# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_m2011
_database_code_depnum_ccdc_archive 'CCDC 1566652'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
# Linda JW Shimon
# Uttam Kumar Das, David Milstein

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N2'
_chemical_formula_sum            'C15 H20 N2'
_chemical_formula_weight         228.33

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'

_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                   14.2280(2)
_cell_length_b                   28.0486(5)
_cell_length_c                   10.06860(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.7934(13)
_cell_angle_gamma                90
_cell_volume                     3970.89(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17643
_cell_measurement_theta_min      4.4500
_cell_measurement_theta_max      79.5650

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.516
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_T_min  0.44165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50218
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.453
_diffrn_reflns_theta_max         74.504
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8088
_reflns_number_gt                7298
_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 1.171.39.22a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2016/4 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0991P)²+1.2128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8088
_refine_ls_number_parameters     484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
N1 N 0.68154(7) 0.39936(4) 0.90057(10) 0.0150(2) Uani 1 1 d . . . . .
H1N H 0.6717(11) 0.4101(6) 0.9850(17) 0.022(4) Uiso 1 1 d . . . . .
N2 N 0.66331(7) 0.39313(4) 0.67900(10) 0.0155(2) Uani 1 1 d . . . . .
C1 C 0.79159(9) 0.33542(4) 0.64970(12) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.74450(9) 0.31699(5) 0.52829(12) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.678477 0.322997 0.502960 0.024 Uiso 1 1 calc R U . . .
C3 C 0.79253(10) 0.29004(5) 0.44404(13) 0.0237(3) Uani 1 1 d . . . . .
H3 H 0.759291 0.277818 0.362110 0.028 Uiso 1 1 calc R U . . .
C4 C 0.88925(10) 0.28100(5) 0.47972(13) 0.0247(3) Uani 1 1 d . . . . .
H4 H 0.922370 0.262822 0.422064 0.030 Uiso 1 1 calc R U . . .
C5 C 0.93689(10) 0.29865(5) 0.59979(14) 0.0247(3) Uani 1 1 d . . . . .
H5A H 1.002741 0.292185 0.625015 0.030 Uiso 1 1 calc R U . . .
C6 C 0.88905(9) 0.32578(5) 0.68376(13) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.922851 0.337963 0.765381 0.026 Uiso 1 1 calc R U . . .
C7 C 0.73948(8) 0.36462(4) 0.73593(12) 0.0162(2) Uani 1 1 d . . . . .
C8 C 0.75153(8) 0.36820(4) 0.87333(12) 0.0158(2) Uani 1 1 d . . . . .
C9 C 0.63063(8) 0.41347(4) 0.78149(11) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.82171(9) 0.34539(5) 0.98106(12) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.849700 0.317405 0.939584 0.023 Uiso 1 1 calc R U . . .
C11 C 0.90364(10) 0.37927(5) 1.03217(15) 0.0315(3) Uani 1 1 d . . . . .
H11A H 0.935384 0.389184 0.956885 0.047 Uiso 1 1 calc R U . . .
H11B H 0.949383 0.362919 1.099649 0.047 Uiso 1 1 calc R U . . .
H11C H 0.878615 0.407408 1.072686 0.047 Uiso 1 1 calc R U . . .
C12 C 0.77530(11) 0.32657(6) 1.09766(14) 0.0315(3) Uani 1 1 d . . . . .
H12A H 0.753332 0.353441 1.147051 0.047 Uiso 1 1 calc R U . . .
H12B H 0.821760 0.307867 1.158184 0.047 Uiso 1 1 calc R U . . .
H12C H 0.721004 0.306326 1.062618 0.047 Uiso 1 1 calc R U . . .
C13 C 0.55049(9) 0.44872(5) 0.77121(12) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.579250 0.481040 0.789352 0.023 Uiso 1 1 calc R U . . .
C14 C 0.49335(10) 0.44964(5) 0.62973(13) 0.0272(3) Uani 1 1 d . . . . .
H14A H 0.535152 0.458669 0.565052 0.041 Uiso 1 1 calc R U . . .
H14B H 0.441648 0.472909 0.626332 0.041 Uiso 1 1 calc R U . . .
H14C H 0.466615 0.417949 0.607116 0.041 Uiso 1 1 calc R U . . .
C15 C 0.48596(10) 0.43972(6) 0.87512(14) 0.0360(4) Uani 1 1 d . . . . .
H15A H 0.456880 0.408105 0.860472 0.054 Uiso 1 1 calc R U . . .
H15B H 0.435991 0.464056 0.866816 0.054 Uiso 1 1 calc R U . . .
H15C H 0.523268 0.441162 0.965296 0.054 Uiso 1 1 calc R U . . .
N3 N 0.67813(7) 0.43215(4) 0.41042(10) 0.0157(2) Uani 1 1 d . . . . .
H3N H 0.6717(11) 0.4206(6) 0.4942(17) 0.023(4) Uiso 1 1 d . . . . .
N4 N 0.65435(7) 0.43667(4) 0.18812(10) 0.0167(2) Uani 1 1 d . . . . .
C16 C 0.78338(9) 0.49298(4) 0.15082(11) 0.0165(2) Uani 1 1 d . . . . .
C17 C 0.73552(9) 0.51022(4) 0.02839(12) 0.0183(3) Uani 1 1 d . . . . .
H17 H 0.669624 0.503719 0.003850 0.022 Uiso 1 1 calc R U . . .
C18 C 0.78252(9) 0.53662(5) -0.05779(12) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.748782 0.547884 -0.140562 0.026 Uiso 1 1 calc R U . . .
C19 C 0.87900(10) 0.54665(5) -0.02321(13) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.911236 0.564858 -0.081843 0.028 Uiso 1 1 calc R U . . .
C20 C 0.92765(9) 0.52980(5) 0.09764(13) 0.0236(3) Uani 1 1 d . . . . .
H20 H 0.993417 0.536674 0.121924 0.028 Uiso 1 1 calc R U . . .
C21 C 0.88091(9) 0.50298(5) 0.18334(12) 0.0202(3) Uani 1 1 d . . . . .
H21 H 0.915366 0.491236 0.265058 0.024 Uiso 1 1 calc R U . . .
C22 C 0.73227(8) 0.46491(4) 0.24032(12) 0.0155(2) Uani 1 1 d . . . . .
C23 C 0.74742(8) 0.46240(4) 0.37824(11) 0.0156(2) Uani 1 1 d . . . . .
C24 C 0.62406(8) 0.41773(4) 0.29464(11) 0.0163(2) Uani 1 1 d . . . . .
C25 C 0.81857(9) 0.48596(5) 0.48311(12) 0.0195(3) Uani 1 1 d . . . . .
H25 H 0.845825 0.513668 0.439416 0.023 Uiso 1 1 calc R U . . .
C26 C 0.90113(10) 0.45238(6) 0.53476(15) 0.0324(3) Uani 1 1 d . . . . .
H26A H 0.876624 0.424412 0.576708 0.049 Uiso 1 1 calc R U . . .
H26B H 0.947037 0.469115 0.601168 0.049 Uiso 1 1 calc R U . . .
H26C H 0.932504 0.442153 0.459431 0.049 Uiso 1 1 calc R U . . .
C27 C 0.77324(11) 0.50551(6) 0.60011(13) 0.0319(3) Uani 1 1 d . . . . .
H27A H 0.718652 0.525566 0.565103 0.048 Uiso 1 1 calc R U . . .
H27B H 0.820114 0.524543 0.658983 0.048 Uiso 1 1 calc R U . . .
H27C H 0.751903 0.478938 0.651244 0.048 Uiso 1 1 calc R U . . .
C28 C 0.53902(9) 0.38610(4) 0.29488(12) 0.0188(3) Uani 1 1 d . . . . .
H28 H 0.540291 0.374212 0.388779 0.023 Uiso 1 1 calc R U . . .
C29 C 0.54151(10) 0.34289(5) 0.20472(14) 0.0290(3) Uani 1 1 d . . . . .
H29A H 0.544216 0.353425 0.112577 0.044 Uiso 1 1 calc R U . . .
H29B H 0.484100 0.323715 0.206198 0.044 Uiso 1 1 calc R U . . .
H29C H 0.597823 0.323633 0.237163 0.044 Uiso 1 1 calc R U . . .
C30 C 0.44635(9) 0.41406(5) 0.25635(13) 0.0255(3) Uani 1 1 d . . . . .
H30A H 0.444067 0.440371 0.319811 0.038 Uiso 1 1 calc R U . . .
H30B H 0.392019 0.392815 0.259281 0.038 Uiso 1 1 calc R U . . .
H30C H 0.443686 0.426873 0.165298 0.038 Uiso 1 1 calc R U . . .
N5 N 0.67317(7) 0.73666(4) -0.09053(10) 0.0145(2) Uani 1 1 d . . . . .
H5N H 0.6654(11) 0.7460(6) -0.0066(16) 0.022(4) Uiso 1 1 d . . . . .
N6 N 0.65865(7) 0.73375(4) -0.31254(9) 0.0157(2) Uani 1 1 d . . . . .
C31 C 0.77842(9) 0.67140(4) -0.34327(12) 0.0171(3) Uani 1 1 d . . . . .
C32 C 0.72886(9) 0.64974(5) -0.45791(12) 0.0203(3) Uani 1 1 d . . . . .
H32 H 0.661750 0.653196 -0.477579 0.024 Uiso 1 1 calc R U . . .
C33 C 0.77633(11) 0.62315(5) -0.54385(13) 0.0257(3) Uani 1 1 d . . . . .
H33 H 0.741785 0.609029 -0.622214 0.031 Uiso 1 1 calc R U . . .
C34 C 0.87446(11) 0.61731(5) -0.51474(14) 0.0272(3) Uani 1 1 d . . . . .
H34 H 0.907116 0.599339 -0.573378 0.033 Uiso 1 1 calc R U . . .
C35 C 0.92427(10) 0.63778(5) -0.40008(14) 0.0263(3) Uani 1 1 d . . . . .
H35 H 0.991090 0.633330 -0.379257 0.032 Uiso 1 1 calc R U . . .
C36 C 0.87699(9) 0.66487(5) -0.31505(13) 0.0219(3) Uani 1 1 d . . . . .
H36 H 0.911976 0.679065 -0.237122 0.026 Uiso 1 1 calc R U . . .
C37 C 0.72781(8) 0.70125(4) -0.25665(12) 0.0151(2) Uani 1 1 d . . . . .
C38 C 0.73716(8) 0.70263(4) -0.11937(11) 0.0146(2) Uani 1 1 d . . . . .
C39 C 0.62784(8) 0.75459(4) -0.20883(11) 0.0155(2) Uani 1 1 d . . . . .
C40 C 0.79729(9) 0.67363(5) -0.01396(12) 0.0202(3) Uani 1 1 d . . . . .
H40 H 0.828272 0.648111 -0.061476 0.024 Uiso 1 1 calc R U . . .
C41 C 0.87658(11) 0.70300(6) 0.06629(16) 0.0373(4) Uani 1 1 d . . . . .
H41A H 0.915677 0.717393 0.004841 0.056 Uiso 1 1 calc R U . . .
H41B H 0.916294 0.682283 0.130257 0.056 Uiso 1 1 calc R U . . .
H41C H 0.848738 0.728201 0.115353 0.056 Uiso 1 1 calc R U . . .
C42 C 0.73733(11) 0.64875(5) 0.07947(14) 0.0318(3) Uani 1 1 d . . . . .
H42A H 0.711007 0.672635 0.134571 0.048 Uiso 1 1 calc R U . . .
H42B H 0.777345 0.626439 0.137984 0.048 Uiso 1 1 calc R U . . .
H42C H 0.685269 0.631261 0.025635 0.048 Uiso 1 1 calc R U . . .
C43 C 0.55656(9) 0.79448(5) -0.21824(12) 0.0197(3) Uani 1 1 d . . . . .
H43 H 0.593085 0.825062 -0.207940 0.024 Uiso 1 1 calc R U . . .
C44 C 0.49396(10) 0.79571(5) -0.35537(12) 0.0245(3) Uani 1 1 d . . . . .
H44A H 0.534036 0.799168 -0.425763 0.037 Uiso 1 1 calc R U . . .
H44B H 0.450042 0.822761 -0.359146 0.037 Uiso 1 1 calc R U . . .
H44C H 0.457584 0.765989 -0.369334 0.037 Uiso 1 1 calc R U . . .
C45 C 0.49502(9) 0.79294(5) -0.10747(12) 0.0228(3) Uani 1 1 d . . . . .
H45A H 0.455025 0.764334 -0.118075 0.034 Uiso 1 1 calc R U . . .
H45B H 0.454539 0.821361 -0.113143 0.034 Uiso 1 1 calc R U . . .
H45C H 0.535824 0.792130 -0.019777 0.034 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
N1 C9 1.3614(14) . ?
N1 C8 1.3834(15) . ?
N1 H1N 0.933(17) . ?
N2 C9 1.3241(15) . ?
N2 C7 1.3973(15) . ?
C1 C2 1.4001(17) . ?
C1 C6 1.4030(17) . ?
C1 C7 1.4735(16) . ?
C2 C3 1.3911(18) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3915(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3840(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3903(18) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3715(17) . ?
C8 C10 1.5006(16) . ?
C9 C13 1.5008(16) . ?
C10 C12 1.5266(18) . ?
C10 C11 1.5308(19) . ?
C10 H10 1.0000 . ?
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 C15 1.5149(18) . ?
C13 C14 1.5286(16) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N3 C24 1.3565(15) . ?
N3 C23 1.3763(15) . ?
N3 H3N 0.921(17) . ?
N4 C24 1.3264(15) . ?
N4 C22 1.3981(15) . ?
C16 C17 1.4001(16) . ?
C16 C21 1.4045(17) . ?
C16 C22 1.4700(16) . ?
C17 C18 1.3878(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3923(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3876(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3887(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.3741(16) . ?
C23 C25 1.4999(16) . ?
C24 C28 1.5008(16) . ?
C25 C27 1.5284(17) . ?
C25 C26 1.5332(19) . ?
C25 H25 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 . ?
C28 C29 1.5179(18) . ?
C28 C30 1.5322(17) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N5 C39 1.3611(14) . ?
N5 C38 1.3802(15) . ?
N5 H5N 0.907(16) . ?
N6 C39 1.3282(15) . ?
N6 C37 1.3951(15) . ?
C31 C32 1.3963(17) . ?
C31 C36 1.3997(17) . ?
C31 C37 1.4740(16) . ?
C32 C33 1.3928(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.3925(18) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.3687(17) . ?
C38 C40 1.4975(16) . ?
C39 C43 1.5034(16) . ?
C40 C41 1.5251(19) . ?
C40 C42 1.5312(18) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C45 1.5201(17) . ?
C43 C44 1.5247(16) . ?
C43 H43 1.0000 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 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
C9 N1 C8 108.13(10) . . ?
C9 N1 H1N 125.0(10) . . ?
C8 N1 H1N 126.8(10) . . ?
C9 N2 C7 105.64(10) . . ?
C2 C1 C6 117.74(11) . . ?
C2 C1 C7 120.19(11) . . ?
C6 C1 C7 122.05(11) . . ?
C3 C2 C1 121.26(12) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 120.02(12) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.55(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.47(12) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 120.95(12) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
C8 C7 N2 109.96(10) . . ?
C8 C7 C1 129.68(11) . . ?
N2 C7 C1 120.33(10) . . ?
C7 C8 N1 105.28(10) . . ?
C7 C8 C10 131.65(11) . . ?
N1 C8 C10 123.07(10) . . ?
N2 C9 N1 110.99(10) . . ?
N2 C9 C13 125.71(10) . . ?
N1 C9 C13 123.27(10) . . ?
C8 C10 C12 112.64(11) . . ?
C8 C10 C11 111.51(11) . . ?
C12 C10 C11 110.66(11) . . ?
C8 C10 H10 107.2 . . ?
C12 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C15 112.14(11) . . ?
C9 C13 C14 111.45(10) . . ?
C15 C13 C14 110.75(11) . . ?
C9 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C14 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C24 N3 C23 108.30(10) . . ?
C24 N3 H3N 124.1(10) . . ?
C23 N3 H3N 127.4(10) . . ?
C24 N4 C22 105.06(10) . . ?
C17 C16 C21 117.80(11) . . ?
C17 C16 C22 120.34(11) . . ?
C21 C16 C22 121.85(11) . . ?
C18 C17 C16 121.25(11) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.16(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.41(12) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.48(12) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.89(12) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C23 C22 N4 110.11(10) . . ?
C23 C22 C16 129.13(11) . . ?
N4 C22 C16 120.74(10) . . ?
C22 C23 N3 105.20(10) . . ?
C22 C23 C25 132.34(11) . . ?
N3 C23 C25 122.45(10) . . ?
N4 C24 N3 111.34(10) . . ?
N4 C24 C28 126.85(10) . . ?
N3 C24 C28 121.76(10) . . ?
C23 C25 C27 112.44(11) . . ?
C23 C25 C26 111.57(11) . . ?
C27 C25 C26 110.52(11) . . ?
C23 C25 H25 107.3 . . ?
C27 C25 H25 107.3 . . ?
C26 C25 H25 107.3 . . ?
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 . . ?
C24 C28 C29 112.24(10) . . ?
C24 C28 C30 111.09(10) . . ?
C29 C28 C30 110.80(11) . . ?
C24 C28 H28 107.5 . . ?
C29 C28 H28 107.5 . . ?
C30 C28 H28 107.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C39 N5 C38 108.12(10) . . ?
C39 N5 H5N 126.8(10) . . ?
C38 N5 H5N 125.0(10) . . ?
C39 N6 C37 105.52(9) . . ?
C32 C31 C36 118.34(11) . . ?
C32 C31 C37 120.37(11) . . ?
C36 C31 C37 121.28(11) . . ?
C33 C32 C31 120.99(12) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C32 119.89(13) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 119.75(12) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.36(13) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.65(12) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C38 C37 N6 110.03(10) . . ?
C38 C37 C31 129.25(11) . . ?
N6 C37 C31 120.71(10) . . ?
C37 C38 N5 105.46(10) . . ?
C37 C38 C40 131.08(11) . . ?
N5 C38 C40 123.39(10) . . ?
N6 C39 N5 110.87(10) . . ?
N6 C39 C43 125.35(10) . . ?
N5 C39 C43 123.71(10) . . ?
C38 C40 C41 112.23(11) . . ?
C38 C40 C42 111.80(11) . . ?
C41 C40 C42 110.93(12) . . ?
C38 C40 H40 107.2 . . ?
C41 C40 H40 107.2 . . ?
C42 C40 H40 107.2 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 C45 113.03(10) . . ?
C39 C43 C44 111.65(10) . . ?
C45 C43 C44 110.05(10) . . ?
C39 C43 H43 107.3 . . ?
C45 C43 H43 107.3 . . ?
C44 C43 H43 107.3 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 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 C1 C2 C3 -0.05(19) . . . . ?
C7 C1 C2 C3 178.84(11) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C2 C1 C6 C5 -0.27(19) . . . . ?
C7 C1 C6 C5 -179.14(12) . . . . ?
C9 N2 C7 C8 0.11(13) . . . . ?
C9 N2 C7 C1 178.36(11) . . . . ?
C2 C1 C7 C8 146.71(13) . . . . ?
C6 C1 C7 C8 -34.5(2) . . . . ?
C2 C1 C7 N2 -31.16(17) . . . . ?
C6 C1 C7 N2 147.68(12) . . . . ?
N2 C7 C8 N1 0.05(13) . . . . ?
C1 C7 C8 N1 -177.99(12) . . . . ?
N2 C7 C8 C10 179.97(12) . . . . ?
C1 C7 C8 C10 1.9(2) . . . . ?
C9 N1 C8 C7 -0.18(13) . . . . ?
C9 N1 C8 C10 179.88(11) . . . . ?
C7 N2 C9 N1 -0.23(13) . . . . ?
C7 N2 C9 C13 177.89(11) . . . . ?
C8 N1 C9 N2 0.26(13) . . . . ?
C8 N1 C9 C13 -177.91(11) . . . . ?
C7 C8 C10 C12 -135.58(14) . . . . ?
N1 C8 C10 C12 44.33(16) . . . . ?
C7 C8 C10 C11 99.29(16) . . . . ?
N1 C8 C10 C11 -80.79(15) . . . . ?
N2 C9 C13 C15 139.10(13) . . . . ?
N1 C9 C13 C15 -42.99(17) . . . . ?
N2 C9 C13 C14 14.29(17) . . . . ?
N1 C9 C13 C14 -167.81(11) . . . . ?
C21 C16 C17 C18 -0.45(18) . . . . ?
C22 C16 C17 C18 -179.74(11) . . . . ?
C16 C17 C18 C19 -0.25(19) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C16 -1.0(2) . . . . ?
C17 C16 C21 C20 1.09(19) . . . . ?
C22 C16 C21 C20 -179.63(11) . . . . ?
C24 N4 C22 C23 -0.02(13) . . . . ?
C24 N4 C22 C16 -178.23(11) . . . . ?
C17 C16 C22 C23 -148.15(13) . . . . ?
C21 C16 C22 C23 32.6(2) . . . . ?
C17 C16 C22 N4 29.69(17) . . . . ?
C21 C16 C22 N4 -149.57(12) . . . . ?
N4 C22 C23 N3 0.20(13) . . . . ?
C16 C22 C23 N3 178.22(12) . . . . ?
N4 C22 C23 C25 -178.46(12) . . . . ?
C16 C22 C23 C25 -0.4(2) . . . . ?
C24 N3 C23 C22 -0.30(13) . . . . ?
C24 N3 C23 C25 178.52(11) . . . . ?
C22 N4 C24 N3 -0.18(13) . . . . ?
C22 N4 C24 C28 177.10(11) . . . . ?
C23 N3 C24 N4 0.31(14) . . . . ?
C23 N3 C24 C28 -177.12(11) . . . . ?
C22 C23 C25 C27 135.09(14) . . . . ?
N3 C23 C25 C27 -43.37(16) . . . . ?
C22 C23 C25 C26 -100.08(16) . . . . ?
N3 C23 C25 C26 81.46(14) . . . . ?
N4 C24 C28 C29 54.41(17) . . . . ?
N3 C24 C28 C29 -128.58(12) . . . . ?
N4 C24 C28 C30 -70.26(16) . . . . ?
N3 C24 C28 C30 106.75(13) . . . . ?
C36 C31 C32 C33 -1.39(19) . . . . ?
C37 C31 C32 C33 177.17(11) . . . . ?
C31 C32 C33 C34 1.0(2) . . . . ?
C32 C33 C34 C35 0.3(2) . . . . ?
C33 C34 C35 C36 -1.1(2) . . . . ?
C34 C35 C36 C31 0.7(2) . . . . ?
C32 C31 C36 C35 0.56(19) . . . . ?
C37 C31 C36 C35 -177.99(12) . . . . ?
C39 N6 C37 C38 0.57(13) . . . . ?
C39 N6 C37 C31 -179.79(11) . . . . ?
C32 C31 C37 C38 136.67(13) . . . . ?
C36 C31 C37 C38 -44.82(19) . . . . ?
C32 C31 C37 N6 -42.90(17) . . . . ?
C36 C31 C37 N6 135.61(12) . . . . ?
N6 C37 C38 N5 -0.33(13) . . . . ?
C31 C37 C38 N5 -179.93(12) . . . . ?
N6 C37 C38 C40 176.70(12) . . . . ?
C31 C37 C38 C40 -2.9(2) . . . . ?
C39 N5 C38 C37 -0.04(13) . . . . ?
C39 N5 C38 C40 -177.35(11) . . . . ?
C37 N6 C39 N5 -0.59(13) . . . . ?
C37 N6 C39 C43 176.29(11) . . . . ?
C38 N5 C39 N6 0.41(14) . . . . ?
C38 N5 C39 C43 -176.54(11) . . . . ?
C37 C38 C40 C41 111.13(15) . . . . ?
N5 C38 C40 C41 -72.31(15) . . . . ?
C37 C38 C40 C42 -123.49(14) . . . . ?
N5 C38 C40 C42 53.07(16) . . . . ?
N6 C39 C43 C45 147.66(12) . . . . ?
N5 C39 C43 C45 -35.84(17) . . . . ?
N6 C39 C43 C44 22.95(17) . . . . ?
N5 C39 C43 C44 -160.55(11) . . . . ?

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
N1 H1N N4_$1 0.933(17) 2.226(17) 3.1575(14) 177.7(14) 1_556
N3 H3N N2 0.921(17) 2.034(17) 2.9546(14) 177.1(15) .
N5 H5N N6_$2 0.907(16) 2.051(17) 2.9568(13) 175.7(14) 4_576

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053

