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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
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#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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data_JULIE1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2'
_chemical_formula_weight         346.41
_chemical_compound_source        'Synthesized by the authors. See text'

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      hexagonal
_symmetry_space_group_name_H-M   P61
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   10.30410(10)
_cell_length_b                   10.30410(10)
_cell_length_c                   29.1806(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2683.15(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9790
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      70.66

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.583
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'

_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 smart diffractometer equiped with an APEX II CCD Detector,
a Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
5.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space


;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\muS Microsource '
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            35626
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         4.956
_diffrn_reflns_theta_max         70.848
_diffrn_reflns_theta_full        67.679
_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 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3318
_reflns_number_gt                3261
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    0.927

_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       'APEX2  (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'

_refine_special_details          
;
 Flack x determined using 1511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.3210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
'Flack, H.D. and Schwarzenbach, D. (1999), XXXX Friedel Pairs'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_number_reflns         3318
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C2 C 0.91234(17) 0.98282(18) 0.11024(6) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.75881(17) 0.75126(18) 0.12675(6) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.77104(17) 0.75976(17) 0.07879(6) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.69658(19) 0.63395(19) 0.05022(6) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.61289(19) 0.49806(19) 0.07289(6) 0.0253(4) Uani 1 1 d . . . . .
H7 H 0.5638 0.4087 0.0553 0.030 Uiso 1 1 calc R U . . .
C8 C 0.59819(18) 0.48777(19) 0.12057(6) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.5400 0.3918 0.1342 0.030 Uiso 1 1 calc R U . . .
C9 C 0.66596(18) 0.61351(18) 0.14882(6) 0.0210(3) Uani 1 1 d . . . . .
C10 C 1.02842(17) 1.14176(18) 0.11380(6) 0.0201(3) Uani 1 1 d . . . . .
C11 C 1.07233(18) 1.23646(19) 0.07558(6) 0.0224(3) Uani 1 1 d . . . . .
H11 H 1.0224 1.2002 0.0471 0.027 Uiso 1 1 calc R U . . .
C12 C 1.18868(19) 1.38323(19) 0.07927(6) 0.0267(4) Uani 1 1 d . . . . .
H12 H 1.2190 1.4465 0.0531 0.032 Uiso 1 1 calc R U . . .
C13 C 1.26119(19) 1.43853(19) 0.12065(7) 0.0286(4) Uani 1 1 d . . . . .
H13 H 1.3406 1.5393 0.1229 0.034 Uiso 1 1 calc R U . . .
C14 C 1.2173(2) 1.3462(2) 0.15872(7) 0.0273(4) Uani 1 1 d . . . . .
H14 H 1.2661 1.3841 0.1873 0.033 Uiso 1 1 calc R U . . .
C15 C 1.10252(18) 1.19852(19) 0.15544(6) 0.0234(3) Uani 1 1 d . . . . .
H15 H 1.0740 1.1355 0.1817 0.028 Uiso 1 1 calc R U . . .
C16 C 0.7081(2) 0.64052(18) -0.00050(6) 0.0250(4) Uani 1 1 d . . . . .
C17 C 0.8470(2) 0.7141(2) -0.02213(6) 0.0272(4) Uani 1 1 d . . . . .
H17 H 0.9354 0.7680 -0.0043 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8576(3) 0.7095(2) -0.06951(6) 0.0356(5) Uani 1 1 d . . . . .
H18 H 0.9532 0.7575 -0.0839 0.043 Uiso 1 1 calc R U . . .
C19 C 0.7290(3) 0.6348(2) -0.09576(7) 0.0419(5) Uani 1 1 d . . . . .
H19 H 0.7362 0.6308 -0.1281 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5901(3) 0.5662(2) -0.07487(7) 0.0418(5) Uani 1 1 d . . . . .
H20 H 0.5018 0.5180 -0.0930 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5793(2) 0.5674(2) -0.02743(7) 0.0333(4) Uani 1 1 d . . . . .
H21 H 0.4835 0.5181 -0.0132 0.040 Uiso 1 1 calc R U . . .
C22 C 0.63032(18) 0.60267(18) 0.19846(6) 0.0219(3) Uani 1 1 d . . . . .
C23 C 0.64080(19) 0.49978(19) 0.22676(6) 0.0262(4) Uani 1 1 d . . . . .
H23 H 0.6768 0.4380 0.2147 0.031 Uiso 1 1 calc R U . . .
C24 C 0.5991(2) 0.4863(2) 0.27271(7) 0.0304(4) Uani 1 1 d . . . . .
H24 H 0.6074 0.4161 0.2918 0.036 Uiso 1 1 calc R U . . .
C25 C 0.5455(2) 0.5749(2) 0.29060(7) 0.0335(4) Uani 1 1 d . . . . .
H25 H 0.5169 0.5657 0.3219 0.040 Uiso 1 1 calc R U . . .
C26 C 0.5337(2) 0.6776(2) 0.26254(7) 0.0322(4) Uani 1 1 d . . . . .
H26 H 0.4963 0.7381 0.2747 0.039 Uiso 1 1 calc R U . . .
C27 C 0.5763(2) 0.6919(2) 0.21695(6) 0.0260(4) Uani 1 1 d . . . . .
H27 H 0.5688 0.7630 0.1981 0.031 Uiso 1 1 calc R U . . .
N1 N 0.86736(15) 0.90952(15) 0.06921(5) 0.0191(3) Uani 1 1 d . . . . .
N3 N 0.84999(15) 0.89202(15) 0.14571(5) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.887(3) 0.951(3) 0.0421(9) 0.032(6) 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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N3 . . 1.326(2) y
C2 N1 . . 1.367(2) y
C2 C10 . . 1.471(2) y
C4 N3 . . 1.389(2) y
C4 C5 . . 1.404(2) y
C4 C9 . . 1.410(2) y
C5 N1 . . 1.383(2) y
C5 C6 . . 1.403(2) y
C6 C7 . . 1.391(2) y
C6 C16 . . 1.484(2) y
C7 C8 . . 1.398(3) y
C7 H7 . . 0.9500 ?
C8 C9 . . 1.393(2) y
C8 H8 . . 0.9500 ?
C9 C22 . . 1.485(2) y
C10 C15 . . 1.398(2) y
C10 C11 . . 1.400(2) y
C11 C12 . . 1.387(2) y
C11 H11 . . 0.9500 ?
C12 C13 . . 1.384(3) y
C12 H12 . . 0.9500 ?
C13 C14 . . 1.383(3) y
C13 H13 . . 0.9500 ?
C14 C15 . . 1.387(2) y
C14 H14 . . 0.9500 ?
C15 H15 . . 0.9500 ?
C16 C17 . . 1.392(3) y
C16 C21 . . 1.395(3) y
C17 C18 . . 1.390(3) y
C17 H17 . . 0.9500 ?
C18 C19 . . 1.384(3) y
C18 H18 . . 0.9500 ?
C19 C20 . . 1.381(4) y
C19 H19 . . 0.9500 ?
C20 C21 . . 1.389(3) y
C20 H20 . . 0.9500 ?
C21 H21 . . 0.9500 ?
C22 C23 . . 1.390(2) y
C22 C27 . . 1.400(2) y
C23 C24 . . 1.394(3) y
C23 H23 . . 0.9500 ?
C24 C25 . . 1.384(3) y
C24 H24 . . 0.9500 ?
C25 C26 . . 1.390(3) y
C25 H25 . . 0.9500 ?
C26 C27 . . 1.385(3) y
C26 H26 . . 0.9500 ?
C27 H27 . . 0.9500 ?
N1 H1 . . 0.87(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C2 N1 . . . 112.51(14) y
N3 C2 C10 . . . 124.60(15) y
N1 C2 C10 . . . 122.63(15) y
N3 C4 C5 . . . 109.81(14) y
N3 C4 C9 . . . 129.32(15) y
C5 C4 C9 . . . 120.86(15) y
N1 C5 C6 . . . 131.79(16) y
N1 C5 C4 . . . 105.26(14) y
C6 C5 C4 . . . 122.95(15) y
C7 C6 C5 . . . 115.14(16) y
C7 C6 C16 . . . 121.03(15) y
C5 C6 C16 . . . 123.79(16) y
C6 C7 C8 . . . 122.61(15) y
C6 C7 H7 . . . 118.7 ?
C8 C7 H7 . . . 118.7 ?
C9 C8 C7 . . . 122.24(16) y
C9 C8 H8 . . . 118.9 ?
C7 C8 H8 . . . 118.9 ?
C8 C9 C4 . . . 116.00(15) y
C8 C9 C22 . . . 121.14(15) y
C4 C9 C22 . . . 122.64(15) y
C15 C10 C11 . . . 118.83(15) y
C15 C10 C2 . . . 119.80(15) y
C11 C10 C2 . . . 121.29(15) y
C12 C11 C10 . . . 120.02(16) y
C12 C11 H11 . . . 120.0 ?
C10 C11 H11 . . . 120.0 ?
C13 C12 C11 . . . 120.74(17) y
C13 C12 H12 . . . 119.6 ?
C11 C12 H12 . . . 119.6 ?
C14 C13 C12 . . . 119.59(16) y
C14 C13 H13 . . . 120.2 ?
C12 C13 H13 . . . 120.2 ?
C13 C14 C15 . . . 120.36(17) y
C13 C14 H14 . . . 119.8 ?
C15 C14 H14 . . . 119.8 ?
C14 C15 C10 . . . 120.44(16) y
C14 C15 H15 . . . 119.8 ?
C10 C15 H15 . . . 119.8 ?
C17 C16 C21 . . . 118.71(18) y
C17 C16 C6 . . . 120.93(16) y
C21 C16 C6 . . . 120.31(17) y
C18 C17 C16 . . . 120.64(18) y
C18 C17 H17 . . . 119.7 ?
C16 C17 H17 . . . 119.7 ?
C19 C18 C17 . . . 120.0(2) y
C19 C18 H18 . . . 120.0 ?
C17 C18 H18 . . . 120.0 ?
C20 C19 C18 . . . 120.0(2) y
C20 C19 H19 . . . 120.0 ?
C18 C19 H19 . . . 120.0 ?
C19 C20 C21 . . . 120.2(2) y
C19 C20 H20 . . . 119.9 ?
C21 C20 H20 . . . 119.9 ?
C20 C21 C16 . . . 120.5(2) y
C20 C21 H21 . . . 119.8 ?
C16 C21 H21 . . . 119.8 ?
C23 C22 C27 . . . 118.70(16) y
C23 C22 C9 . . . 121.77(16) y
C27 C22 C9 . . . 119.43(15) y
C22 C23 C24 . . . 120.65(17) y
C22 C23 H23 . . . 119.7 ?
C24 C23 H23 . . . 119.7 ?
C25 C24 C23 . . . 120.15(17) y
C25 C24 H24 . . . 119.9 ?
C23 C24 H24 . . . 119.9 ?
C24 C25 C26 . . . 119.69(18) y
C24 C25 H25 . . . 120.2 ?
C26 C25 H25 . . . 120.2 ?
C27 C26 C25 . . . 120.21(18) y
C27 C26 H26 . . . 119.9 ?
C25 C26 H26 . . . 119.9 ?
C26 C27 C22 . . . 120.61(17) y
C26 C27 H27 . . . 119.7 ?
C22 C27 H27 . . . 119.7 ?
C2 N1 C5 . . . 107.17(14) y
C2 N1 H1 . . . 126.1(16) ?
C5 N1 H1 . . . 126.4(16) ?
C2 N3 C4 . . . 105.20(14) y

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 C4 C5 N1 . . . . -2.06(17) y
C9 C4 C5 N1 . . . . 178.86(14) y
N3 C4 C5 C6 . . . . 177.32(14) y
C9 C4 C5 C6 . . . . -1.8(2) y
N1 C5 C6 C7 . . . . 177.14(16) y
C4 C5 C6 C7 . . . . -2.1(2) y
N1 C5 C6 C16 . . . . -0.8(3) y
C4 C5 C6 C16 . . . . -179.97(15) y
C5 C6 C7 C8 . . . . 2.8(2) y
C16 C6 C7 C8 . . . . -179.26(16) y
C6 C7 C8 C9 . . . . 0.4(3) y
C7 C8 C9 C4 . . . . -4.1(2) y
C7 C8 C9 C22 . . . . 170.61(15) y
N3 C4 C9 C8 . . . . -174.12(15) y
C5 C4 C9 C8 . . . . 4.8(2) y
N3 C4 C9 C22 . . . . 11.2(3) y
C5 C4 C9 C22 . . . . -169.89(15) y
N3 C2 C10 C15 . . . . 13.5(2) y
N1 C2 C10 C15 . . . . -160.22(15) y
N3 C2 C10 C11 . . . . -169.94(15) y
N1 C2 C10 C11 . . . . 16.4(2) y
C15 C10 C11 C12 . . . . 0.8(2) y
C2 C10 C11 C12 . . . . -175.84(15) y
C10 C11 C12 C13 . . . . -0.9(3) y
C11 C12 C13 C14 . . . . 0.2(3) y
C12 C13 C14 C15 . . . . 0.7(3) y
C13 C14 C15 C10 . . . . -0.8(3) y
C11 C10 C15 C14 . . . . 0.1(2) y
C2 C10 C15 C14 . . . . 176.77(16) y
C7 C6 C16 C17 . . . . -127.76(18) y
C5 C6 C16 C17 . . . . 50.0(2) y
C7 C6 C16 C21 . . . . 49.6(2) y
C5 C6 C16 C21 . . . . -132.62(18) y
C21 C16 C17 C18 . . . . -2.7(3) y
C6 C16 C17 C18 . . . . 174.71(16) y
C16 C17 C18 C19 . . . . 1.9(3) y
C17 C18 C19 C20 . . . . 0.6(3) y
C18 C19 C20 C21 . . . . -2.2(3) y
C19 C20 C21 C16 . . . . 1.4(3) y
C17 C16 C21 C20 . . . . 1.1(3) y
C6 C16 C21 C20 . . . . -176.34(17) y
C8 C9 C22 C23 . . . . 53.2(2) y
C4 C9 C22 C23 . . . . -132.43(18) y
C8 C9 C22 C27 . . . . -123.00(18) y
C4 C9 C22 C27 . . . . 51.4(2) y
C27 C22 C23 C24 . . . . -0.3(3) y
C9 C22 C23 C24 . . . . -176.55(15) y
C22 C23 C24 C25 . . . . 0.5(3) y
C23 C24 C25 C26 . . . . -0.1(3) y
C24 C25 C26 C27 . . . . -0.4(3) y
C25 C26 C27 C22 . . . . 0.6(3) y
C23 C22 C27 C26 . . . . -0.2(3) y
C9 C22 C27 C26 . . . . 176.11(16) y
N3 C2 N1 C5 . . . . -1.21(17) y
C10 C2 N1 C5 . . . . 173.16(14) y
C6 C5 N1 C2 . . . . -177.37(16) y
C4 C5 N1 C2 . . . . 1.94(17) y
N1 C2 N3 C4 . . . . -0.09(17) y
C10 C2 N3 C4 . . . . -174.33(14) y
C5 C4 N3 C2 . . . . 1.35(17) y
C9 C4 N3 C2 . . . . -179.67(16) y

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
_geom_hbond_publ_flag
N1 H1 N3 0.87(2) 2.05(3) 2.916(2) 169(2) 6_564 y





_database_code_depnum_ccdc_archive 'CCDC 1011326'
#######################################################################
#
#                 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_JULIE2

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cl4 N2'
_chemical_formula_weight         502.24
_chemical_compound_source        'Synthesized by the authors. See text'

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_symmetry_space_group_name_H-M   P212121
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.2022(2)
_cell_length_b                   13.4802(4)
_cell_length_c                   23.7766(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2308.40(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9469
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      70.90

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.792
_shelx_estimated_absorpt_T_min   0.514
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.4971
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'

_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 smart diffractometer equiped with an APEX II CCD Detector,
a Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
5.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space


;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\muS Microsource '
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            31032
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.718
_diffrn_reflns_theta_max         71.209
_diffrn_reflns_theta_full        67.679
_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 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4456
_reflns_number_gt                4239
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.999

_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       'APEX2  (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'

_refine_special_details          
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.6880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
'Flack, H.D. and Schwarzenbach, D. (1999), XXXX Friedel Pairs'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.027(7)
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C2 C 0.9778(5) 0.7827(2) 0.01539(15) 0.0186(7) Uani 1 1 d . . . . .
C4 C 0.9860(5) 0.8901(3) 0.08653(15) 0.0196(7) Uani 1 1 d . . . . .
C5 C 0.9570(5) 0.9421(3) 0.03628(15) 0.0190(7) Uani 1 1 d . . . . .
C6 C 0.9360(5) 1.0459(3) 0.03435(16) 0.0205(7) Uani 1 1 d . . . . .
C7 C 0.9332(5) 1.0914(3) 0.08629(16) 0.0235(7) Uani 1 1 d . . . . .
H7 H 0.9153 1.1611 0.0878 0.028 Uiso 1 1 calc R U . . .
C8 C 0.9554(5) 1.0397(3) 0.13677(16) 0.0231(7) Uani 1 1 d . . . . .
H8 H 0.9526 1.0761 0.1710 0.028 Uiso 1 1 calc R U . . .
C9 C 0.9816(5) 0.9370(3) 0.13942(16) 0.0210(7) Uani 1 1 d . . . . .
C10 C 0.9797(5) 0.6906(3) -0.01775(16) 0.0195(7) Uani 1 1 d . . . . .
C11 C 1.0237(5) 0.6944(3) -0.07527(16) 0.0216(7) Uani 1 1 d . . . . .
H11 H 1.0547 0.7559 -0.0924 0.026 Uiso 1 1 calc R U . . .
C12 C 1.0218(5) 0.6080(3) -0.10705(16) 0.0240(7) Uani 1 1 d . . . . .
H12 H 1.0492 0.6104 -0.1461 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9793(5) 0.5175(3) -0.08142(17) 0.0253(8) Uani 1 1 d . . . . .
H13 H 0.9794 0.4583 -0.1031 0.030 Uiso 1 1 calc R U . . .
C14 C 0.9374(5) 0.5137(3) -0.02495(16) 0.0252(8) Uani 1 1 d . . . . .
H14 H 0.9089 0.4519 -0.0079 0.030 Uiso 1 1 calc R U . . .
C15 C 0.9366(5) 0.6001(3) 0.00740(15) 0.0213(7) Uani 1 1 d . . . . .
H15 H 0.9068 0.5972 0.0463 0.026 Uiso 1 1 calc R U . . .
C16 C 0.9308(5) 1.1050(2) -0.01860(15) 0.0209(7) Uani 1 1 d . . . . .
C17 C 1.0453(5) 1.0818(3) -0.06364(15) 0.0231(7) Uani 1 1 d . . . . .
H17 H 1.1191 1.0234 -0.0622 0.028 Uiso 1 1 calc R U . . .
C18 C 1.0539(6) 1.1425(3) -0.11081(17) 0.0286(8) Uani 1 1 d . . . . .
H18 H 1.1332 1.1258 -0.1413 0.034 Uiso 1 1 calc R U . . .
C19 C 0.9450(6) 1.2283(3) -0.11301(17) 0.0304(8) Uani 1 1 d . . . . .
H19 H 0.9507 1.2705 -0.1449 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8294(6) 1.2514(3) -0.06871(18) 0.0295(8) Uani 1 1 d . . . . .
H20 H 0.7553 1.3097 -0.0704 0.035 Uiso 1 1 calc R U . . .
C21 C 0.8200(6) 1.1901(3) -0.02140(17) 0.0259(8) Uani 1 1 d . . . . .
H21 H 0.7387 1.2061 0.0087 0.031 Uiso 1 1 calc R U . . .
C22 C 0.9931(5) 0.8869(3) 0.19467(15) 0.0205(7) Uani 1 1 d . . . . .
C23 C 0.8905(6) 0.9244(3) 0.23979(16) 0.0251(7) Uani 1 1 d . . . . .
H23 H 0.8116 0.9799 0.2339 0.030 Uiso 1 1 calc R U . . .
C24 C 0.9008(6) 0.8830(3) 0.29257(16) 0.0287(8) Uani 1 1 d . . . . .
H24 H 0.8321 0.9108 0.3228 0.034 Uiso 1 1 calc R U . . .
C25 C 1.0124(6) 0.8002(3) 0.30143(17) 0.0293(9) Uani 1 1 d . . . . .
H25 H 1.0187 0.7704 0.3376 0.035 Uiso 1 1 calc R U . . .
C26 C 1.1140(6) 0.7614(3) 0.25722(17) 0.0278(8) Uani 1 1 d . . . . .
H26 H 1.1900 0.7048 0.2632 0.033 Uiso 1 1 calc R U . . .
C27 C 1.1060(6) 0.8048(3) 0.20398(15) 0.0224(7) Uani 1 1 d . . . . .
H27 H 1.1778 0.7782 0.1740 0.027 Uiso 1 1 calc R U . . .
N1 N 0.9527(4) 0.8730(2) -0.00676(13) 0.0183(6) Uani 1 1 d . . . . .
H1 H 0.911(7) 0.878(3) -0.038(2) 0.022 Uiso 1 1 d . U . . .
N3 N 1.0002(4) 0.7900(2) 0.07070(13) 0.0185(6) Uani 1 1 d . . . . .
H3 H 1.031(7) 0.745(4) 0.0918(19) 0.022 Uiso 1 1 d . U . . .
C28 C 0.6077(6) 0.5983(3) 0.20472(16) 0.0284(8) Uani 1 1 d . . . . .
H28 H 0.4986 0.5836 0.1801 0.034 Uiso 1 1 calc R U . . .
Cl2 Cl 0.81384(14) 0.58337(7) 0.16554(4) 0.0320(2) Uani 1 1 d . . . . .
Cl3 Cl 0.60731(17) 0.51577(10) 0.26239(5) 0.0489(3) Uani 1 1 d . . . . .
Cl4 Cl 0.59265(16) 0.72176(8) 0.22872(5) 0.0386(3) Uani 1 1 d . . . . .
Cl1 Cl 0.73779(11) 0.89438(6) 0.88401(3) 0.0211(2) Uani 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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N3 . . 1.329(5) y
C2 N1 . . 1.338(4) y
C2 C10 . . 1.470(5) y
C4 C5 . . 1.401(5) y
C4 N3 . . 1.404(4) y
C4 C9 . . 1.409(5) y
C5 N1 . . 1.384(5) y
C5 C6 . . 1.408(5) y
C6 C7 . . 1.379(5) y
C6 C16 . . 1.490(5) y
C7 C8 . . 1.397(5) y
C7 H7 . . 0.9500 ?
C8 C9 . . 1.398(5) y
C8 H8 . . 0.9500 ?
C9 C22 . . 1.480(5) y
C10 C15 . . 1.394(5) y
C10 C11 . . 1.405(5) y
C11 C12 . . 1.388(5) y
C11 H11 . . 0.9500 ?
C12 C13 . . 1.398(5) y
C12 H12 . . 0.9500 ?
C13 C14 . . 1.377(6) y
C13 H13 . . 0.9500 ?
C14 C15 . . 1.395(5) y
C14 H14 . . 0.9500 ?
C15 H15 . . 0.9500 ?
C16 C17 . . 1.387(5) y
C16 C21 . . 1.399(5) y
C17 C18 . . 1.390(5) y
C17 H17 . . 0.9500 ?
C18 C19 . . 1.399(6) y
C18 H18 . . 0.9500 ?
C19 C20 . . 1.378(6) y
C19 H19 . . 0.9500 ?
C20 C21 . . 1.398(6) y
C20 H20 . . 0.9500 ?
C21 H21 . . 0.9500 ?
C22 C27 . . 1.391(5) y
C22 C23 . . 1.398(5) y
C23 C24 . . 1.375(6) y
C23 H23 . . 0.9500 ?
C24 C25 . . 1.392(6) y
C24 H24 . . 0.9500 ?
C25 C26 . . 1.383(6) y
C25 H25 . . 0.9500 ?
C26 C27 . . 1.396(5) y
C26 H26 . . 0.9500 ?
C27 H27 . . 0.9500 ?
N1 H1 . . 0.79(5) ?
N3 H3 . . 0.82(5) ?
C28 Cl4 . . 1.763(4) y
C28 Cl2 . . 1.764(4) y
C28 Cl3 . . 1.766(4) y
C28 H28 . . 1.0000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C2 N1 . . . 109.8(3) y
N3 C2 C10 . . . 126.3(3) y
N1 C2 C10 . . . 123.9(3) y
C5 C4 N3 . . . 105.2(3) y
C5 C4 C9 . . . 122.2(3) y
N3 C4 C9 . . . 132.3(3) y
N1 C5 C4 . . . 107.3(3) y
N1 C5 C6 . . . 129.9(3) y
C4 C5 C6 . . . 122.8(3) y
C7 C6 C5 . . . 114.5(3) y
C7 C6 C16 . . . 121.2(3) y
C5 C6 C16 . . . 124.2(3) y
C6 C7 C8 . . . 123.1(3) y
C6 C7 H7 . . . 118.5 ?
C8 C7 H7 . . . 118.5 ?
C7 C8 C9 . . . 123.2(3) y
C7 C8 H8 . . . 118.4 ?
C9 C8 H8 . . . 118.4 ?
C8 C9 C4 . . . 114.1(3) y
C8 C9 C22 . . . 120.0(3) y
C4 C9 C22 . . . 125.9(3) y
C15 C10 C11 . . . 120.0(3) y
C15 C10 C2 . . . 120.5(3) y
C11 C10 C2 . . . 119.6(3) y
C12 C11 C10 . . . 119.8(3) y
C12 C11 H11 . . . 120.1 ?
C10 C11 H11 . . . 120.1 ?
C11 C12 C13 . . . 119.8(3) y
C11 C12 H12 . . . 120.1 ?
C13 C12 H12 . . . 120.1 ?
C14 C13 C12 . . . 120.3(3) y
C14 C13 H13 . . . 119.8 ?
C12 C13 H13 . . . 119.8 ?
C13 C14 C15 . . . 120.5(3) y
C13 C14 H14 . . . 119.7 ?
C15 C14 H14 . . . 119.7 ?
C10 C15 C14 . . . 119.5(3) y
C10 C15 H15 . . . 120.2 ?
C14 C15 H15 . . . 120.2 ?
C17 C16 C21 . . . 119.2(3) y
C17 C16 C6 . . . 121.1(3) y
C21 C16 C6 . . . 119.5(3) y
C16 C17 C18 . . . 121.1(4) y
C16 C17 H17 . . . 119.5 ?
C18 C17 H17 . . . 119.5 ?
C17 C18 C19 . . . 119.5(4) y
C17 C18 H18 . . . 120.3 ?
C19 C18 H18 . . . 120.3 ?
C20 C19 C18 . . . 119.8(4) y
C20 C19 H19 . . . 120.1 ?
C18 C19 H19 . . . 120.1 ?
C19 C20 C21 . . . 120.7(4) y
C19 C20 H20 . . . 119.6 ?
C21 C20 H20 . . . 119.6 ?
C20 C21 C16 . . . 119.7(4) y
C20 C21 H21 . . . 120.1 ?
C16 C21 H21 . . . 120.1 ?
C27 C22 C23 . . . 118.3(3) y
C27 C22 C9 . . . 122.5(3) y
C23 C22 C9 . . . 119.1(3) y
C24 C23 C22 . . . 121.7(4) y
C24 C23 H23 . . . 119.2 ?
C22 C23 H23 . . . 119.2 ?
C23 C24 C25 . . . 119.6(4) y
C23 C24 H24 . . . 120.2 ?
C25 C24 H24 . . . 120.2 ?
C26 C25 C24 . . . 119.6(4) y
C26 C25 H25 . . . 120.2 ?
C24 C25 H25 . . . 120.2 ?
C25 C26 C27 . . . 120.6(4) y
C25 C26 H26 . . . 119.7 ?
C27 C26 H26 . . . 119.7 ?
C22 C27 C26 . . . 120.1(4) y
C22 C27 H27 . . . 119.9 ?
C26 C27 H27 . . . 119.9 ?
C2 N1 C5 . . . 108.5(3) y
C2 N1 H1 . . . 119(3) ?
C5 N1 H1 . . . 130(3) ?
C2 N3 C4 . . . 109.1(3) y
C2 N3 H3 . . . 126(3) ?
C4 N3 H3 . . . 125(3) ?
CL4 C28 CL2 . . . 109.3(2) y
CL4 C28 CL3 . . . 110.1(2) y
CL2 C28 CL3 . . . 109.8(2) y
CL4 C28 H28 . . . 109.2 ?
CL2 C28 H28 . . . 109.2 ?
CL3 C28 H28 . . . 109.2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 C4 C5 N1 . . . . 0.7(4) y
C9 C4 C5 N1 . . . . -174.3(3) y
N3 C4 C5 C6 . . . . -179.8(3) y
C9 C4 C5 C6 . . . . 5.1(6) y
N1 C5 C6 C7 . . . . 175.0(4) y
C4 C5 C6 C7 . . . . -4.3(5) y
N1 C5 C6 C16 . . . . -9.4(6) y
C4 C5 C6 C16 . . . . 171.3(3) y
C5 C6 C7 C8 . . . . 2.0(5) y
C16 C6 C7 C8 . . . . -173.8(4) y
C6 C7 C8 C9 . . . . -0.3(6) y
C7 C8 C9 C4 . . . . 0.7(6) y
C7 C8 C9 C22 . . . . -176.4(4) y
C5 C4 C9 C8 . . . . -3.0(5) y
N3 C4 C9 C8 . . . . -176.6(4) y
C5 C4 C9 C22 . . . . 173.9(3) y
N3 C4 C9 C22 . . . . 0.4(6) y
N3 C2 C10 C15 . . . . 24.4(6) y
N1 C2 C10 C15 . . . . -155.7(3) y
N3 C2 C10 C11 . . . . -156.2(4) y
N1 C2 C10 C11 . . . . 23.7(5) y
C15 C10 C11 C12 . . . . 0.8(5) y
C2 C10 C11 C12 . . . . -178.6(3) y
C10 C11 C12 C13 . . . . -1.2(6) y
C11 C12 C13 C14 . . . . 0.7(6) y
C12 C13 C14 C15 . . . . 0.1(6) y
C11 C10 C15 C14 . . . . 0.0(5) y
C2 C10 C15 C14 . . . . 179.3(3) y
C13 C14 C15 C10 . . . . -0.4(6) y
C7 C6 C16 C17 . . . . 136.6(4) y
C5 C6 C16 C17 . . . . -38.7(5) y
C7 C6 C16 C21 . . . . -38.1(5) y
C5 C6 C16 C21 . . . . 146.6(4) y
C21 C16 C17 C18 . . . . 1.1(5) y
C6 C16 C17 C18 . . . . -173.6(3) y
C16 C17 C18 C19 . . . . -0.1(6) y
C17 C18 C19 C20 . . . . -0.5(6) y
C18 C19 C20 C21 . . . . 0.2(6) y
C19 C20 C21 C16 . . . . 0.8(6) y
C17 C16 C21 C20 . . . . -1.5(6) y
C6 C16 C21 C20 . . . . 173.3(3) y
C8 C9 C22 C27 . . . . -145.9(4) y
C4 C9 C22 C27 . . . . 37.3(6) y
C8 C9 C22 C23 . . . . 32.5(5) y
C4 C9 C22 C23 . . . . -144.3(4) y
C27 C22 C23 C24 . . . . 0.8(6) y
C9 C22 C23 C24 . . . . -177.7(4) y
C22 C23 C24 C25 . . . . -1.6(6) y
C23 C24 C25 C26 . . . . 1.0(6) y
C24 C25 C26 C27 . . . . 0.2(6) y
C23 C22 C27 C26 . . . . 0.5(5) y
C9 C22 C27 C26 . . . . 178.9(4) y
C25 C26 C27 C22 . . . . -1.0(6) y
N3 C2 N1 C5 . . . . -0.7(4) y
C10 C2 N1 C5 . . . . 179.4(3) y
C4 C5 N1 C2 . . . . -0.1(4) y
C6 C5 N1 C2 . . . . -179.5(4) y
N1 C2 N3 C4 . . . . 1.1(4) y
C10 C2 N3 C4 . . . . -178.9(3) y
C5 C4 N3 C2 . . . . -1.1(4) y
C9 C4 N3 C2 . . . . 173.2(4) y

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
_geom_hbond_publ_flag
N1 H1 CL1 0.79(5) 2.25(5) 3.037(3) 168(5) 1_554 y
N3 H3 CL1 0.82(5) 2.46(5) 3.204(3) 151(4) 3_566 y





_database_code_depnum_ccdc_archive 'CCDC 1011327'
