data_ia117c
_publ_requested_journal           JACS
_publ_contact_author_name        'Ivan Aprahamian'
_publ_contact_author_address     
'Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.'
_publ_contact_author_email       ivan.aprahamian@dartmouth.edu
_publ_contact_author_phone       '(603) 646-9666'
_publ_contact_author_fax         '(603) 646-3946'
loop_
_publ_author_name
_publ_author_address
'Aprahamian, Ivan'
'Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.'
_audit_creation_date             2017-01-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2014/6
_publ_contact_author_id_orcid    ?
_publ_section_references         
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.9956(2)
_cell_length_b                   9.5201(4)
_cell_length_c                   17.7596(7)
_cell_angle_alpha                102.122(3)
_cell_angle_beta                 92.757(3)
_cell_angle_gamma                90.570(3)
_cell_volume                     824.66(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0689 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.8838. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.023
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9656
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.291
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1690
_reflns_number_total             3011
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      0.977
_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)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_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. Others
 Fixed Sof: C4(0.5) H4(0.5) C4B(0.5) H4B(0.5) C5(0.5) H5(0.5) C5B(0.5)
 H5B(0.5) C7(0.5) H7(0.5) C7B(0.5) H7B(0.5) C8(0.5) H8(0.5) C8B(0.5) H8B(0.5)
 C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C9B(0.5) H9BA(0.5) H9BB(0.5) H9BC(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C10B(0.5) H10D(0.5) H10E(0.5) H10F(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C4B(H4B), C5(H5), C5B(H5B), C7(H7), C7B(H7B), C8(H8), C8B(H8B),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC), C10(H10A,H10B,H10C), C10B(H10D,H10E,
 H10F), C12(H12A,H12B,H12C)
;
_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
O1 O 0.2684(4) 0.7870(2) 0.21393(10) 0.0320(5) Uani 1 1 d . . . . .
O2 O 0.4427(4) 0.6445(2) 0.11241(10) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.7825(5) 0.5310(2) 0.21908(12) 0.0288(5) Uani 1 1 d . . . . .
N2 N 0.8262(5) 0.4771(3) 0.14529(13) 0.0326(6) Uani 1 1 d . . . . .
N3 N 0.4764(6) 0.7762(3) 0.56390(13) 0.0389(6) Uani 1 1 d . . . . .
C1 C 0.4311(5) 0.6846(3) 0.18210(15) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.5989(5) 0.6261(3) 0.23926(15) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.5654(6) 0.6715(3) 0.32351(15) 0.0268(6) Uani 1 1 d . . . . .
C4 C 0.7931(11) 0.6957(6) 0.3737(3) 0.0292(12) Uani 0.5 1 d . . P A 1
H4 H 0.9663 0.6874 0.3535 0.035 Uiso 0.5 1 calc R . P A 1
C4B C 0.5690(11) 0.5682(6) 0.3684(3) 0.0271(12) Uani 0.5 1 d . . P A 2
H4B H 0.5927 0.4709 0.3436 0.033 Uiso 0.5 1 calc R . P A 2
C5 C 0.7676(12) 0.7319(6) 0.4529(3) 0.0320(13) Uani 0.5 1 d . . P A 1
H5 H 0.9241 0.7498 0.4863 0.038 Uiso 0.5 1 calc R . P A 1
C5B C 0.5400(12) 0.5993(6) 0.4468(3) 0.0318(13) Uani 0.5 1 d . . P A 2
H5B H 0.5417 0.5244 0.4748 0.038 Uiso 0.5 1 calc R . P A 2
C6 C 0.5078(6) 0.7429(3) 0.48532(15) 0.0285(6) Uani 1 1 d . . . . .
C7 C 0.2876(11) 0.7208(6) 0.4321(3) 0.0287(12) Uani 0.5 1 d . . P A 1
H7 H 0.1124 0.7309 0.4509 0.034 Uiso 0.5 1 calc R . P A 1
C7B C 0.5057(11) 0.8481(6) 0.4438(3) 0.0287(12) Uani 0.5 1 d . . P A 2
H7B H 0.4870 0.9455 0.4692 0.034 Uiso 0.5 1 calc R . P A 2
C8 C 0.3150(11) 0.6847(6) 0.3530(3) 0.0282(12) Uani 0.5 1 d . . P A 1
H8 H 0.1599 0.6691 0.3190 0.034 Uiso 0.5 1 calc R . P A 1
C8B C 0.5308(11) 0.8134(6) 0.3646(3) 0.0294(12) Uani 0.5 1 d . . P A 2
H8B H 0.5244 0.8886 0.3368 0.035 Uiso 0.5 1 calc R . P A 2
C9 C 0.7159(15) 0.7998(8) 0.6147(3) 0.0512(18) Uani 0.5 1 d . . P B 1
H9A H 0.8253 0.7136 0.6050 0.077 Uiso 0.5 1 calc GR . P B 1
H9B H 0.6651 0.8201 0.6685 0.077 Uiso 0.5 1 calc GR . P B 1
H9C H 0.8192 0.8816 0.6049 0.077 Uiso 0.5 1 calc GR . P B 1
C9B C 0.4712(16) 0.6622(7) 0.6096(3) 0.0493(18) Uani 0.5 1 d . . P B 2
H9BA H 0.3603 0.5806 0.5815 0.074 Uiso 0.5 1 calc GR . P B 2
H9BB H 0.3959 0.7004 0.6595 0.074 Uiso 0.5 1 calc GR . P B 2
H9BC H 0.6541 0.6302 0.6178 0.074 Uiso 0.5 1 calc GR . P B 2
C10 C 0.2190(13) 0.7928(7) 0.5922(3) 0.0408(15) Uani 0.5 1 d . . P B 1
H10A H 0.1304 0.8718 0.5739 0.061 Uiso 0.5 1 calc GR . P B 1
H10B H 0.2324 0.8146 0.6487 0.061 Uiso 0.5 1 calc GR . P B 1
H10C H 0.1140 0.7037 0.5736 0.061 Uiso 0.5 1 calc GR . P B 1
C10B C 0.4791(14) 0.9215(6) 0.6064(3) 0.0440(16) Uani 0.5 1 d . . P B 2
H10D H 0.6424 0.9711 0.5964 0.066 Uiso 0.5 1 calc GR . P B 2
H10E H 0.4753 0.9225 0.6616 0.066 Uiso 0.5 1 calc GR . P B 2
H10F H 0.3217 0.9705 0.5902 0.066 Uiso 0.5 1 calc GR . P B 2
C11 C 0.0935(6) 0.8437(3) 0.16054(15) 0.0348(7) Uani 1 1 d . . . . .
H11A H -0.0240 0.7662 0.1296 0.042 Uiso 1 1 calc R . . . .
H11B H 0.2006 0.8857 0.1250 0.042 Uiso 1 1 calc R . . . .
C12 C -0.0725(7) 0.9575(3) 0.20768(18) 0.0441(8) Uani 1 1 d . . . . .
H12A H -0.2068 0.9911 0.1738 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.0440 1.0384 0.2336 0.066 Uiso 1 1 calc GR . . . .
H12C H -0.1630 0.9172 0.2463 0.066 Uiso 1 1 calc GR . . . .
C13 C 1.0211(6) 0.3730(3) 0.12661(15) 0.0298(6) Uani 1 1 d . . . . .
C14 C 1.1836(6) 0.3303(3) 0.18282(16) 0.0338(7) Uani 1 1 d . . . . .
H14 H 1.1619 0.3703 0.2358 0.041 Uiso 1 1 calc R . . . .
C15 C 1.3778(6) 0.2290(3) 0.16120(16) 0.0378(7) Uani 1 1 d . . . . .
H15 H 1.4906 0.2004 0.1997 0.045 Uiso 1 1 calc R . . . .
C16 C 1.4096(6) 0.1691(3) 0.08414(17) 0.0398(8) Uani 1 1 d . . . . .
H16 H 1.5433 0.0997 0.0696 0.048 Uiso 1 1 calc R . . . .
C17 C 1.2453(7) 0.2112(4) 0.02909(17) 0.0454(9) Uani 1 1 d . . . . .
H17 H 1.2658 0.1701 -0.0238 0.054 Uiso 1 1 calc R . . . .
C18 C 1.0507(7) 0.3123(3) 0.04938(16) 0.0422(8) Uani 1 1 d . . . . .
H18 H 0.9378 0.3401 0.0107 0.051 Uiso 1 1 calc R . . . .
H2 H 0.731(7) 0.502(3) 0.1103(18) 0.047(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.326(3) . ?
O1 C11 1.449(3) . ?
O2 C1 1.221(3) . ?
N1 N2 1.333(3) . ?
N1 C2 1.305(3) . ?
N2 C13 1.397(3) . ?
N2 H2 0.84(3) . ?
N3 C6 1.382(4) . ?
N3 C9 1.450(7) . ?
N3 C9B 1.487(6) . ?
N3 C10 1.401(6) . ?
N3 C10B 1.429(6) . ?
C1 C2 1.486(4) . ?
C2 C3 1.486(4) . ?
C3 C4 1.397(6) . ?
C3 C4B 1.389(6) . ?
C3 C8 1.376(6) . ?
C3 C8B 1.411(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(7) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.377(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.441(6) . ?
C5B H5B 0.9500 . ?
C5B C6 1.409(6) . ?
C6 C7 1.399(6) . ?
C6 C7B 1.362(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(7) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.388(7) . ?
C8 H8 0.9500 . ?
C8B H8B 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.505(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.385(4) . ?
C13 C18 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C11 115.6(2) . . ?
C2 N1 N2 121.8(2) . . ?
N1 N2 C13 119.6(2) . . ?
N1 N2 H2 120(2) . . ?
C13 N2 H2 120(2) . . ?
C6 N3 C9 118.0(4) . . ?
C6 N3 C9B 121.1(3) . . ?
C6 N3 C10 120.0(4) . . ?
C6 N3 C10B 121.8(3) . . ?
C10 N3 C9 122.0(4) . . ?
C10B N3 C9B 116.6(4) . . ?
O1 C1 C2 113.6(2) . . ?
O2 C1 O1 122.7(2) . . ?
O2 C1 C2 123.8(2) . . ?
N1 C2 C1 122.5(2) . . ?
N1 C2 C3 115.6(2) . . ?
C3 C2 C1 121.8(2) . . ?
C4 C3 C2 119.1(3) . . ?
C4B C3 C2 119.1(3) . . ?
C4B C3 C8B 114.8(4) . . ?
C8 C3 C2 121.3(3) . . ?
C8 C3 C4 119.6(4) . . ?
C8B C3 C2 126.1(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4B H4B 118.2 . . ?
C5B C4B C3 123.6(5) . . ?
C5B C4B H4B 118.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C4B C5B H5B 120.2 . . ?
C4B C5B C6 119.5(5) . . ?
C6 C5B H5B 120.2 . . ?
N3 C6 C5 122.4(3) . . ?
N3 C6 C5B 120.5(3) . . ?
N3 C6 C7 121.8(3) . . ?
C7 C6 C5 115.8(4) . . ?
C7B C6 N3 120.5(3) . . ?
C7B C6 C5B 119.0(4) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.6(5) . . ?
C8 C7 H7 118.7 . . ?
C6 C7B H7B 119.9 . . ?
C6 C7B C8B 120.2(5) . . ?
C8B C7B H7B 119.9 . . ?
C3 C8 C7 120.5(5) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C3 C8B H8B 118.6 . . ?
C7B C8B C3 122.9(5) . . ?
C7B C8B H8B 118.6 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C9B H9BA 109.5 . . ?
N3 C9B H9BB 109.5 . . ?
N3 C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C10B H10D 109.5 . . ?
N3 C10B H10E 109.5 . . ?
N3 C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O1 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
O1 C11 C12 107.3(2) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 121.8(2) . . ?
C14 C13 C18 119.9(3) . . ?
C18 C13 N2 118.3(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.6(3) . . ?
C17 C18 H18 120.2 . . ?

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
N2 H2 O2 0.84(3) 1.98(3) 2.626(3) 133(3) .


_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
_journal_coden_cambridge         1078
_journal_name_full               'Private Communication'
_journal_page_first              1
_journal_page_last               2
_journal_volume                  1MSU
_journal_year                    2015
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id BH01917
_olex2_submission_special_instructions 'No special instructions were received'

