# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_muru012
_database_code_depnum_ccdc_archive 'CCDC 1549198'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;



_vrf_PLAT049_muru012             
;
PROBLEM: Calculated Density less than 1.0 gcm-3 .........     0.9641  
RESPONSE: 
Tetraalkylammonium boroydrate salts are known to have a low density 
see for examples: 

Jaron, T. & Grochala, W. (2011). Acta Cryst. E67, o2171.;

Jaron, T., Wegner, W., Cyranski, M. K., Dobrzycki, L. 
& Grochala, W. (2012). J. Solid State Chem. 191, 279--282.;

Maris, T. (2013). Acta Cryst. E69, o1713.

;

_audit_creation_date             2015-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
'N,N,N-Triheptyl-butan-1-aminium (T-4)-(cyano-[kappa]C)tri-hydro-borate'
;
_chemical_formula_moiety         'C28 H60 N, C H3 B N'
_chemical_formula_sum            'C29 H63 B N2'
_chemical_formula_weight         450.62
_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 0.0140 0.0070 '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'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 '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                   9.5425(6)
_cell_length_b                   11.4283(7)
_cell_length_c                   14.5168(9)
_cell_angle_alpha                89.121(4)
_cell_angle_beta                 78.840(3)
_cell_angle_gamma                88.990(3)
_cell_volume                     1552.83(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7706
_cell_measurement_temperature    105
_cell_measurement_theta_max      57.350
_cell_measurement_theta_min      2.700
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.7514
_exptl_absorpt_correction_T_min  0.6115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0888 after correction.
The Ratio of minimum to maximum transmission is 0.8138.
The λ/2 correction factor is 0.00150.
;

_exptl_crystal_colour            'clear light Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.964
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             512
_exptl_crystal_preparation       
;
'Synthesized by reacting tetraheptylammonium bromide 
 with Sodium Cyanoborohydride'
;
_exptl_crystal_recrystallization_method 'Crystallized in Et2O/MeCN/Toluene'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.0944
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33807
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.221
_diffrn_reflns_theta_min         2.699
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2914
_reflns_number_total             6484
_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       
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         6484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1901
_refine_ls_R_factor_gt           0.0860
_refine_ls_restrained_S_all      1.031
_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)+(0.1155P)²+0.1708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2513
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All B(H,H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7477(2) 0.7199(2) 0.48377(16) 0.0467(6) Uani 1 1 d . . . . .
C1 C 0.8601(3) 0.6340(3) 0.4341(2) 0.0497(8) Uani 1 1 d . . . . .
H1A H 0.9405 0.6797 0.3986 0.060 Uiso 1 1 calc R . . . .
H1B H 0.8973 0.5878 0.4826 0.060 Uiso 1 1 calc R . . . .
C2 C 0.8131(3) 0.5493(3) 0.3672(2) 0.0536(8) Uani 1 1 d . . . . .
H2A H 0.7809 0.5935 0.3157 0.064 Uiso 1 1 calc R . . . .
H2B H 0.7316 0.5033 0.4010 0.064 Uiso 1 1 calc R . . . .
C3 C 0.9353(3) 0.4668(3) 0.3264(2) 0.0523(8) Uani 1 1 d . . . . .
H3A H 1.0231 0.5127 0.3059 0.063 Uiso 1 1 calc R . . . .
H3B H 0.9529 0.4111 0.3759 0.063 Uiso 1 1 calc R . . . .
C4 C 0.9049(3) 0.3990(3) 0.2439(2) 0.0526(8) Uani 1 1 d . . . . .
H4A H 0.8976 0.4551 0.1923 0.063 Uiso 1 1 calc R . . . .
H4B H 0.8107 0.3617 0.2629 0.063 Uiso 1 1 calc R . . . .
C5 C 1.0143(3) 0.3048(3) 0.2058(2) 0.0525(8) Uani 1 1 d . . . . .
H5A H 1.1098 0.3405 0.1891 0.063 Uiso 1 1 calc R . . . .
H5B H 1.0179 0.2453 0.2555 0.063 Uiso 1 1 calc R . . . .
C6 C 0.9810(3) 0.2456(3) 0.1205(2) 0.0544(8) Uani 1 1 d . . . . .
H6A H 0.9841 0.3047 0.0696 0.065 Uiso 1 1 calc R . . . .
H6B H 0.8823 0.2159 0.1362 0.065 Uiso 1 1 calc R . . . .
C7 C 1.0806(3) 0.1451(3) 0.0838(2) 0.0617(9) Uani 1 1 d . . . . .
H7A H 1.0450 0.1062 0.0334 0.093 Uiso 1 1 calc GR . . . .
H7B H 1.0849 0.0889 0.1349 0.093 Uiso 1 1 calc GR . . . .
H7C H 1.1763 0.1752 0.0593 0.093 Uiso 1 1 calc GR . . . .
C8 C 0.8281(3) 0.8070(3) 0.5313(2) 0.0505(8) Uani 1 1 d . . . . .
H8A H 0.8911 0.7626 0.5665 0.061 Uiso 1 1 calc R . . . .
H8B H 0.8903 0.8532 0.4819 0.061 Uiso 1 1 calc R . . . .
C9 C 0.7374(3) 0.8908(3) 0.5976(2) 0.0525(8) Uani 1 1 d . . . . .
H9A H 0.6830 0.8469 0.6518 0.063 Uiso 1 1 calc R . . . .
H9B H 0.6683 0.9317 0.5651 0.063 Uiso 1 1 calc R . . . .
C10 C 0.8321(3) 0.9804(3) 0.6322(2) 0.0521(8) Uani 1 1 d . . . . .
H10A H 0.9157 0.9393 0.6495 0.062 Uiso 1 1 calc R . . . .
H10B H 0.8679 1.0361 0.5805 0.062 Uiso 1 1 calc R . . . .
C11 C 0.7542(3) 1.0476(3) 0.7158(2) 0.0550(9) Uani 1 1 d . . . . .
H11A H 0.7162 0.9913 0.7666 0.066 Uiso 1 1 calc R . . . .
H11B H 0.6718 1.0897 0.6978 0.066 Uiso 1 1 calc R . . . .
C12 C 0.8461(3) 1.1359(3) 0.7538(2) 0.0540(8) Uani 1 1 d . . . . .
H12A H 0.9372 1.0973 0.7609 0.065 Uiso 1 1 calc R . . . .
H12B H 0.8690 1.2008 0.7076 0.065 Uiso 1 1 calc R . . . .
C13 C 0.7748(3) 1.1856(3) 0.8467(2) 0.0584(9) Uani 1 1 d . . . . .
H13A H 0.7551 1.1210 0.8934 0.070 Uiso 1 1 calc R . . . .
H13B H 0.6820 1.2215 0.8401 0.070 Uiso 1 1 calc R . . . .
C14 C 0.8634(4) 1.2773(3) 0.8837(3) 0.0715(10) Uani 1 1 d . . . . .
H14A H 0.8810 1.3428 0.8389 0.107 Uiso 1 1 calc GR . . . .
H14B H 0.9549 1.2422 0.8916 0.107 Uiso 1 1 calc GR . . . .
H14C H 0.8115 1.3057 0.9444 0.107 Uiso 1 1 calc GR . . . .
C15 C 0.6690(3) 0.7818(3) 0.4151(2) 0.0492(8) Uani 1 1 d . . . . .
H15A H 0.6117 0.7232 0.3898 0.059 Uiso 1 1 calc R . . . .
H15B H 0.6013 0.8395 0.4503 0.059 Uiso 1 1 calc R . . . .
C16 C 0.7601(3) 0.8446(3) 0.3335(2) 0.0512(8) Uani 1 1 d . . . . .
H16A H 0.8269 0.7880 0.2961 0.061 Uiso 1 1 calc R . . . .
H16B H 0.8174 0.9045 0.3573 0.061 Uiso 1 1 calc R . . . .
C17 C 0.6667(3) 0.9030(3) 0.2712(2) 0.0512(8) Uani 1 1 d . . . . .
H17A H 0.6079 0.8430 0.2490 0.061 Uiso 1 1 calc R . . . .
H17B H 0.6011 0.9603 0.3087 0.061 Uiso 1 1 calc R . . . .
C18 C 0.7551(3) 0.9654(3) 0.1869(2) 0.0596(9) Uani 1 1 d . . . . .
H18A H 0.8222 0.9081 0.1508 0.072 Uiso 1 1 calc R . . . .
H18B H 0.8128 1.0259 0.2098 0.072 Uiso 1 1 calc R . . . .
C19 C 0.6674(3) 1.0236(3) 0.1211(2) 0.0576(9) Uani 1 1 d . . . . .
H19A H 0.7333 1.0499 0.0635 0.069 Uiso 1 1 calc R . . . .
H19B H 0.6039 0.9645 0.1026 0.069 Uiso 1 1 calc R . . . .
C20 C 0.5774(3) 1.1270(3) 0.1623(2) 0.0522(8) Uani 1 1 d . . . . .
H20A H 0.6408 1.1874 0.1793 0.063 Uiso 1 1 calc R . . . .
H20B H 0.5126 1.1016 0.2206 0.063 Uiso 1 1 calc R . . . .
C21 C 0.4887(4) 1.1812(3) 0.0957(2) 0.0657(10) Uani 1 1 d . . . . .
H21A H 0.5522 1.2099 0.0389 0.099 Uiso 1 1 calc GR . . . .
H21B H 0.4312 1.2465 0.1266 0.099 Uiso 1 1 calc GR . . . .
H21C H 0.4254 1.1220 0.0786 0.099 Uiso 1 1 calc GR . . . .
C22 C 0.6349(3) 0.6571(3) 0.5545(2) 0.0487(8) Uani 1 1 d . . . . .
H22A H 0.5592 0.7147 0.5800 0.058 Uiso 1 1 calc R . . . .
H22B H 0.5909 0.5976 0.5207 0.058 Uiso 1 1 calc R . . . .
C23 C 0.6847(3) 0.5970(3) 0.6363(2) 0.0516(8) Uani 1 1 d . . . . .
H23A H 0.7319 0.6543 0.6703 0.062 Uiso 1 1 calc R . . . .
H23B H 0.7550 0.5344 0.6129 0.062 Uiso 1 1 calc R . . . .
C24 C 0.5572(3) 0.5446(3) 0.7030(2) 0.0527(8) Uani 1 1 d . . . . .
H24A H 0.4898 0.6085 0.7281 0.063 Uiso 1 1 calc R . . . .
H24B H 0.5070 0.4918 0.6672 0.063 Uiso 1 1 calc R . . . .
C25 C 0.5985(3) 0.4770(3) 0.7841(2) 0.0581(9) Uani 1 1 d . . . . .
H25A H 0.6441 0.5310 0.8217 0.070 Uiso 1 1 calc R . . . .
H25B H 0.6702 0.4161 0.7589 0.070 Uiso 1 1 calc R . . . .
C26 C 0.4724(3) 0.4182(3) 0.8488(2) 0.0595(9) Uani 1 1 d . . . . .
H26A H 0.4209 0.3711 0.8096 0.071 Uiso 1 1 calc R . . . .
H26B H 0.5108 0.3633 0.8915 0.071 Uiso 1 1 calc R . . . .
C27 C 0.3662(3) 0.4995(3) 0.9074(2) 0.0552(9) Uani 1 1 d . . . . .
H27A H 0.3288 0.5563 0.8656 0.066 Uiso 1 1 calc R . . . .
H27B H 0.4154 0.5441 0.9494 0.066 Uiso 1 1 calc R . . . .
C28 C 0.2421(3) 0.4341(3) 0.9663(2) 0.0658(10) Uani 1 1 d . . . . .
H28A H 0.1919 0.3911 0.9250 0.099 Uiso 1 1 calc GR . . . .
H28B H 0.1760 0.4900 1.0033 0.099 Uiso 1 1 calc GR . . . .
H28C H 0.2785 0.3789 1.0088 0.099 Uiso 1 1 calc GR . . . .
N2 N 0.7527(5) 0.3245(3) 0.5501(3) 0.0969(13) Uani 1 1 d . . . . .
C29 C 0.7380(4) 0.2570(4) 0.5004(3) 0.0815(12) Uani 1 1 d . . . . .
B1 B 0.7138(5) 0.1579(4) 0.4275(4) 0.0688(12) Uani 1 1 d . . . . .
H1C H 0.629(4) 0.096(3) 0.458(3) 0.103 Uiso 1 1 d R . . . .
H1D H 0.800(4) 0.113(3) 0.403(3) 0.103 Uiso 1 1 d R . . . .
H1E H 0.680(4) 0.198(3) 0.366(3) 0.103 Uiso 1 1 d 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
N1 C1 1.522(4) . ?
N1 C8 1.519(3) . ?
N1 C15 1.520(3) . ?
N1 C22 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.515(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.520(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.514(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.510(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.507(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.530(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.508(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.504(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.506(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.521(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.525(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.510(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.522(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.513(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.525(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.510(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.534(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.508(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.521(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N2 C29 1.093(5) . ?
C29 B1 1.611(7) . ?
B1 H1C 1.11(4) . ?
B1 H1D 0.97(4) . ?
B1 H1E 1.10(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 105.8(2) . . ?
C8 N1 C15 110.8(2) . . ?
C15 N1 C1 111.6(2) . . ?
C22 N1 C1 111.0(2) . . ?
C22 N1 C8 111.5(2) . . ?
C22 N1 C15 106.3(2) . . ?
N1 C1 H1A 108.1 . . ?
N1 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
C2 C1 N1 117.0(2) . . ?
C2 C1 H1A 108.1 . . ?
C2 C1 H1B 108.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.5(2) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C3 C4 C5 115.8(2) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.7(2) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C5 C6 C7 114.9(2) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 108.3 . . ?
N1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 N1 116.0(2) . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 110.0(2) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.7(2) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.2(3) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 113.1(3) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.6(3) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 108.2 . . ?
N1 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C16 C15 N1 116.4(2) . . ?
C16 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C15 C16 C17 110.4(2) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 112.0(2) . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.3(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.6(3) . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C19 C20 C21 113.2(3) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 108.1 . . ?
N1 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C23 C22 N1 116.7(2) . . ?
C23 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C22 C23 H23A 109.7 . . ?
C22 C23 H23B 109.7 . . ?
C22 C23 C24 109.8(2) . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 H23A 109.7 . . ?
C24 C23 H23B 109.7 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.3(2) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
C24 C25 C26 113.9(2) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C25 C26 H26A 108.3 . . ?
C25 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C27 C26 C25 115.8(3) . . ?
C27 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
C26 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C26 C27 C28 112.2(3) . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.2 . . ?
C28 C27 H27B 109.2 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 B1 179.1(5) . . ?
C29 B1 H1C 113(2) . . ?
C29 B1 H1D 113(2) . . ?
C29 B1 H1E 111(2) . . ?
H1C B1 H1D 108(3) . . ?
H1C B1 H1E 106(3) . . ?
H1D B1 H1E 105(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23B N2 0.99 2.58 3.380(5) 137.7 .

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
N1 C1 C2 C3 -177.8(2) . . . . ?
N1 C8 C9 C10 -174.4(2) . . . . ?
N1 C15 C16 C17 -179.6(2) . . . . ?
N1 C22 C23 C24 176.9(2) . . . . ?
C1 N1 C8 C9 -171.0(2) . . . . ?
C1 N1 C15 C16 -54.9(3) . . . . ?
C1 N1 C22 C23 63.9(3) . . . . ?
C1 C2 C3 C4 -167.3(2) . . . . ?
C2 C3 C4 C5 -173.5(3) . . . . ?
C3 C4 C5 C6 -176.9(2) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C8 N1 C1 C2 -169.9(2) . . . . ?
C8 N1 C15 C16 62.7(3) . . . . ?
C8 N1 C22 C23 -53.9(3) . . . . ?
C8 C9 C10 C11 -166.0(2) . . . . ?
C9 C10 C11 C12 178.7(2) . . . . ?
C10 C11 C12 C13 -169.5(3) . . . . ?
C11 C12 C13 C14 -177.9(2) . . . . ?
C15 N1 C1 C2 -49.4(3) . . . . ?
C15 N1 C8 C9 67.9(3) . . . . ?
C15 N1 C22 C23 -174.6(3) . . . . ?
C15 C16 C17 C18 -178.9(3) . . . . ?
C16 C17 C18 C19 178.9(3) . . . . ?
C17 C18 C19 C20 67.9(4) . . . . ?
C18 C19 C20 C21 -178.6(3) . . . . ?
C22 N1 C1 C2 69.0(3) . . . . ?
C22 N1 C8 C9 -50.2(3) . . . . ?
C22 N1 C15 C16 -176.1(3) . . . . ?
C22 C23 C24 C25 176.8(3) . . . . ?
C23 C24 C25 C26 -176.9(3) . . . . ?
C24 C25 C26 C27 -69.6(4) . . . . ?
C25 C26 C27 C28 177.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mounted on a Cryoloop'
_olex2_submission_original_sample_id AP-II-61B
_olex2_submission_special_instructions 'No special instructions were received'
