##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2021-07-28
_journal_date_accepted     2021-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2021
_journal_volume     77
_journal_issue      9
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989021007854
_journal_coeditor_code     ZL5021
_publ_contact_author_name     'Allegra L. Liberman-Martin'
_publ_contact_author_address
;
Chemistry and Biochemistry Program, Schmid College of Science and Technology,
Chapman University, 1 University Drive, Orange, CA 92866, USA
;
_publ_contact_author_email     'libermanmartin@chapman.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structure of
2-(2,6-diisopropylphenyl)-N,N-diethyl-3,3-dimethyl-2-\
azaspiro[4.5]decan-1-amine: a diethylamine adduct of a
cyclic(alkyl)(amino)carbene (CAAC)
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Naumann, Roxanne A.' .
;
Chemistry and Biochemistry Program, Schmid College of Science and Technology,
Chapman University, 1 University Drive, Orange, CA 92866, USA
;
    'Ziller, Joseph W.' .
;
Department of Chemistry, University of California, Irvine, Natural Sciences II,
Irvine, CA 92697, USA
;
    'Liberman-Martin, Allegra L.' .
;
Chemistry and Biochemistry Program, Schmid College of Science and Technology,
Chapman University, 1 University Drive, Orange, CA 92866, USA
;
_publ_section_synopsis
;
A diethylamine adduct of a cyclic(alkyl)(amino)carbene was synthesized and
characterized by single-crystal X-ray diffraction and NMR spectroscopy.
;
_chemical_name_systematic
;\
2-(2,6-Diisopropylbenzene)-N,N-diethyl-3,3-dimethyl-\
2-azaspiro[4.5]decan-1-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H46 N2'
_chemical_formula_sum     'C27 H46 N2'
_chemical_formula_iupac     'C27 H46 N2'
_chemical_formula_weight     398.66
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.3319(11)
_cell_length_b     14.4082(13)
_cell_length_c     13.6155(12)
_cell_angle_alpha     90
_cell_angle_beta     96.4589(16)
_cell_angle_gamma     90
_cell_volume     2403.9(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9991
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     30.48
_cell_measurement_temperature     93(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.248
_exptl_crystal_size_min     0.191
_exptl_crystal_density_diffrn     1.102
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     not_measured
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     0.063
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_absorpt_correction_T_min     0.8228
_exptl_absorpt_correction_T_max     0.8622
_diffrn_ambient_temperature     93(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     57200
_diffrn_reflns_av_R_equivalents     0.0690
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_theta_min     2.065
_diffrn_reflns_theta_max     29.575
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
A colorless crystal of approximate dimensions 0.191 x 0.248 x 0.250 mm
was mounted in a cryoloop and transferred to a Bruker SMART APEX II
diffractometer.  The APEX2 program package was used to determine the
unit-cell parameters and for data collection (25 sec/frame scan time).
The raw frame data was processed using SAINT and SADABS to yield the
reflection data file.  Subsequent calculations were carried out using
the SHELXTL program package.  The diffraction symmetry was 2/m and the
systematic absences were consistent with the monoclinic space group
P21/n that was later determined to be correct.
The structure was solved by direct methods and refined on F2 by
full-matrix least-squares techniques.  The analytical scattering factors
for neutral atoms were used throughout the analysis.  Hydrogen atoms
were included using a riding model.
Least-squares analysis yielded wR2 = 0.1207 and Goof = 1.018 for 270
variables refined against 6744 data (0.72 ), R1 = 0.0482 for those 5087
data with I > 2.0sigma(I).
;
_reflns_number_total     6744
_reflns_number_gt     5087
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0721
_refine_ls_R_factor_gt     0.0482
_refine_ls_wR_factor_gt     0.1058
_refine_ls_wR_factor_ref     0.1207
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     6744
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0481P)²+1.1815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.381
_refine_diff_density_min     -0.250
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014/4 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.21509(8) 0.23294(7) 0.51919(7) 0.0098(2) Uani d 1 . .
    N N2 0.19958(8) 0.23854(7) 0.33444(7) 0.0116(2) Uani d 1 . .
    C C1 0.26502(9) 0.25804(8) 0.42898(8) 0.0098(2) Uani d 1 . .
    H H1A 0.2755 0.3269 0.4316 0.012 Uiso calc 1 . .
    C C2 0.38287(9) 0.21455(8) 0.44118(8) 0.0100(2) Uani d 1 . .
    C C3 0.40228(9) 0.19144(8) 0.55256(8) 0.0116(2) Uani d 1 . .
    H H3A 0.4473 0.1347 0.5633 0.014 Uiso calc 1 . .
    H H3B 0.4410 0.2432 0.5892 0.014 Uiso calc 1 . .
    C C4 0.28990(9) 0.17623(8) 0.58916(9) 0.0112(2) Uani d 1 . .
    C C5 0.46257(10) 0.28977(8) 0.41182(9) 0.0127(2) Uani d 1 . .
    H H5A 0.4390 0.3100 0.3433 0.015 Uiso calc 1 . .
    H H5B 0.4585 0.3442 0.4556 0.015 Uiso calc 1 . .
    C C6 0.58148(10) 0.25689(9) 0.41836(9) 0.0149(2) Uani d 1 . .
    H H6A 0.6277 0.3075 0.3970 0.018 Uiso calc 1 . .
    H H6B 0.6078 0.2413 0.4878 0.018 Uiso calc 1 . .
    C C7 0.59148(10) 0.17188(9) 0.35313(9) 0.0149(2) Uani d 1 . .
    H H7A 0.6677 0.1492 0.3614 0.018 Uiso calc 1 . .
    H H7B 0.5725 0.1890 0.2829 0.018 Uiso calc 1 . .
    C C8 0.51526(10) 0.09514(9) 0.38112(9) 0.0140(2) Uani d 1 . .
    H H8A 0.5397 0.0735 0.4490 0.017 Uiso calc 1 . .
    H H8B 0.5193 0.0419 0.3357 0.017 Uiso calc 1 . .
    C C9 0.39694(9) 0.12857(8) 0.37605(9) 0.0122(2) Uani d 1 . .
    H H9A 0.3512 0.0775 0.3973 0.015 Uiso calc 1 . .
    H H9B 0.3703 0.1438 0.3066 0.015 Uiso calc 1 . .
    C C10 0.25722(10) 0.07300(8) 0.58361(9) 0.0144(2) Uani d 1 . .
    H H10A 0.1848 0.0655 0.6058 0.022 Uiso calc 1 . .
    H H10B 0.3107 0.0366 0.6262 0.022 Uiso calc 1 . .
    H H10C 0.2554 0.0512 0.5152 0.022 Uiso calc 1 . .
    C C11 0.29103(10) 0.20714(9) 0.69696(9) 0.0141(2) Uani d 1 . .
    H H11A 0.3137 0.2723 0.7032 0.021 Uiso calc 1 . .
    H H11B 0.3424 0.1685 0.7392 0.021 Uiso calc 1 . .
    H H11C 0.2177 0.2004 0.7174 0.021 Uiso calc 1 . .
    C C12 0.12797(10) 0.31610(9) 0.29816(9) 0.0152(3) Uani d 1 . .
    H H12A 0.1066 0.3513 0.3554 0.018 Uiso calc 1 . .
    H H12B 0.0607 0.2908 0.2612 0.018 Uiso calc 1 . .
    C C13 0.18274(12) 0.38151(10) 0.23150(11) 0.0228(3) Uani d 1 . .
    H H13A 0.1331 0.4328 0.2110 0.034 Uiso calc 1 . .
    H H13B 0.2006 0.3477 0.1730 0.034 Uiso calc 1 . .
    H H13C 0.2498 0.4062 0.2675 0.034 Uiso calc 1 . .
    C C14 0.14360(10) 0.14878(9) 0.32281(9) 0.0142(2) Uani d 1 . .
    H H14A 0.0682 0.1555 0.3404 0.017 Uiso calc 1 . .
    H H14B 0.1821 0.1031 0.3686 0.017 Uiso calc 1 . .
    C C15 0.13992(11) 0.11302(10) 0.21688(9) 0.0196(3) Uani d 1 . .
    H H15A 0.1024 0.0530 0.2114 0.029 Uiso calc 1 . .
    H H15B 0.2145 0.1056 0.1997 0.029 Uiso calc 1 . .
    H H15C 0.1005 0.1575 0.1716 0.029 Uiso calc 1 . .
    C C16 0.13925(9) 0.29785(8) 0.55420(8) 0.0101(2) Uani d 1 . .
    C C17 0.16954(10) 0.39033(8) 0.58137(8) 0.0118(2) Uani d 1 . .
    C C18 0.08998(10) 0.45134(9) 0.60845(9) 0.0150(2) Uani d 1 . .
    H H18A 0.1097 0.5136 0.6250 0.018 Uiso calc 1 . .
    C C19 -0.01697(10) 0.42321(9) 0.61176(9) 0.0167(3) Uani d 1 . .
    H H19A -0.0700 0.4659 0.6298 0.020 Uiso calc 1 . .
    C C20 -0.04562(10) 0.33259(9) 0.58858(9) 0.0153(3) Uani d 1 . .
    H H20A -0.1185 0.3129 0.5927 0.018 Uiso calc 1 . .
    C C21 0.03019(10) 0.26912(8) 0.55924(8) 0.0117(2) Uani d 1 . .
    C C22 0.28572(10) 0.42758(8) 0.58449(9) 0.0124(2) Uani d 1 . .
    H H22A 0.3346 0.3746 0.5717 0.015 Uiso calc 1 . .
    C C23 0.29540(11) 0.50154(9) 0.50440(9) 0.0173(3) Uani d 1 . .
    H H23A 0.2704 0.4754 0.4393 0.026 Uiso calc 1 . .
    H H23B 0.3717 0.5210 0.5060 0.026 Uiso calc 1 . .
    H H23C 0.2503 0.5553 0.5169 0.026 Uiso calc 1 . .
    C C24 0.32675(11) 0.46913(10) 0.68579(10) 0.0192(3) Uani d 1 . .
    H H24A 0.3178 0.4235 0.7377 0.029 Uiso calc 1 . .
    H H24B 0.2845 0.5250 0.6970 0.029 Uiso calc 1 . .
    H H24C 0.4041 0.4854 0.6873 0.029 Uiso calc 1 . .
    C C25 -0.00794(10) 0.17054(9) 0.53442(9) 0.0134(2) Uani d 1 . .
    H H25A 0.0520 0.1375 0.5050 0.016 Uiso calc 1 . .
    C C26 -0.10981(11) 0.16883(10) 0.45862(10) 0.0213(3) Uani d 1 . .
    H H26A -0.0967 0.2062 0.4010 0.032 Uiso calc 1 . .
    H H26B -0.1720 0.1944 0.4886 0.032 Uiso calc 1 . .
    H H26C -0.1259 0.1047 0.4378 0.032 Uiso calc 1 . .
    C C27 -0.03084(11) 0.11760(10) 0.62790(10) 0.0207(3) Uani d 1 . .
    H H27A 0.0339 0.1199 0.6767 0.031 Uiso calc 1 . .
    H H27B -0.0484 0.0528 0.6109 0.031 Uiso calc 1 . .
    H H27C -0.0926 0.1464 0.6557 0.031 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C16 . 1.4412(15) ?
    N1 C1 . 1.4794(15) ?
    N1 C4 . 1.4928(15) ?
    N2 C14 . 1.4662(16) ?
    N2 C1 . 1.4675(14) ?
    N2 C12 . 1.4745(15) ?
    C1 C2 . 1.5741(16) ?
    C1 H1A . 1.0000 ?
    C2 C3 . 1.5449(16) ?
    C2 C9 . 1.5445(16) ?
    C2 C5 . 1.5456(16) ?
    C3 C4 . 1.5402(16) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C11 . 1.5324(17) ?
    C4 C10 . 1.5406(17) ?
    C5 C6 . 1.5340(17) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.5260(17) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.5271(18) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.5307(16) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.5186(19) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 C15 . 1.5274(17) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 C21 . 1.4162(16) ?
    C16 C17 . 1.4215(17) ?
    C17 C18 . 1.3974(17) ?
    C17 C22 . 1.5260(17) ?
    C18 C19 . 1.3853(18) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.3800(19) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.3978(17) ?
    C20 H20A . 0.9500 ?
    C21 C25 . 1.5222(17) ?
    C22 C24 . 1.5361(17) ?
    C22 C23 . 1.5390(17) ?
    C22 H22A . 1.0000 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 C26 . 1.5337(17) ?
    C25 C27 . 1.5370(18) ?
    C25 H25A . 1.0000 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    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_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C16 N1 C1 . . 117.52(9) ?
    C16 N1 C4 . . 121.44(9) ?
    C1 N1 C4 . . 112.25(9) ?
    C14 N2 C1 . . 117.99(9) ?
    C14 N2 C12 . . 112.05(9) ?
    C1 N2 C12 . . 113.47(9) ?
    N2 C1 N1 . . 116.25(9) ?
    N2 C1 C2 . . 115.24(9) ?
    N1 C1 C2 . . 106.30(9) ?
    N2 C1 H1A . . 106.1 ?
    N1 C1 H1A . . 106.1 ?
    C2 C1 H1A . . 106.1 ?
    C3 C2 C9 . . 112.07(10) ?
    C3 C2 C5 . . 111.85(9) ?
    C9 C2 C5 . . 107.34(9) ?
    C3 C2 C1 . . 103.21(9) ?
    C9 C2 C1 . . 114.88(9) ?
    C5 C2 C1 . . 107.46(9) ?
    C4 C3 C2 . . 107.61(9) ?
    C4 C3 H3A . . 110.2 ?
    C2 C3 H3A . . 110.2 ?
    C4 C3 H3B . . 110.2 ?
    C2 C3 H3B . . 110.2 ?
    H3A C3 H3B . . 108.5 ?
    N1 C4 C11 . . 112.99(10) ?
    N1 C4 C3 . . 103.28(9) ?
    C11 C4 C3 . . 110.91(10) ?
    N1 C4 C10 . . 110.96(9) ?
    C11 C4 C10 . . 107.56(10) ?
    C3 C4 C10 . . 111.18(10) ?
    C6 C5 C2 . . 113.58(10) ?
    C6 C5 H5A . . 108.8 ?
    C2 C5 H5A . . 108.8 ?
    C6 C5 H5B . . 108.8 ?
    C2 C5 H5B . . 108.8 ?
    H5A C5 H5B . . 107.7 ?
    C7 C6 C5 . . 110.69(10) ?
    C7 C6 H6A . . 109.5 ?
    C5 C6 H6A . . 109.5 ?
    C7 C6 H6B . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 108.1 ?
    C6 C7 C8 . . 110.10(10) ?
    C6 C7 H7A . . 109.6 ?
    C8 C7 H7A . . 109.6 ?
    C6 C7 H7B . . 109.6 ?
    C8 C7 H7B . . 109.6 ?
    H7A C7 H7B . . 108.2 ?
    C7 C8 C9 . . 111.79(10) ?
    C7 C8 H8A . . 109.3 ?
    C9 C8 H8A . . 109.3 ?
    C7 C8 H8B . . 109.3 ?
    C9 C8 H8B . . 109.3 ?
    H8A C8 H8B . . 107.9 ?
    C8 C9 C2 . . 113.24(10) ?
    C8 C9 H9A . . 108.9 ?
    C2 C9 H9A . . 108.9 ?
    C8 C9 H9B . . 108.9 ?
    C2 C9 H9B . . 108.9 ?
    H9A C9 H9B . . 107.7 ?
    C4 C10 H10A . . 109.5 ?
    C4 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C4 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C4 C11 H11A . . 109.5 ?
    C4 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C4 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 C13 . . 112.38(10) ?
    N2 C12 H12A . . 109.1 ?
    C13 C12 H12A . . 109.1 ?
    N2 C12 H12B . . 109.1 ?
    C13 C12 H12B . . 109.1 ?
    H12A C12 H12B . . 107.9 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N2 C14 C15 . . 111.30(10) ?
    N2 C14 H14A . . 109.4 ?
    C15 C14 H14A . . 109.4 ?
    N2 C14 H14B . . 109.4 ?
    C15 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C21 C16 C17 . . 118.98(11) ?
    C21 C16 N1 . . 118.78(10) ?
    C17 C16 N1 . . 122.22(10) ?
    C18 C17 C16 . . 119.12(11) ?
    C18 C17 C22 . . 117.14(11) ?
    C16 C17 C22 . . 123.73(10) ?
    C19 C18 C17 . . 121.59(12) ?
    C19 C18 H18A . . 119.2 ?
    C17 C18 H18A . . 119.2 ?
    C20 C19 C18 . . 119.31(12) ?
    C20 C19 H19A . . 120.3 ?
    C18 C19 H19A . . 120.3 ?
    C19 C20 C21 . . 121.47(12) ?
    C19 C20 H20A . . 119.3 ?
    C21 C20 H20A . . 119.3 ?
    C20 C21 C16 . . 119.47(11) ?
    C20 C21 C25 . . 118.29(11) ?
    C16 C21 C25 . . 122.23(11) ?
    C17 C22 C24 . . 112.06(10) ?
    C17 C22 C23 . . 111.79(10) ?
    C24 C22 C23 . . 108.81(10) ?
    C17 C22 H22A . . 108.0 ?
    C24 C22 H22A . . 108.0 ?
    C23 C22 H22A . . 108.0 ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C22 C24 H24A . . 109.5 ?
    C22 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C22 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C21 C25 C26 . . 111.94(10) ?
    C21 C25 C27 . . 111.11(10) ?
    C26 C25 C27 . . 109.66(11) ?
    C21 C25 H25A . . 108.0 ?
    C26 C25 H25A . . 108.0 ?
    C27 C25 H25A . . 108.0 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C25 C27 H27A . . 109.5 ?
    C25 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C25 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C14 N2 C1 N1 . . . . -44.13(14) ?
    C12 N2 C1 N1 . . . . 89.84(12) ?
    C14 N2 C1 C2 . . . . 81.21(13) ?
    C12 N2 C1 C2 . . . . -144.82(10) ?
    C16 N1 C1 N2 . . . . -82.53(12) ?
    C4 N1 C1 N2 . . . . 129.41(10) ?
    C16 N1 C1 C2 . . . . 147.71(10) ?
    C4 N1 C1 C2 . . . . -0.35(12) ?
    N2 C1 C2 C3 . . . . -146.18(10) ?
    N1 C1 C2 C3 . . . . -15.85(11) ?
    N2 C1 C2 C9 . . . . -23.88(14) ?
    N1 C1 C2 C9 . . . . 106.45(11) ?
    N2 C1 C2 C5 . . . . 95.48(11) ?
    N1 C1 C2 C5 . . . . -134.18(10) ?
    C9 C2 C3 C4 . . . . -97.89(11) ?
    C5 C2 C3 C4 . . . . 141.50(10) ?
    C1 C2 C3 C4 . . . . 26.27(12) ?
    C16 N1 C4 C11 . . . . -10.30(15) ?
    C1 N1 C4 C11 . . . . 136.35(10) ?
    C16 N1 C4 C3 . . . . -130.19(11) ?
    C1 N1 C4 C3 . . . . 16.45(12) ?
    C16 N1 C4 C10 . . . . 110.60(12) ?
    C1 N1 C4 C10 . . . . -102.76(11) ?
    C2 C3 C4 N1 . . . . -26.48(12) ?
    C2 C3 C4 C11 . . . . -147.79(10) ?
    C2 C3 C4 C10 . . . . 92.57(11) ?
    C3 C2 C5 C6 . . . . 68.34(13) ?
    C9 C2 C5 C6 . . . . -54.98(13) ?
    C1 C2 C5 C6 . . . . -179.06(9) ?
    C2 C5 C6 C7 . . . . 57.69(13) ?
    C5 C6 C7 C8 . . . . -55.75(13) ?
    C6 C7 C8 C9 . . . . 55.59(13) ?
    C7 C8 C9 C2 . . . . -56.42(13) ?
    C3 C2 C9 C8 . . . . -69.22(13) ?
    C5 C2 C9 C8 . . . . 53.96(13) ?
    C1 C2 C9 C8 . . . . 173.39(10) ?
    C14 N2 C12 C13 . . . . -132.20(11) ?
    C1 N2 C12 C13 . . . . 91.09(13) ?
    C1 N2 C14 C15 . . . . -145.42(11) ?
    C12 N2 C14 C15 . . . . 79.99(13) ?
    C1 N1 C16 C21 . . . . 118.88(11) ?
    C4 N1 C16 C21 . . . . -96.14(13) ?
    C1 N1 C16 C17 . . . . -59.47(14) ?
    C4 N1 C16 C17 . . . . 85.51(14) ?
    C21 C16 C17 C18 . . . . -2.55(16) ?
    N1 C16 C17 C18 . . . . 175.80(10) ?
    C21 C16 C17 C22 . . . . 176.45(10) ?
    N1 C16 C17 C22 . . . . -5.21(17) ?
    C16 C17 C18 C19 . . . . 1.60(18) ?
    C22 C17 C18 C19 . . . . -177.46(11) ?
    C17 C18 C19 C20 . . . . 0.55(19) ?
    C18 C19 C20 C21 . . . . -1.75(19) ?
    C19 C20 C21 C16 . . . . 0.76(18) ?
    C19 C20 C21 C25 . . . . -179.70(11) ?
    C17 C16 C21 C20 . . . . 1.40(16) ?
    N1 C16 C21 C20 . . . . -177.00(10) ?
    C17 C16 C21 C25 . . . . -178.12(10) ?
    N1 C16 C21 C25 . . . . 3.48(16) ?
    C18 C17 C22 C24 . . . . 54.13(14) ?
    C16 C17 C22 C24 . . . . -124.88(12) ?
    C18 C17 C22 C23 . . . . -68.32(14) ?
    C16 C17 C22 C23 . . . . 112.66(13) ?
    C20 C21 C25 C26 . . . . 52.45(15) ?
    C16 C21 C25 C26 . . . . -128.02(12) ?
    C20 C21 C25 C27 . . . . -70.53(14) ?
    C16 C21 C25 C27 . . . . 109.01(13) ?
_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.
;
_shelx_estimated_absorpt_T_min     0.984
_shelx_estimated_absorpt_T_max     0.988
