# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_demb23
_database_code_depnum_ccdc_archive 'CCDC 929587'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (Z)-1-phenyl-3-(phenylamino)-4-(4-methylphenyl)but-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N O'
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.9333(3)
_cell_length_b                   6.7797(2)
_cell_length_c                   12.1298(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.667(1)
_cell_angle_gamma                90.00
_cell_volume                     876.97(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4927
_cell_measurement_theta_min      4.077
_cell_measurement_theta_max      67.691

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8426
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12455
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         68.02
_reflns_number_total             3024
_reflns_number_gt                2828
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

All nonhydrogen atoms were located in a difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.  The N-H hydrogen atom
 was located in a diff map and refined isotropically with Uiso = 1.2xUeqiv
 and restrained to a N-H distance of 0.84(2) ang. 

 The hydroegen atoms located on methyl C17 were modeled with two part disorder
 (50:50). 

 It should be noted that despite the parent molecule is achiral, it organizes 
 in the noncentrosymmetric space group P21.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.1186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33964(9) 0.50784(16) 0.06453(9) 0.0224(2) Uani 1 1 d . . .
N1 N 0.55036(11) 0.70694(19) 0.16628(11) 0.0201(3) Uani 1 1 d D . .
H1 H 0.5048(14) 0.600(2) 0.1514(15) 0.024 Uiso 1 1 d D . .
C1 C 0.28808(13) 0.6697(2) 0.01923(12) 0.0200(3) Uani 1 1 d . . .
C2 C 0.35358(13) 0.8528(2) 0.04374(12) 0.0190(3) Uani 1 1 d . . .
H2 H 0.3073 0.9690 0.0070 0.023 Uiso 1 1 calc R . .
C3 C 0.48091(13) 0.8697(2) 0.11822(12) 0.0186(3) Uani 1 1 d . . .
C4 C 0.54075(13) 1.0722(2) 0.15249(13) 0.0200(3) Uani 1 1 d . . .
H4A H 0.4834 1.1719 0.0953 0.024 Uiso 1 1 calc R . .
H4B H 0.6195 1.0739 0.1440 0.024 Uiso 1 1 calc R . .
C5 C 0.15001(13) 0.6685(2) -0.06464(12) 0.0206(3) Uani 1 1 d . . .
C6 C 0.07262(14) 0.5390(3) -0.04127(14) 0.0260(3) Uani 1 1 d . . .
H6 H 0.1075 0.4532 0.0280 0.031 Uiso 1 1 calc R . .
C7 C -0.05531(14) 0.5346(3) -0.11875(14) 0.0298(4) Uani 1 1 d . . .
H7 H -0.1081 0.4490 -0.1009 0.036 Uiso 1 1 calc R . .
C8 C -0.10625(14) 0.6549(3) -0.22223(15) 0.0293(4) Uani 1 1 d . . .
H8 H -0.1937 0.6505 -0.2758 0.035 Uiso 1 1 calc R . .
C9 C -0.02955(14) 0.7812(3) -0.24727(15) 0.0297(4) Uani 1 1 d . . .
H9 H -0.0642 0.8622 -0.3188 0.036 Uiso 1 1 calc R . .
C10 C 0.09824(14) 0.7901(2) -0.16808(13) 0.0241(3) Uani 1 1 d . . .
H10 H 0.1502 0.8793 -0.1846 0.029 Uiso 1 1 calc R . .
C11 C 0.56911(12) 1.1250(2) 0.28480(12) 0.0176(3) Uani 1 1 d . . .
C12 C 0.68855(13) 1.1031(2) 0.38196(13) 0.0209(3) Uani 1 1 d . . .
H12 H 0.7560 1.0632 0.3657 0.025 Uiso 1 1 calc R . .
C13 C 0.71008(14) 1.1390(2) 0.50230(13) 0.0231(3) Uani 1 1 d . . .
H13 H 0.7924 1.1230 0.5673 0.028 Uiso 1 1 calc R . .
C14 C 0.61432(13) 1.1977(2) 0.53016(13) 0.0230(3) Uani 1 1 d . . .
C15 C 0.49608(14) 1.2283(2) 0.43217(14) 0.0246(3) Uani 1 1 d . . .
H15 H 0.4297 1.2743 0.4483 0.029 Uiso 1 1 calc R . .
C16 C 0.47373(13) 1.1926(2) 0.31125(13) 0.0219(3) Uani 1 1 d . . .
H16 H 0.3924 1.2146 0.2459 0.026 Uiso 1 1 calc R . .
C17 C 0.63783(16) 1.2240(3) 0.66216(14) 0.0310(4) Uani 1 1 d . . .
H17A H 0.5601 1.2655 0.6642 0.046 Uiso 0.50 1 calc PR . .
H17B H 0.7025 1.3249 0.7017 0.046 Uiso 0.50 1 calc PR . .
H17C H 0.6662 1.0988 0.7064 0.046 Uiso 0.50 1 calc PR . .
H17D H 0.7258 1.1940 0.7174 0.046 Uiso 0.50 1 calc PR . .
H17E H 0.5834 1.1346 0.6798 0.046 Uiso 0.50 1 calc PR . .
H17F H 0.6196 1.3607 0.6751 0.046 Uiso 0.50 1 calc PR . .
C18 C 0.68106(13) 0.6952(2) 0.24773(12) 0.0199(3) Uani 1 1 d . . .
C19 C 0.71826(13) 0.6033(2) 0.36111(13) 0.0218(3) Uani 1 1 d . . .
H19 H 0.6575 0.5470 0.3822 0.026 Uiso 1 1 calc R . .
C20 C 0.84422(14) 0.5942(2) 0.44307(13) 0.0244(3) Uani 1 1 d . . .
H20 H 0.8699 0.5309 0.5205 0.029 Uiso 1 1 calc R . .
C21 C 0.93306(13) 0.6764(3) 0.41322(13) 0.0258(3) Uani 1 1 d . . .
H21 H 1.0192 0.6740 0.4712 0.031 Uiso 1 1 calc R . .
C22 C 0.89610(13) 0.7626(2) 0.29837(14) 0.0243(3) Uani 1 1 d . . .
H22 H 0.9573 0.8170 0.2773 0.029 Uiso 1 1 calc R . .
C23 C 0.77004(13) 0.7696(2) 0.21398(13) 0.0212(3) Uani 1 1 d . . .
H23 H 0.7449 0.8245 0.1343 0.025 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.258(2) . ?
N1 C3 1.3457(19) . ?
N1 C18 1.4254(17) . ?
N1 H1 0.876(14) . ?
C1 C2 1.425(2) . ?
C1 C5 1.4983(18) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.517(2) . ?
C4 C11 1.5265(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.393(2) . ?
C5 C10 1.393(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.3909(19) . ?
C11 C16 1.392(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C17 1.507(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 C19 1.389(2) . ?
C18 C23 1.393(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C18 127.99(13) . . ?
C3 N1 H1 112.7(11) . . ?
C18 N1 H1 118.8(11) . . ?
O1 C1 C2 123.64(12) . . ?
O1 C1 C5 117.72(14) . . ?
C2 C1 C5 118.65(14) . . ?
C3 C2 C1 123.24(13) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 C2 119.90(13) . . ?
N1 C3 C4 120.06(12) . . ?
C2 C3 C4 119.92(13) . . ?
C3 C4 C11 110.80(11) . . ?
C3 C4 H4A 109.5 . . ?
C11 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C11 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C10 119.35(13) . . ?
C6 C5 C1 119.53(13) . . ?
C10 C5 C1 121.09(13) . . ?
C7 C6 C5 120.26(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.13(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.88(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.23(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.10(14) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C16 118.22(13) . . ?
C12 C11 C4 121.69(12) . . ?
C16 C11 C4 120.08(12) . . ?
C13 C12 C11 120.60(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.56(13) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 117.67(13) . . ?
C13 C14 C17 120.79(13) . . ?
C15 C14 C17 121.53(14) . . ?
C16 C15 C14 121.05(13) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.77(13) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C14 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C14 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C19 C18 C23 120.43(12) . . ?
C19 C18 N1 118.38(12) . . ?
C23 C18 N1 121.16(12) . . ?
C20 C19 C18 119.57(13) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.53(14) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 119.82(13) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.35(13) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 119.16(13) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 1.2(2) . . . . ?
C5 C1 C2 C3 -179.10(12) . . . . ?
C18 N1 C3 C2 -177.72(13) . . . . ?
C18 N1 C3 C4 -1.7(2) . . . . ?
C1 C2 C3 N1 3.59(19) . . . . ?
C1 C2 C3 C4 -172.41(13) . . . . ?
N1 C3 C4 C11 -72.44(16) . . . . ?
C2 C3 C4 C11 103.55(14) . . . . ?
O1 C1 C5 C6 35.20(19) . . . . ?
C2 C1 C5 C6 -144.56(14) . . . . ?
O1 C1 C5 C10 -142.60(14) . . . . ?
C2 C1 C5 C10 37.64(19) . . . . ?
C10 C5 C6 C7 -1.5(2) . . . . ?
C1 C5 C6 C7 -179.36(14) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C5 1.5(2) . . . . ?
C6 C5 C10 C9 -0.2(2) . . . . ?
C1 C5 C10 C9 177.58(14) . . . . ?
C3 C4 C11 C12 99.16(15) . . . . ?
C3 C4 C11 C16 -79.33(16) . . . . ?
C16 C11 C12 C13 3.0(2) . . . . ?
C4 C11 C12 C13 -175.51(14) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -2.8(2) . . . . ?
C12 C13 C14 C17 176.25(15) . . . . ?
C13 C14 C15 C16 2.8(2) . . . . ?
C17 C14 C15 C16 -176.24(15) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C12 C11 C16 C15 -3.0(2) . . . . ?
C4 C11 C16 C15 175.55(14) . . . . ?
C3 N1 C18 C19 121.81(16) . . . . ?
C3 N1 C18 C23 -59.7(2) . . . . ?
C23 C18 C19 C20 3.1(2) . . . . ?
N1 C18 C19 C20 -178.42(14) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C22 -2.4(2) . . . . ?
C20 C21 C22 C23 1.1(2) . . . . ?
C21 C22 C23 C18 2.2(2) . . . . ?
C19 C18 C23 C22 -4.3(2) . . . . ?
N1 C18 C23 C22 177.27(14) . . . . ?

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
N1 H1 O1 0.876(14) 1.876(14) 2.6235(15) 142.2(16) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        68.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_demb26
_database_code_depnum_ccdc_archive 'CCDC 929589'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cl N O'
_chemical_formula_sum            'C18 H18 Cl N O'
_chemical_formula_weight         299.78

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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8282(2)
_cell_length_b                   10.3586(3)
_cell_length_c                   13.2061(4)
_cell_angle_alpha                77.465(2)
_cell_angle_beta                 86.009(2)
_cell_angle_gamma                76.595(1)
_cell_volume                     756.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8132
_cell_measurement_theta_min      3.426
_cell_measurement_theta_max      68.202

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4289
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15426
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         67.62
_reflns_number_total             2658
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.3165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34444(5) 0.83859(3) 0.41226(3) 0.02691(12) Uani 1 1 d . . .
O1 O -0.63251(17) 1.14064(9) -0.05658(7) 0.0242(2) Uani 1 1 d . . .
N1 N -0.3834(2) 1.14670(11) 0.10460(9) 0.0210(2) Uani 1 1 d D . .
H3 H -0.415(3) 1.1029(16) 0.0613(12) 0.025 Uiso 1 1 d D . .
C1 C -0.8621(3) 1.31657(15) -0.23953(12) 0.0315(3) Uani 1 1 d . . .
H1A H -0.7208 1.3520 -0.2622 0.047 Uiso 1 1 calc R . .
H1B H -0.9924 1.3665 -0.2856 0.047 Uiso 1 1 calc R . .
H1C H -0.8298 1.2201 -0.2419 0.047 Uiso 1 1 calc R . .
C2 C -0.9289(3) 1.33379(16) -0.12977(12) 0.0331(4) Uani 1 1 d . . .
H2A H -1.0732 1.2993 -0.1078 0.040 Uiso 1 1 calc R . .
H2B H -0.9656 1.4316 -0.1284 0.040 Uiso 1 1 calc R . .
C3 C -0.7351(2) 1.25984(14) -0.05322(10) 0.0226(3) Uani 1 1 d . . .
C4 C -0.6789(2) 1.33031(14) 0.01980(10) 0.0229(3) Uani 1 1 d . . .
H4 H -0.7622 1.4216 0.0163 0.027 Uiso 1 1 calc R . .
C5 C -0.5113(2) 1.27456(13) 0.09534(10) 0.0204(3) Uani 1 1 d . . .
C6 C -0.4683(2) 1.35998(13) 0.16839(11) 0.0223(3) Uani 1 1 d . . .
H6A H -0.4941 1.4555 0.1304 0.027 Uiso 1 1 calc R . .
H6B H -0.3007 1.3306 0.1886 0.027 Uiso 1 1 calc R . .
C7 C -0.6215(2) 1.35420(12) 0.26667(10) 0.0195(3) Uani 1 1 d . . .
C8 C -0.8117(2) 1.29163(13) 0.28223(11) 0.0209(3) Uani 1 1 d . . .
H8 H -0.8521 1.2522 0.2293 0.025 Uiso 1 1 calc R . .
C9 C -0.9430(2) 1.28621(13) 0.37428(11) 0.0228(3) Uani 1 1 d . . .
H9 H -1.0716 1.2425 0.3840 0.027 Uiso 1 1 calc R . .
C10 C -0.8877(2) 1.34413(13) 0.45203(11) 0.0232(3) Uani 1 1 d . . .
H10 H -0.9767 1.3397 0.5152 0.028 Uiso 1 1 calc R . .
C11 C -0.7007(2) 1.40867(14) 0.43633(11) 0.0248(3) Uani 1 1 d . . .
H11 H -0.6630 1.4500 0.4887 0.030 Uiso 1 1 calc R . .
C12 C -0.5688(2) 1.41324(13) 0.34492(11) 0.0231(3) Uani 1 1 d . . .
H12 H -0.4405 1.4572 0.3354 0.028 Uiso 1 1 calc R . .
C13 C -0.2088(2) 1.07683(13) 0.18008(10) 0.0193(3) Uani 1 1 d . . .
C14 C 0.0200(2) 1.02718(13) 0.14632(10) 0.0212(3) Uani 1 1 d . . .
H14 H 0.0589 1.0437 0.0743 0.025 Uiso 1 1 calc R . .
C15 C 0.1917(2) 0.95355(14) 0.21744(11) 0.0220(3) Uani 1 1 d . . .
H15 H 0.3478 0.9191 0.1948 0.026 Uiso 1 1 calc R . .
C16 C 0.1309(2) 0.93138(13) 0.32200(11) 0.0204(3) Uani 1 1 d . . .
C17 C -0.0960(2) 0.97933(13) 0.35701(10) 0.0207(3) Uani 1 1 d . . .
H17 H -0.1342 0.9630 0.4291 0.025 Uiso 1 1 calc R . .
C18 C -0.2666(2) 1.05166(13) 0.28521(10) 0.0204(3) Uani 1 1 d . . .
H18 H -0.4234 1.0840 0.3081 0.024 Uiso 1 1 calc R . .


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

All nonhydrogen atoms were located in a difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.  The N-H hydrogen atom
 was located in a diff map and refined isotropically with Uiso = 1.2xUeqiv
 and restrained to 0.85(2) ang. 
;

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
Cl1 C16 1.7459(14) . ?
O1 C3 1.2496(17) . ?
N1 C5 1.3451(17) . ?
N1 C13 1.4282(17) . ?
N1 H3 0.856(13) . ?
C1 C2 1.512(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.425(2) . ?
C4 C5 1.3811(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.5110(19) . ?
C6 C7 1.5217(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.3908(19) . ?
C7 C12 1.3935(19) . ?
C8 C9 1.3882(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3860(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3883(19) . ?
C13 C14 1.3932(19) . ?
C14 C15 1.3897(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3846(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3853(19) . ?
C17 C18 1.3880(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C13 126.99(12) . . ?
C5 N1 H3 115.3(11) . . ?
C13 N1 H3 117.6(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 112.79(12) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C4 122.91(12) . . ?
O1 C3 C2 119.05(12) . . ?
C4 C3 C2 118.04(12) . . ?
C5 C4 C3 124.24(12) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
N1 C5 C4 121.59(12) . . ?
N1 C5 C6 119.25(12) . . ?
C4 C5 C6 119.16(12) . . ?
C5 C6 C7 115.45(11) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C12 118.39(12) . . ?
C8 C7 C6 122.81(12) . . ?
C12 C7 C6 118.81(12) . . ?
C9 C8 C7 120.69(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.46(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.14(13) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.40(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 120.90(12) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 119.93(12) . . ?
C18 C13 N1 121.14(12) . . ?
C14 C13 N1 118.84(12) . . ?
C15 C14 C13 120.34(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 118.71(12) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 121.77(12) . . ?
C15 C16 Cl1 119.24(10) . . ?
C17 C16 Cl1 118.98(10) . . ?
C16 C17 C18 119.02(12) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.21(12) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

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
C1 C2 C3 O1 -45.62(19) . . . . ?
C1 C2 C3 C4 134.56(14) . . . . ?
O1 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C4 C5 178.30(13) . . . . ?
C13 N1 C5 C4 -178.80(12) . . . . ?
C13 N1 C5 C6 2.03(19) . . . . ?
C3 C4 C5 N1 0.9(2) . . . . ?
C3 C4 C5 C6 -179.92(12) . . . . ?
N1 C5 C6 C7 -91.73(15) . . . . ?
C4 C5 C6 C7 89.08(14) . . . . ?
C5 C6 C7 C8 -9.20(18) . . . . ?
C5 C6 C7 C12 170.39(12) . . . . ?
C12 C7 C8 C9 -1.10(19) . . . . ?
C6 C7 C8 C9 178.49(12) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C7 0.4(2) . . . . ?
C8 C7 C12 C11 0.63(19) . . . . ?
C6 C7 C12 C11 -178.97(12) . . . . ?
C5 N1 C13 C18 62.21(18) . . . . ?
C5 N1 C13 C14 -121.29(14) . . . . ?
C18 C13 C14 C15 -0.61(19) . . . . ?
N1 C13 C14 C15 -177.16(11) . . . . ?
C13 C14 C15 C16 -0.32(19) . . . . ?
C14 C15 C16 C17 0.67(19) . . . . ?
C14 C15 C16 Cl1 179.80(10) . . . . ?
C15 C16 C17 C18 -0.08(19) . . . . ?
Cl1 C16 C17 C18 -179.20(10) . . . . ?
C16 C17 C18 C13 -0.88(19) . . . . ?
C14 C13 C18 C17 1.22(19) . . . . ?
N1 C13 C18 C17 177.68(11) . . . . ?

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
N1 H3 O1 0.856(13) 1.991(15) 2.6781(15) 136.6(15) .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        67.62
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_demb33
_database_code_depnum_ccdc_archive 'CCDC 1477555'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N3 O2'
_chemical_formula_sum            'C23 H19 N3 O2'
_chemical_formula_weight         369.41

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   21.4737(10)
_cell_length_b                   16.0302(8)
_cell_length_c                   5.5546(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1912.05(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4714
_cell_measurement_theta_min      3.440
_cell_measurement_theta_max      67.609

_exptl_crystal_description       'transparent rod'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28119
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.440
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3485
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.986

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
TWINABS (Bruker, 2012) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3485
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91318(14) 0.26405(19) 0.7521(7) 0.0728(9) Uani 1 1 d . . . . .
O2 O 0.82867(13) 0.21890(17) 0.5777(6) 0.0652(8) Uani 1 1 d . . . . .
N1 N 0.89334(13) 0.53085(18) -0.0776(6) 0.0479(8) Uani 1 1 d . . . . .
N5 N 0.78961(13) 0.40461(18) -0.1098(6) 0.0482(8) Uani 1 1 d . . . . .
N7 N 0.87247(16) 0.2675(2) 0.5928(7) 0.0567(9) Uani 1 1 d . . . . .
C2 C 0.84635(16) 0.5733(2) -0.1578(8) 0.0459(9) Uani 1 1 d . . . . .
C3 C 0.78161(15) 0.5552(2) -0.0615(8) 0.0483(9) Uani 1 1 d . . . . .
H3A H 0.7821 0.5502 0.1162 0.058 Uiso 1 1 calc R U . . .
H3B H 0.7521 0.5997 -0.1080 0.058 Uiso 1 1 calc R U . . .
C4 C 0.76404(16) 0.4732(2) -0.1771(7) 0.0456(9) Uani 1 1 d . . . . .
C6 C 0.83431(16) 0.3394(2) 0.2344(8) 0.0475(9) Uani 1 1 d . . . . .
H6 H 0.8032 0.2975 0.2210 0.057 Uiso 1 1 calc R U . . .
C7 C 0.87839(16) 0.3351(2) 0.4142(7) 0.0475(9) Uani 1 1 d . . . . .
C8 C 0.92729(17) 0.3917(2) 0.4309(8) 0.0551(10) Uani 1 1 d . . . . .
H8 H 0.9577 0.3866 0.5543 0.066 Uiso 1 1 calc R U . . .
C9 C 0.93071(17) 0.4549(2) 0.2651(8) 0.0526(10) Uani 1 1 d . . . . .
H9 H 0.9649 0.4925 0.2705 0.063 Uiso 1 1 calc R U . . .
C10 C 0.88453(16) 0.4654(2) 0.0867(8) 0.0455(9) Uani 1 1 d . . . . .
C11 C 0.83564(16) 0.4058(2) 0.0722(8) 0.0457(9) Uani 1 1 d . . . . .
C12 C 0.85580(16) 0.6357(2) -0.3508(7) 0.0461(10) Uani 1 1 d . . . . .
C13 C 0.80594(17) 0.6756(2) -0.4652(8) 0.0567(11) Uani 1 1 d . . . . .
H13 H 0.7646 0.6642 -0.4142 0.068 Uiso 1 1 calc R U . . .
C14 C 0.81584(19) 0.7314(2) -0.6506(9) 0.0630(12) Uani 1 1 d . . . . .
H14 H 0.7813 0.7578 -0.7255 0.076 Uiso 1 1 calc R U . . .
C15 C 0.87541(18) 0.7491(3) -0.7284(10) 0.0635(12) Uani 1 1 d . . . . .
H15 H 0.8822 0.7873 -0.8564 0.076 Uiso 1 1 calc R U . . .
C16 C 0.92560(19) 0.7097(3) -0.6158(9) 0.0667(13) Uani 1 1 d . . . . .
H16 H 0.9669 0.7214 -0.6677 0.080 Uiso 1 1 calc R U . . .
C17 C 0.91586(16) 0.6541(2) -0.4297(9) 0.0570(11) Uani 1 1 d . . . . .
H17 H 0.9505 0.6281 -0.3545 0.068 Uiso 1 1 calc R U . . .
C18 C 0.71691(17) 0.4724(2) -0.3764(8) 0.0511(10) Uani 1 1 d . . . . .
H18A H 0.7090 0.4141 -0.4264 0.061 Uiso 1 1 calc R U . . .
H18B H 0.7338 0.5030 -0.5169 0.061 Uiso 1 1 calc R U . . .
C19 C 0.65610(16) 0.5124(2) -0.2991(7) 0.0464(9) Uani 1 1 d . . . . .
C20 C 0.62606(17) 0.4845(3) -0.0909(8) 0.0555(11) Uani 1 1 d . . . . .
H20 H 0.6432 0.4397 -0.0008 0.067 Uiso 1 1 calc R U . . .
C21 C 0.57111(18) 0.5223(3) -0.0153(8) 0.0581(11) Uani 1 1 d . . . . .
H21 H 0.5510 0.5022 0.1254 0.070 Uiso 1 1 calc R U . . .
C22 C 0.54507(17) 0.5883(3) -0.1392(8) 0.0541(10) Uani 1 1 d . . . . .
C23 C 0.48573(18) 0.6296(3) -0.0518(9) 0.0717(13) Uani 1 1 d . . . . .
H23A H 0.4574 0.5870 0.0120 0.107 Uiso 1 1 calc R U . . .
H23B H 0.4657 0.6586 -0.1862 0.107 Uiso 1 1 calc R U . . .
H23C H 0.4958 0.6698 0.0754 0.107 Uiso 1 1 calc R U . . .
C24 C 0.57481(17) 0.6156(3) -0.3454(8) 0.0571(11) Uani 1 1 d . . . . .
H24 H 0.5576 0.6606 -0.4344 0.069 Uiso 1 1 calc R U . . .
C25 C 0.62976(17) 0.5781(2) -0.4253(8) 0.0545(10) Uani 1 1 d . . . . .
H25 H 0.6493 0.5978 -0.5678 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N7 1.245(5) . ?
O2 N7 1.224(4) . ?
N1 C2 1.296(5) . ?
N1 C10 1.404(5) . ?
N5 C4 1.284(4) . ?
N5 C11 1.414(5) . ?
N7 C7 1.475(5) . ?
C2 C12 1.480(5) . ?
C2 C3 1.518(5) . ?
C3 C4 1.511(5) . ?
C4 C18 1.500(6) . ?
C6 C7 1.378(5) . ?
C6 C11 1.394(5) . ?
C7 C8 1.390(5) . ?
C8 C9 1.371(5) . ?
C9 C10 1.412(5) . ?
C10 C11 1.422(5) . ?
C12 C17 1.394(5) . ?
C12 C13 1.400(5) . ?
C13 C14 1.380(6) . ?
C14 C15 1.380(5) . ?
C15 C16 1.396(6) . ?
C16 C17 1.381(6) . ?
C18 C19 1.517(5) . ?
C19 C25 1.385(5) . ?
C19 C20 1.398(5) . ?
C20 C21 1.391(5) . ?
C21 C22 1.379(6) . ?
C22 C24 1.383(6) . ?
C22 C23 1.516(5) . ?
C24 C25 1.397(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
C2 N1 C10 120.7(3) . . ?
C4 N5 C11 119.7(3) . . ?
O2 N7 O1 124.0(4) . . ?
O2 N7 C7 119.2(4) . . ?
O1 N7 C7 116.8(3) . . ?
N1 C2 C12 119.8(3) . . ?
N1 C2 C3 119.4(3) . . ?
C12 C2 C3 120.7(3) . . ?
C4 C3 C2 104.2(3) . . ?
N5 C4 C18 119.8(3) . . ?
N5 C4 C3 120.9(3) . . ?
C18 C4 C3 119.3(3) . . ?
C7 C6 C11 119.5(3) . . ?
C6 C7 C8 122.3(3) . . ?
C6 C7 N7 117.7(3) . . ?
C8 C7 N7 120.0(4) . . ?
C9 C8 C7 118.6(4) . . ?
C8 C9 C10 121.4(3) . . ?
N1 C10 C9 116.8(3) . . ?
N1 C10 C11 124.4(3) . . ?
C9 C10 C11 118.6(3) . . ?
C6 C11 N5 115.9(3) . . ?
C6 C11 C10 119.4(4) . . ?
N5 C11 C10 124.5(3) . . ?
C17 C12 C13 117.9(4) . . ?
C17 C12 C2 119.8(3) . . ?
C13 C12 C2 122.2(3) . . ?
C14 C13 C12 121.1(4) . . ?
C15 C14 C13 120.6(4) . . ?
C14 C15 C16 118.9(4) . . ?
C17 C16 C15 120.6(4) . . ?
C16 C17 C12 120.8(4) . . ?
C4 C18 C19 111.6(3) . . ?
C25 C19 C20 118.2(4) . . ?
C25 C19 C18 121.9(4) . . ?
C20 C19 C18 119.8(3) . . ?
C21 C20 C19 120.1(4) . . ?
C22 C21 C20 121.8(4) . . ?
C21 C22 C24 117.9(4) . . ?
C21 C22 C23 121.0(4) . . ?
C24 C22 C23 121.0(4) . . ?
C22 C24 C25 121.1(4) . . ?
C19 C25 C24 120.7(4) . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_demb31
_database_code_depnum_ccdc_archive 'CCDC 1477556'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O'
_chemical_formula_sum            'C24 H24 N2 O'
_chemical_formula_weight         356.45

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

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

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

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

_cell_length_a                   12.2036(7)
_cell_length_b                   10.1274(5)
_cell_length_c                   15.5213(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.535(3)
_cell_angle_gamma                90
_cell_volume                     1914.64(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      3.674
_cell_measurement_theta_max      66.301

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.192
_exptl_absorpt_coefficient_mu    0.590
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27874
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.629
_diffrn_reflns_theta_max         68.135
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3493
_reflns_number_gt                2918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

All nonhydrogen atoms were located in a single difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with O-H bond distances restrained to 0.85(2) angstroms.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.5822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3493
_refine_ls_number_parameters     255
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02065(8) 0.19866(10) 0.98767(6) 0.0292(2) Uani 1 1 d . . . . .
N1 N -0.11090(10) 0.29597(12) 0.86249(8) 0.0260(3) Uani 1 1 d D . . . .
H1 H -0.0884(13) 0.2845(16) 0.9171(9) 0.031 Uiso 1 1 d D U . . .
N2 N -0.07963(11) 0.55247(13) 0.92174(9) 0.0320(3) Uani 1 1 d D . . . .
H2A H -0.0223(13) 0.5016(17) 0.9186(11) 0.038 Uiso 1 1 d D U . . .
H2B H -0.0700(14) 0.6333(15) 0.9415(11) 0.038 Uiso 1 1 d D U . . .
C1 C 0.07325(11) 0.14303(13) 0.92924(9) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.03935(11) 0.15227(13) 0.83943(9) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.0784 0.1026 0.7994 0.031 Uiso 1 1 calc R U . . .
C3 C -0.04827(11) 0.23069(13) 0.80777(9) 0.0252(3) Uani 1 1 d . . . . .
C4 C -0.07392(12) 0.24346(14) 0.71116(9) 0.0272(3) Uani 1 1 d . . . . .
H4A H -0.0045 0.2362 0.6818 0.033 Uiso 1 1 calc R U . . .
H4B H -0.1044 0.3326 0.6990 0.033 Uiso 1 1 calc R U . . .
C5 C -0.15485(11) 0.14079(14) 0.67245(9) 0.0257(3) Uani 1 1 d . . . . .
C6 C -0.16978(12) 0.01662(14) 0.70985(9) 0.0303(3) Uani 1 1 d . . . . .
H6 H -0.1275 -0.0067 0.7611 0.036 Uiso 1 1 calc R U . . .
C7 C -0.24587(12) -0.07344(15) 0.67301(9) 0.0308(3) Uani 1 1 d . . . . .
H7 H -0.2548 -0.1566 0.7000 0.037 Uiso 1 1 calc R U . . .
C8 C -0.30926(11) -0.04357(14) 0.59701(9) 0.0276(3) Uani 1 1 d . . . . .
C9 C -0.29156(12) 0.07917(15) 0.55831(9) 0.0289(3) Uani 1 1 d . . . . .
H9 H -0.3321 0.1015 0.5061 0.035 Uiso 1 1 calc R U . . .
C10 C -0.21546(12) 0.16937(14) 0.59500(9) 0.0277(3) Uani 1 1 d . . . . .
H10 H -0.2047 0.2513 0.5670 0.033 Uiso 1 1 calc R U . . .
C11 C -0.39388(13) -0.14002(16) 0.55875(10) 0.0346(4) Uani 1 1 d . . . . .
H11A H -0.3568 -0.2198 0.5398 0.052 Uiso 1 1 calc R U . . .
H11B H -0.4344 -0.0991 0.5093 0.052 Uiso 1 1 calc R U . . .
H11C H -0.4451 -0.1636 0.6025 0.052 Uiso 1 1 calc R U . . .
C12 C 0.17556(11) 0.06753(13) 0.95805(9) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.25774(12) 0.03458(14) 0.90220(10) 0.0297(3) Uani 1 1 d . . . . .
H13 H 0.2490 0.0573 0.8428 0.036 Uiso 1 1 calc R U . . .
C14 C 0.35243(12) -0.03159(15) 0.93397(10) 0.0339(4) Uani 1 1 d . . . . .
H14 H 0.4077 -0.0537 0.8959 0.041 Uiso 1 1 calc R U . . .
C15 C 0.36640(12) -0.06540(15) 1.02110(11) 0.0352(4) Uani 1 1 d . . . . .
H15 H 0.4310 -0.1100 1.0423 0.042 Uiso 1 1 calc R U . . .
C16 C 0.28509(13) -0.03347(15) 1.07690(10) 0.0338(3) Uani 1 1 d . . . . .
H16 H 0.2941 -0.0567 1.1362 0.041 Uiso 1 1 calc R U . . .
C17 C 0.19046(12) 0.03270(14) 1.04551(10) 0.0305(3) Uani 1 1 d . . . . .
H17 H 0.1355 0.0544 1.0839 0.037 Uiso 1 1 calc R U . . .
C18 C -0.19524(11) 0.39213(14) 0.84298(9) 0.0241(3) Uani 1 1 d . . . . .
C19 C -0.17656(11) 0.52114(14) 0.87565(9) 0.0245(3) Uani 1 1 d . . . . .
C20 C -0.26103(11) 0.61521(14) 0.86203(9) 0.0271(3) Uani 1 1 d . . . . .
H20 H -0.2487 0.7032 0.8815 0.033 Uiso 1 1 calc R U . . .
C21 C -0.36220(12) 0.58260(15) 0.82081(9) 0.0290(3) Uani 1 1 d . . . . .
C22 C -0.37967(12) 0.45339(15) 0.79053(9) 0.0302(3) Uani 1 1 d . . . . .
H22 H -0.4484 0.4297 0.7627 0.036 Uiso 1 1 calc R U . . .
C23 C -0.29620(12) 0.35965(14) 0.80123(9) 0.0289(3) Uani 1 1 d . . . . .
H23 H -0.3082 0.2726 0.7798 0.035 Uiso 1 1 calc R U . . .
C24 C -0.45242(13) 0.68572(16) 0.80820(11) 0.0380(4) Uani 1 1 d . . . . .
H24A H -0.4271 0.7694 0.8341 0.057 Uiso 1 1 calc R U . . .
H24B H -0.5179 0.6556 0.8360 0.057 Uiso 1 1 calc R U . . .
H24C H -0.4704 0.6985 0.7464 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2743(17) . ?
N1 C3 1.3500(18) . ?
N1 C18 1.4357(17) . ?
N1 H1 0.882(13) . ?
N2 C19 1.3810(19) . ?
N2 H2A 0.872(14) . ?
N2 H2B 0.879(14) . ?
C1 C2 1.432(2) . ?
C1 C12 1.5082(19) . ?
C2 C3 1.3967(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.5183(19) . ?
C4 C5 1.5312(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.402(2) . ?
C5 C10 1.4023(19) . ?
C6 C7 1.399(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(2) . ?
C8 C11 1.516(2) . ?
C9 C10 1.399(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.403(2) . ?
C12 C13 1.406(2) . ?
C13 C14 1.399(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.3955(19) . ?
C18 C19 1.4149(19) . ?
C19 C20 1.4101(19) . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.402(2) . ?
C21 C24 1.521(2) . ?
C22 C23 1.395(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C3 N1 C18 128.75(12) . . ?
C3 N1 H1 112.6(11) . . ?
C18 N1 H1 118.0(11) . . ?
C19 N2 H2A 120.0(12) . . ?
C19 N2 H2B 119.1(11) . . ?
H2A N2 H2B 118.6(17) . . ?
O1 C1 C2 122.40(13) . . ?
O1 C1 C12 117.21(12) . . ?
C2 C1 C12 120.38(12) . . ?
C3 C2 C1 123.26(13) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 C2 120.53(13) . . ?
N1 C3 C4 119.30(12) . . ?
C2 C3 C4 120.18(12) . . ?
C3 C4 C5 114.74(11) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C10 117.72(13) . . ?
C6 C5 C4 122.95(12) . . ?
C10 C5 C4 119.31(12) . . ?
C7 C6 C5 121.05(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.39(14) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 117.36(13) . . ?
C9 C8 C11 121.49(13) . . ?
C7 C8 C11 121.15(13) . . ?
C10 C9 C8 121.35(13) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 121.07(13) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.82(13) . . ?
C17 C12 C1 118.01(13) . . ?
C13 C12 C1 123.14(13) . . ?
C14 C13 C12 120.11(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.53(14) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.73(14) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.95(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.87(14) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 120.15(13) . . ?
C23 C18 N1 122.62(12) . . ?
C19 C18 N1 116.94(12) . . ?
N2 C19 C20 121.15(13) . . ?
N2 C19 C18 120.79(13) . . ?
C20 C19 C18 118.03(13) . . ?
C21 C20 C19 121.81(13) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 119.13(13) . . ?
C20 C21 C24 120.63(14) . . ?
C22 C21 C24 120.24(14) . . ?
C23 C22 C21 120.02(14) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 120.81(14) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.2(2) . . . . ?
C12 C1 C2 C3 -173.73(12) . . . . ?
C18 N1 C3 C2 172.06(13) . . . . ?
C18 N1 C3 C4 -7.9(2) . . . . ?
C1 C2 C3 N1 -4.5(2) . . . . ?
C1 C2 C3 C4 175.39(12) . . . . ?
N1 C3 C4 C5 -89.87(15) . . . . ?
C2 C3 C4 C5 90.21(16) . . . . ?
C3 C4 C5 C6 -25.32(19) . . . . ?
C3 C4 C5 C10 156.29(12) . . . . ?
C10 C5 C6 C7 -2.6(2) . . . . ?
C4 C5 C6 C7 179.00(13) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 1.4(2) . . . . ?
C6 C7 C8 C11 -178.26(13) . . . . ?
C7 C8 C9 C10 -1.3(2) . . . . ?
C11 C8 C9 C10 178.31(13) . . . . ?
C8 C9 C10 C5 -0.7(2) . . . . ?
C6 C5 C10 C9 2.6(2) . . . . ?
C4 C5 C10 C9 -178.90(12) . . . . ?
O1 C1 C12 C17 16.92(18) . . . . ?
C2 C1 C12 C17 -164.11(13) . . . . ?
O1 C1 C12 C13 -160.92(13) . . . . ?
C2 C1 C12 C13 18.1(2) . . . . ?
C17 C12 C13 C14 -0.1(2) . . . . ?
C1 C12 C13 C14 177.73(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C1 C12 C17 C16 -177.90(13) . . . . ?
C3 N1 C18 C23 69.78(19) . . . . ?
C3 N1 C18 C19 -116.39(15) . . . . ?
C23 C18 C19 N2 175.98(13) . . . . ?
N1 C18 C19 N2 1.99(19) . . . . ?
C23 C18 C19 C20 -2.1(2) . . . . ?
N1 C18 C19 C20 -176.08(12) . . . . ?
N2 C19 C20 C21 -175.52(13) . . . . ?
C18 C19 C20 C21 2.6(2) . . . . ?
C19 C20 C21 C22 -1.3(2) . . . . ?
C19 C20 C21 C24 179.08(13) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C24 C21 C22 C23 179.16(13) . . . . ?
C21 C22 C23 C18 0.9(2) . . . . ?
C19 C18 C23 C22 0.4(2) . . . . ?
N1 C18 C23 C22 174.06(13) . . . . ?

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
N1 H1 O1 0.882(13) 1.883(15) 2.6342(15) 141.9(15) .
N2 H2B O1 0.879(14) 2.095(15) 2.9533(16) 165.3(16) 3_567

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_demb35
_database_code_depnum_ccdc_archive 'CCDC 1477557'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.5902(3)
_cell_length_b                   14.0682(5)
_cell_length_c                   18.3473(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.945(3)
_cell_angle_gamma                90
_cell_volume                     1940.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5389
_cell_measurement_theta_min      3.833
_cell_measurement_theta_max      68.195

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    0.538
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29080
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.974
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3504
_reflns_number_gt                2997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.4476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25717(14) 0.55508(7) 0.39381(6) 0.0216(2) Uani 1 1 d . . . . .
N5 N 0.49219(14) 0.72903(7) 0.40535(6) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.40883(17) 0.52089(9) 0.38307(7) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.58204(17) 0.56214(9) 0.42089(7) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.5819 0.5650 0.4748 0.026 Uiso 1 1 calc R U . . .
H3B H 0.6842 0.5230 0.4106 0.026 Uiso 1 1 calc R U . . .
C4 C 0.59302(17) 0.66110(9) 0.38931(7) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.31882(18) 0.78761(9) 0.49616(7) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.17827(18) 0.77879(9) 0.53575(7) 0.0252(3) Uani 1 1 d . . . . .
H7 H 0.1579 0.8280 0.5690 0.030 Uiso 1 1 calc R U . . .
C8 C 0.06379(18) 0.69989(9) 0.52886(7) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.09757(17) 0.62908(9) 0.48060(7) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.0189 0.5764 0.4734 0.028 Uiso 1 1 calc R U . . .
C10 C 0.24454(17) 0.63237(9) 0.44169(7) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.35671(17) 0.71271(9) 0.44888(7) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.4343(2) 0.87502(10) 0.50353(9) 0.0344(4) Uani 1 1 d . . . . .
H12A H 0.3852 0.9215 0.5351 0.052 Uiso 1 1 calc R U . . .
H12B H 0.4379 0.9028 0.4548 0.052 Uiso 1 1 calc R U . . .
H12C H 0.5551 0.8577 0.5255 0.052 Uiso 1 1 calc R U . . .
C13 C -0.0913(2) 0.69310(11) 0.57160(9) 0.0352(4) Uani 1 1 d . . . . .
H13A H -0.1870 0.7350 0.5494 0.053 Uiso 1 1 calc R U . . .
H13B H -0.0534 0.7125 0.6227 0.053 Uiso 1 1 calc R U . . .
H13C H -0.1344 0.6274 0.5706 0.053 Uiso 1 1 calc R U . . .
C14 C 0.40905(17) 0.43765(9) 0.33309(7) 0.0212(3) Uani 1 1 d . . . . .
C15 C 0.53434(18) 0.36557(9) 0.34761(8) 0.0266(3) Uani 1 1 d . . . . .
H15 H 0.6284 0.3723 0.3872 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5231(2) 0.28357(10) 0.30457(8) 0.0315(3) Uani 1 1 d . . . . .
H16 H 0.6081 0.2342 0.3154 0.038 Uiso 1 1 calc R U . . .
C17 C 0.38832(19) 0.27411(10) 0.24613(8) 0.0306(3) Uani 1 1 d . . . . .
H17 H 0.3805 0.2182 0.2168 0.037 Uiso 1 1 calc R U . . .
C18 C 0.26445(19) 0.34636(10) 0.23032(8) 0.0297(3) Uani 1 1 d . . . . .
H18 H 0.1730 0.3404 0.1897 0.036 Uiso 1 1 calc R U . . .
C19 C 0.27415(18) 0.42722(10) 0.27379(7) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.1880 0.4761 0.2631 0.031 Uiso 1 1 calc R U . . .
C20 C 0.72278(18) 0.67860(9) 0.33606(7) 0.0257(3) Uani 1 1 d . . . . .
H20A H 0.8455 0.6714 0.3619 0.031 Uiso 1 1 calc R U . . .
H20B H 0.7090 0.7446 0.3174 0.031 Uiso 1 1 calc R U . . .
C21 C 0.69410(18) 0.60991(9) 0.27172(7) 0.0238(3) Uani 1 1 d . . . . .
C22 C 0.81719(19) 0.53942(10) 0.26292(8) 0.0291(3) Uani 1 1 d . . . . .
H22 H 0.9226 0.5343 0.2973 0.035 Uiso 1 1 calc R U . . .
C23 C 0.7876(2) 0.47624(10) 0.20429(8) 0.0323(3) Uani 1 1 d . . . . .
H23 H 0.8740 0.4289 0.1989 0.039 Uiso 1 1 calc R U . . .
C24 C 0.6340(2) 0.48096(10) 0.15339(8) 0.0293(3) Uani 1 1 d . . . . .
C25 C 0.51069(19) 0.55189(10) 0.16282(8) 0.0285(3) Uani 1 1 d . . . . .
H25 H 0.4045 0.5566 0.1289 0.034 Uiso 1 1 calc R U . . .
C26 C 0.54045(18) 0.61564(9) 0.22077(7) 0.0262(3) Uani 1 1 d . . . . .
H26 H 0.4552 0.6638 0.2258 0.031 Uiso 1 1 calc R U . . .
C27 C 0.5990(2) 0.41133(11) 0.09082(9) 0.0399(4) Uani 1 1 d . . . . .
H27A H 0.7112 0.3817 0.0823 0.060 Uiso 1 1 calc R U . . .
H27B H 0.5463 0.4448 0.0462 0.060 Uiso 1 1 calc R U . . .
H27C H 0.5167 0.3621 0.1032 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.2876(17) . ?
N1 C10 1.4094(16) . ?
N5 C4 1.2837(17) . ?
N5 C11 1.4054(17) . ?
C2 C14 1.4875(17) . ?
C2 C3 1.5148(17) . ?
C3 C4 1.5147(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C20 1.5004(19) . ?
C6 C7 1.377(2) . ?
C6 C11 1.4193(18) . ?
C6 C12 1.5055(19) . ?
C7 C8 1.4046(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3801(18) . ?
C8 C13 1.505(2) . ?
C9 C10 1.4059(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4101(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3905(18) . ?
C14 C19 1.3949(19) . ?
C15 C16 1.3938(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3855(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5178(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.3872(19) . ?
C21 C26 1.3925(19) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.395(2) . ?
C24 C27 1.505(2) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 121.52(11) . . ?
C4 N5 C11 120.99(11) . . ?
N1 C2 C14 117.75(11) . . ?
N1 C2 C3 121.63(11) . . ?
C14 C2 C3 120.60(11) . . ?
C4 C3 C2 105.49(10) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
N5 C4 C20 119.53(12) . . ?
N5 C4 C3 122.04(12) . . ?
C20 C4 C3 118.40(11) . . ?
C7 C6 C11 119.53(12) . . ?
C7 C6 C12 120.68(12) . . ?
C11 C6 C12 119.78(12) . . ?
C6 C7 C8 122.59(12) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 117.43(13) . . ?
C9 C8 C13 121.10(12) . . ?
C7 C8 C13 121.46(12) . . ?
C8 C9 C10 122.20(12) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 N1 114.72(11) . . ?
C9 C10 C11 119.35(12) . . ?
N1 C10 C11 125.76(12) . . ?
N5 C11 C10 123.89(12) . . ?
N5 C11 C6 116.87(11) . . ?
C10 C11 C6 118.78(12) . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.79(12) . . ?
C15 C14 C2 121.00(12) . . ?
C19 C14 C2 120.02(12) . . ?
C14 C15 C16 120.55(13) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.99(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.94(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.03(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.68(13) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C4 C20 C21 111.44(11) . . ?
C4 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C4 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C26 118.57(13) . . ?
C22 C21 C20 121.28(12) . . ?
C26 C21 C20 120.14(12) . . ?
C21 C22 C23 120.54(13) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.33(13) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 117.73(13) . . ?
C23 C24 C27 121.62(14) . . ?
C25 C24 C27 120.64(14) . . ?
C26 C25 C24 121.14(13) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C21 120.69(13) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C14 178.43(11) . . . . ?
C10 N1 C2 C3 -0.37(18) . . . . ?
N1 C2 C3 C4 -66.49(15) . . . . ?
C14 C2 C3 C4 114.73(12) . . . . ?
C11 N5 C4 C20 173.31(11) . . . . ?
C11 N5 C4 C3 -4.93(18) . . . . ?
C2 C3 C4 N5 71.54(15) . . . . ?
C2 C3 C4 C20 -106.72(12) . . . . ?
C11 C6 C7 C8 -3.1(2) . . . . ?
C12 C6 C7 C8 177.97(13) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C6 C7 C8 C13 -178.63(13) . . . . ?
C7 C8 C9 C10 2.71(19) . . . . ?
C13 C8 C9 C10 -178.07(13) . . . . ?
C8 C9 C10 N1 -178.93(12) . . . . ?
C8 C9 C10 C11 -3.40(19) . . . . ?
C2 N1 C10 C9 -145.18(12) . . . . ?
C2 N1 C10 C11 39.62(18) . . . . ?
C4 N5 C11 C10 -41.40(18) . . . . ?
C4 N5 C11 C6 146.50(12) . . . . ?
C9 C10 C11 N5 -171.16(12) . . . . ?
N1 C10 C11 N5 3.8(2) . . . . ?
C9 C10 C11 C6 0.80(18) . . . . ?
N1 C10 C11 C6 175.79(12) . . . . ?
C7 C6 C11 N5 174.85(11) . . . . ?
C12 C6 C11 N5 -6.20(18) . . . . ?
C7 C6 C11 C10 2.33(19) . . . . ?
C12 C6 C11 C10 -178.72(12) . . . . ?
N1 C2 C14 C15 -142.95(13) . . . . ?
C3 C2 C14 C15 35.87(17) . . . . ?
N1 C2 C14 C19 32.00(17) . . . . ?
C3 C2 C14 C19 -149.18(12) . . . . ?
C19 C14 C15 C16 -1.3(2) . . . . ?
C2 C14 C15 C16 173.74(12) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C18 C19 C14 0.9(2) . . . . ?
C15 C14 C19 C18 0.31(19) . . . . ?
C2 C14 C19 C18 -174.76(12) . . . . ?
N5 C4 C20 C21 -123.43(13) . . . . ?
C3 C4 C20 C21 54.88(15) . . . . ?
C4 C20 C21 C22 -110.77(14) . . . . ?
C4 C20 C21 C26 68.03(15) . . . . ?
C26 C21 C22 C23 0.2(2) . . . . ?
C20 C21 C22 C23 179.05(13) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
C22 C23 C24 C27 -178.51(14) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C27 C24 C25 C26 179.17(13) . . . . ?
C24 C25 C26 C21 -0.6(2) . . . . ?
C22 C21 C26 C25 0.42(19) . . . . ?
C20 C21 C26 C25 -178.41(12) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038

