# 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
#  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_amsm1327

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H30 Li N3'
_chemical_formula_sum            'C14 H30 Li N3'
_chemical_formula_weight         247.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Li Li -0.0003 0.0001 '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'
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'

_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                   7.7542(7)
_cell_length_b                   12.7074(9)
_cell_length_c                   17.2355(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.159(9)
_cell_angle_gamma                90
_cell_volume                     1660.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      2.8952
_cell_measurement_theta_max      30.1328

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.990
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.99830
_shelx_estimated_absorpt_T_max   1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   tube
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17768
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.901
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3275
_reflns_number_gt                2186
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0463P)²+0.0137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3275
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
Li1 Li 0.9765(4) 0.7036(2) 0.30831(19) 0.0300(8) Uani 1 1 d . . . . .
N1 N 0.78699(19) 0.64529(11) 0.23433(8) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.9877(2) 0.84270(11) 0.37260(9) 0.0258(4) Uani 1 1 d . . . . .
N3 N 1.2194(2) 0.66387(12) 0.37871(10) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.6946(2) 0.55773(14) 0.24653(10) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.5607(2) 0.51125(14) 0.19438(11) 0.0264(5) Uani 1 1 d . . . . .
H2 H 0.5037 0.4516 0.2107 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5010(2) 0.55205(15) 0.11163(11) 0.0282(5) Uani 1 1 d . . . . .
H3A H 0.3916 0.5938 0.1076 0.034 Uiso 1 1 calc R U . . .
H3B H 0.4758 0.4926 0.0738 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6464(2) 0.62080(13) 0.09153(10) 0.0241(4) Uani 1 1 d . . . . .
H4A H 0.5992 0.6604 0.0422 0.029 Uiso 1 1 calc R U . . .
H4B H 0.7434 0.5754 0.0818 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7195(2) 0.69860(13) 0.15834(10) 0.0234(4) Uani 1 1 d . . . . .
C6 C 0.7578(3) 0.50977(15) 0.32820(11) 0.0325(5) Uani 1 1 d . . . . .
H6A H 0.6890 0.4463 0.3330 0.049 Uiso 1 1 calc R U . . .
H6B H 0.7423 0.5608 0.3688 0.049 Uiso 1 1 calc R U . . .
H6C H 0.8829 0.4913 0.3355 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8734(3) 0.75966(14) 0.13715(12) 0.0321(5) Uani 1 1 d . . . . .
H7A H 0.9651 0.7102 0.1292 0.048 Uiso 1 1 calc R U . . .
H7B H 0.9223 0.8081 0.1804 0.048 Uiso 1 1 calc R U . . .
H7C H 0.8313 0.7998 0.0883 0.048 Uiso 1 1 calc R U . . .
C8 C 0.5745(3) 0.77719(15) 0.16738(12) 0.0339(5) Uani 1 1 d . . . . .
H8A H 0.5316 0.8134 0.1168 0.051 Uiso 1 1 calc R U . . .
H8B H 0.6227 0.8289 0.2084 0.051 Uiso 1 1 calc R U . . .
H8C H 0.4767 0.7394 0.1827 0.051 Uiso 1 1 calc R U . . .
C9 C 1.2327(3) 0.73488(16) 0.44662(13) 0.0461(6) Uani 1 1 d . . . . .
H9A H 1.3574 0.7389 0.4752 0.055 Uiso 1 1 calc R U . . .
H9B H 1.1630 0.7056 0.4836 0.055 Uiso 1 1 calc R U . . .
C10 C 1.1670(3) 0.84477(15) 0.42235(12) 0.0366(5) Uani 1 1 d . . . . .
H10A H 1.1670 0.8873 0.4705 0.044 Uiso 1 1 calc R U . . .
H10B H 1.2481 0.8787 0.3926 0.044 Uiso 1 1 calc R U . . .
C11 C 1.3408(3) 0.69534(19) 0.32819(17) 0.0651(8) Uani 1 1 d . . . . .
H11A H 1.3366 0.6433 0.2859 0.098 Uiso 1 1 calc R U . . .
H11B H 1.4610 0.6994 0.3602 0.098 Uiso 1 1 calc R U . . .
H11C H 1.3058 0.7644 0.3047 0.098 Uiso 1 1 calc R U . . .
C12 C 1.2606(3) 0.55587(16) 0.40635(16) 0.0570(7) Uani 1 1 d . . . . .
H12A H 1.2444 0.5084 0.3606 0.085 Uiso 1 1 calc R U . . .
H12B H 1.1816 0.5348 0.4411 0.085 Uiso 1 1 calc R U . . .
H12C H 1.3832 0.5523 0.4358 0.085 Uiso 1 1 calc R U . . .
C13 C 0.8556(3) 0.81893(17) 0.41963(14) 0.0497(7) Uani 1 1 d . . . . .
H13A H 0.7380 0.8179 0.3849 0.075 Uiso 1 1 calc R U . . .
H13B H 0.8596 0.8730 0.4605 0.075 Uiso 1 1 calc R U . . .
H13C H 0.8809 0.7500 0.4450 0.075 Uiso 1 1 calc R U . . .
C14 C 0.9456(3) 0.94570(14) 0.33514(12) 0.0338(5) Uani 1 1 d . . . . .
H14A H 1.0342 0.9640 0.3044 0.051 Uiso 1 1 calc R U . . .
H14B H 0.9457 0.9990 0.3762 0.051 Uiso 1 1 calc R U . . .
H14C H 0.8288 0.9430 0.2998 0.051 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
Li1 N1 1.883(4) . ?
Li1 N3 2.077(4) . ?
Li1 N2 2.078(3) . ?
N1 C1 1.363(2) . ?
N1 C5 1.469(2) . ?
N2 C14 1.465(2) . ?
N2 C13 1.466(2) . ?
N2 C10 1.472(2) . ?
N3 C9 1.464(3) . ?
N3 C12 1.466(2) . ?
N3 C11 1.466(3) . ?
C1 C2 1.357(3) . ?
C1 C6 1.517(2) . ?
C2 C3 1.496(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.533(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.531(2) . ?
C5 C8 1.536(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 Li1 N3 141.48(18) . . ?
N1 Li1 N2 129.43(18) . . ?
N3 Li1 N2 87.95(14) . . ?
C1 N1 C5 114.44(15) . . ?
C1 N1 Li1 125.26(15) . . ?
C5 N1 Li1 120.17(14) . . ?
C14 N2 C13 108.11(15) . . ?
C14 N2 C10 109.64(15) . . ?
C13 N2 C10 111.46(16) . . ?
C14 N2 Li1 122.98(15) . . ?
C13 N2 Li1 99.43(14) . . ?
C10 N2 Li1 104.74(14) . . ?
C9 N3 C12 110.09(17) . . ?
C9 N3 C11 111.15(17) . . ?
C12 N3 C11 108.97(17) . . ?
C9 N3 Li1 102.69(15) . . ?
C12 N3 Li1 121.76(16) . . ?
C11 N3 Li1 101.73(16) . . ?
C2 C1 N1 127.35(17) . . ?
C2 C1 C6 119.49(16) . . ?
N1 C1 C6 113.15(16) . . ?
C1 C2 C3 121.36(16) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 108.68(16) . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 C5 111.94(14) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C7 107.30(15) . . ?
N1 C5 C4 112.22(13) . . ?
C7 C5 C4 109.35(14) . . ?
N1 C5 C8 109.88(14) . . ?
C7 C5 C8 108.59(15) . . ?
C4 C5 C8 109.42(15) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 112.61(17) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C9 111.44(16) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N3 Li1 N1 C1 54.0(3) . . . . ?
N2 Li1 N1 C1 -109.4(2) . . . . ?
N3 Li1 N1 C5 -130.3(2) . . . . ?
N2 Li1 N1 C5 66.2(2) . . . . ?
C5 N1 C1 C2 6.1(2) . . . . ?
Li1 N1 C1 C2 -178.05(17) . . . . ?
C5 N1 C1 C6 -175.17(14) . . . . ?
Li1 N1 C1 C6 0.7(2) . . . . ?
N1 C1 C2 C3 2.3(3) . . . . ?
C6 C1 C2 C3 -176.39(16) . . . . ?
C1 C2 C3 C4 18.8(2) . . . . ?
C2 C3 C4 C5 -46.6(2) . . . . ?
C1 N1 C5 C7 -155.16(14) . . . . ?
Li1 N1 C5 C7 28.7(2) . . . . ?
C1 N1 C5 C4 -35.03(19) . . . . ?
Li1 N1 C5 C4 148.87(15) . . . . ?
C1 N1 C5 C8 86.96(17) . . . . ?
Li1 N1 C5 C8 -89.15(19) . . . . ?
C3 C4 C5 N1 57.07(19) . . . . ?
C3 C4 C5 C7 176.01(15) . . . . ?
C3 C4 C5 C8 -65.17(19) . . . . ?
C12 N3 C9 C10 -171.96(18) . . . . ?
C11 N3 C9 C10 67.2(2) . . . . ?
Li1 N3 C9 C10 -40.9(2) . . . . ?
C14 N2 C10 C9 -166.63(15) . . . . ?
C13 N2 C10 C9 73.7(2) . . . . ?
Li1 N2 C10 C9 -32.9(2) . . . . ?
N3 C9 C10 N2 53.1(2) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1002045'
#######################################################################
#
#                 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_amc90smart

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H60 N6 Na2'
_chemical_formula_sum            'C28 H60 N6 Na2'
_chemical_formula_weight         526.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Na Na 0.1353 0.1239 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7005(3)
_cell_length_b                   15.6464(5)
_cell_length_c                   19.4063(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3249.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6667
_cell_measurement_theta_min      3.6257
_cell_measurement_theta_max      73.0000

_exptl_crystal_description       'cut plate'
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.723
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   tube
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22031
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.557
_diffrn_reflns_theta_max         73.151
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3254
_reflns_number_gt                2483
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0761P)²+0.8908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3254
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
Na1 Na 0.08776(6) 0.04709(4) 0.94779(4) 0.0339(2) Uani 1 1 d . . . . .
N1 N 0.10160(14) 0.04103(10) 1.07287(8) 0.0368(4) Uani 1 1 d . . . . .
N2 N 0.31128(15) 0.05022(11) 0.90596(8) 0.0419(4) Uani 1 1 d . . . . .
N3 N 0.10843(15) 0.16970(10) 0.85866(9) 0.0425(4) Uani 1 1 d . . . . .
C1 C 0.18921(18) -0.01256(14) 1.09903(11) 0.0436(5) Uani 1 1 d . . . . .
C2 C 0.2681(2) 0.00228(19) 1.15337(12) 0.0628(7) Uani 1 1 d . . . . .
H2 H 0.3203 -0.0426 1.1694 0.075 Uiso 1 1 calc R U . . .
C3 C 0.1993(2) -0.09710(15) 1.06219(14) 0.0589(6) Uani 1 1 d . . . . .
H3A H 0.2134 -0.0871 1.0130 0.088 Uiso 1 1 calc R U . . .
H3B H 0.1216 -0.1294 1.0684 0.088 Uiso 1 1 calc R U . . .
H3C H 0.2694 -0.1298 1.0812 0.088 Uiso 1 1 calc R U . . .
C4 C 0.2737(2) 0.0869(2) 1.18760(13) 0.0761(9) Uani 1 1 d . . . . .
H4A H 0.3618 0.1025 1.1969 0.091 Uiso 1 1 calc R U . . .
H4B H 0.2286 0.0847 1.2321 0.091 Uiso 1 1 calc R U . . .
C5 C 0.2137(2) 0.15381(17) 1.14054(13) 0.0635(7) Uani 1 1 d . . . . .
H5A H 0.2711 0.1669 1.1019 0.076 Uiso 1 1 calc R U . . .
H5B H 0.1997 0.2072 1.1668 0.076 Uiso 1 1 calc R U . . .
C6 C 0.08864(19) 0.12157(14) 1.11168(11) 0.0455(5) Uani 1 1 d . . . . .
C7 C -0.0050(3) 0.11073(18) 1.16998(14) 0.0698(8) Uani 1 1 d . . . . .
H7A H -0.0883 0.1005 1.1507 0.105 Uiso 1 1 calc R U . . .
H7B H -0.0065 0.1627 1.1981 0.105 Uiso 1 1 calc R U . . .
H7C H 0.0196 0.0620 1.1987 0.105 Uiso 1 1 calc R U . . .
C8 C 0.0408(3) 0.19077(15) 1.06271(14) 0.0698(7) Uani 1 1 d . . . . .
H8A H 0.1005 0.1984 1.0249 0.105 Uiso 1 1 calc R U . . .
H8B H 0.0316 0.2447 1.0879 0.105 Uiso 1 1 calc R U . . .
H8C H -0.0404 0.1736 1.0439 0.105 Uiso 1 1 calc R U . . .
C9 C 0.3202(2) 0.10516(17) 0.84507(12) 0.0550(6) Uani 1 1 d . . . . .
H9A H 0.2940 0.0719 0.8042 0.066 Uiso 1 1 calc R U . . .
H9B H 0.4087 0.1216 0.8384 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2430(2) 0.18442(15) 0.84886(12) 0.0544(6) Uani 1 1 d . . . . .
H10A H 0.2741 0.2200 0.8874 0.065 Uiso 1 1 calc R U . . .
H10B H 0.2551 0.2174 0.8058 0.065 Uiso 1 1 calc R U . . .
C11 C 0.3767(2) 0.08778(14) 0.96472(11) 0.0468(5) Uani 1 1 d . . . . .
H11A H 0.4658 0.0931 0.9539 0.070 Uiso 1 1 calc R U . . .
H11B H 0.3662 0.0510 1.0051 0.070 Uiso 1 1 calc R U . . .
H11C H 0.3420 0.1444 0.9745 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3697(2) -0.03275(16) 0.89101(14) 0.0591(6) Uani 1 1 d . . . . .
H12A H 0.3261 -0.0600 0.8524 0.089 Uiso 1 1 calc R U . . .
H12B H 0.3641 -0.0695 0.9318 0.089 Uiso 1 1 calc R U . . .
H12C H 0.4577 -0.0241 0.8789 0.089 Uiso 1 1 calc R U . . .
C13 C 0.0536(2) 0.13104(16) 0.79724(11) 0.0543(6) Uani 1 1 d . . . . .
H13A H 0.0688 0.1680 0.7574 0.081 Uiso 1 1 calc R U . . .
H13B H -0.0366 0.1241 0.8039 0.081 Uiso 1 1 calc R U . . .
H13C H 0.0918 0.0750 0.7892 0.081 Uiso 1 1 calc R U . . .
C14 C 0.0488(2) 0.25193(14) 0.87136(14) 0.0644(7) Uani 1 1 d . . . . .
H14A H 0.0642 0.2901 0.8322 0.097 Uiso 1 1 calc R U . . .
H14B H 0.0836 0.2774 0.9133 0.097 Uiso 1 1 calc R U . . .
H14C H -0.0413 0.2436 0.8771 0.097 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
Na1 N1 2.4338(17) . ?
Na1 N1 2.4835(16) 5_557 ?
Na1 N2 2.5262(17) . ?
Na1 N3 2.5924(17) . ?
Na1 Na1 3.1314(13) 5_557 ?
N1 C1 1.356(2) . ?
N1 C6 1.475(2) . ?
N1 Na1 2.4835(16) 5_557 ?
N2 C11 1.461(3) . ?
N2 C9 1.464(3) . ?
N2 C12 1.470(3) . ?
N3 C14 1.457(3) . ?
N3 C13 1.460(3) . ?
N3 C10 1.471(3) . ?
C1 C2 1.370(3) . ?
C1 C3 1.507(3) . ?
C2 C4 1.483(4) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.530(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.536(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.521(3) . ?
C6 C8 1.529(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.492(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 Na1 N1 100.90(5) . 5_557 ?
N1 Na1 N2 105.28(6) . . ?
N1 Na1 N2 137.00(6) 5_557 . ?
N1 Na1 N3 133.56(6) . . ?
N1 Na1 N3 111.88(6) 5_557 . ?
N2 Na1 N3 71.97(5) . . ?
N1 Na1 Na1 51.15(4) . 5_557 ?
N1 Na1 Na1 49.75(4) 5_557 5_557 ?
N2 Na1 Na1 141.71(5) . 5_557 ?
N3 Na1 Na1 146.22(5) . 5_557 ?
C1 N1 C6 113.71(17) . . ?
C1 N1 Na1 116.07(13) . . ?
C6 N1 Na1 118.06(12) . . ?
C1 N1 Na1 106.33(12) . 5_557 ?
C6 N1 Na1 118.70(11) . 5_557 ?
Na1 N1 Na1 79.10(5) . 5_557 ?
C11 N2 C9 111.25(17) . . ?
C11 N2 C12 107.80(17) . . ?
C9 N2 C12 109.36(18) . . ?
C11 N2 Na1 102.17(12) . . ?
C9 N2 Na1 109.40(12) . . ?
C12 N2 Na1 116.66(13) . . ?
C14 N3 C13 109.16(18) . . ?
C14 N3 C10 108.19(17) . . ?
C13 N3 C10 110.66(18) . . ?
C14 N3 Na1 120.22(14) . . ?
C13 N3 Na1 101.76(12) . . ?
C10 N3 Na1 106.60(12) . . ?
N1 C1 C2 127.5(2) . . ?
N1 C1 C3 114.48(18) . . ?
C2 C1 C3 118.0(2) . . ?
C1 C2 C4 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
C4 C2 H2 119.3 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 109.05(19) . . ?
C2 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C2 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 C6 111.0(2) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C7 110.28(17) . . ?
N1 C6 C8 108.61(17) . . ?
C7 C6 C8 108.7(2) . . ?
N1 C6 C5 112.63(18) . . ?
C7 C6 C5 109.84(19) . . ?
C8 C6 C5 106.6(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 114.35(18) . . ?
N2 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
N2 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 C9 114.71(18) . . ?
N3 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
N3 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C6 N1 C1 C2 -3.8(3) . . . . ?
Na1 N1 C1 C2 138.13(19) . . . . ?
Na1 N1 C1 C2 -136.23(19) 5_557 . . . ?
C6 N1 C1 C3 177.07(17) . . . . ?
Na1 N1 C1 C3 -41.0(2) . . . . ?
Na1 N1 C1 C3 44.60(19) 5_557 . . . ?
N1 C1 C2 C4 -5.7(3) . . . . ?
C3 C1 C2 C4 173.4(2) . . . . ?
C1 C2 C4 C5 -17.0(3) . . . . ?
C2 C4 C5 C6 46.4(3) . . . . ?
C1 N1 C6 C7 -87.9(2) . . . . ?
Na1 N1 C6 C7 131.02(18) . . . . ?
Na1 N1 C6 C7 38.3(2) 5_557 . . . ?
C1 N1 C6 C8 153.06(19) . . . . ?
Na1 N1 C6 C8 12.0(2) . . . . ?
Na1 N1 C6 C8 -80.7(2) 5_557 . . . ?
C1 N1 C6 C5 35.2(2) . . . . ?
Na1 N1 C6 C5 -105.88(18) . . . . ?
Na1 N1 C6 C5 161.40(14) 5_557 . . . ?
C4 C5 C6 N1 -58.0(3) . . . . ?
C4 C5 C6 C7 65.4(3) . . . . ?
C4 C5 C6 C8 -177.0(2) . . . . ?
C11 N2 C9 C10 -72.4(2) . . . . ?
C12 N2 C9 C10 168.66(19) . . . . ?
Na1 N2 C9 C10 39.8(2) . . . . ?
C14 N3 C10 C9 171.8(2) . . . . ?
C13 N3 C10 C9 -68.6(2) . . . . ?
Na1 N3 C10 C9 41.2(2) . . . . ?
N2 C9 C10 N3 -58.5(3) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1002046'
