128
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.551
_diffrn_reflns_theta_min         2.844
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00  -60.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -      -42.5607 -147.0000   70.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -16.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   87.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  -71.00   23.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   61.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   28.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   47.00   74.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00   91.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00  150.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -15.0000 -120.0000 123

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   89.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   76.00  109.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  137.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000    0.0000 99

#__ type_ start__ end____ width___ exp.time_
 12 omega   93.00  121.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   83.00  171.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 14 omega  101.00  174.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  -90.0000 73

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00  120.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00   73.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00  107.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1916140000
_diffrn_orient_matrix_UB_12      -0.0372494000
_diffrn_orient_matrix_UB_13      -0.0101525000
_diffrn_orient_matrix_UB_21      0.0754684000
_diffrn_orient_matrix_UB_22      0.0088086000
_diffrn_orient_matrix_UB_23      0.0983398000
_diffrn_orient_matrix_UB_31      -0.1121989000
_diffrn_orient_matrix_UB_32      -0.0970083000
_diffrn_orient_matrix_UB_33      0.0075714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4927
_reflns_number_total             6195
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.013
_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)+(0.0520P)²+0.2941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C105(H105)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C101(H10A,H10B), C104(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C108(H108), C109(H109), C110(H110), C111(H111), C113(H113), C114(H114),
 C116(H116), C117(H117)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C18(H18A,H18B,H18C), C106(H10E,H10F,H10G), C118(H11A,H11B,
 H11C)
;
_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 0.2873(2) 0.04677(9) 0.28741(9) 0.0187(3) Uani 1 1 d . . . . .
H1A H 0.1699 0.0436 0.3163 0.022 Uiso 1 1 calc R . . . .
H1B H 0.2843 -0.0145 0.2627 0.022 Uiso 1 1 calc R . . . .
C2 C 0.4835(2) 0.11489(9) 0.42773(9) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.7065(2) 0.15588(9) 0.46678(9) 0.0167(3) Uani 1 1 d . . . . .
C4 C 0.8220(2) 0.10643(9) 0.41395(9) 0.0186(3) Uani 1 1 d . . . . .
H4A H 0.8525 0.0501 0.4410 0.022 Uiso 1 1 calc R . . . .
H4B H 0.9513 0.1453 0.4078 0.022 Uiso 1 1 calc R . . . .
C5 C 0.67628(19) 0.08513(9) 0.32610(9) 0.0167(3) Uani 1 1 d . . . . .
H5 H 0.6927 0.1393 0.2904 0.020 Uiso 1 1 calc R . . . .
C6 C 0.7606(2) 0.14695(10) 0.56295(9) 0.0208(3) Uani 1 1 d . . . . .
H6A H 0.9033 0.1748 0.5842 0.031 Uiso 1 1 calc GR . . . .
H6B H 0.7407 0.0827 0.5757 0.031 Uiso 1 1 calc GR . . . .
H6C H 0.6730 0.1775 0.5912 0.031 Uiso 1 1 calc GR . . . .
C7 C 0.70247(19) 0.00377(9) 0.27587(9) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.7337(2) 0.01293(10) 0.19202(9) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.7373 0.0712 0.1691 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7521(2) -0.13579(10) 0.17476(9) 0.0213(3) Uani 1 1 d . . . . .
H9 H 0.7685 -0.1849 0.1399 0.026 Uiso 1 1 calc R . . . .
C10 C 0.7221(2) -0.15234(10) 0.25771(10) 0.0221(3) Uani 1 1 d . . . . .
H10 H 0.7186 -0.2114 0.2788 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6974(2) -0.08169(10) 0.30920(9) 0.0192(3) Uani 1 1 d . . . . .
H11 H 0.6774 -0.0913 0.3663 0.023 Uiso 1 1 calc R . . . .
C12 C 0.2663(2) 0.11176(9) 0.21543(9) 0.0178(3) Uani 1 1 d . . . . .
C13 C 0.2845(2) 0.20389(10) 0.23275(10) 0.0249(3) Uani 1 1 d . . . . .
H13 H 0.3088 0.2263 0.2908 0.030 Uiso 1 1 calc R . . . .
C14 C 0.2679(2) 0.26432(10) 0.16698(10) 0.0255(3) Uani 1 1 d . . . . .
H14 H 0.2824 0.3273 0.1802 0.031 Uiso 1 1 calc R . . . .
C15 C 0.2299(2) 0.23164(10) 0.08204(9) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.2091(2) 0.13919(10) 0.06347(9) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.1821 0.1165 0.0054 0.029 Uiso 1 1 calc R . . . .
C17 C 0.2277(2) 0.08037(10) 0.12978(9) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.2139 0.0174 0.1166 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2281(3) 0.38006(11) 0.02904(11) 0.0323(4) Uani 1 1 d . . . . .
H18A H 0.2060 0.4101 -0.0256 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.3646 0.4045 0.0621 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.1261 0.3909 0.0621 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.47584(16) 0.07409(8) 0.35105(7) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.75902(19) -0.05433(9) 0.14137(8) 0.0232(3) Uani 1 1 d . . . . .
O1 O 0.33465(15) 0.12221(7) 0.45994(6) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.73286(15) 0.24845(7) 0.44333(6) 0.0195(2) Uani 1 1 d . . . . .
H2 H 0.699(3) 0.2833(15) 0.4807(14) 0.042(6) Uiso 1 1 d . . . . .
O3 O 0.21001(18) 0.28502(8) 0.01231(7) 0.0292(3) Uani 1 1 d . . . . .
C101 C 0.6897(2) 0.45703(9) 0.72271(9) 0.0184(3) Uani 1 1 d . . . . .
H10A H 0.6758 0.5096 0.7581 0.022 Uiso 1 1 calc R . . . .
H10B H 0.8106 0.4749 0.6965 0.022 Uiso 1 1 calc R . . . .
C102 C 0.5110(2) 0.39163(9) 0.57858(9) 0.0166(3) Uani 1 1 d . . . . .
C103 C 0.2918(2) 0.34904(9) 0.53592(9) 0.0165(3) Uani 1 1 d . . . . .
C104 C 0.1676(2) 0.39926(9) 0.58352(9) 0.0180(3) Uani 1 1 d . . . . .
H10C H 0.0348 0.3611 0.5860 0.022 Uiso 1 1 calc R . . . .
H10D H 0.1435 0.4559 0.5555 0.022 Uiso 1 1 calc R . . . .
C105 C 0.30119(19) 0.41942(9) 0.67396(9) 0.0163(3) Uani 1 1 d . . . . .
H105 H 0.2812 0.3645 0.7084 0.020 Uiso 1 1 calc R . . . .
C106 C 0.2483(2) 0.35397(10) 0.43919(9) 0.0203(3) Uani 1 1 d . . . . .
H10E H 0.1084 0.3236 0.4158 0.030 Uiso 1 1 calc GR . . . .
H10F H 0.3432 0.3240 0.4150 0.030 Uiso 1 1 calc GR . . . .
H10G H 0.2650 0.4175 0.4241 0.030 Uiso 1 1 calc GR . . . .
C107 C 0.26359(19) 0.49912(9) 0.72291(9) 0.0170(3) Uani 1 1 d . . . . .
C108 C 0.2230(2) 0.48900(10) 0.80547(9) 0.0209(3) Uani 1 1 d . . . . .
H108 H 0.2228 0.4311 0.8289 0.025 Uiso 1 1 calc R . . . .
C109 C 0.1843(2) 0.63534(10) 0.81915(10) 0.0267(3) Uani 1 1 d . . . . .
H109 H 0.1577 0.6834 0.8523 0.032 Uiso 1 1 calc R . . . .
C110 C 0.2208(2) 0.65296(10) 0.73755(10) 0.0256(3) Uani 1 1 d . . . . .
H110 H 0.2173 0.7113 0.7155 0.031 Uiso 1 1 calc R . . . .
C111 C 0.2625(2) 0.58403(10) 0.68866(9) 0.0209(3) Uani 1 1 d . . . . .
H111 H 0.2898 0.5944 0.6327 0.025 Uiso 1 1 calc R . . . .
C112 C 0.7205(2) 0.37871(9) 0.77976(9) 0.0179(3) Uani 1 1 d . . . . .
C113 C 0.7913(2) 0.30528(10) 0.74889(9) 0.0191(3) Uani 1 1 d . . . . .
H113 H 0.8283 0.3073 0.6941 0.023 Uiso 1 1 calc R . . . .
C114 C 0.8084(2) 0.22986(10) 0.79638(9) 0.0200(3) Uani 1 1 d . . . . .
H114 H 0.8569 0.1806 0.7742 0.024 Uiso 1 1 calc R . . . .
C115 C 0.7546(2) 0.22565(10) 0.87711(9) 0.0199(3) Uani 1 1 d . . . . .
C116 C 0.6893(2) 0.29899(10) 0.91016(9) 0.0230(3) Uani 1 1 d . . . . .
H116 H 0.6565 0.2976 0.9658 0.028 Uiso 1 1 calc R . . . .
C117 C 0.6722(2) 0.37456(10) 0.86112(9) 0.0218(3) Uani 1 1 d . . . . .
H117 H 0.6265 0.4244 0.8838 0.026 Uiso 1 1 calc R . . . .
C118 C 0.7053(2) 0.13600(11) 0.99702(10) 0.0265(3) Uani 1 1 d . . . . .
H11A H 0.7890 0.1822 1.0394 0.040 Uiso 1 1 calc GR . . . .
H11B H 0.7194 0.0757 1.0175 0.040 Uiso 1 1 calc GR . . . .
H11C H 0.5624 0.1428 0.9891 0.040 Uiso 1 1 calc GR . . . .
N101 N 0.50752(16) 0.43294(8) 0.65430(7) 0.0162(2) Uani 1 1 d . . . . .
N102 N 0.1844(2) 0.55481(9) 0.85421(8) 0.0265(3) Uani 1 1 d . . . . .
O101 O 0.66549(14) 0.38509(7) 0.55046(6) 0.0209(2) Uani 1 1 d . . . . .
O102 O 0.26536(15) 0.25762(7) 0.56282(6) 0.0195(2) Uani 1 1 d . . . . .
H102 H 0.303(3) 0.2202(15) 0.5258(14) 0.045(6) Uiso 1 1 d . . . . .
O103 O 0.77091(16) 0.14657(7) 0.91698(7) 0.0244(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C12 1.5142(19) . ?
C1 N1 1.4621(16) . ?
C2 C3 1.5382(18) . ?
C2 N1 1.3417(18) . ?
C2 O1 1.2398(17) . ?
C3 C4 1.5209(19) . ?
C3 C6 1.5114(19) . ?
C3 O2 1.4342(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5392(18) . ?
C5 H5 1.0000 . ?
C5 C7 1.5044(19) . ?
C5 N1 1.4756(16) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.391(2) . ?
C7 C11 1.3923(19) . ?
C8 H8 0.9500 . ?
C8 N2 1.3367(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C9 N2 1.3367(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 C17 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 C16 1.392(2) . ?
C15 O3 1.3741(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O3 1.428(2) . ?
O2 H2 0.87(2) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C101 C112 1.5127(19) . ?
C101 N101 1.4688(16) . ?
C102 C103 1.5356(18) . ?
C102 N101 1.3501(18) . ?
C102 O101 1.2370(17) . ?
C103 C104 1.5189(19) . ?
C103 C106 1.5102(19) . ?
C103 O102 1.4352(16) . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C104 C105 1.5369(19) . ?
C105 H105 1.0000 . ?
C105 C107 1.5029(19) . ?
C105 N101 1.4774(16) . ?
C106 H10E 0.9800 . ?
C106 H10F 0.9800 . ?
C106 H10G 0.9800 . ?
C107 C108 1.394(2) . ?
C107 C111 1.394(2) . ?
C108 H108 0.9500 . ?
C108 N102 1.3385(19) . ?
C109 H109 0.9500 . ?
C109 C110 1.384(2) . ?
C109 N102 1.338(2) . ?
C110 H110 0.9500 . ?
C110 C111 1.385(2) . ?
C111 H111 0.9500 . ?
C112 C113 1.396(2) . ?
C112 C117 1.391(2) . ?
C113 H113 0.9500 . ?
C113 C114 1.378(2) . ?
C114 H114 0.9500 . ?
C114 C115 1.397(2) . ?
C115 C116 1.389(2) . ?
C115 O103 1.3648(18) . ?
C116 H116 0.9500 . ?
C116 C117 1.394(2) . ?
C117 H117 0.9500 . ?
C118 H11A 0.9800 . ?
C118 H11B 0.9800 . ?
C118 H11C 0.9800 . ?
C118 O103 1.4267(18) . ?
O102 H102 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 107.9 . . ?
C12 C1 H1A 109.2 . . ?
C12 C1 H1B 109.2 . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C12 112.26(11) . . ?
N1 C2 C3 108.73(11) . . ?
O1 C2 C3 125.54(12) . . ?
O1 C2 N1 125.65(12) . . ?
C4 C3 C2 102.23(10) . . ?
C6 C3 C2 113.12(11) . . ?
C6 C3 C4 115.23(12) . . ?
O2 C3 C2 105.52(10) . . ?
O2 C3 C4 107.32(11) . . ?
O2 C3 C6 112.48(11) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.16(11) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 H5 108.9 . . ?
C7 C5 C4 115.32(11) . . ?
C7 C5 H5 108.9 . . ?
N1 C5 C4 101.63(10) . . ?
N1 C5 H5 108.9 . . ?
N1 C5 C7 112.79(11) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.38(12) . . ?
C8 C7 C11 117.46(13) . . ?
C11 C7 C5 123.15(12) . . ?
C7 C8 H8 117.6 . . ?
N2 C8 C7 124.70(13) . . ?
N2 C8 H8 117.6 . . ?
C10 C9 H9 118.3 . . ?
N2 C9 H9 118.3 . . ?
N2 C9 C10 123.39(13) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.07(13) . . ?
C11 C10 H10 120.5 . . ?
C7 C11 H11 120.6 . . ?
C10 C11 C7 118.78(13) . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C1 121.16(13) . . ?
C13 C12 C17 118.14(13) . . ?
C17 C12 C1 120.69(13) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.57(14) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.36(14) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 119.82(14) . . ?
O3 C15 C14 124.21(14) . . ?
O3 C15 C16 115.97(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.92(14) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.19(14) . . ?
C16 C17 H17 119.4 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
C1 N1 C5 121.19(11) . . ?
C2 N1 C1 123.30(11) . . ?
C2 N1 C5 112.94(11) . . ?
C9 N2 C8 116.59(12) . . ?
C3 O2 H2 111.5(14) . . ?
C15 O3 C18 117.41(12) . . ?
H10A C101 H10B 108.0 . . ?
C112 C101 H10A 109.4 . . ?
C112 C101 H10B 109.4 . . ?
N101 C101 H10A 109.4 . . ?
N101 C101 H10B 109.4 . . ?
N101 C101 C112 111.35(11) . . ?
N101 C102 C103 108.41(11) . . ?
O101 C102 C103 125.72(12) . . ?
O101 C102 N101 125.78(12) . . ?
C104 C103 C102 102.17(11) . . ?
C106 C103 C102 113.47(11) . . ?
C106 C103 C104 115.67(12) . . ?
O102 C103 C102 105.04(10) . . ?
O102 C103 C104 106.92(11) . . ?
O102 C103 C106 112.51(11) . . ?
C103 C104 H10C 111.0 . . ?
C103 C104 H10D 111.0 . . ?
C103 C104 C105 103.64(11) . . ?
H10C C104 H10D 109.0 . . ?
C105 C104 H10C 111.0 . . ?
C105 C104 H10D 111.0 . . ?
C104 C105 H105 109.1 . . ?
C107 C105 C104 114.93(11) . . ?
C107 C105 H105 109.1 . . ?
N101 C105 C104 101.38(10) . . ?
N101 C105 H105 109.1 . . ?
N101 C105 C107 112.94(11) . . ?
C103 C106 H10E 109.5 . . ?
C103 C106 H10F 109.5 . . ?
C103 C106 H10G 109.5 . . ?
H10E C106 H10F 109.5 . . ?
H10E C106 H10G 109.5 . . ?
H10F C106 H10G 109.5 . . ?
C108 C107 C105 119.81(12) . . ?
C111 C107 C105 122.82(13) . . ?
C111 C107 C108 117.35(13) . . ?
C107 C108 H108 117.6 . . ?
N102 C108 C107 124.85(14) . . ?
N102 C108 H108 117.6 . . ?
C110 C109 H109 118.0 . . ?
N102 C109 H109 118.0 . . ?
N102 C109 C110 124.06(14) . . ?
C109 C110 H110 120.6 . . ?
C109 C110 C111 118.79(14) . . ?
C111 C110 H110 120.6 . . ?
C107 C111 H111 120.6 . . ?
C110 C111 C107 118.85(14) . . ?
C110 C111 H111 120.6 . . ?
C113 C112 C101 119.39(13) . . ?
C117 C112 C101 122.57(13) . . ?
C117 C112 C113 117.97(13) . . ?
C112 C113 H113 119.4 . . ?
C114 C113 C112 121.28(13) . . ?
C114 C113 H113 119.4 . . ?
C113 C114 H114 119.9 . . ?
C113 C114 C115 120.15(13) . . ?
C115 C114 H114 119.9 . . ?
C116 C115 C114 119.55(13) . . ?
O103 C115 C114 115.08(13) . . ?
O103 C115 C116 125.37(13) . . ?
C115 C116 H116 120.2 . . ?
C115 C116 C117 119.50(13) . . ?
C117 C116 H116 120.2 . . ?
C112 C117 C116 121.50(14) . . ?
C112 C117 H117 119.2 . . ?
C116 C117 H117 119.2 . . ?
H11A C118 H11B 109.5 . . ?
H11A C118 H11C 109.5 . . ?
H11B C118 H11C 109.5 . . ?
O103 C118 H11A 109.5 . . ?
O103 C118 H11B 109.5 . . ?
O103 C118 H11C 109.5 . . ?
C101 N101 C105 121.17(11) . . ?
C102 N101 C101 122.53(11) . . ?
C102 N101 C105 112.43(11) . . ?
C109 N102 C108 116.09(13) . . ?
C103 O102 H102 111.1(13) . . ?
C115 O103 C118 117.59(12) . . ?

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
O2 H2 O101 0.87(2) 1.95(2) 2.8000(15) 165(2) .
O102 H102 O1 0.91(2) 1.86(2) 2.7495(14) 166(2) .

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 C12 C13 C14 179.19(14) . . . . ?
C1 C12 C17 C16 -179.71(13) . . . . ?
C2 C3 C4 C5 29.43(13) . . . . ?
C3 C2 N1 C1 -165.11(11) . . . . ?
C3 C2 N1 C5 -3.16(15) . . . . ?
C3 C4 C5 C7 -153.44(11) . . . . ?
C3 C4 C5 N1 -31.10(13) . . . . ?
C4 C5 C7 C8 -125.61(13) . . . . ?
C4 C5 C7 C11 54.29(17) . . . . ?
C4 C5 N1 C1 -175.87(11) . . . . ?
C4 C5 N1 C2 21.75(14) . . . . ?
C5 C7 C8 N2 179.94(13) . . . . ?
C5 C7 C11 C10 179.69(12) . . . . ?
C6 C3 C4 C5 152.54(11) . . . . ?
C7 C5 N1 C1 -51.82(16) . . . . ?
C7 C5 N1 C2 145.81(12) . . . . ?
C7 C8 N2 C9 0.4(2) . . . . ?
C8 C7 C11 C10 -0.41(19) . . . . ?
C9 C10 C11 C7 0.3(2) . . . . ?
C10 C9 N2 C8 -0.5(2) . . . . ?
C11 C7 C8 N2 0.0(2) . . . . ?
C12 C1 N1 C2 102.11(15) . . . . ?
C12 C1 N1 C5 -58.40(16) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C13 C14 C15 O3 179.74(14) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C14 C15 O3 C18 -0.5(2) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C16 C15 O3 C18 179.26(13) . . . . ?
C17 C12 C13 C14 -0.9(2) . . . . ?
N1 C1 C12 C13 -52.85(17) . . . . ?
N1 C1 C12 C17 127.26(14) . . . . ?
N1 C2 C3 C4 -17.09(14) . . . . ?
N1 C2 C3 C6 -141.61(12) . . . . ?
N1 C2 C3 O2 95.01(12) . . . . ?
N1 C5 C7 C8 118.25(13) . . . . ?
N1 C5 C7 C11 -61.85(16) . . . . ?
N2 C9 C10 C11 0.1(2) . . . . ?
O1 C2 C3 C4 166.13(13) . . . . ?
O1 C2 C3 C6 41.61(19) . . . . ?
O1 C2 C3 O2 -81.77(16) . . . . ?
O1 C2 N1 C1 11.7(2) . . . . ?
O1 C2 N1 C5 173.61(13) . . . . ?
O2 C3 C4 C5 -81.33(12) . . . . ?
O3 C15 C16 C17 179.73(13) . . . . ?
C101 C112 C113 C114 -175.55(12) . . . . ?
C101 C112 C117 C116 175.70(13) . . . . ?
C102 C103 C104 C105 -31.62(13) . . . . ?
C103 C102 N101 C101 161.55(11) . . . . ?
C103 C102 N101 C105 3.53(15) . . . . ?
C103 C104 C105 C107 155.60(11) . . . . ?
C103 C104 C105 N101 33.46(13) . . . . ?
C104 C105 C107 C108 126.94(13) . . . . ?
C104 C105 C107 C111 -51.51(17) . . . . ?
C104 C105 N101 C101 178.18(11) . . . . ?
C104 C105 N101 C102 -23.46(14) . . . . ?
C105 C107 C108 N102 -178.94(13) . . . . ?
C105 C107 C111 C110 178.21(13) . . . . ?
C106 C103 C104 C105 -155.39(11) . . . . ?
C107 C105 N101 C101 54.67(16) . . . . ?
C107 C105 N101 C102 -146.97(12) . . . . ?
C107 C108 N102 C109 0.5(2) . . . . ?
C108 C107 C111 C110 -0.3(2) . . . . ?
C109 C110 C111 C107 0.8(2) . . . . ?
C110 C109 N102 C108 0.1(2) . . . . ?
C111 C107 C108 N102 -0.4(2) . . . . ?
C112 C101 N101 C102 -86.10(15) . . . . ?
C112 C101 N101 C105 70.06(15) . . . . ?
C112 C113 C114 C115 0.0(2) . . . . ?
C113 C112 C117 C116 -1.3(2) . . . . ?
C113 C114 C115 C116 -1.8(2) . . . . ?
C113 C114 C115 O103 177.79(12) . . . . ?
C114 C115 C116 C117 2.0(2) . . . . ?
C114 C115 O103 C118 -175.95(12) . . . . ?
C115 C116 C117 C112 -0.5(2) . . . . ?
C116 C115 O103 C118 3.6(2) . . . . ?
C117 C112 C113 C114 1.5(2) . . . . ?
N101 C101 C112 C113 74.11(15) . . . . ?
N101 C101 C112 C117 -102.84(15) . . . . ?
N101 C102 C103 C104 18.24(14) . . . . ?
N101 C102 C103 C106 143.48(12) . . . . ?
N101 C102 C103 O102 -93.24(12) . . . . ?
N101 C105 C107 C108 -117.40(14) . . . . ?
N101 C105 C107 C111 64.16(17) . . . . ?
N102 C109 C110 C111 -0.8(2) . . . . ?
O101 C102 C103 C104 -165.23(13) . . . . ?
O101 C102 C103 C106 -40.00(19) . . . . ?
O101 C102 C103 O102 83.29(16) . . . . ?
O101 C102 N101 C101 -15.0(2) . . . . ?
O101 C102 N101 C105 -172.99(13) . . . . ?
O102 C103 C104 C105 78.44(12) . . . . ?
O103 C115 C116 C117 -177.51(13) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 -1 -10 0.0084 1.0036 -0.9896 -10.0062 0.3307 -0.9170 -0.0924
-1 1 10 0.0214 -1.0036 0.9896 10.0062 -0.3307 0.9170 0.0924
-4 0 2 0.0631 -3.9995 -0.0020 1.9973 -0.7866 -0.1054 0.4641
0 -10 1 0.0737 -0.0003 -10.0016 0.9918 0.3624 0.0094 0.9778
4 1 -2 0.0377 3.9995 1.0020 -1.9964 0.7493 0.1143 -0.5611
4 3 -2 0.0395 3.9995 3.0022 -1.9947 0.6748 0.1321 -0.7551
-4 5 1 0.0705 -3.9992 4.9994 1.0011 -0.9627 -0.1593 -0.0287

_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_6q-cis
_database_code_depnum_ccdc_archive 'CCDC 1028127'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H14 N2 O2'
_chemical_formula_sum            'C11 H14 N2 O2'
_chemical_formula_weight         206.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H14 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'

_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                   7.5414(3)
_cell_length_b                   11.8446(5)
_cell_length_c                   12.2635(5)
_cell_angle_alpha                80.154(4)
_cell_angle_beta                 88.093(4)
_cell_angle_gamma                88.519(3)
_cell_volume                     1078.48(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1380
_cell_measurement_theta_min      3.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.1447
_exptl_crystal_size_mid          0.0816
_exptl_crystal_size_min          0.0337
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7212
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_min         3.660
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1210706000
_diffrn_orient_matrix_UB_12      0.0614208000
_diffrn_orient_matrix_UB_13      0.0760325000
_diffrn_orient_matrix_UB_21      0.0822099000
_diffrn_orient_matrix_UB_22      0.1154447000
_diffrn_orient_matrix_UB_23      -0.0512703000
_diffrn_orient_matrix_UB_31      -0.1427501000
_diffrn_orient_matrix_UB_32      0.0182631000
_diffrn_orient_matrix_UB_33      -0.0886606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3649
_reflns_number_total             4221
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.028
_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)+(0.0480P)²+0.3700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C105(H105)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C104(H10D,H10E)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C108(H108), C109(H109), C110(H110),
 C111(H111)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C101(H10A,H10B,H10C), C106(H10F,H10G,H10H)
;
_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 0.14392(19) 0.60399(13) 0.07201(11) 0.0220(3) Uani 1 1 d . . . . .
H1A H 0.1479 0.5452 0.0245 0.033 Uiso 1 1 calc GR . . . .
H1B H 0.0625 0.6664 0.0415 0.033 Uiso 1 1 calc GR . . . .
H1C H 0.1023 0.5701 0.1467 0.033 Uiso 1 1 calc GR . . . .
C2 C 0.42274(18) 0.62421(11) 0.16608(11) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.61223(18) 0.66391(12) 0.13320(11) 0.0189(3) Uani 1 1 d . . . . .
C4 C 0.58456(18) 0.74591(12) 0.02491(11) 0.0208(3) Uani 1 1 d . . . . .
H4A H 0.6895 0.7451 -0.0257 0.025 Uiso 1 1 calc R . . . .
H4B H 0.5622 0.8251 0.0384 0.025 Uiso 1 1 calc R . . . .
C5 C 0.42097(18) 0.69996(11) -0.02373(10) 0.0173(3) Uani 1 1 d . . . . .
H5 H 0.4592 0.6384 -0.0665 0.021 Uiso 1 1 calc R . . . .
C6 C 0.6990(2) 0.71452(13) 0.22330(12) 0.0246(3) Uani 1 1 d . . . . .
H6A H 0.6282 0.7805 0.2394 0.037 Uiso 1 1 calc GR . . . .
H6B H 0.8188 0.7392 0.1982 0.037 Uiso 1 1 calc GR . . . .
H6C H 0.7060 0.6565 0.2904 0.037 Uiso 1 1 calc GR . . . .
C7 C 0.31506(17) 0.79107(12) -0.09681(11) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.29839(18) 0.78522(12) -0.20806(11) 0.0202(3) Uani 1 1 d . . . . .
H8 H 0.3492 0.7205 -0.2346 0.024 Uiso 1 1 calc R . . . .
C9 C 0.1404(2) 0.95374(13) -0.24080(12) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.0799 1.0110 -0.2906 0.031 Uiso 1 1 calc R . . . .
C10 C 0.1462(2) 0.96674(13) -0.13056(12) 0.0254(3) Uani 1 1 d . . . . .
H10 H 0.0898 1.0308 -0.1058 0.030 Uiso 1 1 calc R . . . .
C11 C 0.23615(19) 0.88439(12) -0.05739(11) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.2438 0.8915 0.0183 0.026 Uiso 1 1 calc R . . . .
N1 N 0.32093(15) 0.64897(10) 0.07695(9) 0.0171(2) Uani 1 1 d . . . . .
N2 N 0.21502(17) 0.86527(11) -0.28047(10) 0.0244(3) Uani 1 1 d . . . . .
O1 O 0.37572(14) 0.57358(9) 0.25848(8) 0.0241(2) Uani 1 1 d . . . . .
O2 O 0.70825(14) 0.56624(9) 0.10706(8) 0.0231(2) Uani 1 1 d . . . . .
C101 C 0.63556(18) 0.37910(13) 0.45764(12) 0.0221(3) Uani 1 1 d . . . . .
H10A H 0.6083 0.4378 0.3935 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.6163 0.4112 0.5257 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.5579 0.3137 0.4594 0.033 Uiso 1 1 calc GR . . . .
C102 C 0.92705(18) 0.37579(11) 0.36107(11) 0.0180(3) Uani 1 1 d . . . . .
C103 C 1.11626(18) 0.33114(11) 0.38729(11) 0.0197(3) Uani 1 1 d . . . . .
C104 C 1.08560(18) 0.23960(12) 0.48942(11) 0.0207(3) Uani 1 1 d . . . . .
H10D H 1.1867 0.2346 0.5397 0.025 Uiso 1 1 calc R . . . .
H10E H 1.0696 0.1636 0.4682 0.025 Uiso 1 1 calc R . . . .
C105 C 0.91511(18) 0.28018(12) 0.54488(11) 0.0179(3) Uani 1 1 d . . . . .
H105 H 0.9460 0.3355 0.5940 0.021 Uiso 1 1 calc R . . . .
C106 C 1.21044(18) 0.28905(12) 0.28758(12) 0.0205(3) Uani 1 1 d . . . . .
H10F H 1.1421 0.2276 0.2659 0.031 Uiso 1 1 calc GR . . . .
H10G H 1.3297 0.2599 0.3082 0.031 Uiso 1 1 calc GR . . . .
H10H H 1.2194 0.3529 0.2253 0.031 Uiso 1 1 calc GR . . . .
C107 C 0.80969(17) 0.18413(11) 0.61080(11) 0.0172(3) Uani 1 1 d . . . . .
C108 C 0.79465(18) 0.17313(12) 0.72516(11) 0.0194(3) Uani 1 1 d . . . . .
H108 H 0.8492 0.2291 0.7591 0.023 Uiso 1 1 calc R . . . .
C109 C 0.6306(2) 0.01165(13) 0.74133(12) 0.0236(3) Uani 1 1 d . . . . .
H109 H 0.5682 -0.0487 0.7863 0.028 Uiso 1 1 calc R . . . .
C110 C 0.6364(2) 0.01523(13) 0.62777(12) 0.0241(3) Uani 1 1 d . . . . .
H110 H 0.5784 -0.0411 0.5961 0.029 Uiso 1 1 calc R . . . .
C111 C 0.7283(2) 0.10239(12) 0.56102(11) 0.0212(3) Uani 1 1 d . . . . .
H111 H 0.7356 0.1063 0.4830 0.025 Uiso 1 1 calc R . . . .
N101 N 0.81987(15) 0.34131(10) 0.44915(9) 0.0174(2) Uani 1 1 d . . . . .
N102 N 0.70828(17) 0.08868(11) 0.79100(9) 0.0229(3) Uani 1 1 d . . . . .
O101 O 0.88508(14) 0.43701(9) 0.27380(8) 0.0246(2) Uani 1 1 d . . . . .
O102 O 1.20918(14) 0.42198(9) 0.42130(9) 0.0245(2) Uani 1 1 d . . . . .
H2 H 0.748(3) 0.5261(19) 0.1681(18) 0.038(5) Uiso 1 1 d . . . . .
H102 H 1.244(3) 0.474(2) 0.356(2) 0.057(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4570(18) . ?
C2 C3 1.5353(19) . ?
C2 N1 1.3435(17) . ?
C2 O1 1.2333(17) . ?
C3 C4 1.5223(18) . ?
C3 C6 1.5175(19) . ?
C3 O2 1.4261(17) . ?
C4 C5 1.5390(19) . ?
C5 C7 1.5093(18) . ?
C5 N1 1.4714(16) . ?
C7 C8 1.3878(19) . ?
C7 C11 1.393(2) . ?
C8 N2 1.3421(19) . ?
C9 C10 1.389(2) . ?
C9 N2 1.333(2) . ?
C10 C11 1.387(2) . ?
C101 N101 1.4551(18) . ?
C102 C103 1.5338(19) . ?
C102 N101 1.3398(17) . ?
C102 O101 1.2315(17) . ?
C103 C104 1.5255(18) . ?
C103 C106 1.5429(19) . ?
C103 O102 1.4265(17) . ?
C104 C105 1.5389(19) . ?
C105 C107 1.5064(18) . ?
C105 N101 1.4686(16) . ?
C107 C108 1.3872(18) . ?
C107 C111 1.394(2) . ?
C108 N102 1.3413(19) . ?
C109 C110 1.385(2) . ?
C109 N102 1.337(2) . ?
C110 C111 1.388(2) . ?

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
N1 C2 C3 108.86(11) . . ?
O1 C2 C3 124.81(12) . . ?
O1 C2 N1 126.26(13) . . ?
C4 C3 C2 102.18(11) . . ?
C6 C3 C2 112.52(11) . . ?
C6 C3 C4 115.59(12) . . ?
O2 C3 C2 106.32(11) . . ?
O2 C3 C4 107.28(11) . . ?
O2 C3 C6 112.10(11) . . ?
C3 C4 C5 104.23(10) . . ?
C7 C5 C4 113.75(11) . . ?
N1 C5 C4 101.82(10) . . ?
N1 C5 C7 112.62(11) . . ?
C8 C7 C5 119.93(12) . . ?
C8 C7 C11 117.84(12) . . ?
C11 C7 C5 122.20(12) . . ?
N2 C8 C7 124.11(13) . . ?
N2 C9 C10 123.56(13) . . ?
C11 C10 C9 118.68(14) . . ?
C10 C11 C7 118.83(13) . . ?
C1 N1 C5 121.68(11) . . ?
C2 N1 C1 123.56(11) . . ?
C2 N1 C5 112.94(11) . . ?
C9 N2 C8 116.95(12) . . ?
N101 C102 C103 109.07(11) . . ?
O101 C102 C103 124.35(12) . . ?
O101 C102 N101 126.53(13) . . ?
C102 C103 C106 112.06(11) . . ?
C104 C103 C102 102.18(11) . . ?
C104 C103 C106 115.50(11) . . ?
O102 C103 C102 107.11(11) . . ?
O102 C103 C104 107.47(11) . . ?
O102 C103 C106 111.80(11) . . ?
C103 C104 C105 104.28(11) . . ?
C107 C105 C104 113.78(11) . . ?
N101 C105 C104 101.79(10) . . ?
N101 C105 C107 112.75(11) . . ?
C108 C107 C105 120.08(12) . . ?
C108 C107 C111 117.74(13) . . ?
C111 C107 C105 122.16(12) . . ?
N102 C108 C107 124.37(13) . . ?
N102 C109 C110 123.46(13) . . ?
C109 C110 C111 118.96(13) . . ?
C110 C111 C107 118.67(12) . . ?
C101 N101 C105 122.26(11) . . ?
C102 N101 C101 123.68(11) . . ?
C102 N101 C105 113.02(11) . . ?
C109 N102 C108 116.79(12) . . ?

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
O2 H2 O101 0.87(2) 1.85(2) 2.7034(14) 165(2) .
O102 H102 O1 0.95(3) 1.82(3) 2.7409(14) 161(2) 1_655

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
C2 C3 C4 C5 -28.99(13) . . . . ?
C3 C2 N1 C1 167.61(12) . . . . ?
C3 C2 N1 C5 2.80(15) . . . . ?
C3 C4 C5 C7 151.96(11) . . . . ?
C3 C4 C5 N1 30.53(13) . . . . ?
C4 C5 C7 C8 117.17(14) . . . . ?
C4 C5 C7 C11 -60.86(17) . . . . ?
C4 C5 N1 C1 173.70(12) . . . . ?
C4 C5 N1 C2 -21.16(14) . . . . ?
C5 C7 C8 N2 -176.33(13) . . . . ?
C5 C7 C11 C10 177.72(13) . . . . ?
C6 C3 C4 C5 -151.53(12) . . . . ?
C7 C5 N1 C1 51.50(17) . . . . ?
C7 C5 N1 C2 -143.37(12) . . . . ?
C7 C8 N2 C9 -1.9(2) . . . . ?
C8 C7 C11 C10 -0.3(2) . . . . ?
C9 C10 C11 C7 -0.9(2) . . . . ?
C10 C9 N2 C8 0.5(2) . . . . ?
C11 C7 C8 N2 1.8(2) . . . . ?
N1 C2 C3 C4 17.03(14) . . . . ?
N1 C2 C3 C6 141.63(12) . . . . ?
N1 C2 C3 O2 -95.29(12) . . . . ?
N1 C5 C7 C8 -127.63(13) . . . . ?
N1 C5 C7 C11 54.34(17) . . . . ?
N2 C9 C10 C11 0.8(2) . . . . ?
O1 C2 C3 C4 -165.77(13) . . . . ?
O1 C2 C3 C6 -41.17(19) . . . . ?
O1 C2 C3 O2 81.91(16) . . . . ?
O1 C2 N1 C1 -9.5(2) . . . . ?
O1 C2 N1 C5 -174.34(13) . . . . ?
O2 C3 C4 C5 82.61(13) . . . . ?
C102 C103 C104 C105 -28.00(13) . . . . ?
C103 C102 N101 C101 172.79(12) . . . . ?
C103 C102 N101 C105 4.25(15) . . . . ?
C103 C104 C105 C107 151.89(11) . . . . ?
C103 C104 C105 N101 30.31(13) . . . . ?
C104 C105 C107 C108 112.47(14) . . . . ?
C104 C105 C107 C111 -65.93(17) . . . . ?
C104 C105 N101 C101 169.30(12) . . . . ?
C104 C105 N101 C102 -21.98(14) . . . . ?
C105 C107 C108 N102 -177.93(13) . . . . ?
C105 C107 C111 C110 178.75(13) . . . . ?
C106 C103 C104 C105 -149.91(12) . . . . ?
C107 C105 N101 C101 47.01(17) . . . . ?
C107 C105 N101 C102 -144.26(12) . . . . ?
C107 C108 N102 C109 -0.8(2) . . . . ?
C108 C107 C111 C110 0.3(2) . . . . ?
C109 C110 C111 C107 -0.8(2) . . . . ?
C110 C109 N102 C108 0.3(2) . . . . ?
C111 C107 C108 N102 0.5(2) . . . . ?
N101 C102 C103 C104 15.57(14) . . . . ?
N101 C102 C103 C106 139.80(12) . . . . ?
N101 C102 C103 O102 -97.25(12) . . . . ?
N101 C105 C107 C108 -132.26(13) . . . . ?
N101 C105 C107 C111 49.34(17) . . . . ?
N102 C109 C110 C111 0.5(2) . . . . ?
O101 C102 C103 C104 -166.88(13) . . . . ?
O101 C102 C103 C106 -42.65(18) . . . . ?
O101 C102 C103 O102 80.30(16) . . . . ?
O101 C102 N101 C101 -4.7(2) . . . . ?
O101 C102 N101 C105 -173.23(13) . . . . ?
O102 C103 C104 C105 84.55(13) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 2 7 0.0537 -2.0000 2.0000 7.0000 0.8972 -0.2924 -0.2986
-5 1 0 0.0440 -5.0000 1.0000 0.0000 0.6668 -0.2956 0.7320
5 -1 0 0.0255 5.0000 -1.0000 -0.0000 -0.6668 0.2956 -0.7320
4 -2 -4 0.0302 4.0000 -2.0000 -4.0000 -0.9113 0.3030 -0.2529
-2 -1 -7 0.0664 -2.0000 -1.0000 -7.0000 -0.3515 0.0790 0.8879
0 -8 0 0.0084 -0.0000 -8.0000 -0.0000 -0.4914 -0.9236 -0.1461
-1 7 0 0.0203 -1.0000 7.0000 0.0000 0.5510 0.7259 0.2706


####################################################################### 
# 
# 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_11a
_database_code_depnum_ccdc_archive 'CCDC 1028128'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C46 H42 N2 O'
_chemical_formula_sum            'C46 H42 N2 O'
_chemical_formula_weight         638.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H21 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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.55604(14)
_cell_length_b                   15.09459(13)
_cell_length_c                   18.96430(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.8657(10)
_cell_angle_gamma                90
_cell_volume                     3457.35(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19536
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      4.6540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2615
_exptl_crystal_size_mid          0.1421
_exptl_crystal_size_min          0.0885
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         4.689
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   77.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega -113.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607 -139.0000 -113.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
  8 omega   25.00  109.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00  122.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
 10 omega   32.00   91.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 12 omega   25.00  109.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000   90.0000 117

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00  122.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
 20 omega   36.00  134.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
 21 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  -90.0000 105

#__ type_ start__ end____ width___ exp.time_
 22 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
 23 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 24 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
 25 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  -30.0000 105

#__ type_ start__ end____ width___ exp.time_
 26 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 27 omega   61.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000 -120.0000 117

#__ type_ start__ end____ width___ exp.time_
 28 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 29 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  177.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 31 omega   79.00  177.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
 32 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 33 omega   79.00  127.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 34 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0393431000
_diffrn_orient_matrix_UB_12      -0.0944538000
_diffrn_orient_matrix_UB_13      -0.0108436000
_diffrn_orient_matrix_UB_21      0.0372694000
_diffrn_orient_matrix_UB_22      -0.0131864000
_diffrn_orient_matrix_UB_23      0.0837390000
_diffrn_orient_matrix_UB_31      -0.1154170000
_diffrn_orient_matrix_UB_32      -0.0363900000
_diffrn_orient_matrix_UB_33      -0.0021494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3248
_reflns_number_total             3515
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.038
_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)+(0.0440P)²+2.7440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_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 0.28711(9) 0.91564(7) 0.24301(6) 0.0183(2) Uani 1 1 d . . . . .
H1A H 0.2100 0.9273 0.2139 0.022 Uiso 1 1 calc R . . . .
H1B H 0.3371 0.9497 0.2208 0.022 Uiso 1 1 calc R . . . .
C2 C 0.42413(8) 0.79697(7) 0.27613(5) 0.0149(2) Uani 1 1 d . . . . .
H2 H 0.4394 0.8018 0.3306 0.018 Uiso 1 1 calc R . . . .
C3 C 0.43908(8) 0.70023(7) 0.25280(5) 0.0140(2) Uani 1 1 d . . . . .
C4 C 0.34986(8) 0.69594(7) 0.17639(5) 0.0159(2) Uani 1 1 d . . . . .
H4A H 0.3858 0.6847 0.1368 0.019 Uiso 1 1 calc R . . . .
H4B H 0.2963 0.6477 0.1761 0.019 Uiso 1 1 calc R . . . .
C5 C 0.29037(8) 0.78657(7) 0.16488(5) 0.0158(2) Uani 1 1 d . . . . .
H5 H 0.3270 0.8263 0.1363 0.019 Uiso 1 1 calc R . . . .
C6 C 0.41338(8) 0.63427(7) 0.30734(5) 0.0149(2) Uani 1 1 d . . . . .
C7 C 0.32174(8) 0.64970(7) 0.33447(5) 0.0174(2) Uani 1 1 d . . . . .
H7 H 0.2747 0.6988 0.3166 0.021 Uiso 1 1 calc R . . . .
C8 C 0.29839(9) 0.59450(7) 0.38703(6) 0.0191(2) Uani 1 1 d . . . . .
H8 H 0.2359 0.6062 0.4046 0.023 Uiso 1 1 calc R . . . .
C9 C 0.36590(9) 0.52243(7) 0.41389(6) 0.0189(2) Uani 1 1 d . . . . .
H9 H 0.3512 0.4857 0.4508 0.023 Uiso 1 1 calc R . . . .
C10 C 0.45504(9) 0.50460(7) 0.38616(6) 0.0183(2) Uani 1 1 d . . . . .
H10 H 0.5006 0.4545 0.4034 0.022 Uiso 1 1 calc R . . . .
C11 C 0.47827(8) 0.55954(7) 0.33329(5) 0.0167(2) Uani 1 1 d . . . . .
H11 H 0.5392 0.5461 0.3145 0.020 Uiso 1 1 calc R . . . .
C12 C 0.16858(8) 0.77844(7) 0.12522(5) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.09098(9) 0.75373(7) 0.16186(6) 0.0214(2) Uani 1 1 d . . . . .
H13 H 0.1138 0.7449 0.2134 0.026 Uiso 1 1 calc R . . . .
C14 C -0.01951(9) 0.74193(8) 0.12370(7) 0.0253(2) Uani 1 1 d . . . . .
H14 H -0.0716 0.7249 0.1493 0.030 Uiso 1 1 calc R . . . .
C15 C -0.05423(9) 0.75491(8) 0.04828(7) 0.0261(3) Uani 1 1 d . . . . .
H15 H -0.1297 0.7463 0.0222 0.031 Uiso 1 1 calc R . . . .
C16 C 0.02202(10) 0.78049(8) 0.01131(6) 0.0246(2) Uani 1 1 d . . . . .
H16 H -0.0013 0.7901 -0.0401 0.030 Uiso 1 1 calc R . . . .
C17 C 0.13275(9) 0.79200(7) 0.04962(6) 0.0197(2) Uani 1 1 d . . . . .
H17 H 0.1846 0.8093 0.0239 0.024 Uiso 1 1 calc R . . . .
C18 C 0.30203(8) 0.94649(7) 0.32061(6) 0.0177(2) Uani 1 1 d . . . . .
C19 C 0.38143(9) 1.00977(7) 0.35252(6) 0.0216(2) Uani 1 1 d . . . . .
H19 H 0.4279 1.0335 0.3252 0.026 Uiso 1 1 calc R . . . .
C20 C 0.39337(10) 1.03850(8) 0.42404(6) 0.0255(2) Uani 1 1 d . . . . .
H20 H 0.4471 1.0822 0.4451 0.031 Uiso 1 1 calc R . . . .
C21 C 0.32695(10) 1.00338(8) 0.46450(6) 0.0252(2) Uani 1 1 d . . . . .
H21 H 0.3354 1.0226 0.5134 0.030 Uiso 1 1 calc R . . . .
C22 C 0.24791(10) 0.93990(8) 0.43334(6) 0.0248(2) Uani 1 1 d . . . . .
H22 H 0.2025 0.9154 0.4611 0.030 Uiso 1 1 calc R . . . .
C23 C 0.23536(9) 0.91233(7) 0.36180(6) 0.0217(2) Uani 1 1 d . . . . .
H23 H 0.1805 0.8695 0.3406 0.026 Uiso 1 1 calc R . . . .
N1 N 0.31105(7) 0.82046(6) 0.24002(4) 0.01554(19) Uani 1 1 d . . . . .
O1 O 0.5000 0.85026(7) 0.2500 0.0182(2) Uani 1 2 d S T P . .


_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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C18 1.5054(14) . ?
C1 N1 1.4721(13) . ?
C2 H2 1.0000 . ?
C2 C3 1.5520(13) . ?
C2 N1 1.4418(12) . ?
C2 O1 1.4346(11) . ?
C3 C3 1.5622(19) 2_655 ?
C3 C4 1.5720(13) . ?
C3 C6 1.5322(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5453(14) . ?
C5 H5 1.0000 . ?
C5 C12 1.5134(13) . ?
C5 N1 1.4688(12) . ?
C6 C7 1.4024(14) . ?
C6 C11 1.3998(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.3904(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3877(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3869(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3922(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3934(15) . ?
C12 C17 1.3953(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.3897(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3905(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3871(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3924(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3939(15) . ?
C18 C23 1.3908(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3923(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3839(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.3898(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3864(15) . ?
C23 H23 0.9500 . ?
O1 C2 1.4346(11) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.0 . . ?
C18 C1 H1A 109.3 . . ?
C18 C1 H1B 109.3 . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C18 111.55(8) . . ?
C3 C2 H2 111.0 . . ?
N1 C2 H2 111.0 . . ?
N1 C2 C3 106.03(8) . . ?
O1 C2 H2 111.0 . . ?
O1 C2 C3 106.60(8) . . ?
O1 C2 N1 111.03(7) . . ?
C2 C3 C3 102.49(5) . 2_655 ?
C2 C3 C4 100.97(7) . . ?
C3 C3 C4 113.68(10) 2_655 . ?
C6 C3 C2 110.78(8) . . ?
C6 C3 C3 115.90(8) . 2_655 ?
C6 C3 C4 111.53(8) . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C3 106.79(8) . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C4 C5 H5 109.3 . . ?
C12 C5 C4 112.47(8) . . ?
C12 C5 H5 109.3 . . ?
N1 C5 C4 102.76(8) . . ?
N1 C5 H5 109.3 . . ?
N1 C5 C12 113.39(8) . . ?
C7 C6 C3 119.02(9) . . ?
C11 C6 C3 123.45(9) . . ?
C11 C6 C7 117.51(9) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.23(10) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.37(10) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.22(10) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.48(10) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.12(10) . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C5 121.54(9) . . ?
C13 C12 C17 118.60(10) . . ?
C17 C12 C5 119.80(10) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.61(10) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.35(11) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.57(10) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.98(10) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.88(11) . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C1 121.30(10) . . ?
C23 C18 C1 120.08(10) . . ?
C23 C18 C19 118.62(10) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.68(10) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.00(11) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.79(10) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.99(11) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.90(10) . . ?
C22 C23 H23 119.5 . . ?
C2 N1 C1 113.99(8) . . ?
C2 N1 C5 105.37(8) . . ?
C5 N1 C1 113.17(8) . . ?
C2 O1 C2 111.79(10) . 2_655 ?

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 C18 C19 C20 179.18(10) . . . . ?
C1 C18 C23 C22 179.97(10) . . . . ?
C2 C3 C4 C5 -2.33(10) . . . . ?
C2 C3 C6 C7 41.93(12) . . . . ?
C2 C3 C6 C11 -136.59(9) . . . . ?
C3 C2 N1 C1 -167.99(8) . . . . ?
C3 C2 N1 C5 -43.31(9) . . . . ?
C3 C2 O1 C2 -10.30(4) . . . 2_655 ?
C3 C3 C4 C5 -111.33(6) 2_655 . . . ?
C3 C3 C6 C7 158.13(9) 2_655 . . . ?
C3 C3 C6 C11 -20.39(13) 2_655 . . . ?
C3 C4 C5 C12 -144.44(8) . . . . ?
C3 C4 C5 N1 -22.14(10) . . . . ?
C3 C6 C7 C8 -176.48(9) . . . . ?
C3 C6 C11 C10 176.12(9) . . . . ?
C4 C3 C6 C7 -69.69(11) . . . . ?
C4 C3 C6 C11 111.79(10) . . . . ?
C4 C5 C12 C13 80.47(12) . . . . ?
C4 C5 C12 C17 -96.63(11) . . . . ?
C4 C5 N1 C1 165.37(8) . . . . ?
C4 C5 N1 C2 40.18(10) . . . . ?
C5 C12 C13 C14 -176.44(10) . . . . ?
C5 C12 C17 C16 176.70(10) . . . . ?
C6 C3 C4 C5 115.38(9) . . . . ?
C6 C7 C8 C9 0.00(15) . . . . ?
C7 C6 C11 C10 -2.42(14) . . . . ?
C7 C8 C9 C10 -1.87(15) . . . . ?
C8 C9 C10 C11 1.57(15) . . . . ?
C9 C10 C11 C6 0.61(15) . . . . ?
C11 C6 C7 C8 2.12(15) . . . . ?
C12 C5 N1 C1 -72.96(11) . . . . ?
C12 C5 N1 C2 161.84(8) . . . . ?
C12 C13 C14 C15 -0.20(17) . . . . ?
C13 C12 C17 C16 -0.49(16) . . . . ?
C13 C14 C15 C16 -0.53(17) . . . . ?
C14 C15 C16 C17 0.73(17) . . . . ?
C15 C16 C17 C12 -0.23(17) . . . . ?
C17 C12 C13 C14 0.70(16) . . . . ?
C18 C1 N1 C2 -63.38(11) . . . . ?
C18 C1 N1 C5 176.22(8) . . . . ?
C18 C19 C20 C21 0.81(17) . . . . ?
C19 C18 C23 C22 -0.53(16) . . . . ?
C19 C20 C21 C22 -0.46(18) . . . . ?
C20 C21 C22 C23 -0.37(18) . . . . ?
C21 C22 C23 C18 0.87(17) . . . . ?
C23 C18 C19 C20 -0.31(16) . . . . ?
N1 C1 C18 C19 117.37(11) . . . . ?
N1 C1 C18 C23 -63.14(12) . . . . ?
N1 C2 C3 C3 144.45(9) . . . 2_655 ?
N1 C2 C3 C4 26.94(9) . . . . ?
N1 C2 C3 C6 -91.31(9) . . . . ?
N1 C2 O1 C2 -125.34(8) . . . 2_655 ?
N1 C5 C12 C13 -35.60(13) . . . . ?
N1 C5 C12 C17 147.30(9) . . . . ?
O1 C2 C3 C3 26.08(10) . . . 2_655 ?
O1 C2 C3 C4 -91.43(8) . . . . ?
O1 C2 C3 C6 150.31(7) . . . . ?
O1 C2 N1 C1 -52.60(11) . . . . ?
O1 C2 N1 C5 72.08(9) . . . . ?




loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -12 0.0443 0.0000 -0.0000 -12.0000 0.1301 -1.0049 0.0258
0 0 12 0.0443 -0.0000 0.0000 12.0000 -0.1301 1.0049 -0.0258
7 3 0 0.0708 7.0000 3.0000 0.0000 -0.0080 0.2213 -0.9171
-7 -3 7 0.0643 -7.0000 -3.0000 7.0000 -0.0679 0.3648 0.9020
-6 -7 3 0.0420 -6.0000 -7.0000 3.0000 0.3926 0.1199 0.9408
8 2 -3 0.0666 8.0000 2.0000 -3.0000 0.1584 0.0206 -0.9897
6 -6 -1 0.1019 6.0000 -6.0000 -1.0000 0.8136 0.2190 -0.4720
0 10 -2 0.0934 0.0000 10.0000 -2.0000 -0.9229 -0.2993 -0.3596
-3 7 8 0.0923 -3.0000 7.0000 8.0000 -0.8660 0.4658 0.0743

_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_11b
_database_code_depnum_ccdc_archive 'CCDC 1028129'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H46 N2 O3'
_chemical_formula_sum            'C48 H46 N2 O3'
_chemical_formula_weight         698.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H46 N2 O3'
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                   10.1705(3)
_cell_length_b                   10.2903(3)
_cell_length_c                   19.4528(5)
_cell_angle_alpha                99.778(2)
_cell_angle_beta                 99.679(2)
_cell_angle_gamma                106.888(2)
_cell_volume                     1868.03(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16193
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      74.1680
_cell_measurement_theta_min      4.5710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.1859
_exptl_crystal_size_mid          0.1062
_exptl_crystal_size_min          0.0726
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31249
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.062
_diffrn_reflns_theta_min         7.122
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   82.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.8107   38.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega   97.00  124.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -78.4862 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  100.00  126.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -143.9027 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  108.00  176.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega  144.00  170.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  111.00  177.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega  134.00  160.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   63.0000  -23.6666 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  122.00  149.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000   21.8378 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   76.00  166.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  177.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega   79.00  105.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   63.0000  -23.6666 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  157.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  169.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  175.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
 16 omega   76.00  152.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 17 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  102.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   75.00  129.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 21 omega   52.00   79.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   72.0000 -175.3215 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   51.00   77.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000 -146.5494 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   63.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -143.9027 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -114.2179 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00   72.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   68.0000  -74.0308 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   43.00   70.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -31.9960 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   65.00   92.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000   21.8378 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   59.00   88.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       90.0000   74.0000   75.6551 29

#__ type_ start__ end____ width___ exp.time_
 29 omega   53.00   79.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   67.0000  156.4616 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   67.00  164.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   63.0000  168.4610 97

#__ type_ start__ end____ width___ exp.time_
 31 omega   52.00   77.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   76.0000  113.0487 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   45.00   70.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   70.0000   71.5699 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   51.9120 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   40.00   65.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000    7.6433 25

#__ type_ start__ end____ width___ exp.time_
 35 omega   32.00   58.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000    7.3912 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   35.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -42.3615 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -78.4862 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   17.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000 -164.7459 26

#__ type_ start__ end____ width___ exp.time_
 39 omega    8.00   33.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.0000   85.0000  -42.6889 25

#__ type_ start__ end____ width___ exp.time_
 40 omega   18.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000   54.3015 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   13.00   38.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000   21.1604 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   18.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  119.2219 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   31.00   57.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  120.2191 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  137.3951 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   35.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  174.1956 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   33.00  137.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
 47 omega   51.00  122.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
 48 omega   36.00   83.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 49 omega   34.00  111.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 50 omega   28.00  112.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -102.0000  -89.0000 84

#__ type_ start__ end____ width___ exp.time_
 51 omega   23.00   98.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.8107 -125.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 52 omega  -68.00   25.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107   57.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
 53 omega -114.00  -22.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -38.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
 54 omega -113.00  -16.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -57.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 55 omega -114.00   24.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107    0.0000  -30.0000 138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1310477000
_diffrn_orient_matrix_UB_12      0.0488299000
_diffrn_orient_matrix_UB_13      0.0627250000
_diffrn_orient_matrix_UB_21      0.0787428000
_diffrn_orient_matrix_UB_22      -0.0688542000
_diffrn_orient_matrix_UB_23      -0.0480433000
_diffrn_orient_matrix_UB_31      0.0556377000
_diffrn_orient_matrix_UB_32      0.1368975000
_diffrn_orient_matrix_UB_33      -0.0240464000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6174
_reflns_number_total             7054
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0863
_refine_ls_restrained_S_all      1.157
_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)+(0.0460P)²+8.5290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2303
_refine_ls_wR_factor_ref         0.2339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C19(H19), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39),
 C40(H40), C43(H43), C44(H44), C46(H46), C47(H47)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C48(H48A,H48B,H48C)
;
_atom_sites_solution_hydrogens   geom
_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 0.3589(4) 0.1524(5) 0.7335(2) 0.0272(9) Uani 1 1 d . . . . .
H1A H 0.2698 0.0758 0.7093 0.033 Uiso 1 1 calc R . . . .
H1B H 0.3730 0.2221 0.7037 0.033 Uiso 1 1 calc R . . . .
C2 C 0.6144(4) 0.1961(4) 0.7687(2) 0.0216(8) Uani 1 1 d . . . . .
H2 H 0.6287 0.2291 0.8217 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7214(4) 0.1223(4) 0.7506(2) 0.0203(8) Uani 1 1 d . . . . .
C4 C 0.6334(4) 0.0197(4) 0.6767(2) 0.0227(8) Uani 1 1 d . . . . .
H4A H 0.6772 0.0468 0.6373 0.027 Uiso 1 1 calc R . . . .
H4B H 0.6300 -0.0772 0.6776 0.027 Uiso 1 1 calc R . . . .
C5 C 0.4826(4) 0.0298(4) 0.6653(2) 0.0242(8) Uani 1 1 d . . . . .
H5 H 0.4740 0.0936 0.6326 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7570(4) 0.0398(4) 0.8055(2) 0.0213(8) Uani 1 1 d . . . . .
C7 C 0.6525(4) -0.0299(4) 0.8376(2) 0.0252(9) Uani 1 1 d . . . . .
H7 H 0.5615 -0.0203 0.8274 0.030 Uiso 1 1 calc R . . . .
C8 C 0.6792(5) -0.1120(4) 0.8836(2) 0.0273(9) Uani 1 1 d . . . . .
H8 H 0.6058 -0.1601 0.9037 0.033 Uiso 1 1 calc R . . . .
C9 C 0.8124(5) -0.1255(4) 0.9012(2) 0.0274(9) Uani 1 1 d . . . . .
H9 H 0.8300 -0.1828 0.9327 0.033 Uiso 1 1 calc R . . . .
C10 C 0.9177(4) -0.0545(4) 0.8722(2) 0.0255(9) Uani 1 1 d . . . . .
H10 H 1.0097 -0.0609 0.8847 0.031 Uiso 1 1 calc R . . . .
C11 C 0.8908(4) 0.0271(4) 0.8244(2) 0.0244(8) Uani 1 1 d . . . . .
H11 H 0.9647 0.0746 0.8045 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3670(4) -0.1099(4) 0.6346(2) 0.0238(8) Uani 1 1 d . . . . .
C13 C 0.3400(5) -0.2094(5) 0.6744(2) 0.0299(9) Uani 1 1 d . . . . .
H13 H 0.3912 -0.1884 0.7227 0.036 Uiso 1 1 calc R . . . .
C14 C 0.2396(5) -0.3390(5) 0.6450(3) 0.0346(10) Uani 1 1 d . . . . .
H14 H 0.2218 -0.4069 0.6729 0.042 Uiso 1 1 calc R . . . .
C15 C 0.1641(5) -0.3699(5) 0.5738(3) 0.0342(10) Uani 1 1 d . . . . .
H15 H 0.0964 -0.4598 0.5530 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1872(5) -0.2722(5) 0.5342(3) 0.0377(11) Uani 1 1 d . . . . .
H16 H 0.1343 -0.2931 0.4862 0.045 Uiso 1 1 calc R . . . .
C17 C 0.2894(5) -0.1401(5) 0.5644(2) 0.0319(10) Uani 1 1 d . . . . .
H17 H 0.3055 -0.0714 0.5369 0.038 Uiso 1 1 calc R . . . .
C18 C 0.7973(4) 0.5939(4) 0.7537(2) 0.0247(8) Uani 1 1 d . . . . .
H18A H 0.8649 0.6830 0.7845 0.030 Uiso 1 1 calc R . . . .
H18B H 0.7139 0.5688 0.7748 0.030 Uiso 1 1 calc R . . . .
C19 C 0.7733(4) 0.3460(4) 0.7166(2) 0.0214(8) Uani 1 1 d . . . . .
H19 H 0.7622 0.3361 0.6637 0.026 Uiso 1 1 calc R . . . .
C20 C 0.8474(4) 0.2436(4) 0.7426(2) 0.0197(8) Uani 1 1 d . . . . .
C21 C 0.9464(4) 0.3365(4) 0.8165(2) 0.0215(8) Uani 1 1 d . . . . .
H21A H 0.9275 0.2888 0.8557 0.026 Uiso 1 1 calc R . . . .
H21B H 1.0468 0.3548 0.8150 0.026 Uiso 1 1 calc R . . . .
C22 C 0.9128(4) 0.4736(4) 0.8284(2) 0.0222(8) Uani 1 1 d . . . . .
H22 H 0.8330 0.4628 0.8531 0.027 Uiso 1 1 calc R . . . .
C23 C 0.9348(4) 0.2039(4) 0.6904(2) 0.0204(8) Uani 1 1 d . . . . .
C24 C 1.0228(4) 0.3093(4) 0.6663(2) 0.0232(8) Uani 1 1 d . . . . .
H24 H 1.0276 0.4033 0.6828 0.028 Uiso 1 1 calc R . . . .
C25 C 1.1038(4) 0.2797(5) 0.6186(2) 0.0263(9) Uani 1 1 d . . . . .
H25 H 1.1643 0.3534 0.6036 0.032 Uiso 1 1 calc R . . . .
C26 C 1.0965(4) 0.1438(4) 0.5929(2) 0.0254(9) Uani 1 1 d . . . . .
H26 H 1.1497 0.1235 0.5593 0.030 Uiso 1 1 calc R . . . .
C27 C 1.0113(4) 0.0370(4) 0.6164(2) 0.0250(9) Uani 1 1 d . . . . .
H27 H 1.0064 -0.0568 0.5992 0.030 Uiso 1 1 calc R . . . .
C28 C 0.9324(4) 0.0674(4) 0.6655(2) 0.0227(8) Uani 1 1 d . . . . .
H28 H 0.8762 -0.0062 0.6823 0.027 Uiso 1 1 calc R . . . .
C29 C 1.0354(4) 0.6003(4) 0.8707(2) 0.0228(8) Uani 1 1 d . . . . .
C30 C 1.1507(5) 0.6541(4) 0.8432(2) 0.0286(9) Uani 1 1 d . . . . .
H30 H 1.1531 0.6102 0.7965 0.034 Uiso 1 1 calc R . . . .
C31 C 1.2630(5) 0.7707(5) 0.8819(3) 0.0342(10) Uani 1 1 d . . . . .
H31 H 1.3413 0.8063 0.8619 0.041 Uiso 1 1 calc R . . . .
C32 C 1.2602(5) 0.8356(5) 0.9505(2) 0.0322(10) Uani 1 1 d . . . . .
H32 H 1.3375 0.9145 0.9778 0.039 Uiso 1 1 calc R . . . .
C33 C 1.1450(5) 0.7847(5) 0.9786(2) 0.0323(10) Uani 1 1 d . . . . .
H33 H 1.1421 0.8301 1.0248 0.039 Uiso 1 1 calc R . . . .
C34 C 1.0334(5) 0.6678(4) 0.9396(2) 0.0267(9) Uani 1 1 d . . . . .
H34 H 0.9548 0.6329 0.9595 0.032 Uiso 1 1 calc R . . . .
C35 C 0.3444(4) 0.2203(5) 0.8055(2) 0.0248(9) Uani 1 1 d . . . . .
C36 C 0.3058(5) 0.1416(5) 0.8552(2) 0.0314(10) Uani 1 1 d . . . . .
H36 H 0.2902 0.0440 0.8439 0.038 Uiso 1 1 calc R . . . .
C37 C 0.2904(5) 0.2038(5) 0.9201(2) 0.0314(10) Uani 1 1 d . . . . .
H37 H 0.2642 0.1491 0.9534 0.038 Uiso 1 1 calc R . . . .
C38 C 0.3130(4) 0.3470(5) 0.9376(2) 0.0273(9) Uani 1 1 d . . . . .
C39 C 0.3495(5) 0.4263(5) 0.8890(2) 0.0303(9) Uani 1 1 d . . . . .
H39 H 0.3634 0.5236 0.9000 0.036 Uiso 1 1 calc R . . . .
C40 C 0.3657(4) 0.3612(5) 0.8234(2) 0.0293(9) Uani 1 1 d . . . . .
H40 H 0.3922 0.4159 0.7901 0.035 Uiso 1 1 calc R . . . .
C41 C 0.3176(5) 0.5454(5) 1.0224(3) 0.0375(11) Uani 1 1 d . . . . .
H41A H 0.2389 0.5627 0.9933 0.056 Uiso 1 1 calc GR . . . .
H41B H 0.4066 0.5986 1.0127 0.056 Uiso 1 1 calc GR . . . .
H41C H 0.3196 0.5747 1.0733 0.056 Uiso 1 1 calc GR . . . .
C42 C 0.7512(4) 0.6161(4) 0.6801(2) 0.0222(8) Uani 1 1 d . . . . .
C43 C 0.8437(4) 0.6345(4) 0.6341(2) 0.0257(9) Uani 1 1 d . . . . .
H43 H 0.9360 0.6302 0.6490 0.031 Uiso 1 1 calc R . . . .
C44 C 0.8027(4) 0.6590(4) 0.5673(2) 0.0260(9) Uani 1 1 d . . . . .
H44 H 0.8661 0.6702 0.5364 0.031 Uiso 1 1 calc R . . . .
C45 C 0.6684(4) 0.6672(4) 0.5456(2) 0.0237(8) Uani 1 1 d . . . . .
C46 C 0.5758(4) 0.6512(4) 0.5907(2) 0.0252(9) Uani 1 1 d . . . . .
H46 H 0.4845 0.6579 0.5763 0.030 Uiso 1 1 calc R . . . .
C47 C 0.6180(4) 0.6251(4) 0.6571(2) 0.0253(9) Uani 1 1 d . . . . .
H47 H 0.5540 0.6131 0.6878 0.030 Uiso 1 1 calc R . . . .
C48 C 0.5029(5) 0.7037(5) 0.4548(2) 0.0305(9) Uani 1 1 d . . . . .
H48A H 0.4889 0.7090 0.4044 0.046 Uiso 1 1 calc GR . . . .
H48B H 0.4975 0.7887 0.4840 0.046 Uiso 1 1 calc GR . . . .
H48C H 0.4293 0.6223 0.4599 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.4763(3) 0.0959(4) 0.73772(18) 0.0232(7) Uani 1 1 d . . . . .
N2 N 0.8640(3) 0.4848(3) 0.75467(17) 0.0217(7) Uani 1 1 d . . . . .
O1 O 0.6380(3) 0.3113(3) 0.73413(16) 0.0266(6) Uani 1 1 d . . . . .
O2 O 0.2999(3) 0.3992(3) 1.00489(17) 0.0359(7) Uani 1 1 d . . . . .
O3 O 0.6379(3) 0.6909(3) 0.47824(16) 0.0290(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C35 1.506(6) . ?
C1 N1 1.470(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.550(5) . ?
C2 N1 1.436(5) . ?
C2 O1 1.441(5) . ?
C3 C4 1.577(5) . ?
C3 C6 1.532(5) . ?
C3 C20 1.559(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.549(5) . ?
C5 H5 1.0000 . ?
C5 C12 1.515(6) . ?
C5 N1 1.476(5) . ?
C6 C7 1.402(6) . ?
C6 C11 1.399(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(6) . ?
C12 C17 1.391(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.359(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(7) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C42 1.506(5) . ?
C18 N2 1.472(5) . ?
C19 H19 1.0000 . ?
C19 C20 1.565(5) . ?
C19 N2 1.444(5) . ?
C19 O1 1.433(5) . ?
C20 C21 1.575(5) . ?
C20 C23 1.537(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.536(5) . ?
C22 H22 1.0000 . ?
C22 C29 1.509(6) . ?
C22 N2 1.472(5) . ?
C23 C24 1.395(6) . ?
C23 C28 1.397(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.399(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(6) . ?
C29 C34 1.408(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.397(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.379(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.385(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.397(6) . ?
C35 C40 1.375(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.371(6) . ?
C37 H37 0.9500 . ?
C37 C38 1.395(6) . ?
C38 C39 1.378(6) . ?
C38 O2 1.372(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.396(6) . ?
C40 H40 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C41 O2 1.435(6) . ?
C42 C43 1.399(6) . ?
C42 C47 1.389(6) . ?
C43 H43 0.9500 . ?
C43 C44 1.384(6) . ?
C44 H44 0.9500 . ?
C44 C45 1.391(6) . ?
C45 C46 1.387(6) . ?
C45 O3 1.374(5) . ?
C46 H46 0.9500 . ?
C46 C47 1.388(6) . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C48 O3 1.423(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 107.7 . . ?
C35 C1 H1A 108.8 . . ?
C35 C1 H1B 108.8 . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
N1 C1 C35 113.6(3) . . ?
C3 C2 H2 111.3 . . ?
N1 C2 H2 111.3 . . ?
N1 C2 C3 106.4(3) . . ?
N1 C2 O1 110.6(3) . . ?
O1 C2 H2 111.3 . . ?
O1 C2 C3 105.6(3) . . ?
C2 C3 C4 100.2(3) . . ?
C2 C3 C20 103.1(3) . . ?
C6 C3 C2 112.9(3) . . ?
C6 C3 C4 110.4(3) . . ?
C6 C3 C20 116.0(3) . . ?
C20 C3 C4 112.9(3) . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 C3 107.1(3) . . ?
C5 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C4 C5 H5 109.1 . . ?
C12 C5 C4 113.6(3) . . ?
C12 C5 H5 109.1 . . ?
N1 C5 C4 103.3(3) . . ?
N1 C5 H5 109.1 . . ?
N1 C5 C12 112.4(3) . . ?
C7 C6 C3 120.1(3) . . ?
C11 C6 C3 122.7(4) . . ?
C11 C6 C7 117.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.9(4) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C5 121.1(4) . . ?
C13 C12 C17 119.3(4) . . ?
C17 C12 C5 119.6(4) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(4) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.0(4) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
H18A C18 H18B 107.6 . . ?
C42 C18 H18A 108.7 . . ?
C42 C18 H18B 108.7 . . ?
N2 C18 H18A 108.7 . . ?
N2 C18 H18B 108.7 . . ?
N2 C18 C42 114.1(3) . . ?
C20 C19 H19 110.4 . . ?
N2 C19 H19 110.4 . . ?
N2 C19 C20 106.1(3) . . ?
O1 C19 H19 110.4 . . ?
O1 C19 C20 107.2(3) . . ?
O1 C19 N2 112.1(3) . . ?
C3 C20 C19 102.7(3) . . ?
C3 C20 C21 113.4(3) . . ?
C19 C20 C21 101.4(3) . . ?
C23 C20 C3 116.4(3) . . ?
C23 C20 C19 110.9(3) . . ?
C23 C20 C21 110.8(3) . . ?
C20 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
C22 C21 C20 106.3(3) . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C21 C22 H22 109.1 . . ?
C29 C22 C21 114.8(3) . . ?
C29 C22 H22 109.1 . . ?
N2 C22 C21 102.5(3) . . ?
N2 C22 H22 109.1 . . ?
N2 C22 C29 112.0(3) . . ?
C24 C23 C20 118.7(3) . . ?
C24 C23 C28 117.4(4) . . ?
C28 C23 C20 123.8(4) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.7(4) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.9(4) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 121.3(4) . . ?
C23 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C22 121.6(4) . . ?
C30 C29 C34 118.2(4) . . ?
C34 C29 C22 120.1(4) . . ?
C29 C30 H30 119.2 . . ?
C29 C30 C31 121.6(4) . . ?
C31 C30 H30 119.2 . . ?
C30 C31 H31 120.3 . . ?
C30 C31 C32 119.4(4) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.9(4) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.3(4) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 H34 119.7 . . ?
C33 C34 C29 120.6(4) . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C1 121.0(4) . . ?
C40 C35 C1 120.7(4) . . ?
C40 C35 C36 118.3(4) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.6(4) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.5(4) . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 119.9(4) . . ?
O2 C38 C37 115.6(4) . . ?
O2 C38 C39 124.6(4) . . ?
C38 C39 H39 120.6 . . ?
C38 C39 C40 118.9(4) . . ?
C40 C39 H39 120.6 . . ?
C35 C40 C39 121.9(4) . . ?
C35 C40 H40 119.0 . . ?
C39 C40 H40 119.0 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O2 C41 H41A 109.5 . . ?
O2 C41 H41B 109.5 . . ?
O2 C41 H41C 109.5 . . ?
C43 C42 C18 120.9(4) . . ?
C47 C42 C18 121.0(4) . . ?
C47 C42 C43 118.0(4) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 C42 120.9(4) . . ?
C44 C43 H43 119.6 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 119.9(4) . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 120.1(4) . . ?
O3 C45 C44 115.3(4) . . ?
O3 C45 C46 124.5(4) . . ?
C45 C46 H46 120.4 . . ?
C45 C46 C47 119.2(4) . . ?
C47 C46 H46 120.4 . . ?
C42 C47 H47 119.1 . . ?
C46 C47 C42 121.8(4) . . ?
C46 C47 H47 119.1 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O3 C48 H48A 109.5 . . ?
O3 C48 H48B 109.5 . . ?
O3 C48 H48C 109.5 . . ?
C1 N1 C5 110.4(3) . . ?
C2 N1 C1 115.6(3) . . ?
C2 N1 C5 105.3(3) . . ?
C19 N2 C18 114.9(3) . . ?
C19 N2 C22 105.4(3) . . ?
C22 N2 C18 111.2(3) . . ?
C19 O1 C2 111.8(3) . . ?
C38 O2 C41 116.0(4) . . ?
C45 O3 C48 117.0(3) . . ?

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 C35 C36 C37 -178.8(4) . . . . ?
C1 C35 C40 C39 178.3(4) . . . . ?
C2 C3 C4 C5 -7.5(4) . . . . ?
C2 C3 C6 C7 36.0(5) . . . . ?
C2 C3 C6 C11 -145.8(4) . . . . ?
C2 C3 C20 C19 -28.9(4) . . . . ?
C2 C3 C20 C21 79.5(4) . . . . ?
C2 C3 C20 C23 -150.2(3) . . . . ?
C3 C2 N1 C1 -166.2(3) . . . . ?
C3 C2 N1 C5 -44.1(4) . . . . ?
C3 C2 O1 C19 -18.8(4) . . . . ?
C3 C4 C5 C12 -139.1(3) . . . . ?
C3 C4 C5 N1 -17.0(4) . . . . ?
C3 C6 C7 C8 175.8(4) . . . . ?
C3 C6 C11 C10 -176.9(4) . . . . ?
C3 C20 C21 C22 -105.1(4) . . . . ?
C3 C20 C23 C24 163.1(3) . . . . ?
C3 C20 C23 C28 -17.3(5) . . . . ?
C4 C3 C6 C7 -75.2(4) . . . . ?
C4 C3 C6 C11 103.0(4) . . . . ?
C4 C3 C20 C19 78.3(4) . . . . ?
C4 C3 C20 C21 -173.3(3) . . . . ?
C4 C3 C20 C23 -43.0(4) . . . . ?
C4 C5 C12 C13 68.7(5) . . . . ?
C4 C5 C12 C17 -109.4(4) . . . . ?
C4 C5 N1 C1 162.7(3) . . . . ?
C4 C5 N1 C2 37.3(4) . . . . ?
C5 C12 C13 C14 -176.6(4) . . . . ?
C5 C12 C17 C16 176.6(4) . . . . ?
C6 C3 C4 C5 111.7(4) . . . . ?
C6 C3 C20 C19 -152.9(3) . . . . ?
C6 C3 C20 C21 -44.4(4) . . . . ?
C6 C3 C20 C23 85.9(4) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
C7 C6 C11 C10 1.4(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 -1.6(6) . . . . ?
C9 C10 C11 C6 0.7(6) . . . . ?
C11 C6 C7 C8 -2.5(6) . . . . ?
C12 C5 N1 C1 -74.5(4) . . . . ?
C12 C5 N1 C2 160.1(3) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C13 C12 C17 C16 -1.6(6) . . . . ?
C13 C14 C15 C16 -1.4(7) . . . . ?
C14 C15 C16 C17 1.3(7) . . . . ?
C15 C16 C17 C12 0.2(7) . . . . ?
C17 C12 C13 C14 1.5(6) . . . . ?
C18 C42 C43 C44 -178.1(4) . . . . ?
C18 C42 C47 C46 177.3(4) . . . . ?
C19 C20 C21 C22 4.2(4) . . . . ?
C19 C20 C23 C24 46.2(5) . . . . ?
C19 C20 C23 C28 -134.1(4) . . . . ?
C20 C3 C4 C5 -116.5(3) . . . . ?
C20 C3 C6 C7 154.7(3) . . . . ?
C20 C3 C6 C11 -27.1(5) . . . . ?
C20 C19 N2 C18 -163.8(3) . . . . ?
C20 C19 N2 C22 -41.0(4) . . . . ?
C20 C19 O1 C2 -0.3(4) . . . . ?
C20 C21 C22 C29 -149.4(3) . . . . ?
C20 C21 C22 N2 -27.8(4) . . . . ?
C20 C23 C24 C25 -179.5(4) . . . . ?
C20 C23 C28 C27 178.1(4) . . . . ?
C21 C20 C23 C24 -65.5(4) . . . . ?
C21 C20 C23 C28 114.2(4) . . . . ?
C21 C22 C29 C30 68.3(5) . . . . ?
C21 C22 C29 C34 -112.5(4) . . . . ?
C21 C22 N2 C18 167.8(3) . . . . ?
C21 C22 N2 C19 42.6(4) . . . . ?
C22 C29 C30 C31 179.7(4) . . . . ?
C22 C29 C34 C33 -179.5(4) . . . . ?
C23 C20 C21 C22 121.9(3) . . . . ?
C23 C24 C25 C26 1.2(6) . . . . ?
C24 C23 C28 C27 -2.2(6) . . . . ?
C24 C25 C26 C27 -1.9(6) . . . . ?
C25 C26 C27 C28 0.5(6) . . . . ?
C26 C27 C28 C23 1.6(6) . . . . ?
C28 C23 C24 C25 0.8(6) . . . . ?
C29 C22 N2 C18 -68.7(4) . . . . ?
C29 C22 N2 C19 166.2(3) . . . . ?
C29 C30 C31 C32 0.2(7) . . . . ?
C30 C29 C34 C33 -0.4(6) . . . . ?
C30 C31 C32 C33 -1.2(7) . . . . ?
C31 C32 C33 C34 1.4(7) . . . . ?
C32 C33 C34 C29 -0.7(7) . . . . ?
C34 C29 C30 C31 0.6(6) . . . . ?
C35 C1 N1 C2 -61.3(5) . . . . ?
C35 C1 N1 C5 179.3(3) . . . . ?
C35 C36 C37 C38 0.0(7) . . . . ?
C36 C35 C40 C39 -0.2(6) . . . . ?
C36 C37 C38 C39 0.7(7) . . . . ?
C36 C37 C38 O2 -177.6(4) . . . . ?
C37 C38 C39 C40 -1.2(6) . . . . ?
C37 C38 O2 C41 -177.8(4) . . . . ?
C38 C39 C40 C35 0.9(6) . . . . ?
C39 C38 O2 C41 4.0(6) . . . . ?
C40 C35 C36 C37 -0.3(6) . . . . ?
C42 C18 N2 C19 -63.2(5) . . . . ?
C42 C18 N2 C22 177.1(3) . . . . ?
C42 C43 C44 C45 0.8(6) . . . . ?
C43 C42 C47 C46 0.2(6) . . . . ?
C43 C44 C45 C46 0.1(6) . . . . ?
C43 C44 C45 O3 -179.6(4) . . . . ?
C44 C45 C46 C47 -0.9(6) . . . . ?
C44 C45 O3 C48 -178.3(4) . . . . ?
C45 C46 C47 C42 0.7(6) . . . . ?
C46 C45 O3 C48 1.9(6) . . . . ?
C47 C42 C43 C44 -0.9(6) . . . . ?
N1 C1 C35 C36 -66.7(5) . . . . ?
N1 C1 C35 C40 114.9(4) . . . . ?
N1 C2 C3 C4 30.8(4) . . . . ?
N1 C2 C3 C6 -86.6(4) . . . . ?
N1 C2 C3 C20 147.4(3) . . . . ?
N1 C2 O1 C19 -133.6(3) . . . . ?
N1 C5 C12 C13 -48.1(5) . . . . ?
N1 C5 C12 C17 133.8(4) . . . . ?
N2 C18 C42 C43 -49.9(5) . . . . ?
N2 C18 C42 C47 133.1(4) . . . . ?
N2 C19 C20 C3 138.9(3) . . . . ?
N2 C19 C20 C21 21.6(4) . . . . ?
N2 C19 C20 C23 -96.1(4) . . . . ?
N2 C19 O1 C2 -116.4(3) . . . . ?
N2 C22 C29 C30 -48.0(5) . . . . ?
N2 C22 C29 C34 131.1(4) . . . . ?
O1 C2 C3 C4 -86.9(3) . . . . ?
O1 C2 C3 C6 155.7(3) . . . . ?
O1 C2 C3 C20 29.8(4) . . . . ?
O1 C2 N1 C1 -51.9(4) . . . . ?
O1 C2 N1 C5 70.2(4) . . . . ?
O1 C19 C20 C3 18.9(4) . . . . ?
O1 C19 C20 C21 -98.5(3) . . . . ?
O1 C19 C20 C23 143.9(3) . . . . ?
O1 C19 N2 C18 -47.0(4) . . . . ?
O1 C19 N2 C22 75.8(4) . . . . ?
O2 C38 C39 C40 177.0(4) . . . . ?
O3 C45 C46 C47 178.9(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6 -1 2 0.0250 -6.0000 -1.0000 2.0000 -0.7097 -0.4997 -0.5188
5 3 -4 0.0453 5.0000 3.0000 -4.0000 0.5508 0.3793 0.7851
-5 5 -5 0.0732 -5.0000 5.0000 -5.0000 -0.7247 -0.4978 0.5265
-1 -6 7 0.0838 -0.5000 -5.5000 7.0000 0.1050 0.0030 -0.9491
2 5 -6 0.0689 1.5000 5.5000 -6.0000 0.0888 0.0277 0.9807
3 -2 -11 0.0592 2.5000 -2.5000 -11.0000 -0.4844 0.8975 0.0614
-3 0 12 0.0332 -2.5000 0.5000 12.0000 0.4495 -0.8078 -0.3592
1 6 -3 0.0606 0.5000 6.5000 -3.0000 0.1947 -0.2640 0.9898
2 -5 -7 0.0712 2.0000 -5.0000 -7.0000 -0.4211 0.8381 -0.4049
-4 -2 -4 0.0352 -3.5000 -2.5000 -4.0000 -0.8316 0.0887 -0.4408
4 0 8 0.0492 3.5000 0.5000 8.0000 0.9849 -0.1432 0.0708
3 5 -2 0.0484 3.0000 5.0000 -2.0000 0.5118 -0.0120 0.8995
6 -1 1 0.0453 6.0000 -1.0000 1.0000 0.8002 0.4933 0.1729
6 -1 -8 0.0279 5.5000 -0.5000 -8.0000 0.1945 0.8519 0.4299

_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_11c
_database_code_depnum_ccdc_archive 'CCDC 1028130'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_audit_creation_date             2014-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H34 N2 O'
_chemical_formula_sum            'C34 H34 N2 O'
_chemical_formula_weight         486.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C34H34N2O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.9986(2)
_cell_length_b                   10.60180(16)
_cell_length_c                   20.9045(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.8514(19)
_cell_angle_gamma                90
_cell_volume                     2570.37(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7780
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2370
_cell_measurement_theta_min      3.7770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3228
_exptl_crystal_size_mid          0.2557
_exptl_crystal_size_min          0.1293
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.419
_diffrn_reflns_theta_min         3.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   32.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega   26.00  105.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega   72.00  119.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00   97.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00  172.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  8 omega   92.00  178.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  134.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00  109.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   55.00  108.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   89.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   98.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   97.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00   91.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 17 omega   52.00   84.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega -129.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857    0.0000  -90.0000 138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0258841000
_diffrn_orient_matrix_UB_12      -0.0105824000
_diffrn_orient_matrix_UB_13      0.0759281000
_diffrn_orient_matrix_UB_21      -0.0099896000
_diffrn_orient_matrix_UB_22      -0.1446678000
_diffrn_orient_matrix_UB_23      -0.0058804000
_diffrn_orient_matrix_UB_31      0.1297850000
_diffrn_orient_matrix_UB_32      -0.0089099000
_diffrn_orient_matrix_UB_33      0.0043158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4414
_reflns_number_total             5186
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.030
_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)+(0.0579P)²+0.8834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C19(H19), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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 0.40165(11) 1.02385(13) 0.72690(7) 0.0216(3) Uani 1 1 d . . . . .
H1A H 0.3396 1.0640 0.7403 0.032 Uiso 1 1 calc GR . . . .
H1B H 0.4376 1.0837 0.7041 0.032 Uiso 1 1 calc GR . . . .
H1C H 0.4574 0.9931 0.7652 0.032 Uiso 1 1 calc GR . . . .
C2 C 0.44339(10) 0.84330(12) 0.66468(6) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.4891 0.7962 0.7028 0.020 Uiso 1 1 calc R . . . .
C3 C 0.37714(10) 0.75233(12) 0.60943(6) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.26522(10) 0.83286(12) 0.57924(6) 0.0171(3) Uani 1 1 d . . . . .
H4A H 0.2588 0.8512 0.5330 0.021 Uiso 1 1 calc R . . . .
H4B H 0.1969 0.7871 0.5826 0.021 Uiso 1 1 calc R . . . .
C5 C 0.27749(10) 0.95602(12) 0.61960(6) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.3151 1.0198 0.5984 0.021 Uiso 1 1 calc R . . . .
C6 C 0.34588(10) 0.62862(12) 0.63823(6) 0.0165(2) Uani 1 1 d . . . . .
C7 C 0.30644(10) 0.63248(13) 0.69582(6) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.3012 0.7097 0.7160 0.023 Uiso 1 1 calc R . . . .
C8 C 0.27512(11) 0.52288(13) 0.72331(6) 0.0223(3) Uani 1 1 d . . . . .
H8 H 0.2506 0.5275 0.7620 0.027 Uiso 1 1 calc R . . . .
C9 C 0.28010(11) 0.40677(13) 0.69372(7) 0.0229(3) Uani 1 1 d . . . . .
H9 H 0.2576 0.3338 0.7117 0.028 Uiso 1 1 calc R . . . .
C10 C 0.31935(11) 0.40127(13) 0.63672(7) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.3237 0.3239 0.6166 0.026 Uiso 1 1 calc R . . . .
C11 C 0.35227(10) 0.51065(12) 0.60957(6) 0.0187(3) Uani 1 1 d . . . . .
H11 H 0.3790 0.5051 0.5717 0.022 Uiso 1 1 calc R . . . .
C12 C 0.16578(10) 1.00911(12) 0.62900(7) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.10499(11) 0.94645(13) 0.66799(7) 0.0226(3) Uani 1 1 d . . . . .
H13 H 0.1322 0.8698 0.6875 0.027 Uiso 1 1 calc R . . . .
C14 C 0.00436(12) 0.99718(14) 0.67803(7) 0.0264(3) Uani 1 1 d . . . . .
H14 H -0.0356 0.9544 0.7041 0.032 Uiso 1 1 calc R . . . .
C15 C -0.03694(12) 1.11158(14) 0.64930(9) 0.0314(3) Uani 1 1 d . . . . .
H15 H -0.1036 1.1464 0.6567 0.038 Uiso 1 1 calc R . . . .
C16 C 0.02130(13) 1.17336(15) 0.60970(10) 0.0373(4) Uani 1 1 d . . . . .
H16 H -0.0068 1.2495 0.5898 0.045 Uiso 1 1 calc R . . . .
C17 C 0.12229(12) 1.12198(14) 0.59932(8) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.1608 1.1638 0.5722 0.036 Uiso 1 1 calc R . . . .
C18 C 0.71205(10) 0.95978(12) 0.58253(7) 0.0197(3) Uani 1 1 d . . . . .
H18A H 0.7852 0.9388 0.5746 0.030 Uiso 1 1 calc GR . . . .
H18B H 0.7229 0.9830 0.6281 0.030 Uiso 1 1 calc GR . . . .
H18C H 0.6785 1.0292 0.5547 0.030 Uiso 1 1 calc GR . . . .
C19 C 0.51882(10) 0.87360(12) 0.57107(6) 0.0162(2) Uani 1 1 d . . . . .
H19 H 0.4791 0.9316 0.5361 0.019 Uiso 1 1 calc R . . . .
C20 C 0.45990(10) 0.74212(11) 0.56290(6) 0.0156(2) Uani 1 1 d . . . . .
C21 C 0.56744(10) 0.65405(12) 0.59079(6) 0.0171(3) Uani 1 1 d . . . . .
H21A H 0.5575 0.6062 0.6285 0.020 Uiso 1 1 calc R . . . .
H21B H 0.5773 0.5955 0.5570 0.020 Uiso 1 1 calc R . . . .
C22 C 0.67269(10) 0.74257(12) 0.61161(6) 0.0173(3) Uani 1 1 d . . . . .
H22 H 0.6808 0.7695 0.6574 0.021 Uiso 1 1 calc R . . . .
C23 C 0.40317(10) 0.71352(11) 0.49006(6) 0.0163(2) Uani 1 1 d . . . . .
C24 C 0.46112(11) 0.74347(12) 0.44173(6) 0.0194(3) Uani 1 1 d . . . . .
H24 H 0.5341 0.7795 0.4546 0.023 Uiso 1 1 calc R . . . .
C25 C 0.41180(11) 0.72053(13) 0.37507(7) 0.0220(3) Uani 1 1 d . . . . .
H25 H 0.4514 0.7430 0.3439 0.026 Uiso 1 1 calc R . . . .
C26 C 0.30409(11) 0.66445(13) 0.35452(6) 0.0212(3) Uani 1 1 d . . . . .
H26 H 0.2717 0.6480 0.3099 0.025 Uiso 1 1 calc R . . . .
C27 C 0.24548(11) 0.63322(12) 0.40157(6) 0.0191(3) Uani 1 1 d . . . . .
H27 H 0.1731 0.5958 0.3884 0.023 Uiso 1 1 calc R . . . .
C28 C 0.29406(10) 0.65744(11) 0.46817(6) 0.0177(3) Uani 1 1 d . . . . .
H28 H 0.2534 0.6360 0.4990 0.021 Uiso 1 1 calc R . . . .
C29 C 0.78649(10) 0.68935(12) 0.60576(6) 0.0182(3) Uani 1 1 d . . . . .
C30 C 0.80610(11) 0.66600(13) 0.54410(7) 0.0216(3) Uani 1 1 d . . . . .
H30 H 0.7478 0.6815 0.5060 0.026 Uiso 1 1 calc R . . . .
C31 C 0.91168(12) 0.61975(13) 0.53869(7) 0.0252(3) Uani 1 1 d . . . . .
H31 H 0.9237 0.6045 0.4972 0.030 Uiso 1 1 calc R . . . .
C32 C 0.99940(11) 0.59630(13) 0.59539(8) 0.0256(3) Uani 1 1 d . . . . .
H32 H 1.0703 0.5657 0.5920 0.031 Uiso 1 1 calc R . . . .
C33 C 0.98036(11) 0.61894(13) 0.65696(7) 0.0245(3) Uani 1 1 d . . . . .
H33 H 1.0386 0.6030 0.6950 0.029 Uiso 1 1 calc R . . . .
C34 C 0.87446(11) 0.66549(12) 0.66218(7) 0.0211(3) Uani 1 1 d . . . . .
H34 H 0.8625 0.6807 0.7037 0.025 Uiso 1 1 calc R . . . .
N1 N 0.35650(9) 0.91847(10) 0.68282(5) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.63548(8) 0.85104(10) 0.56759(5) 0.0167(2) Uani 1 1 d . . . . .
O1 O 0.51593(7) 0.91962(8) 0.63529(4) 0.0188(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N1 1.4612(16) . ?
C2 H2 0.9800 . ?
C2 C3 1.5574(17) . ?
C2 N1 1.4382(15) . ?
C2 O1 1.4367(14) . ?
C3 C4 1.5798(16) . ?
C3 C6 1.5294(17) . ?
C3 C20 1.5618(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5411(17) . ?
C5 H5 0.9800 . ?
C5 C12 1.5122(17) . ?
C5 N1 1.4702(16) . ?
C6 C7 1.4026(17) . ?
C6 C11 1.3973(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3900(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.3902(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.3921(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.3939(19) . ?
C12 C17 1.387(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.3860(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.395(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 N2 1.4572(16) . ?
C19 H19 0.9800 . ?
C19 C20 1.5525(16) . ?
C19 N2 1.4402(15) . ?
C19 O1 1.4370(15) . ?
C20 C21 1.5783(16) . ?
C20 C23 1.5305(17) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.5437(17) . ?
C22 H22 0.9800 . ?
C22 C29 1.5111(16) . ?
C22 N2 1.4691(16) . ?
C23 C24 1.4018(17) . ?
C23 C28 1.4034(17) . ?
C24 H24 0.9300 . ?
C24 C25 1.3887(19) . ?
C25 H25 0.9300 . ?
C25 C26 1.3869(19) . ?
C26 H26 0.9300 . ?
C26 C27 1.3879(19) . ?
C27 H27 0.9300 . ?
C27 C28 1.3884(18) . ?
C28 H28 0.9300 . ?
C29 C30 1.3906(18) . ?
C29 C34 1.3897(18) . ?
C30 H30 0.9300 . ?
C30 C31 1.3897(18) . ?
C31 H31 0.9300 . ?
C31 C32 1.391(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.385(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.3933(18) . ?
C34 H34 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
C3 C2 H2 111.1 . . ?
N1 C2 H2 111.1 . . ?
N1 C2 C3 105.78(9) . . ?
O1 C2 H2 111.1 . . ?
O1 C2 C3 106.36(9) . . ?
O1 C2 N1 111.11(10) . . ?
C2 C3 C4 100.46(9) . . ?
C2 C3 C20 102.69(9) . . ?
C6 C3 C2 111.66(10) . . ?
C6 C3 C4 110.59(9) . . ?
C6 C3 C20 116.42(10) . . ?
C20 C3 C4 113.56(10) . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C3 106.68(10) . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C4 C5 H5 109.1 . . ?
C12 C5 C4 115.03(10) . . ?
C12 C5 H5 109.1 . . ?
N1 C5 C4 102.23(10) . . ?
N1 C5 H5 109.1 . . ?
N1 C5 C12 111.89(10) . . ?
C7 C6 C3 118.92(11) . . ?
C11 C6 C3 123.56(11) . . ?
C11 C6 C7 117.51(11) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.13(12) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.72(12) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.86(12) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.56(13) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.21(12) . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C5 120.84(12) . . ?
C17 C12 C5 120.50(12) . . ?
C17 C12 C13 118.65(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.69(13) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.14(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.71(13) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.14(14) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.64(14) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
C20 C19 H19 111.1 . . ?
N2 C19 H19 111.1 . . ?
N2 C19 C20 105.45(10) . . ?
O1 C19 H19 111.1 . . ?
O1 C19 C20 106.76(9) . . ?
O1 C19 N2 111.11(10) . . ?
C3 C20 C21 113.65(10) . . ?
C19 C20 C3 102.33(9) . . ?
C19 C20 C21 100.63(9) . . ?
C23 C20 C3 116.21(10) . . ?
C23 C20 C19 111.18(10) . . ?
C23 C20 C21 111.31(10) . . ?
C20 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
C22 C21 C20 106.07(10) . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C21 C22 H22 108.8 . . ?
C29 C22 C21 116.17(10) . . ?
C29 C22 H22 108.8 . . ?
N2 C22 C21 101.77(9) . . ?
N2 C22 H22 108.8 . . ?
N2 C22 C29 112.17(10) . . ?
C24 C23 C20 119.73(11) . . ?
C24 C23 C28 117.03(11) . . ?
C28 C23 C20 123.24(11) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.40(12) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.63(12) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 118.94(12) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.52(12) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 119.3 . . ?
C27 C28 C23 121.47(12) . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C22 120.85(11) . . ?
C34 C29 C22 120.31(11) . . ?
C34 C29 C30 118.83(12) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.84(13) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.01(13) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.47(12) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.35(13) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 120.50(12) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C1 N1 C5 114.16(10) . . ?
C2 N1 C1 114.41(10) . . ?
C2 N1 C5 104.90(9) . . ?
C18 N2 C22 114.29(10) . . ?
C19 N2 C18 115.17(10) . . ?
C19 N2 C22 103.98(9) . . ?
C2 O1 C19 111.75(9) . . ?

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
C2 C3 C4 C5 -0.94(12) . . . . ?
C2 C3 C6 C7 41.11(14) . . . . ?
C2 C3 C6 C11 -140.14(12) . . . . ?
C2 C3 C20 C19 -31.11(11) . . . . ?
C2 C3 C20 C21 76.45(12) . . . . ?
C2 C3 C20 C23 -152.42(10) . . . . ?
C3 C2 N1 C1 -170.84(10) . . . . ?
C3 C2 N1 C5 -44.98(12) . . . . ?
C3 C2 O1 C19 -10.07(12) . . . . ?
C3 C4 C5 C12 -145.90(11) . . . . ?
C3 C4 C5 N1 -24.42(12) . . . . ?
C3 C6 C7 C8 178.92(11) . . . . ?
C3 C6 C11 C10 -177.98(11) . . . . ?
C3 C20 C21 C22 -108.28(11) . . . . ?
C3 C20 C23 C24 158.75(11) . . . . ?
C3 C20 C23 C28 -21.42(17) . . . . ?
C4 C3 C6 C7 -69.86(14) . . . . ?
C4 C3 C6 C11 108.88(13) . . . . ?
C4 C3 C20 C19 76.43(11) . . . . ?
C4 C3 C20 C21 -176.01(10) . . . . ?
C4 C3 C20 C23 -44.89(14) . . . . ?
C4 C5 C12 C13 68.01(16) . . . . ?
C4 C5 C12 C17 -112.54(14) . . . . ?
C4 C5 N1 C1 168.70(10) . . . . ?
C4 C5 N1 C2 42.68(12) . . . . ?
C5 C12 C13 C14 178.15(12) . . . . ?
C5 C12 C17 C16 -177.83(14) . . . . ?
C6 C3 C4 C5 117.12(11) . . . . ?
C6 C3 C20 C19 -153.41(10) . . . . ?
C6 C3 C20 C21 -45.85(14) . . . . ?
C6 C3 C20 C23 85.28(13) . . . . ?
C6 C7 C8 C9 -1.18(19) . . . . ?
C7 C6 C11 C10 0.78(18) . . . . ?
C7 C8 C9 C10 1.36(19) . . . . ?
C8 C9 C10 C11 -0.48(19) . . . . ?
C9 C10 C11 C6 -0.60(19) . . . . ?
C11 C6 C7 C8 0.10(18) . . . . ?
C12 C5 N1 C1 -67.69(13) . . . . ?
C12 C5 N1 C2 166.29(10) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C12 C17 C16 1.6(2) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C17 C12 C13 C14 -1.3(2) . . . . ?
C19 C20 C21 C22 0.35(12) . . . . ?
C19 C20 C23 C24 42.27(15) . . . . ?
C19 C20 C23 C28 -137.90(12) . . . . ?
C20 C3 C4 C5 -109.86(11) . . . . ?
C20 C3 C6 C7 158.58(11) . . . . ?
C20 C3 C6 C11 -22.68(16) . . . . ?
C20 C19 N2 C18 -172.51(10) . . . . ?
C20 C19 N2 C22 -46.69(11) . . . . ?
C20 C19 O1 C2 -10.59(12) . . . . ?
C20 C21 C22 C29 -148.97(10) . . . . ?
C20 C21 C22 N2 -26.84(12) . . . . ?
C20 C23 C24 C25 -179.12(12) . . . . ?
C20 C23 C28 C27 179.89(11) . . . . ?
C21 C20 C23 C24 -69.03(14) . . . . ?
C21 C20 C23 C28 110.79(13) . . . . ?
C21 C22 C29 C30 69.08(16) . . . . ?
C21 C22 C29 C34 -112.34(13) . . . . ?
C21 C22 N2 C18 171.58(10) . . . . ?
C21 C22 N2 C19 45.19(11) . . . . ?
C22 C29 C30 C31 178.53(12) . . . . ?
C22 C29 C34 C33 -178.64(12) . . . . ?
C23 C20 C21 C22 118.23(11) . . . . ?
C23 C24 C25 C26 -1.4(2) . . . . ?
C24 C23 C28 C27 -0.27(18) . . . . ?
C24 C25 C26 C27 0.9(2) . . . . ?
C25 C26 C27 C28 -0.18(19) . . . . ?
C26 C27 C28 C23 -0.15(19) . . . . ?
C28 C23 C24 C25 1.04(18) . . . . ?
C29 C22 N2 C18 -63.58(13) . . . . ?
C29 C22 N2 C19 170.04(10) . . . . ?
C29 C30 C31 C32 0.0(2) . . . . ?
C30 C29 C34 C33 0.0(2) . . . . ?
C30 C31 C32 C33 0.2(2) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 C29 0.2(2) . . . . ?
C34 C29 C30 C31 -0.1(2) . . . . ?
N1 C2 C3 C4 27.04(12) . . . . ?
N1 C2 C3 C6 -90.23(11) . . . . ?
N1 C2 C3 C20 144.31(10) . . . . ?
N1 C2 O1 C19 -124.73(10) . . . . ?
N1 C5 C12 C13 -48.06(16) . . . . ?
N1 C5 C12 C17 131.39(13) . . . . ?
N2 C19 C20 C3 144.60(9) . . . . ?
N2 C19 C20 C21 27.30(11) . . . . ?
N2 C19 C20 C23 -90.68(11) . . . . ?
N2 C19 O1 C2 -125.07(10) . . . . ?
N2 C22 C29 C30 -47.39(16) . . . . ?
N2 C22 C29 C34 131.20(12) . . . . ?
O1 C2 C3 C4 -91.20(10) . . . . ?
O1 C2 C3 C6 151.54(10) . . . . ?
O1 C2 C3 C20 26.08(12) . . . . ?
O1 C2 N1 C1 -55.82(14) . . . . ?
O1 C2 N1 C5 70.04(12) . . . . ?
O1 C19 C20 C3 26.35(11) . . . . ?
O1 C19 C20 C21 -90.96(10) . . . . ?
O1 C19 C20 C23 151.06(9) . . . . ?
O1 C19 N2 C18 -57.22(13) . . . . ?
O1 C19 N2 C22 68.61(12) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 5 8 0.1511 0.0058 5.0044 7.9718 0.5525 -0.7709 -0.0094
8 0 -2 0.1206 8.0024 0.0001 -2.0148 0.0542 -0.0681 1.0299
-8 -1 0 0.1126 -8.0038 -1.0013 0.0209 -0.1950 0.2247 -1.0298
1 2 -13 0.0493 0.9916 1.9905 -12.9946 -0.9821 -0.2215 0.0549
2 -2 10 0.0514 2.0077 -1.9921 9.9917 0.8317 0.2094 0.3214
1 -7 2 0.1437 1.0015 -6.9967 2.0220 0.2535 0.9903 0.2010
0 7 -2 0.1447 -0.0010 6.9968 -2.0241 -0.2278 -1.0003 -0.0712
-8 -2 3 0.1250 -8.0018 -1.9989 3.0212 0.0434 0.3513 -1.0077
0 -6 -7 0.1459 -0.0051 -6.0034 -6.9692 -0.4658 0.9095 0.0227
-7 -2 7 0.1276 -6.9986 -1.9959 7.0144 0.3726 0.3174 -0.8603
0 4 -10 0.0738 -0.0067 3.9920 -10.0035 -0.8020 -0.5186 -0.0796
-7 1 0 0.1451 -7.0032 0.9984 0.0112 -0.1910 -0.0745 -0.9178
-8 0 4 0.1385 -8.0010 0.0013 4.0125 0.0975 0.0561 -1.0211
0 -4 10 0.0988 0.0067 -3.9920 10.0035 0.8020 0.5186 0.0796
1 -1 12 0.0473 1.0087 -0.9911 11.9877 0.9468 0.0628 0.1915
-1 -1 13 0.0656 -0.9916 -0.9908 12.9908 0.9712 0.0769 -0.0638

_olex2_submission_special_instructions 'No special instructions were received'


#==========================================================================END
