# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_chzhm1120
_audit_creation_date             2013-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4713)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 N3 O'
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.709(3)
_cell_length_b                   8.4319(16)
_cell_length_c                   12.274(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.34(2)
_cell_angle_gamma                90
_cell_volume                     1615.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1394
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2330
_cell_measurement_theta_min      3.7950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.288
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   75.00  102.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000   30.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   87.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   50.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -77.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   97.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075 -178.0000 -120.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0101380000
_diffrn_orient_matrix_UB_12      -0.0685458000
_diffrn_orient_matrix_UB_13      -0.0291930000
_diffrn_orient_matrix_UB_21      0.0410324000
_diffrn_orient_matrix_UB_22      0.0321064000
_diffrn_orient_matrix_UB_23      -0.0063138000
_diffrn_orient_matrix_UB_31      0.0169975000
_diffrn_orient_matrix_UB_32      -0.0364556000
_diffrn_orient_matrix_UB_33      0.0498329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1988
_reflns_number_total             3179
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.052
_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)+(0.0617P)²+0.0879P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1694
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
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), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.72107(11) 0.1566(2) 0.14674(13) 0.0619(5) Uani 1 1 d . . . . .
N1 N 0.83203(14) 0.4139(2) 0.31102(17) 0.0558(6) Uani 1 1 d . . . . .
N2 N 0.86975(13) 0.5356(3) 0.34226(18) 0.0552(6) Uani 1 1 d . . . . .
N3 N 0.90424(17) 0.6523(3) 0.3599(2) 0.0847(8) Uani 1 1 d . . . . .
C1 C 0.83048(15) 0.2847(3) 0.39500(19) 0.0432(6) Uani 1 1 d . . . . .
H1 H 0.7889 0.3126 0.4458 0.052 Uiso 1 1 calc R . . . .
C2 C 0.91922(15) 0.2643(3) 0.4601(2) 0.0538(7) Uani 1 1 d . . . . .
H2A H 0.9384 0.3662 0.4902 0.065 Uiso 1 1 calc R . . . .
H2B H 0.9142 0.1929 0.5210 0.065 Uiso 1 1 calc R . . . .
C3 C 0.98632(16) 0.1995(3) 0.3916(2) 0.0585(7) Uani 1 1 d . . . . .
H3A H 1.0391 0.1786 0.4382 0.070 Uiso 1 1 calc R . . . .
H3B H 0.9982 0.2770 0.3369 0.070 Uiso 1 1 calc R . . . .
C4 C 0.95342(16) 0.0469(3) 0.3356(2) 0.0586(7) Uani 1 1 d . . . . .
H4A H 0.9961 0.0054 0.2917 0.070 Uiso 1 1 calc R . . . .
H4B H 0.9438 -0.0318 0.3906 0.070 Uiso 1 1 calc R . . . .
C5 C 0.87026(15) 0.0770(3) 0.2625(2) 0.0491(6) Uani 1 1 d . . . . .
H5A H 0.8520 -0.0208 0.2254 0.059 Uiso 1 1 calc R . . . .
H5B H 0.8807 0.1543 0.2070 0.059 Uiso 1 1 calc R . . . .
C6 C 0.79707(14) 0.1385(3) 0.32667(17) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.76438(13) 0.0010(3) 0.39432(18) 0.0387(5) Uani 1 1 d . . . . .
C8 C 0.72410(15) -0.1268(3) 0.3376(2) 0.0492(6) Uani 1 1 d . . . . .
H8 H 0.7176 -0.1256 0.2614 0.059 Uiso 1 1 calc R . . . .
C9 C 0.69359(17) -0.2550(3) 0.3917(2) 0.0625(8) Uani 1 1 d . . . . .
H9 H 0.6664 -0.3378 0.3518 0.075 Uiso 1 1 calc R . . . .
C10 C 0.70329(19) -0.2606(3) 0.5039(3) 0.0674(8) Uani 1 1 d . . . . .
H10 H 0.6842 -0.3482 0.5403 0.081 Uiso 1 1 calc R . . . .
C11 C 0.74160(18) -0.1353(4) 0.5623(2) 0.0652(8) Uani 1 1 d . . . . .
H11 H 0.7476 -0.1379 0.6385 0.078 Uiso 1 1 calc R . . . .
C12 C 0.77155(15) -0.0045(3) 0.50826(19) 0.0497(6) Uani 1 1 d . . . . .
H12 H 0.7966 0.0798 0.5488 0.060 Uiso 1 1 calc R . . . .
C13 C 0.72065(15) 0.1907(3) 0.24349(18) 0.0421(6) Uani 1 1 d . . . . .
C14 C 0.64480(15) 0.2772(3) 0.27784(19) 0.0420(5) Uani 1 1 d . . . . .
C15 C 0.59380(16) 0.3617(3) 0.1976(2) 0.0558(7) Uani 1 1 d . . . . .
H15 H 0.6092 0.3657 0.1266 0.067 Uiso 1 1 calc R . . . .
C16 C 0.52123(18) 0.4393(4) 0.2217(3) 0.0702(8) Uani 1 1 d . . . . .
H16 H 0.4884 0.4958 0.1672 0.084 Uiso 1 1 calc R . . . .
C17 C 0.49690(18) 0.4338(4) 0.3254(3) 0.0667(8) Uani 1 1 d . . . . .
H17 H 0.4473 0.4853 0.3411 0.080 Uiso 1 1 calc R . . . .
C18 C 0.54613(17) 0.3516(3) 0.4065(2) 0.0601(7) Uani 1 1 d . . . . .
H18 H 0.5296 0.3478 0.4769 0.072 Uiso 1 1 calc R . . . .
C19 C 0.61997(15) 0.2748(3) 0.3840(2) 0.0484(6) Uani 1 1 d . . . . .
H19 H 0.6533 0.2214 0.4396 0.058 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 C13 1.223(3) . ?
N1 N2 1.225(3) . ?
N1 C1 1.501(3) . ?
N2 N3 1.133(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.538(3) . ?
C1 C6 1.550(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.522(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.553(3) . ?
C6 C7 1.547(3) . ?
C6 C13 1.552(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.496(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.401(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 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
N2 N1 C1 115.9(2) . . ?
N3 N2 N1 172.8(3) . . ?
N1 C1 H1 109.0 . . ?
N1 C1 C2 110.83(19) . . ?
N1 C1 C6 103.63(18) . . ?
C2 C1 H1 109.0 . . ?
C2 C1 C6 115.17(19) . . ?
C6 C1 H1 109.0 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.4(2) . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C2 C3 C4 109.4(2) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.6(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C4 C5 C6 113.10(19) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C1 C6 C5 108.34(18) . . ?
C1 C6 C13 108.74(17) . . ?
C7 C6 C1 114.75(18) . . ?
C7 C6 C5 109.29(18) . . ?
C7 C6 C13 106.71(17) . . ?
C13 C6 C5 108.88(17) . . ?
C8 C7 C6 118.0(2) . . ?
C12 C7 C6 124.7(2) . . ?
C12 C7 C8 117.2(2) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 120.7(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C6 119.1(2) . . ?
O1 C13 C14 118.6(2) . . ?
C14 C13 C6 122.36(18) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 C19 117.8(2) . . ?
C19 C14 C13 124.6(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -21.9(3) . . . . ?
O1 C13 C14 C19 156.0(2) . . . . ?
N1 C1 C2 C3 -67.7(3) . . . . ?
N1 C1 C6 C5 74.3(2) . . . . ?
N1 C1 C6 C7 -163.26(18) . . . . ?
N1 C1 C6 C13 -43.9(2) . . . . ?
N2 N1 C1 C2 -44.2(3) . . . . ?
N2 N1 C1 C6 -168.3(2) . . . . ?
C1 C2 C3 C4 -53.5(3) . . . . ?
C1 C6 C7 C8 172.61(19) . . . . ?
C1 C6 C7 C12 -6.9(3) . . . . ?
C1 C6 C13 O1 128.8(2) . . . . ?
C1 C6 C13 C14 -53.2(3) . . . . ?
C2 C1 C6 C5 -46.9(2) . . . . ?
C2 C1 C6 C7 75.5(2) . . . . ?
C2 C1 C6 C13 -165.08(18) . . . . ?
C2 C3 C4 C5 59.1(3) . . . . ?
C3 C4 C5 C6 -61.1(3) . . . . ?
C4 C5 C6 C1 52.9(3) . . . . ?
C4 C5 C6 C7 -72.8(3) . . . . ?
C4 C5 C6 C13 171.00(19) . . . . ?
C5 C6 C7 C8 -65.5(3) . . . . ?
C5 C6 C7 C12 115.0(2) . . . . ?
C5 C6 C13 O1 11.0(3) . . . . ?
C5 C6 C13 C14 -171.05(19) . . . . ?
C6 C1 C2 C3 49.5(3) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C12 C11 -178.7(2) . . . . ?
C6 C13 C14 C15 160.2(2) . . . . ?
C6 C13 C14 C19 -22.0(3) . . . . ?
C7 C6 C13 O1 -106.9(2) . . . . ?
C7 C6 C13 C14 71.1(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C7 C12 C11 1.8(3) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C12 C7 C8 C9 -1.0(4) . . . . ?
C13 C6 C7 C8 52.1(2) . . . . ?
C13 C6 C7 C12 -127.4(2) . . . . ?
C13 C14 C15 C16 177.5(2) . . . . ?
C13 C14 C19 C18 -176.5(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C14 C19 C18 1.4(4) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C14 -1.2(4) . . . . ?
C19 C14 C15 C16 -0.5(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 997264'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_chzhm1104
_audit_creation_date             2013-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4713)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H26 N6 O2 Si'
_chemical_formula_sum            'C21 H26 N6 O2 Si'
_chemical_formula_weight         422.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   8.7189(3)
_cell_length_b                   9.0660(4)
_cell_length_c                   27.8157(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.003(4)
_cell_angle_gamma                90
_cell_volume                     2198.38(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2621
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2270
_cell_measurement_theta_min      3.5350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9627
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.633
_diffrn_reflns_theta_min         3.242
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0305403000
_diffrn_orient_matrix_UB_12      0.0674731000
_diffrn_orient_matrix_UB_13      -0.0088274000
_diffrn_orient_matrix_UB_21      0.0252138000
_diffrn_orient_matrix_UB_22      -0.0178216000
_diffrn_orient_matrix_UB_23      -0.0233893000
_diffrn_orient_matrix_UB_31      -0.0711196000
_diffrn_orient_matrix_UB_32      -0.0353292000
_diffrn_orient_matrix_UB_33      -0.0050135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3233
_reflns_number_total             4974
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0464P)²+0.1519P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1314
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Si1 Si -0.12466(7) 0.24764(7) 0.65750(2) 0.04452(19) Uani 1 1 d . . . . .
O2 O 0.00196(14) 0.20484(15) 0.61647(5) 0.0352(3) Uani 1 1 d . . . . .
O1 O 0.04358(15) -0.08503(15) 0.63774(5) 0.0389(4) Uani 1 1 d . . . . .
N1 N 0.02965(19) -0.0332(2) 0.55325(6) 0.0411(4) Uani 1 1 d . . . . .
N2 N -0.1061(2) 0.0037(2) 0.55438(7) 0.0473(5) Uani 1 1 d . . . . .
N3 N 0.4807(2) -0.1936(2) 0.62572(7) 0.0525(5) Uani 1 1 d . . . . .
N4 N 0.3817(2) -0.1010(2) 0.62261(7) 0.0515(5) Uani 1 1 d . . . . .
N5 N 0.5788(3) -0.2711(3) 0.63308(10) 0.1018(11) Uani 1 1 d . . . . .
C6 C 0.1517(2) 0.1430(2) 0.61100(7) 0.0313(4) Uani 1 1 d . . . . .
C7 C 0.1223(2) -0.0254(2) 0.59881(7) 0.0343(5) Uani 1 1 d . . . . .
C8 C 0.2210(2) 0.2168(2) 0.56664(7) 0.0334(5) Uani 1 1 d . . . . .
C9 C 0.2464(2) 0.1800(2) 0.65681(7) 0.0329(5) Uani 1 1 d . . . . .
C10 C -0.2525(3) 0.3744(3) 0.62371(10) 0.0608(7) Uani 1 1 d . . . . .
H10A H -0.1985 0.4640 0.6169 0.091 Uiso 1 1 calc GR . . . .
H10B H -0.3408 0.3964 0.6426 0.091 Uiso 1 1 calc GR . . . .
H10C H -0.2848 0.3287 0.5941 0.091 Uiso 1 1 calc GR . . . .
N11 N -0.2318(2) 0.0297(3) 0.54944(9) 0.0760(7) Uani 1 1 d . . . . .
C12 C 0.1313(3) 0.3014(2) 0.53586(8) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.0271 0.3117 0.5416 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3761(2) 0.2020(2) 0.55658(8) 0.0418(5) Uani 1 1 d . . . . .
H13 H 0.4386 0.1451 0.5767 0.050 Uiso 1 1 calc R . . . .
C14 C 0.2531(3) 0.0931(3) 0.69772(8) 0.0449(5) Uani 1 1 d . . . . .
H14 H 0.2085 -0.0001 0.6972 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2626(2) -0.1198(2) 0.58485(8) 0.0407(5) Uani 1 1 d . . . . .
H15 H 0.3023 -0.0831 0.5544 0.049 Uiso 1 1 calc R . . . .
C16 C 0.3484(3) 0.3567(3) 0.48736(9) 0.0533(6) Uani 1 1 d . . . . .
H16 H 0.3912 0.4047 0.4613 0.064 Uiso 1 1 calc R . . . .
C17 C 0.3150(2) 0.3183(2) 0.65923(8) 0.0430(5) Uani 1 1 d . . . . .
H17 H 0.3129 0.3787 0.6322 0.052 Uiso 1 1 calc R . . . .
C18 C 0.4383(3) 0.2707(3) 0.51715(9) 0.0503(6) Uani 1 1 d . . . . .
H18 H 0.5419 0.2587 0.5107 0.060 Uiso 1 1 calc R . . . .
C19 C 0.1946(3) 0.3711(3) 0.49644(8) 0.0496(6) Uani 1 1 d . . . . .
H19 H 0.1327 0.4279 0.4761 0.060 Uiso 1 1 calc R . . . .
C20 C 0.3255(3) 0.1433(3) 0.73940(8) 0.0546(6) Uani 1 1 d . . . . .
H20 H 0.3289 0.0833 0.7665 0.066 Uiso 1 1 calc R . . . .
C21 C -0.2359(4) 0.0865(3) 0.67831(13) 0.0971(12) Uani 1 1 d . . . . .
H21A H -0.2739 0.0321 0.6510 0.146 Uiso 1 1 calc GR . . . .
H21B H -0.3205 0.1199 0.6971 0.146 Uiso 1 1 calc GR . . . .
H21C H -0.1708 0.0241 0.6977 0.146 Uiso 1 1 calc GR . . . .
C22 C 0.3862(3) 0.3679(3) 0.70107(9) 0.0545(6) Uani 1 1 d . . . . .
H22 H 0.4303 0.4613 0.7019 0.065 Uiso 1 1 calc R . . . .
C23 C 0.3923(3) 0.2805(3) 0.74120(9) 0.0588(7) Uani 1 1 d . . . . .
H23 H 0.4409 0.3135 0.7692 0.071 Uiso 1 1 calc R . . . .
C24 C -0.0056(3) -0.2363(2) 0.63222(10) 0.0513(6) Uani 1 1 d . . . . .
H24A H -0.0806 -0.2428 0.6061 0.062 Uiso 1 1 calc R . . . .
H24B H -0.0544 -0.2687 0.6615 0.062 Uiso 1 1 calc R . . . .
C25 C 0.1283(3) -0.3368(3) 0.62170(10) 0.0599(7) Uani 1 1 d . . . . .
H25A H 0.0911 -0.4359 0.6154 0.072 Uiso 1 1 calc R . . . .
H25B H 0.1972 -0.3405 0.6494 0.072 Uiso 1 1 calc R . . . .
C26 C -0.0433(3) 0.3463(4) 0.71052(10) 0.0901(11) Uani 1 1 d . . . . .
H26A H 0.0115 0.2778 0.7308 0.135 Uiso 1 1 calc GR . . . .
H26B H -0.1248 0.3904 0.7283 0.135 Uiso 1 1 calc GR . . . .
H26C H 0.0256 0.4218 0.7000 0.135 Uiso 1 1 calc GR . . . .
C27 C 0.2141(3) -0.2804(2) 0.57826(9) 0.0516(6) Uani 1 1 d . . . . .
H27A H 0.1487 -0.2889 0.5498 0.062 Uiso 1 1 calc R . . . .
H27B H 0.3043 -0.3408 0.5734 0.062 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
Si1 O2 1.6480(14) . ?
Si1 C10 1.847(2) . ?
Si1 C21 1.852(3) . ?
Si1 C26 1.855(3) . ?
O2 C6 1.431(2) . ?
O1 C7 1.401(2) . ?
O1 C24 1.444(2) . ?
N1 N2 1.230(2) . ?
N1 C7 1.492(2) . ?
N2 N11 1.127(2) . ?
N3 N4 1.206(2) . ?
N3 N5 1.123(3) . ?
N4 C15 1.474(3) . ?
C6 C7 1.584(3) . ?
C6 C8 1.537(3) . ?
C6 C9 1.543(3) . ?
C7 C15 1.548(3) . ?
C8 C12 1.382(3) . ?
C8 C13 1.392(3) . ?
C9 C14 1.385(3) . ?
C9 C17 1.390(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C19 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C18 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C20 1.387(3) . ?
C15 H15 0.9800 . ?
C15 C27 1.526(3) . ?
C16 H16 0.9300 . ?
C16 C18 1.373(3) . ?
C16 C19 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C22 1.385(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C23 1.374(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.369(3) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.513(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C27 1.521(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Si1 C10 101.53(9) . . ?
O2 Si1 C21 113.05(11) . . ?
O2 Si1 C26 114.36(11) . . ?
C10 Si1 C21 109.59(14) . . ?
C10 Si1 C26 108.87(13) . . ?
C21 Si1 C26 109.09(17) . . ?
C6 O2 Si1 142.11(12) . . ?
C7 O1 C24 115.65(16) . . ?
N2 N1 C7 118.15(18) . . ?
N11 N2 N1 170.8(2) . . ?
N5 N3 N4 172.1(3) . . ?
N3 N4 C15 117.73(19) . . ?
O2 C6 C7 104.80(15) . . ?
O2 C6 C8 106.70(15) . . ?
O2 C6 C9 107.63(15) . . ?
C8 C6 C7 108.19(15) . . ?
C8 C6 C9 110.85(16) . . ?
C9 C6 C7 117.96(16) . . ?
O1 C7 N1 111.91(15) . . ?
O1 C7 C6 106.64(15) . . ?
O1 C7 C15 112.35(17) . . ?
N1 C7 C6 108.10(15) . . ?
N1 C7 C15 100.31(16) . . ?
C15 C7 C6 117.45(16) . . ?
C12 C8 C6 120.83(18) . . ?
C12 C8 C13 118.0(2) . . ?
C13 C8 C6 121.12(18) . . ?
C14 C9 C6 124.68(19) . . ?
C14 C9 C17 117.49(19) . . ?
C17 C9 C6 117.37(18) . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C12 H12 119.6 . . ?
C8 C12 C19 120.9(2) . . ?
C19 C12 H12 119.6 . . ?
C8 C13 H13 119.6 . . ?
C18 C13 C8 120.9(2) . . ?
C18 C13 H13 119.6 . . ?
C9 C14 H14 119.6 . . ?
C9 C14 C20 120.8(2) . . ?
C20 C14 H14 119.6 . . ?
N4 C15 C7 107.89(17) . . ?
N4 C15 H15 108.8 . . ?
N4 C15 C27 112.72(18) . . ?
C7 C15 H15 108.8 . . ?
C27 C15 C7 109.83(17) . . ?
C27 C15 H15 108.8 . . ?
C18 C16 H16 120.3 . . ?
C18 C16 C19 119.4(2) . . ?
C19 C16 H16 120.3 . . ?
C9 C17 H17 119.3 . . ?
C22 C17 C9 121.3(2) . . ?
C22 C17 H17 119.3 . . ?
C13 C18 H18 119.8 . . ?
C16 C18 C13 120.5(2) . . ?
C16 C18 H18 119.8 . . ?
C12 C19 H19 119.9 . . ?
C16 C19 C12 120.3(2) . . ?
C16 C19 H19 119.9 . . ?
C14 C20 H20 119.5 . . ?
C23 C20 C14 120.9(2) . . ?
C23 C20 H20 119.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22 119.7 . . ?
C23 C22 C17 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C20 C23 H23 120.5 . . ?
C22 C23 C20 118.9(2) . . ?
C22 C23 H23 120.5 . . ?
O1 C24 H24A 109.4 . . ?
O1 C24 H24B 109.4 . . ?
O1 C24 C25 111.36(19) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C24 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C24 C25 C27 110.0(2) . . ?
H25A C25 H25B 108.2 . . ?
C27 C25 H25A 109.7 . . ?
C27 C25 H25B 109.7 . . ?
Si1 C26 H26A 109.5 . . ?
Si1 C26 H26B 109.5 . . ?
Si1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 C27 H27A 109.4 . . ?
C15 C27 H27B 109.4 . . ?
C25 C27 C15 111.39(19) . . ?
C25 C27 H27A 109.4 . . ?
C25 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?

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
Si1 O2 C6 C7 96.3(2) . . . . ?
Si1 O2 C6 C8 -149.05(16) . . . . ?
Si1 O2 C6 C9 -30.0(3) . . . . ?
O2 C6 C7 O1 -59.92(17) . . . . ?
O2 C6 C7 N1 60.58(19) . . . . ?
O2 C6 C7 C15 173.03(16) . . . . ?
O2 C6 C8 C12 -11.4(3) . . . . ?
O2 C6 C8 C13 167.81(18) . . . . ?
O2 C6 C9 C14 89.2(2) . . . . ?
O2 C6 C9 C17 -82.9(2) . . . . ?
O1 C7 C15 N4 -71.8(2) . . . . ?
O1 C7 C15 C27 51.4(2) . . . . ?
O1 C24 C25 C27 -54.4(3) . . . . ?
N1 C7 C15 N4 169.17(17) . . . . ?
N1 C7 C15 C27 -67.6(2) . . . . ?
N2 N1 C7 O1 45.3(2) . . . . ?
N2 N1 C7 C6 -71.8(2) . . . . ?
N2 N1 C7 C15 164.66(19) . . . . ?
N3 N4 C15 C7 160.0(2) . . . . ?
N3 N4 C15 C27 38.6(3) . . . . ?
N4 C15 C27 C25 68.3(2) . . . . ?
C6 C7 C15 N4 52.4(2) . . . . ?
C6 C7 C15 C27 175.62(17) . . . . ?
C6 C8 C12 C19 178.36(19) . . . . ?
C6 C8 C13 C18 -178.83(19) . . . . ?
C6 C9 C14 C20 -171.9(2) . . . . ?
C6 C9 C17 C22 172.1(2) . . . . ?
C7 O1 C24 C25 56.4(3) . . . . ?
C7 C6 C8 C12 100.9(2) . . . . ?
C7 C6 C8 C13 -79.9(2) . . . . ?
C7 C6 C9 C14 -29.0(3) . . . . ?
C7 C6 C9 C17 158.97(18) . . . . ?
C7 C15 C27 C25 -52.1(2) . . . . ?
C8 C6 C7 O1 -173.48(14) . . . . ?
C8 C6 C7 N1 -52.99(19) . . . . ?
C8 C6 C7 C15 59.5(2) . . . . ?
C8 C6 C9 C14 -154.5(2) . . . . ?
C8 C6 C9 C17 33.5(2) . . . . ?
C8 C12 C19 C16 0.2(3) . . . . ?
C8 C13 C18 C16 0.8(4) . . . . ?
C9 C6 C7 O1 59.7(2) . . . . ?
C9 C6 C7 N1 -179.76(16) . . . . ?
C9 C6 C7 C15 -67.3(2) . . . . ?
C9 C6 C8 C12 -128.31(19) . . . . ?
C9 C6 C8 C13 50.9(2) . . . . ?
C9 C14 C20 C23 0.1(4) . . . . ?
C9 C17 C22 C23 0.7(4) . . . . ?
C10 Si1 O2 C6 163.0(2) . . . . ?
C12 C8 C13 C18 0.4(3) . . . . ?
C13 C8 C12 C19 -0.9(3) . . . . ?
C14 C9 C17 C22 -0.5(3) . . . . ?
C14 C20 C23 C22 0.1(4) . . . . ?
C17 C9 C14 C20 0.1(3) . . . . ?
C17 C22 C23 C20 -0.5(4) . . . . ?
C18 C16 C19 C12 1.1(4) . . . . ?
C19 C16 C18 C13 -1.5(4) . . . . ?
C21 Si1 O2 C6 -79.7(2) . . . . ?
C24 O1 C7 N1 57.3(2) . . . . ?
C24 O1 C7 C6 175.32(15) . . . . ?
C24 O1 C7 C15 -54.7(2) . . . . ?
C24 C25 C27 C15 54.4(3) . . . . ?
C26 Si1 O2 C6 45.9(2) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 997265'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_chenzhm_0328
_audit_creation_date             2014-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_weight         307.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.6242(13)
_cell_length_b                   10.2987(12)
_cell_length_c                   10.3691(14)
_cell_angle_alpha                61.409(13)
_cell_angle_beta                 80.700(12)
_cell_angle_gamma                86.903(11)
_cell_volume                     797.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1579
_cell_measurement_temperature    294.52(10)
_cell_measurement_theta_max      24.5650
_cell_measurement_theta_min      3.8780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5760
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.648
_diffrn_reflns_theta_min         3.030
_diffrn_ambient_temperature      294.52(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0044633000
_diffrn_orient_matrix_UB_12      -0.0781356000
_diffrn_orient_matrix_UB_13      0.0395556000
_diffrn_orient_matrix_UB_21      0.0731405000
_diffrn_orient_matrix_UB_22      0.0038829000
_diffrn_orient_matrix_UB_23      -0.0444609000
_diffrn_orient_matrix_UB_31      0.0397655000
_diffrn_orient_matrix_UB_32      0.0060551000
_diffrn_orient_matrix_UB_33      0.0517382000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2089
_reflns_number_total             3576
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.182
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.063
_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)+(0.0525P)²+0.1167P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1729
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_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
O1 O 0.00335(17) 0.38150(15) 0.22158(17) 0.0465(4) Uani 1 1 d . . . . .
O2 O -0.3095(2) 0.18687(19) 0.48915(19) 0.0618(5) Uani 1 1 d . . . . .
N1 N -0.1472(3) 0.3434(2) 0.5966(2) 0.0559(6) Uani 1 1 d . . . . .
N2 N -0.1919(3) 0.2255(2) 0.7071(3) 0.0572(6) Uani 1 1 d . . . . .
N3 N -0.2409(3) 0.1261(3) 0.8145(3) 0.0836(8) Uani 1 1 d . . . . .
C1 C -0.4259(3) 0.1688(3) 0.2660(3) 0.0583(7) Uani 1 1 d . . . . .
H1 H -0.4531 0.0942 0.3634 0.070 Uiso 1 1 calc R . . . .
C2 C -0.4930(3) 0.1692(3) 0.1538(4) 0.0721(9) Uani 1 1 d . . . . .
H2 H -0.5643 0.0942 0.1757 0.087 Uiso 1 1 calc R . . . .
C3 C -0.4554(3) 0.2795(4) 0.0105(4) 0.0753(9) Uani 1 1 d . . . . .
H3 H -0.5030 0.2804 -0.0643 0.090 Uiso 1 1 calc R . . . .
C4 C -0.3475(3) 0.3888(3) -0.0231(3) 0.0692(8) Uani 1 1 d . . . . .
H4 H -0.3204 0.4626 -0.1209 0.083 Uiso 1 1 calc R . . . .
C5 C -0.2792(3) 0.3891(3) 0.0884(3) 0.0555(7) Uani 1 1 d . . . . .
H5 H -0.2068 0.4638 0.0651 0.067 Uiso 1 1 calc R . . . .
C6 C -0.3170(3) 0.2801(2) 0.2342(3) 0.0442(5) Uani 1 1 d . . . . .
C7 C -0.2537(3) 0.2747(2) 0.3625(3) 0.0434(5) Uani 1 1 d . . . . .
C8 C -0.1170(3) 0.3797(2) 0.3354(2) 0.0408(5) Uani 1 1 d . . . . .
C9 C -0.1750(3) 0.5381(2) 0.2784(2) 0.0416(5) Uani 1 1 d . . . . .
C10 C -0.0878(3) 0.6552(2) 0.1583(3) 0.0504(6) Uani 1 1 d . . . . .
H10 H 0.0053 0.6373 0.1107 0.061 Uiso 1 1 calc R . . . .
C11 C -0.1393(3) 0.7988(3) 0.1092(3) 0.0602(7) Uani 1 1 d . . . . .
H11 H -0.0818 0.8766 0.0271 0.072 Uiso 1 1 calc R . . . .
C12 C -0.2748(4) 0.8270(3) 0.1811(3) 0.0623(7) Uani 1 1 d . . . . .
H12 H -0.3079 0.9236 0.1484 0.075 Uiso 1 1 calc R . . . .
C13 C -0.3606(3) 0.7126(3) 0.3007(3) 0.0632(7) Uani 1 1 d . . . . .
H13 H -0.4517 0.7317 0.3499 0.076 Uiso 1 1 calc R . . . .
C14 C -0.3118(3) 0.5682(3) 0.3488(3) 0.0553(6) Uani 1 1 d . . . . .
H14 H -0.3717 0.4908 0.4290 0.066 Uiso 1 1 calc R . . . .
C15 C -0.0384(3) 0.3337(2) 0.4751(2) 0.0454(6) Uani 1 1 d . . . . .
H15 H 0.0450 0.4084 0.4443 0.054 Uiso 1 1 calc R . . . .
C16 C 0.0442(3) 0.1872(2) 0.5233(3) 0.0540(6) Uani 1 1 d . . . . .
H16A H 0.0996 0.1673 0.6049 0.065 Uiso 1 1 calc R . . . .
H16B H -0.0325 0.1076 0.5571 0.065 Uiso 1 1 calc R . . . .
C17 C 0.1597(3) 0.1948(3) 0.3926(3) 0.0610(7) Uani 1 1 d . . . . .
H17A H 0.2444 0.2650 0.3678 0.073 Uiso 1 1 calc R . . . .
H17B H 0.2049 0.0985 0.4195 0.073 Uiso 1 1 calc R . . . .
C18 C 0.0779(3) 0.2416(3) 0.2597(3) 0.0558(6) Uani 1 1 d . . . . .
H18A H 0.1538 0.2504 0.1758 0.067 Uiso 1 1 calc R . . . .
H18B H -0.0006 0.1669 0.2817 0.067 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 C8 1.433(3) . ?
O1 C18 1.443(2) . ?
O2 C7 1.217(3) . ?
N1 N2 1.230(3) . ?
N1 C15 1.486(3) . ?
N2 N3 1.127(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(4) . ?
C1 C6 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 C7 1.493(3) . ?
C7 C8 1.543(3) . ?
C8 C9 1.532(3) . ?
C8 C15 1.552(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.385(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C15 C16 1.521(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.518(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.507(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C18 114.41(16) . . ?
N2 N1 C15 116.4(2) . . ?
N3 N2 N1 172.7(3) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 117.1(2) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 124.6(2) . . ?
O2 C7 C6 120.1(2) . . ?
O2 C7 C8 119.58(19) . . ?
C6 C7 C8 120.31(19) . . ?
O1 C8 C7 109.86(17) . . ?
O1 C8 C9 106.72(16) . . ?
O1 C8 C15 106.90(17) . . ?
C7 C8 C15 113.34(17) . . ?
C9 C8 C7 109.81(17) . . ?
C9 C8 C15 109.97(17) . . ?
C10 C9 C8 120.4(2) . . ?
C14 C9 C8 120.8(2) . . ?
C14 C9 C10 118.7(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.7(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C8 112.20(18) . . ?
N1 C15 H15 105.6 . . ?
N1 C15 C16 114.22(19) . . ?
C8 C15 H15 105.6 . . ?
C16 C15 C8 112.67(18) . . ?
C16 C15 H15 105.6 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 C15 109.17(19) . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 C16 110.27(19) . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O1 C18 C17 110.72(19) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?

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 C8 C9 C10 -15.4(3) . . . . ?
O1 C8 C9 C14 167.09(19) . . . . ?
O1 C8 C15 N1 173.80(16) . . . . ?
O1 C8 C15 C16 -55.6(2) . . . . ?
O2 C7 C8 O1 134.0(2) . . . . ?
O2 C7 C8 C9 -108.9(2) . . . . ?
O2 C7 C8 C15 14.5(3) . . . . ?
N1 C15 C16 C17 -176.17(19) . . . . ?
N2 N1 C15 C8 110.4(2) . . . . ?
N2 N1 C15 C16 -19.4(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C6 C7 O2 -8.2(3) . . . . ?
C1 C6 C7 C8 171.59(19) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 O2 169.6(2) . . . . ?
C5 C6 C7 C8 -10.5(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C7 C8 O1 -45.8(2) . . . . ?
C6 C7 C8 C9 71.2(2) . . . . ?
C6 C7 C8 C15 -165.33(18) . . . . ?
C7 C8 C9 C10 -134.4(2) . . . . ?
C7 C8 C9 C14 48.1(3) . . . . ?
C7 C8 C15 N1 -65.0(2) . . . . ?
C7 C8 C15 C16 65.6(2) . . . . ?
C8 O1 C18 C17 -62.0(2) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C14 C13 177.3(2) . . . . ?
C8 C15 C16 C17 54.3(3) . . . . ?
C9 C8 C15 N1 58.3(2) . . . . ?
C9 C8 C15 C16 -171.10(19) . . . . ?
C9 C10 C11 C12 1.6(4) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C9 1.1(4) . . . . ?
C14 C9 C10 C11 -1.0(3) . . . . ?
C15 C8 C9 C10 100.2(2) . . . . ?
C15 C8 C9 C14 -77.3(3) . . . . ?
C15 C16 C17 C18 -53.5(3) . . . . ?
C16 C17 C18 O1 56.6(3) . . . . ?
C18 O1 C8 C7 -64.1(2) . . . . ?
C18 O1 C8 C9 176.94(16) . . . . ?
C18 O1 C8 C15 59.3(2) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 997266'
