# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cqnn-ortho_a
_database_code_depnum_ccdc_archive 'CCDC 1872167'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H26 N2'
_chemical_formula_sum            'C41 H26 N2'
_chemical_formula_weight         546.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   24.211(3)
_cell_length_b                   11.3310(17)
_cell_length_c                   10.5117(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2883.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5988
_cell_measurement_theta_min      1.984
_cell_measurement_theta_max      26.508

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38547
_diffrn_reflns_av_unetI/netI     0.1229
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         26.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5909
_reflns_number_gt                3133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.995

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0641P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     389
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N1 N 0.56692(16) 0.3107(4) 0.3800(4) 0.0462(10) Uani 1 1 d . . . . .
N2 N 0.67103(17) 0.3366(4) 0.2809(4) 0.0541(12) Uani 1 1 d . . . . .
C2 C 0.5167(2) 0.2992(4) 0.4287(5) 0.0436(12) Uani 1 1 d . . . . .
C3 C 0.5072(2) 0.2727(4) 0.5572(5) 0.0470(13) Uani 1 1 d . . . . .
H3 H 0.471087 0.271668 0.587277 0.056 Uiso 1 1 calc R U . . .
C4 C 0.54948(18) 0.2483(4) 0.6399(4) 0.0424(12) Uani 1 1 d . . . . .
C5 C 0.6518(2) 0.2192(5) 0.6574(5) 0.0555(14) Uani 1 1 d . . . . .
H5 H 0.648412 0.193409 0.740985 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7028(2) 0.2247(5) 0.6020(5) 0.0639(16) Uani 1 1 d . . . . .
H6 H 0.733728 0.200383 0.647420 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7090(2) 0.2665(5) 0.4781(5) 0.0591(15) Uani 1 1 d . . . . .
H7 H 0.744089 0.272837 0.442892 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6642(2) 0.2978(4) 0.4084(5) 0.0494(13) Uani 1 1 d . . . . .
C9 C 0.6102(2) 0.2887(4) 0.4596(5) 0.0450(12) Uani 1 1 d . . . . .
C10 C 0.6041(2) 0.2525(4) 0.5882(5) 0.0450(12) Uani 1 1 d . . . . .
C11 C 0.6603(2) 0.4510(5) 0.2360(5) 0.0548(14) Uani 1 1 d . . . . .
C11A C 0.6934(2) 0.2707(5) 0.1820(6) 0.0580(15) Uani 1 1 d . . . . .
C12 C 0.6381(2) 0.5457(6) 0.2996(6) 0.0691(17) Uani 1 1 d . . . . .
H12 H 0.627218 0.539669 0.384162 0.083 Uiso 1 1 calc R U . . .
C12A C 0.7092(2) 0.1536(6) 0.1816(7) 0.0717(17) Uani 1 1 d . . . . .
H12A H 0.705790 0.106804 0.253768 0.086 Uiso 1 1 calc R U . . .
C13 C 0.6326(3) 0.6505(6) 0.2331(8) 0.0820(19) Uani 1 1 d . . . . .
H13 H 0.618448 0.716468 0.274313 0.098 Uiso 1 1 calc R U . . .
C13A C 0.7306(3) 0.1086(7) 0.0683(8) 0.090(2) Uani 1 1 d . . . . .
H13A H 0.741196 0.029838 0.063653 0.108 Uiso 1 1 calc R U . . .
C14 C 0.6475(3) 0.6589(8) 0.1083(9) 0.092(2) Uani 1 1 d . . . . .
H14 H 0.643202 0.730470 0.066149 0.111 Uiso 1 1 calc R U . . .
C14A C 0.7359(3) 0.1808(9) -0.0372(8) 0.099(3) Uani 1 1 d . . . . .
H14A H 0.750968 0.149376 -0.111253 0.118 Uiso 1 1 calc R U . . .
C15 C 0.6687(3) 0.5642(8) 0.0437(7) 0.085(2) Uani 1 1 d . . . . .
H15 H 0.677867 0.570524 -0.041929 0.103 Uiso 1 1 calc R U . . .
C15A C 0.7201(3) 0.2953(8) -0.0366(7) 0.088(2) Uani 1 1 d . . . . .
H15A H 0.724392 0.341291 -0.109220 0.106 Uiso 1 1 calc R U . . .
C16 C 0.6763(2) 0.4585(6) 0.1086(6) 0.0626(16) Uani 1 1 d . . . . .
C16A C 0.6973(2) 0.3443(6) 0.0741(5) 0.0663(17) Uani 1 1 d . . . . .
C17 C 0.47017(19) 0.3198(4) 0.3387(4) 0.0442(12) Uani 1 1 d . . . . .
C18 C 0.4702(2) 0.4188(5) 0.2642(6) 0.0586(15) Uani 1 1 d . . . . .
H18 H 0.499311 0.472022 0.270802 0.070 Uiso 1 1 calc R U . . .
C19 C 0.4273(3) 0.4416(5) 0.1783(6) 0.0689(17) Uani 1 1 d . . . . .
H19 H 0.428856 0.507948 0.126381 0.083 Uiso 1 1 calc R U . . .
C20 C 0.3837(2) 0.3678(5) 0.1704(6) 0.0666(16) Uani 1 1 d . . . . .
H20 H 0.354625 0.385951 0.116122 0.080 Uiso 1 1 calc R U . . .
C21 C 0.3376(2) 0.1817(6) 0.2315(6) 0.0616(16) Uani 1 1 d . . . . .
H21 H 0.308285 0.199146 0.177612 0.074 Uiso 1 1 calc R U . . .
C22 C 0.3376(2) 0.0787(6) 0.2972(6) 0.0676(17) Uani 1 1 d . . . . .
H22 H 0.307807 0.027369 0.290618 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3825(2) 0.0498(5) 0.3749(6) 0.0620(15) Uani 1 1 d . . . . .
H23 H 0.382807 -0.022052 0.417722 0.074 Uiso 1 1 calc R U . . .
C24 C 0.4254(2) 0.1252(4) 0.3886(5) 0.0499(13) Uani 1 1 d . . . . .
H24 H 0.455147 0.103627 0.439579 0.060 Uiso 1 1 calc R U . . .
C25 C 0.42605(19) 0.2365(4) 0.3269(5) 0.0438(12) Uani 1 1 d . . . . .
C26 C 0.3817(2) 0.2628(5) 0.2437(5) 0.0509(13) Uani 1 1 d . . . . .
C27 C 0.5383(2) 0.2276(5) 0.7772(5) 0.0471(13) Uani 1 1 d . . . . .
C28 C 0.5659(2) 0.2920(5) 0.8675(5) 0.0543(14) Uani 1 1 d . . . . .
H28 H 0.593808 0.343261 0.842144 0.065 Uiso 1 1 calc R U . . .
C29 C 0.5532(2) 0.2825(6) 0.9966(5) 0.0639(16) Uani 1 1 d . . . . .
H29 H 0.572968 0.326405 1.055978 0.077 Uiso 1 1 calc R U . . .
C30 C 0.5124(3) 0.2097(5) 1.0358(6) 0.0639(16) Uani 1 1 d . . . . .
H30 H 0.504115 0.204770 1.122032 0.077 Uiso 1 1 calc R U . . .
C31 C 0.4380(2) 0.0691(5) 0.9870(6) 0.0623(16) Uani 1 1 d . . . . .
H31 H 0.428136 0.066482 1.072412 0.075 Uiso 1 1 calc R U . . .
C32 C 0.4098(3) 0.0037(5) 0.9026(6) 0.0689(16) Uani 1 1 d . . . . .
H32 H 0.379562 -0.040205 0.929497 0.083 Uiso 1 1 calc R U . . .
C33 C 0.4255(2) 0.0010(6) 0.7752(6) 0.0676(16) Uani 1 1 d . . . . .
H33 H 0.407059 -0.048148 0.718486 0.081 Uiso 1 1 calc R U . . .
C34 C 0.4681(2) 0.0705(5) 0.7331(5) 0.0549(14) Uani 1 1 d . . . . .
H34 H 0.478536 0.067277 0.648015 0.066 Uiso 1 1 calc R U . . .
C35 C 0.4964(2) 0.1474(4) 0.8174(5) 0.0468(12) Uani 1 1 d . . . . .
C36 C 0.4823(2) 0.1416(5) 0.9486(5) 0.0506(13) 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.325(6) . ?
N1 C9 1.365(6) . ?
N2 C11A 1.390(7) . ?
N2 C11 1.403(7) . ?
N2 C8 1.420(7) . ?
C2 C3 1.403(7) . ?
C2 C17 1.490(7) . ?
C3 C4 1.371(7) . ?
C3 H3 0.9300 . ?
C4 C10 1.430(6) . ?
C4 C27 1.486(7) . ?
C5 C6 1.367(7) . ?
C5 C10 1.416(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(7) . ?
C9 C10 1.420(7) . ?
C11 C12 1.373(8) . ?
C11 C16 1.397(7) . ?
C11A C12A 1.381(8) . ?
C11A C16A 1.410(8) . ?
C12 C13 1.384(8) . ?
C12 H12 0.9300 . ?
C12A C13A 1.394(9) . ?
C12A H12A 0.9300 . ?
C13 C14 1.364(10) . ?
C13 H13 0.9300 . ?
C13A C14A 1.384(10) . ?
C13A H13A 0.9300 . ?
C14 C15 1.369(11) . ?
C14 H14 0.9300 . ?
C14A C15A 1.353(10) . ?
C14A H14A 0.9300 . ?
C15 C16 1.390(9) . ?
C15 H15 0.9300 . ?
C15A C16A 1.404(9) . ?
C15A H15A 0.9300 . ?
C16 C16A 1.437(9) . ?
C17 C18 1.368(7) . ?
C17 C25 1.431(7) . ?
C18 C19 1.401(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(8) . ?
C19 H19 0.9300 . ?
C20 C26 1.417(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(8) . ?
C21 C26 1.415(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.398(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.354(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.418(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.417(7) . ?
C27 C28 1.371(7) . ?
C27 C35 1.427(7) . ?
C28 C29 1.396(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.351(8) . ?
C29 H29 0.9300 . ?
C30 C36 1.402(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.342(8) . ?
C31 C36 1.411(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.393(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.370(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.420(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.422(7) . ?

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
C2 N1 C9 116.7(4) . . ?
C11A N2 C11 108.5(4) . . ?
C11A N2 C8 125.8(5) . . ?
C11 N2 C8 125.5(4) . . ?
N1 C2 C3 122.9(5) . . ?
N1 C2 C17 115.7(4) . . ?
C3 C2 C17 121.4(4) . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C10 116.3(4) . . ?
C3 C4 C27 120.8(4) . . ?
C10 C4 C27 122.8(4) . . ?
C6 C5 C10 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 N2 119.8(5) . . ?
C9 C8 N2 119.3(5) . . ?
N1 C9 C8 117.5(4) . . ?
N1 C9 C10 123.8(4) . . ?
C8 C9 C10 118.7(4) . . ?
C5 C10 C9 118.7(4) . . ?
C5 C10 C4 123.4(4) . . ?
C9 C10 C4 117.9(4) . . ?
C12 C11 C16 121.8(6) . . ?
C12 C11 N2 129.1(5) . . ?
C16 C11 N2 109.1(5) . . ?
C12A C11A N2 128.8(6) . . ?
C12A C11A C16A 123.2(6) . . ?
N2 C11A C16A 108.1(5) . . ?
C11 C12 C13 117.5(6) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C11A C12A C13A 117.2(7) . . ?
C11A C12A H12A 121.4 . . ?
C13A C12A H12A 121.4 . . ?
C14 C13 C12 121.4(8) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C14A C13A C12A 120.2(7) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C13 C14 C15 121.4(8) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C15A C14A C13A 122.4(7) . . ?
C15A C14A H14A 118.8 . . ?
C13A C14A H14A 118.8 . . ?
C14 C15 C16 118.8(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C14A C15A C16A 119.7(8) . . ?
C14A C15A H15A 120.2 . . ?
C16A C15A H15A 120.2 . . ?
C15 C16 C11 119.1(7) . . ?
C15 C16 C16A 134.4(6) . . ?
C11 C16 C16A 106.5(5) . . ?
C15A C16A C11A 117.3(7) . . ?
C15A C16A C16 134.8(7) . . ?
C11A C16A C16 107.8(5) . . ?
C18 C17 C25 119.5(4) . . ?
C18 C17 C2 119.4(5) . . ?
C25 C17 C2 121.1(4) . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 120.4(6) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C26 120.9(5) . . ?
C19 C20 H20 119.5 . . ?
C26 C20 H20 119.5 . . ?
C22 C21 C26 120.9(5) . . ?
C22 C21 H21 119.6 . . ?
C26 C21 H21 119.6 . . ?
C21 C22 C23 120.0(5) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 121.4(5) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 117.5(5) . . ?
C26 C25 C17 118.7(4) . . ?
C24 C25 C17 123.7(4) . . ?
C21 C26 C25 119.4(5) . . ?
C21 C26 C20 121.5(5) . . ?
C25 C26 C20 119.1(5) . . ?
C28 C27 C35 118.7(5) . . ?
C28 C27 C4 120.0(5) . . ?
C35 C27 C4 121.1(5) . . ?
C27 C28 C29 121.7(5) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C30 C29 C28 120.3(5) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C36 121.1(5) . . ?
C29 C30 H30 119.5 . . ?
C36 C30 H30 119.5 . . ?
C32 C31 C36 121.3(5) . . ?
C32 C31 H31 119.3 . . ?
C36 C31 H31 119.3 . . ?
C31 C32 C33 120.6(6) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 121.0(5) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C36 117.5(5) . . ?
C34 C35 C27 123.4(5) . . ?
C36 C35 C27 119.2(5) . . ?
C30 C36 C31 121.9(5) . . ?
C30 C36 C35 119.0(5) . . ?
C31 C36 C35 119.1(5) . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_CQNN_a
_database_code_depnum_ccdc_archive 'CCDC 1872168'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_CQNN_a              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.71 eA-3
RESPONSE: The above alerts due to the crystal growth was very  difficult in this case and after repeated crystallization we  could obtain  crystals which were of not very good quality.  Moreover, the H positions could not be obtained accurately  from X-ray diffraction data.
;
_vrf_PLAT230_CQNN_a              
;
PROBLEM: Hirshfeld Test Diff for    C27      --C28      .        8.6 s.u.
RESPONSE: Structural observation does not indicate any problems in the thermal ellipsoids. Since the Hirshfeld test is  performed relative to the esd of the thermal parameters. The alert might be caused by the low esd of the heavy atom position. ;
;
_vrf_PLAT230_CQNN_a_2            
;
PROBLEM: Hirshfeld Test Diff for    C34      --C35      .        9.2 s.u.
RESPONSE: Structural observation does not indicate any problems in the thermal ellipsoids. Since the Hirshfeld test is  performed relative to the esd of the thermal parameters. The alert might be caused by the low esd of the heavy atom position. ;
;
_vrf_PLAT369_CQNN_a              
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C4       - C27      .       1.57 Ang.
RESPONSE: Conjugated systems may cause higher bond distance
;
_vrf_PLAT369_CQNN_a_2            
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C34      - C35      .       1.57 Ang.
RESPONSE: Conjugated systems may cause higher bond distance
;
# Added during the CSD deposition process: Tuesday 08 January 2019 05:30 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H26 N2'
_chemical_formula_sum            'C41 H26 N2'
_chemical_formula_weight         546.64
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.8272(6)
_cell_length_b                   27.987(2)
_cell_length_c                   11.8174(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.951(3)
_cell_angle_gamma                90
_cell_volume                     2891.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5925
_cell_measurement_theta_min      1.886
_cell_measurement_theta_max      26.434


_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49555
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         26.434
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5925
_reflns_number_gt                2726
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1190P)²+3.7193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5925
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1805
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.3298
_refine_ls_wR_factor_gt          0.2516
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
N1 N 0.4483(4) 0.67821(14) 0.5705(3) 0.0758(11) Uani 1 1 d . . . . .
N2 N 0.4112(4) 0.77428(12) 0.6228(3) 0.0678(10) Uani 1 1 d . . . . .
C2 C 0.4675(7) 0.63244(19) 0.5487(6) 0.1062(15) Uani 1 1 d . . . . .
C3 C 0.4016(7) 0.59577(19) 0.6085(6) 0.1062(15) Uani 1 1 d . . . . .
H3 H 0.419145 0.564019 0.591022 0.127 Uiso 1 1 calc R U . . .
C4 C 0.3125(7) 0.60604(19) 0.6915(6) 0.1052(15) Uani 1 1 d . . . . .
C5 C 0.1945(7) 0.66903(19) 0.7958(6) 0.1052(15) Uani 1 1 d . . . . .
H5 H 0.145354 0.646065 0.834465 0.126 Uiso 1 1 calc R U . . .
C6 C 0.1781(6) 0.71541(18) 0.8198(5) 0.0866(16) Uani 1 1 d . . . . .
H6 H 0.119131 0.724389 0.875617 0.104 Uiso 1 1 calc R U . . .
C7 C 0.2498(5) 0.75036(17) 0.7609(4) 0.0745(13) Uani 1 1 d . . . . .
H7 H 0.237078 0.782474 0.777558 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3378(5) 0.73789(15) 0.6797(4) 0.0661(12) Uani 1 1 d . . . . .
C9 C 0.3576(5) 0.68927(16) 0.6523(4) 0.0700(12) Uani 1 1 d . . . . .
C10 C 0.2845(6) 0.65475(17) 0.7132(5) 0.0865(16) Uani 1 1 d . . . . .
C11 C 0.5634(6) 0.78769(17) 0.6496(4) 0.0739(13) Uani 1 1 d . . . . .
C11A C 0.3368(6) 0.80744(16) 0.5464(4) 0.0691(12) Uani 1 1 d . . . . .
C12 C 0.6772(6) 0.7669(2) 0.7254(5) 0.0950(17) Uani 1 1 d . . . . .
H12 H 0.658862 0.739629 0.766206 0.114 Uiso 1 1 calc R U . . .
C12A C 0.1859(7) 0.80887(19) 0.4984(5) 0.0888(15) Uani 1 1 d . . . . .
H12A H 0.115588 0.786342 0.516471 0.107 Uiso 1 1 calc R U . . .
C13 C 0.8201(7) 0.7884(3) 0.7384(6) 0.119(2) Uani 1 1 d . . . . .
H13 H 0.898855 0.775567 0.789828 0.142 Uiso 1 1 calc R U . . .
C13A C 0.1442(8) 0.8451(2) 0.4226(6) 0.1084(19) Uani 1 1 d . . . . .
H13A H 0.042994 0.847188 0.388375 0.130 Uiso 1 1 calc R U . . .
C14 C 0.8473(9) 0.8284(3) 0.6766(8) 0.130(3) Uani 1 1 d . . . . .
H14 H 0.944971 0.841566 0.685844 0.156 Uiso 1 1 calc R U . . .
C14A C 0.2479(10) 0.8785(2) 0.3958(6) 0.116(2) Uani 1 1 d . . . . .
H14A H 0.215701 0.902449 0.343293 0.140 Uiso 1 1 calc R U . . .
C15 C 0.7348(8) 0.8493(2) 0.6019(6) 0.107(2) Uani 1 1 d . . . . .
H15 H 0.754985 0.876497 0.561192 0.129 Uiso 1 1 calc R U . . .
C15A C 0.3978(9) 0.87719(19) 0.4450(6) 0.1000(19) Uani 1 1 d . . . . .
H15A H 0.466639 0.900152 0.426684 0.120 Uiso 1 1 calc R U . . .
C16 C 0.5878(6) 0.82901(17) 0.5879(4) 0.0795(15) Uani 1 1 d . . . . .
C16A C 0.4455(6) 0.84131(16) 0.5221(4) 0.0749(14) Uani 1 1 d . . . . .
C17 C 0.5640(7) 0.61953(18) 0.4588(5) 0.0923(17) Uani 1 1 d . . . . .
C18 C 0.5071(8) 0.5861(2) 0.3799(7) 0.127(2) Uani 1 1 d . . . . .
H18 H 0.412070 0.572398 0.384005 0.153 Uiso 1 1 calc R U . . .
C19 C 0.5932(10) 0.5721(2) 0.2906(6) 0.129(2) Uani 1 1 d . . . . .
H19 H 0.553252 0.549808 0.236232 0.155 Uiso 1 1 calc R U . . .
C20 C 0.7312(9) 0.5913(2) 0.2861(6) 0.114(2) Uani 1 1 d . . . . .
H20 H 0.785567 0.582309 0.227482 0.137 Uiso 1 1 calc R U . . .
C21 C 0.9464(7) 0.6424(2) 0.3656(6) 0.103(2) Uani 1 1 d . . . . .
H21 H 1.002607 0.632553 0.308855 0.124 Uiso 1 1 calc R U . . .
C22 C 1.0094(8) 0.6736(3) 0.4455(6) 0.111(2) Uani 1 1 d . . . . .
H22 H 1.107945 0.685048 0.443621 0.134 Uiso 1 1 calc R U . . .
C23 C 0.9277(7) 0.6883(2) 0.5294(6) 0.1049(19) Uani 1 1 d . . . . .
H23 H 0.972119 0.709664 0.584510 0.126 Uiso 1 1 calc R U . . .
C24 C 0.7812(6) 0.67217(19) 0.5345(5) 0.0896(16) Uani 1 1 d . . . . .
H24 H 0.728319 0.683190 0.592172 0.108 Uiso 1 1 calc R U . . .
C25 C 0.7106(6) 0.63943(18) 0.4541(5) 0.0865(11) Uani 1 1 d . . . . .
C26 C 0.7950(7) 0.62416(18) 0.3660(5) 0.0865(11) Uani 1 1 d . . . . .
C27 C 0.2573(9) 0.5667(2) 0.7708(7) 0.111(2) Uani 1 1 d . . . . .
C28 C 0.3417(8) 0.5544(2) 0.8701(6) 0.1002(18) Uani 1 1 d . . . . .
H28 H 0.435361 0.569603 0.890161 0.120 Uiso 1 1 calc R U . . .
C29 C 0.2960(11) 0.5196(3) 0.9463(7) 0.137(3) Uani 1 1 d . . . . .
H29 H 0.357247 0.512355 1.014691 0.164 Uiso 1 1 calc R U . . .
C30 C 0.1503(10) 0.4958(2) 0.9136(7) 0.115(2) Uani 1 1 d . . . . .
H30 H 0.112882 0.472570 0.958659 0.138 Uiso 1 1 calc R U . . .
C31 C -0.0726(11) 0.4910(3) 0.7691(10) 0.144(3) Uani 1 1 d . . . . .
H31 H -0.109022 0.467830 0.814930 0.172 Uiso 1 1 calc R U . . .
C32 C -0.1611(15) 0.5025(4) 0.6722(13) 0.203(5) Uani 1 1 d . . . . .
H32 H -0.256891 0.488741 0.651764 0.243 Uiso 1 1 calc R U . . .
C33 C -0.1056(10) 0.5342(3) 0.6073(9) 0.167(4) Uani 1 1 d . . . . .
H33 H -0.166752 0.540699 0.538441 0.200 Uiso 1 1 calc R U . . .
C34 C 0.0266(8) 0.5586(2) 0.6254(6) 0.116(2) Uani 1 1 d . . . . .
H34 H 0.055469 0.580860 0.574050 0.139 Uiso 1 1 calc R U . . .
C35 C 0.1277(8) 0.54601(18) 0.7413(6) 0.1062(16) Uani 1 1 d . . . . .
C36 C 0.0695(9) 0.51086(18) 0.8072(7) 0.1062(16) 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.322(6) . ?
N1 C9 1.373(5) . ?
N2 C11 1.388(6) . ?
N2 C11A 1.394(6) . ?
N2 C8 1.425(5) . ?
C2 C3 1.416(7) . ?
C2 C17 1.494(7) . ?
C3 C4 1.370(7) . ?
C3 H3 0.9300 . ?
C4 C10 1.415(7) . ?
C4 C27 1.567(8) . ?
C5 C6 1.341(7) . ?
C5 C10 1.399(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(6) . ?
C9 C10 1.413(6) . ?
C11 C12 1.379(7) . ?
C11 C16 1.399(7) . ?
C11A C12A 1.375(7) . ?
C11A C16A 1.406(6) . ?
C12 C13 1.386(8) . ?
C12 H12 0.9300 . ?
C12A C13A 1.369(8) . ?
C12A H12A 0.9300 . ?
C13 C14 1.376(10) . ?
C13 H13 0.9300 . ?
C13A C14A 1.377(9) . ?
C13A H13A 0.9300 . ?
C14 C15 1.366(10) . ?
C14 H14 0.9300 . ?
C14A C15A 1.370(9) . ?
C14A H14A 0.9300 . ?
C15 C16 1.405(8) . ?
C15 H15 0.9300 . ?
C15A C16A 1.382(8) . ?
C15A H15A 0.9300 . ?
C16 C16A 1.424(7) . ?
C17 C18 1.366(8) . ?
C17 C25 1.417(7) . ?
C18 C19 1.438(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.339(9) . ?
C19 H19 0.9300 . ?
C20 C26 1.381(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.348(9) . ?
C21 C26 1.432(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.403(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.426(7) . ?
C27 C35 1.286(9) . ?
C27 C28 1.345(9) . ?
C28 C29 1.423(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.453(10) . ?
C29 H29 0.9300 . ?
C30 C36 1.421(10) . ?
C30 H30 0.9300 . ?
C31 C32 1.333(13) . ?
C31 C36 1.389(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.312(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.344(9) . ?
C33 H33 0.9300 . ?
C34 C35 1.568(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.396(8) . ?

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
C2 N1 C9 117.3(4) . . ?
C11 N2 C11A 108.8(4) . . ?
C11 N2 C8 125.1(4) . . ?
C11A N2 C8 125.2(4) . . ?
N1 C2 C3 122.1(5) . . ?
N1 C2 C17 118.3(5) . . ?
C3 C2 C17 119.5(5) . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C10 117.6(5) . . ?
C3 C4 C27 122.5(5) . . ?
C10 C4 C27 119.5(5) . . ?
C6 C5 C10 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C5 C6 C7 120.1(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 N2 119.4(4) . . ?
C9 C8 N2 120.1(4) . . ?
N1 C9 C10 123.8(4) . . ?
N1 C9 C8 118.7(4) . . ?
C10 C9 C8 117.5(4) . . ?
C5 C10 C9 120.2(4) . . ?
C5 C10 C4 122.1(4) . . ?
C9 C10 C4 117.6(4) . . ?
C12 C11 N2 129.0(5) . . ?
C12 C11 C16 122.4(5) . . ?
N2 C11 C16 108.6(5) . . ?
C12A C11A N2 129.0(4) . . ?
C12A C11A C16A 123.1(5) . . ?
N2 C11A C16A 107.9(4) . . ?
C11 C12 C13 117.4(6) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C13A C12A C11A 116.7(6) . . ?
C13A C12A H12A 121.7 . . ?
C11A C12A H12A 121.7 . . ?
C14 C13 C12 121.1(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12A C13A C14A 121.8(7) . . ?
C12A C13A H13A 119.1 . . ?
C14A C13A H13A 119.1 . . ?
C15 C14 C13 121.8(7) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C15A C14A C13A 121.2(6) . . ?
C15A C14A H14A 119.4 . . ?
C13A C14A H14A 119.4 . . ?
C14 C15 C16 118.7(6) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C14A C15A C16A 119.2(6) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 120.4 . . ?
C11 C16 C15 118.6(6) . . ?
C11 C16 C16A 107.2(4) . . ?
C15 C16 C16A 134.1(6) . . ?
C15A C16A C11A 118.0(6) . . ?
C15A C16A C16 134.5(5) . . ?
C11A C16A C16 107.5(4) . . ?
C18 C17 C25 119.6(5) . . ?
C18 C17 C2 117.3(5) . . ?
C25 C17 C2 123.1(5) . . ?
C17 C18 C19 120.4(6) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.7(7) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C26 121.8(6) . . ?
C19 C20 H20 119.1 . . ?
C26 C20 H20 119.1 . . ?
C22 C21 C26 121.6(6) . . ?
C22 C21 H21 119.2 . . ?
C26 C21 H21 119.2 . . ?
C21 C22 C23 119.6(6) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 121.7(7) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 121.0(5) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C17 123.5(5) . . ?
C24 C25 C26 117.5(5) . . ?
C17 C25 C26 118.9(5) . . ?
C20 C26 C25 119.6(6) . . ?
C20 C26 C21 121.8(6) . . ?
C25 C26 C21 118.5(6) . . ?
C35 C27 C28 119.1(7) . . ?
C35 C27 C4 119.5(8) . . ?
C28 C27 C4 121.4(7) . . ?
C27 C28 C29 123.7(7) . . ?
C27 C28 H28 118.1 . . ?
C29 C28 H28 118.1 . . ?
C28 C29 C30 117.6(7) . . ?
C28 C29 H29 121.2 . . ?
C30 C29 H29 121.2 . . ?
C36 C30 C29 114.7(6) . . ?
C36 C30 H30 122.7 . . ?
C29 C30 H30 122.7 . . ?
C32 C31 C36 125.3(10) . . ?
C32 C31 H31 117.4 . . ?
C36 C31 H31 117.4 . . ?
C33 C32 C31 116.4(11) . . ?
C33 C32 H32 121.8 . . ?
C31 C32 H32 121.8 . . ?
C32 C33 C34 129.6(11) . . ?
C32 C33 H33 115.2 . . ?
C34 C33 H33 115.2 . . ?
C33 C34 C35 113.7(7) . . ?
C33 C34 H34 123.1 . . ?
C35 C34 H34 123.1 . . ?
C27 C35 C36 123.2(8) . . ?
C27 C35 C34 120.9(6) . . ?
C36 C35 C34 115.9(7) . . ?
C31 C36 C35 119.2(9) . . ?
C31 C36 C30 119.2(7) . . ?
C35 C36 C30 121.6(7) . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_platon_tw
_database_code_depnum_ccdc_archive 'CCDC 1878663'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H24 N2'
_chemical_formula_sum            'C37 H24 N2'
_chemical_formula_weight         496.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   11.7976(11)
_cell_length_b                   20.678(2)
_cell_length_c                   10.8197(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.169(4)
_cell_angle_gamma                90
_cell_volume                     2628.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4994
_cell_measurement_theta_min      1.970
_cell_measurement_theta_max      25.682

_exptl_crystal_description       cubic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   SADBAS
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4994
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.970
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4993
_reflns_number_gt                2562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+0.9495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4993
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.2222
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
N1 N 0.3383(2) 0.36693(14) 0.4984(3) 0.0520(7) Uani 1 1 d . . . . .
N2 N 0.1404(2) 0.40774(16) 0.3586(3) 0.0574(8) Uani 1 1 d . . . . .
C2 C 0.4309(3) 0.34590(17) 0.5649(3) 0.0493(9) Uani 1 1 d . . . . .
C3 C 0.4363(3) 0.33878(18) 0.6952(3) 0.0539(9) Uani 1 1 d . . . . .
H3 H 0.503647 0.324624 0.738025 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3451(3) 0.35222(17) 0.7593(3) 0.0501(9) Uani 1 1 d . . . . .
C5 C 0.1424(3) 0.38896(19) 0.7454(4) 0.0630(11) Uani 1 1 d . . . . .
H5 H 0.141479 0.385804 0.831054 0.076 Uiso 1 1 calc R U . . .
C6 C 0.0477(4) 0.4085(2) 0.6763(4) 0.0720(12) Uani 1 1 d . . . . .
H6 H -0.017955 0.418055 0.714363 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0480(3) 0.4146(2) 0.5473(4) 0.0700(12) Uani 1 1 d . . . . .
H7 H -0.017531 0.427894 0.500018 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1440(3) 0.40096(18) 0.4906(3) 0.0533(9) Uani 1 1 d . . . . .
C9 C 0.2443(3) 0.37993(16) 0.5597(3) 0.0484(9) Uani 1 1 d . . . . .
C10 C 0.2430(3) 0.37315(17) 0.6904(3) 0.0489(9) Uani 1 1 d . . . . .
C11 C 0.1758(3) 0.4618(2) 0.2964(3) 0.0593(10) Uani 1 1 d . . . . .
C11A C 0.0790(3) 0.3679(2) 0.2739(3) 0.0585(10) Uani 1 1 d . . . . .
C12 C 0.2392(3) 0.5135(2) 0.3422(4) 0.0769(13) Uani 1 1 d . . . . .
H12 H 0.263354 0.516419 0.426223 0.092 Uiso 1 1 calc R U . . .
C12A C 0.0323(3) 0.3075(2) 0.2933(4) 0.0724(12) Uani 1 1 d . . . . .
H12A H 0.038068 0.288672 0.371687 0.087 Uiso 1 1 calc R U . . .
C13 C 0.2661(4) 0.5609(3) 0.2604(6) 0.1000(17) Uani 1 1 d . . . . .
H13 H 0.309220 0.596328 0.289155 0.120 Uiso 1 1 calc R U . . .
C13A C -0.0223(4) 0.2768(2) 0.1933(5) 0.0877(14) Uani 1 1 d . . . . .
H13A H -0.052920 0.235920 0.203953 0.105 Uiso 1 1 calc R U . . .
C14 C 0.2289(5) 0.5561(3) 0.1344(6) 0.1057(18) Uani 1 1 d . . . . .
H14 H 0.248803 0.588292 0.080299 0.127 Uiso 1 1 calc R U . . .
C14A C -0.0334(4) 0.3048(3) 0.0762(5) 0.0955(17) Uani 1 1 d . . . . .
H14A H -0.072550 0.282969 0.010327 0.115 Uiso 1 1 calc R U . . .
C15 C 0.1635(4) 0.5048(3) 0.0887(4) 0.0910(16) Uani 1 1 d . . . . .
H15 H 0.138592 0.502525 0.004798 0.109 Uiso 1 1 calc R U . . .
C15A C 0.0129(4) 0.3643(3) 0.0569(4) 0.0832(15) Uani 1 1 d . . . . .
H15A H 0.005083 0.382927 -0.021655 0.100 Uiso 1 1 calc R U . . .
C16 C 0.1353(3) 0.4565(2) 0.1702(3) 0.0635(11) Uani 1 1 d . . . . .
C16A C 0.0726(3) 0.3970(2) 0.1569(3) 0.0622(11) Uani 1 1 d . . . . .
C17 C 0.5316(3) 0.32791(19) 0.4988(3) 0.0544(9) Uani 1 1 d . . . . .
C18 C 0.5763(3) 0.2675(2) 0.5187(4) 0.0712(12) Uani 1 1 d . . . . .
H18 H 0.544774 0.240084 0.574527 0.085 Uiso 1 1 calc R U . . .
C19 C 0.6682(4) 0.2461(2) 0.4574(5) 0.0927(15) Uani 1 1 d . . . . .
H19 H 0.695986 0.204341 0.470654 0.111 Uiso 1 1 calc R U . . .
C20 C 0.7173(4) 0.2863(2) 0.3779(5) 0.0921(15) Uani 1 1 d . . . . .
H20 H 0.777587 0.271451 0.335978 0.111 Uiso 1 1 calc R U . . .
C21 C 0.7307(4) 0.3939(3) 0.2806(5) 0.0870(14) Uani 1 1 d . . . . .
H21 H 0.792338 0.380119 0.239675 0.104 Uiso 1 1 calc R U . . .
C22 C 0.6933(4) 0.4553(3) 0.2646(4) 0.0827(14) Uani 1 1 d . . . . .
H22 H 0.730627 0.483600 0.215256 0.099 Uiso 1 1 calc R U . . .
C23 C 0.5986(4) 0.4763(2) 0.3221(4) 0.0715(12) Uani 1 1 d . . . . .
H23 H 0.572285 0.518368 0.309391 0.086 Uiso 1 1 calc R U . . .
C24 C 0.5439(3) 0.43559(19) 0.3971(3) 0.0587(10) Uani 1 1 d . . . . .
H24 H 0.481285 0.450458 0.435145 0.070 Uiso 1 1 calc R U . . .
C25 C 0.5817(3) 0.37130(19) 0.4174(3) 0.0552(9) Uani 1 1 d . . . . .
C26 C 0.6780(3) 0.3498(2) 0.3587(4) 0.0685(11) Uani 1 1 d . . . . .
C27 C 0.3501(3) 0.34703(18) 0.8968(3) 0.0536(9) Uani 1 1 d . . . . .
C28 C 0.4189(4) 0.3888(2) 0.9703(4) 0.0756(12) Uani 1 1 d . . . . .
H28 H 0.464430 0.418701 0.933935 0.091 Uiso 1 1 calc R U . . .
C29 C 0.4195(5) 0.3857(3) 1.0974(4) 0.0902(15) Uani 1 1 d . . . . .
H29 H 0.464961 0.414082 1.146582 0.108 Uiso 1 1 calc R U . . .
C30 C 0.3541(4) 0.3413(3) 1.1524(4) 0.0814(14) Uani 1 1 d . . . . .
H30 H 0.354354 0.340078 1.238386 0.098 Uiso 1 1 calc R U . . .
C31 C 0.2897(4) 0.2997(2) 1.0818(4) 0.0700(11) Uani 1 1 d . . . . .
H31 H 0.246509 0.268953 1.119348 0.084 Uiso 1 1 calc R U . . .
C32 C 0.2867(3) 0.30192(19) 0.9541(3) 0.0607(10) Uani 1 1 d . . . . .
H32 H 0.241521 0.272751 0.906323 0.073 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 C2 1.326(4) . ?
N1 C9 1.369(4) . ?
N2 C11A 1.386(5) . ?
N2 C11 1.388(5) . ?
N2 C8 1.432(4) . ?
C2 C3 1.413(5) . ?
C2 C17 1.488(5) . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C10 1.425(5) . ?
C4 C27 1.487(5) . ?
C5 C6 1.350(5) . ?
C5 C10 1.413(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(5) . ?
C9 C10 1.423(4) . ?
C11 C12 1.371(6) . ?
C11 C16 1.410(5) . ?
C11A C12A 1.389(5) . ?
C11A C16A 1.397(5) . ?
C12 C13 1.377(6) . ?
C12 H12 0.9300 . ?
C12A C13A 1.366(6) . ?
C12A H12A 0.9300 . ?
C13 C14 1.397(7) . ?
C13 H13 0.9300 . ?
C13A C14A 1.389(7) . ?
C13A H13A 0.9300 . ?
C14 C15 1.377(7) . ?
C14 H14 0.9300 . ?
C14A C15A 1.369(7) . ?
C14A H14A 0.9300 . ?
C15 C16 1.393(6) . ?
C15 H15 0.9300 . ?
C15A C16A 1.410(6) . ?
C15A H15A 0.9300 . ?
C16 C16A 1.436(6) . ?
C17 C18 1.365(5) . ?
C17 C25 1.422(5) . ?
C18 C19 1.394(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.362(6) . ?
C19 H19 0.9300 . ?
C20 C26 1.402(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.349(6) . ?
C21 C26 1.423(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.413(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.422(5) . ?
C27 C32 1.377(5) . ?
C27 C28 1.385(5) . ?
C28 C29 1.376(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.369(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.341(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

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
C2 N1 C9 117.7(3) . . ?
C11A N2 C11 108.7(3) . . ?
C11A N2 C8 124.6(3) . . ?
C11 N2 C8 125.4(3) . . ?
N1 C2 C3 122.5(3) . . ?
N1 C2 C17 118.4(3) . . ?
C3 C2 C17 119.1(3) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C10 117.7(3) . . ?
C3 C4 C27 122.2(3) . . ?
C10 C4 C27 120.0(3) . . ?
C6 C5 C10 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 N2 118.5(3) . . ?
C9 C8 N2 120.5(3) . . ?
N1 C9 C8 118.8(3) . . ?
N1 C9 C10 123.0(3) . . ?
C8 C9 C10 118.3(3) . . ?
C5 C10 C9 118.7(3) . . ?
C5 C10 C4 123.5(3) . . ?
C9 C10 C4 117.8(3) . . ?
C12 C11 N2 129.1(4) . . ?
C12 C11 C16 122.5(4) . . ?
N2 C11 C16 108.4(3) . . ?
N2 C11A C12A 128.7(4) . . ?
N2 C11A C16A 109.0(4) . . ?
C12A C11A C16A 122.3(4) . . ?
C11 C12 C13 118.2(5) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C13A C12A C11A 117.7(4) . . ?
C13A C12A H12A 121.2 . . ?
C11A C12A H12A 121.2 . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C12A C13A C14A 121.9(5) . . ?
C12A C13A H13A 119.1 . . ?
C14A C13A H13A 119.1 . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C15A C14A C13A 120.5(5) . . ?
C15A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
C14 C15 C16 118.9(5) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C14A C15A C16A 119.5(5) . . ?
C14A C15A H15A 120.3 . . ?
C16A C15A H15A 120.3 . . ?
C15 C16 C11 118.5(4) . . ?
C15 C16 C16A 134.6(4) . . ?
C11 C16 C16A 106.9(3) . . ?
C11A C16A C15A 118.2(4) . . ?
C11A C16A C16 107.0(3) . . ?
C15A C16A C16 134.8(4) . . ?
C18 C17 C25 119.9(3) . . ?
C18 C17 C2 117.8(3) . . ?
C25 C17 C2 122.3(3) . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C26 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C26 C20 H20 119.6 . . ?
C22 C21 C26 121.6(4) . . ?
C22 C21 H21 119.2 . . ?
C26 C21 H21 119.2 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C17 123.2(3) . . ?
C24 C25 C26 118.5(4) . . ?
C17 C25 C26 118.2(4) . . ?
C20 C26 C25 119.5(4) . . ?
C20 C26 C21 122.2(4) . . ?
C25 C26 C21 118.3(4) . . ?
C32 C27 C28 118.5(3) . . ?
C32 C27 C4 121.6(3) . . ?
C28 C27 C4 119.8(3) . . ?
C29 C28 C27 119.6(4) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 120.9(5) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 119.7(4) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.7(4) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C27 C32 C31 120.5(4) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_CQPN
_database_code_depnum_ccdc_archive 'CCDC 1878664'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H24 N2'
_chemical_formula_sum            'C37 H24 N2'
_chemical_formula_weight         496.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   10.6994(7)
_cell_length_b                   26.4284(15)
_cell_length_c                   9.3265(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.560(2)
_cell_angle_gamma                90
_cell_volume                     2620.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5366
_cell_measurement_theta_min      2.065
_cell_measurement_theta_max      26.395

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39624
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5366
_reflns_number_gt                2659
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0785P)²+0.6538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0101(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5359
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1997
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N1 N 0.69165(18) 0.34951(7) 0.5113(2) 0.0628(6) Uani 1 1 d . . . . .
N2 N 0.90768(19) 0.35171(8) 0.6997(3) 0.0711(6) Uani 1 1 d . . . . .
C2 C 0.5845(2) 0.35053(9) 0.4248(3) 0.0622(7) Uani 1 1 d . . . . .
C3 C 0.5083(2) 0.30679(9) 0.4016(3) 0.0705(7) Uani 1 1 d . . . . .
H3 H 0.431919 0.309107 0.343349 0.085 Uiso 1 1 calc R U . . .
C4 C 0.5440(2) 0.26142(9) 0.4624(3) 0.0650(7) Uani 1 1 d . . . . .
C5 C 0.7017(2) 0.21605(10) 0.6335(3) 0.0694(7) Uani 1 1 d . . . . .
H5 H 0.656759 0.185981 0.619758 0.083 Uiso 1 1 calc R U . . .
C6 C 0.8090(3) 0.21738(11) 0.7273(3) 0.0756(8) Uani 1 1 d . . . . .
H6 H 0.836730 0.188338 0.777540 0.091 Uiso 1 1 calc R U . . .
C7 C 0.8780(2) 0.26264(11) 0.7484(3) 0.0747(8) Uani 1 1 d . . . . .
H7 H 0.950945 0.263249 0.813034 0.090 Uiso 1 1 calc R U . . .
C8 C 0.8396(2) 0.30544(10) 0.6756(3) 0.0669(7) Uani 1 1 d . . . . .
C9 C 0.7276(2) 0.30528(9) 0.5783(3) 0.0597(6) Uani 1 1 d . . . . .
C10 C 0.6580(2) 0.25980(9) 0.5571(3) 0.0611(6) Uani 1 1 d . . . . .
C11 C 0.8727(3) 0.39028(12) 0.7890(4) 0.0802(8) Uani 1 1 d . . . . .
C11A C 0.9889(3) 0.37213(11) 0.6083(3) 0.0749(8) Uani 1 1 d . . . . .
C12 C 0.7969(3) 0.38717(15) 0.8976(4) 0.1019(11) Uani 1 1 d . . . . .
H12 H 0.758328 0.356865 0.917834 0.122 Uiso 1 1 calc R U . . .
C12A C 1.0487(3) 0.34839(13) 0.5031(4) 0.0916(10) Uani 1 1 d . . . . .
H12A H 1.033591 0.314502 0.480445 0.110 Uiso 1 1 calc R U . . .
C13 C 0.7794(4) 0.4304(2) 0.9760(5) 0.1359(16) Uani 1 1 d . . . . .
H13 H 0.728029 0.429412 1.049895 0.163 Uiso 1 1 calc R U . . .
C13A C 1.1318(3) 0.37655(18) 0.4325(4) 0.1141(12) Uani 1 1 d . . . . .
H13A H 1.173216 0.361382 0.361394 0.137 Uiso 1 1 calc R U . . .
C14 C 0.8376(5) 0.4750(2) 0.9455(7) 0.145(2) Uani 1 1 d . . . . .
H14 H 0.824515 0.503757 0.999477 0.174 Uiso 1 1 calc R U . . .
C14A C 1.1543(4) 0.4272(2) 0.4663(5) 0.1254(15) Uani 1 1 d . . . . .
H14A H 1.210947 0.445375 0.417784 0.150 Uiso 1 1 calc R U . . .
C15 C 0.9151(4) 0.47821(15) 0.8366(6) 0.1239(15) Uani 1 1 d . . . . .
H15 H 0.953514 0.508657 0.817369 0.149 Uiso 1 1 calc R U . . .
C15A C 1.0946(4) 0.45070(15) 0.5695(5) 0.1107(13) Uani 1 1 d . . . . .
H15A H 1.110222 0.484634 0.591114 0.133 Uiso 1 1 calc R U . . .
C16 C 0.9347(3) 0.43501(12) 0.7561(4) 0.0898(10) Uani 1 1 d . . . . .
C16A C 1.0100(3) 0.42343(12) 0.6423(4) 0.0844(9) Uani 1 1 d . . . . .
C17 C 0.5505(2) 0.39920(9) 0.3519(3) 0.0666(7) Uani 1 1 d . . . . .
C18 C 0.6090(3) 0.44321(11) 0.3992(4) 0.1106(13) Uani 1 1 d . . . . .
H18 H 0.669989 0.442476 0.478630 0.133 Uiso 1 1 calc R U . . .
C19 C 0.5787(4) 0.48866(13) 0.3308(5) 0.1349(17) Uani 1 1 d . . . . .
H19 H 0.619412 0.518114 0.364867 0.162 Uiso 1 1 calc R U . . .
C20 C 0.4905(4) 0.49081(12) 0.2147(4) 0.1151(13) Uani 1 1 d . . . . .
H20 H 0.469874 0.521511 0.169331 0.138 Uiso 1 1 calc R U . . .
C21 C 0.4330(3) 0.44764(12) 0.1659(4) 0.1140(13) Uani 1 1 d . . . . .
H21 H 0.373032 0.448644 0.085525 0.137 Uiso 1 1 calc R U . . .
C22 C 0.4620(3) 0.40225(11) 0.2335(4) 0.0912(10) Uani 1 1 d . . . . .
H22 H 0.420788 0.373030 0.198398 0.109 Uiso 1 1 calc R U . . .
C23 C 0.4678(2) 0.21464(9) 0.4241(3) 0.0653(7) Uani 1 1 d . . . . .
C24 C 0.5100(3) 0.18045(10) 0.3324(3) 0.0739(8) Uani 1 1 d . . . . .
H24 H 0.588614 0.185571 0.301401 0.089 Uiso 1 1 calc R U . . .
C25 C 0.4408(3) 0.13786(10) 0.2824(3) 0.0827(8) Uani 1 1 d . . . . .
H25 H 0.472834 0.115385 0.219100 0.099 Uiso 1 1 calc R U . . .
C26 C 0.3252(3) 0.12964(11) 0.3276(3) 0.0830(9) Uani 1 1 d . . . . .
H26 H 0.277606 0.101846 0.293159 0.100 Uiso 1 1 calc R U . . .
C27 C 0.1619(3) 0.15450(13) 0.4783(4) 0.0867(9) Uani 1 1 d . . . . .
H27 H 0.114639 0.126327 0.446381 0.104 Uiso 1 1 calc R U . . .
C28 C 0.1184(3) 0.18634(14) 0.5736(4) 0.1006(11) Uani 1 1 d . . . . .
H28 H 0.041433 0.179838 0.607262 0.121 Uiso 1 1 calc R U . . .
C29 C 0.1874(3) 0.22904(12) 0.6224(4) 0.0883(9) Uani 1 1 d . . . . .
H29 H 0.156036 0.250487 0.688856 0.106 Uiso 1 1 calc R U . . .
C30 C 0.2997(3) 0.23973(11) 0.5744(3) 0.0771(8) Uani 1 1 d . . . . .
H30 H 0.343968 0.268607 0.606661 0.093 Uiso 1 1 calc R U . . .
C31 C 0.3498(2) 0.20635(9) 0.4738(3) 0.0638(7) Uani 1 1 d . . . . .
C32 C 0.2778(2) 0.16338(10) 0.4269(3) 0.0667(7) 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.325(3) . ?
N1 C9 1.360(3) . ?
N2 C11A 1.394(4) . ?
N2 C11 1.394(4) . ?
N2 C8 1.428(3) . ?
C2 C3 1.417(3) . ?
C2 C17 1.480(3) . ?
C3 C4 1.363(3) . ?
C3 H3 0.9300 . ?
C4 C10 1.423(3) . ?
C4 C23 1.502(3) . ?
C5 C6 1.362(4) . ?
C5 C10 1.409(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.418(3) . ?
C9 C10 1.416(3) . ?
C11 C12 1.370(5) . ?
C11 C16 1.407(4) . ?
C11A C12A 1.382(4) . ?
C11A C16A 1.405(4) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C12A C13A 1.382(4) . ?
C12A H12A 0.9300 . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
C13A C14A 1.390(6) . ?
C13A H13A 0.9300 . ?
C14 C15 1.386(7) . ?
C14 H14 0.9300 . ?
C14A C15A 1.364(6) . ?
C14A H14A 0.9300 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9300 . ?
C15A C16A 1.393(5) . ?
C15A H15A 0.9300 . ?
C16 C16A 1.436(5) . ?
C17 C18 1.369(4) . ?
C17 C22 1.373(4) . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.350(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.357(4) . ?
C23 C31 1.410(4) . ?
C24 C25 1.398(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(4) . ?
C25 H25 0.9300 . ?
C26 C32 1.421(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.345(4) . ?
C27 C32 1.399(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.359(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.436(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.414(3) . ?

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
C2 N1 C9 118.5(2) . . ?
C11A N2 C11 108.1(2) . . ?
C11A N2 C8 125.3(2) . . ?
C11 N2 C8 123.6(2) . . ?
N1 C2 C3 121.3(2) . . ?
N1 C2 C17 116.6(2) . . ?
C3 C2 C17 122.2(2) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C10 117.7(2) . . ?
C3 C4 C23 120.4(2) . . ?
C10 C4 C23 121.8(2) . . ?
C6 C5 C10 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 N2 121.0(2) . . ?
C9 C8 N2 118.8(2) . . ?
N1 C9 C10 123.3(2) . . ?
N1 C9 C8 117.7(2) . . ?
C10 C9 C8 119.0(2) . . ?
C5 C10 C9 119.2(2) . . ?
C5 C10 C4 123.3(2) . . ?
C9 C10 C4 117.4(2) . . ?
C12 C11 N2 128.3(3) . . ?
C12 C11 C16 123.1(3) . . ?
N2 C11 C16 108.6(3) . . ?
C12A C11A N2 129.1(3) . . ?
C12A C11A C16A 121.6(3) . . ?
N2 C11A C16A 109.3(3) . . ?
C11 C12 C13 118.0(4) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C13A C12A C11A 117.9(3) . . ?
C13A C12A H12A 121.0 . . ?
C11A C12A H12A 121.0 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C12A C13A C14A 121.0(4) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C15A C14A C13A 121.0(4) . . ?
C15A C14A H14A 119.5 . . ?
C13A C14A H14A 119.5 . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C14A C15A C16A 119.4(4) . . ?
C14A C15A H15A 120.3 . . ?
C16A C15A H15A 120.3 . . ?
C15 C16 C11 117.8(4) . . ?
C15 C16 C16A 134.7(4) . . ?
C11 C16 C16A 107.5(3) . . ?
C15A C16A C11A 119.0(4) . . ?
C15A C16A C16 134.4(4) . . ?
C11A C16A C16 106.5(3) . . ?
C18 C17 C22 117.2(3) . . ?
C18 C17 C2 120.7(2) . . ?
C22 C17 C2 122.1(2) . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 121.3(3) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C31 118.6(2) . . ?
C24 C23 C4 119.2(2) . . ?
C31 C23 C4 122.1(2) . . ?
C23 C24 C25 123.0(3) . . ?
C23 C24 H24 118.5 . . ?
C25 C24 H24 118.5 . . ?
C26 C25 C24 119.2(3) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C32 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C32 C26 H26 119.9 . . ?
C28 C27 C32 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C32 C27 H27 119.7 . . ?
C27 C28 C29 120.7(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C23 C31 C32 120.0(3) . . ?
C23 C31 C30 122.3(2) . . ?
C32 C31 C30 117.7(2) . . ?
C27 C32 C31 120.1(3) . . ?
C27 C32 C26 121.0(3) . . ?
C31 C32 C26 118.9(3) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

