# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_2-Tolene
_database_code_depnum_ccdc_archive 'CCDC 1940315'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C48H32N2,C7H8
_chemical_formula_sum            'C55 H40 N2'
_chemical_formula_weight         728.89

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.4653(9)
_cell_length_b                   14.009(3)
_cell_length_c                   15.061(3)
_cell_angle_alpha                115.001(5)
_cell_angle_beta                 89.766(6)
_cell_angle_gamma                100.874(5)
_cell_volume                     1022.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2508
_cell_measurement_theta_min      0.986
_cell_measurement_theta_max      0.997

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7668
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3764
_reflns_number_gt                2508
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.1851P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.075(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     356
_refine_ls_number_restraints     290
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.2988(5) 0.0199(2) 0.3822(2) 0.0934(8) Uani 1 1 d . . . . .
H1 H 0.178748 0.020977 0.426340 0.112 Uiso 1 1 calc R U . . .
C2 C 0.3983(7) -0.0706(2) 0.3320(3) 0.1094(10) Uani 1 1 d . . . . .
H2 H 0.343645 -0.131400 0.343025 0.131 Uiso 1 1 calc R U . . .
C3 C 0.5760(7) -0.0733(3) 0.2661(3) 0.1105(10) Uani 1 1 d . . . . .
H3 H 0.641819 -0.134708 0.234855 0.133 Uiso 1 1 calc R U . . .
C4 C 0.6561(6) 0.0138(2) 0.2465(2) 0.0934(8) Uani 1 1 d . . . . .
H4 H 0.773460 0.011237 0.201026 0.112 Uiso 1 1 calc R U . . .
C5 C 0.7635(5) 0.2542(2) 0.24017(16) 0.0788(7) Uani 1 1 d . . . . .
H5 H 0.865614 0.214435 0.196010 0.095 Uiso 1 1 calc R U . . .
C6 C 0.7682(5) 0.3589(2) 0.25701(18) 0.0847(8) Uani 1 1 d . . . . .
H6 H 0.874886 0.390226 0.224026 0.102 Uiso 1 1 calc R U . . .
C7 C 0.6160(5) 0.4184(2) 0.32250(18) 0.0781(7) Uani 1 1 d . . . . .
H7 H 0.621958 0.489036 0.332384 0.094 Uiso 1 1 calc R U . . .
C8 C 0.4561(4) 0.37551(18) 0.37326(16) 0.0669(6) Uani 1 1 d . . . . .
H8 H 0.354495 0.415973 0.417073 0.080 Uiso 1 1 calc R U . . .
N9 N 0.3178(3) 0.20953(14) 0.40189(13) 0.0639(5) Uani 1 1 d . . . . .
C10 C 0.3862(4) 0.10901(18) 0.36371(17) 0.0683(6) Uani 1 1 d . . . . .
C11 C 0.5607(4) 0.10612(18) 0.29494(16) 0.0691(6) Uani 1 1 d . . . . .
C12 C 0.6025(4) 0.20840(18) 0.29061(15) 0.0632(6) Uani 1 1 d . . . . .
C13 C 0.4513(4) 0.27034(17) 0.35712(14) 0.0573(5) Uani 1 1 d . . . . .
C14 C 0.1881(4) 0.25192(17) 0.48761(15) 0.0599(6) Uani 1 1 d D . . . .
C15 C 0.0080(4) 0.30994(17) 0.49106(15) 0.0608(6) Uani 1 1 d D . . . .
H15 H -0.032503 0.320200 0.436259 0.073 Uiso 1 1 calc R U . . .
C16 C -0.1124(4) 0.35286(18) 0.57518(16) 0.0639(6) Uani 1 1 d D . . . .
H16 H -0.232784 0.392324 0.576774 0.077 Uiso 1 1 calc R U . . .
C17 C -0.0558(4) 0.33779(18) 0.65791(16) 0.0638(6) Uani 1 1 d D . . . .
C18 C 0.1254(4) 0.2793(2) 0.65337(17) 0.0738(7) Uani 1 1 d D . . . .
H18 H 0.165582 0.268428 0.707892 0.089 Uiso 1 1 calc R U . . .
C19 C 0.2474(4) 0.2367(2) 0.56957(18) 0.0734(7) Uani 1 1 d D . . . .
H19 H 0.369145 0.197892 0.567969 0.088 Uiso 1 1 calc R U . . .
C20 C -0.1785(4) 0.38173(19) 0.74627(18) 0.0697(6) Uani 1 1 d . . . . .
C21 C -0.2774(5) 0.41561(19) 0.82020(17) 0.0716(6) Uani 1 1 d . . . . .
C22 C -0.3919(4) 0.45736(18) 0.91192(16) 0.0666(6) Uani 1 1 d . . . . .
C23 C -0.3518(4) 0.42231(19) 0.98419(17) 0.0687(6) Uani 1 1 d . . . . .
C24 C -0.5375(5) 0.53321(19) 0.92899(16) 0.0722(7) Uani 1 1 d . . . . .
H24 H -0.561791 0.555207 0.880018 0.087 Uiso 1 1 calc R U . . .
C25 C -0.1939(5) 0.3409(2) 0.9682(2) 0.0930(8) Uani 1 1 d . . . . .
H25A H -0.177486 0.331106 1.027066 0.140 Uiso 1 1 calc R U . . .
H25B H -0.031406 0.365808 0.952125 0.140 Uiso 1 1 calc R U . . .
H25C H -0.271584 0.273701 0.915148 0.140 Uiso 1 1 calc R U . . .
C31 C 0.065(3) 0.0534(11) 0.0044(15) 0.097(2) Uani 0.25 1 d D U P A -1
C32 C -0.149(4) -0.0154(15) -0.049(2) 0.095(3) Uani 0.25 1 d D U P A -1
H32 H -0.238881 0.002937 -0.090145 0.114 Uiso 0.25 1 calc R U P A -1
C33 C -0.233(2) -0.1117(11) -0.0435(11) 0.096(3) Uani 0.25 1 d D U P A -1
H33 H -0.381894 -0.156633 -0.078585 0.115 Uiso 0.25 1 calc R U P A -1
C34 C -0.097(4) -0.1420(14) 0.0148(19) 0.097(3) Uani 0.25 1 d D U P A -1
H34 H -0.146061 -0.209038 0.015371 0.116 Uiso 0.25 1 calc R U P A -1
C35 C 0.112(3) -0.0709(12) 0.0712(11) 0.100(3) Uani 0.25 1 d D U P A -1
H35 H 0.201671 -0.088835 0.112160 0.120 Uiso 0.25 1 calc R U P A -1
C36 C 0.191(4) 0.0274(15) 0.0680(19) 0.099(3) Uani 0.25 1 d D U P A -1
H36 H 0.328342 0.076177 0.108819 0.118 Uiso 0.25 1 calc R U P A -1
C37 C 0.159(5) 0.1589(17) 0.000(3) 0.109(4) Uani 0.25 1 d D U P A -1
H37A H 0.330245 0.164124 -0.015014 0.164 Uiso 0.25 1 calc R U P A -1
H37B H 0.147556 0.216635 0.063080 0.164 Uiso 0.25 1 calc R U P A -1
H37C H 0.059418 0.163680 -0.049301 0.164 Uiso 0.25 1 calc R U P A -1
C31B C -0.116(3) -0.0751(11) -0.0202(17) 0.096(2) Uani 0.25 1 d D U P B -2
C32B C 0.117(3) -0.0364(10) 0.0304(13) 0.098(3) Uani 0.25 1 d D U P B -2
H32B H 0.185267 -0.078097 0.053970 0.117 Uiso 0.25 1 calc R U P B -2
C33B C 0.250(2) 0.0643(11) 0.0461(13) 0.101(3) Uani 0.25 1 d D U P B -2
H33B H 0.407009 0.089923 0.080216 0.122 Uiso 0.25 1 calc R U P B -2
C34B C 0.152(4) 0.1280(12) 0.0117(19) 0.101(3) Uani 0.25 1 d D U P B -2
H34B H 0.239625 0.196542 0.023871 0.121 Uiso 0.25 1 calc R U P B -2
C35B C -0.080(3) 0.0874(12) -0.0410(13) 0.100(3) Uani 0.25 1 d D U P B -2
H35B H -0.142562 0.126255 -0.069370 0.120 Uiso 0.25 1 calc R U P B -2
C36B C -0.218(3) -0.0108(14) -0.0518(17) 0.098(3) Uani 0.25 1 d D U P B -2
H36B H -0.381480 -0.033712 -0.080589 0.118 Uiso 0.25 1 calc R U P B -2
C37B C -0.261(3) -0.1848(10) -0.0398(12) 0.106(4) Uani 0.25 1 d D U P B -2
H37D H -0.377677 -0.179008 0.009173 0.159 Uiso 0.25 1 calc R U P B -2
H37E H -0.148566 -0.228826 -0.037555 0.159 Uiso 0.25 1 calc R U P B -2
H37F H -0.350595 -0.216930 -0.103686 0.159 Uiso 0.25 1 calc R U P B -2


_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
C1 C2 1.387(4) . ?
C1 C10 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C11 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 C12 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.383(3) . ?
C8 H8 0.9300 . ?
N9 C13 1.400(3) . ?
N9 C10 1.402(3) . ?
N9 C14 1.423(3) . ?
C10 C11 1.398(3) . ?
C11 C12 1.437(3) . ?
C12 C13 1.403(3) . ?
C14 C15 1.378(3) . ?
C14 C19 1.388(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 C20 1.434(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.184(3) . ?
C21 C22 1.446(3) . ?
C22 C24 1.384(3) . ?
C22 C23 1.403(3) . ?
C23 C24 1.383(3) 2_467 ?
C23 C25 1.496(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C31 C32 1.373(8) . ?
C31 C36 1.383(8) . ?
C31 C37 1.497(9) . ?
C32 C33 1.380(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.397(9) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.384(8) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C31B C32B 1.375(8) . ?
C31B C36B 1.381(8) . ?
C31B C37B 1.496(9) . ?
C32B C33B 1.381(8) . ?
C32B H32B 0.9300 . ?
C33B C34B 1.387(9) . ?
C33B H33B 0.9300 . ?
C34B C35B 1.381(9) . ?
C34B H34B 0.9300 . ?
C35B C36B 1.382(8) . ?
C35B H35B 0.9300 . ?
C36B H36B 0.9300 . ?
C37B H37D 0.9600 . ?
C37B H37E 0.9600 . ?
C37B H37F 0.9600 . ?

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 C1 C10 117.2(3) . . ?
C2 C1 H1 121.4 . . ?
C10 C1 H1 121.4 . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C11 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C11 C4 H4 120.3 . . ?
C6 C5 C12 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C12 C5 H5 120.6 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C13 117.9(2) . . ?
C7 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
C13 N9 C10 107.87(17) . . ?
C13 N9 C14 124.89(17) . . ?
C10 N9 C14 125.45(18) . . ?
C1 C10 C11 121.3(2) . . ?
C1 C10 N9 129.7(2) . . ?
C11 C10 N9 108.9(2) . . ?
C4 C11 C10 119.6(2) . . ?
C4 C11 C12 133.2(2) . . ?
C10 C11 C12 107.3(2) . . ?
C5 C12 C13 119.4(2) . . ?
C5 C12 C11 133.4(2) . . ?
C13 C12 C11 107.14(19) . . ?
C8 C13 N9 129.7(2) . . ?
C8 C13 C12 121.4(2) . . ?
N9 C13 C12 108.83(19) . . ?
C15 C14 C19 119.5(2) . . ?
C15 C14 N9 120.8(2) . . ?
C19 C14 N9 119.7(2) . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 C20 120.1(2) . . ?
C16 C17 C20 121.7(2) . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 119.9(2) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C21 C20 C17 177.8(3) . . ?
C20 C21 C22 178.5(3) . . ?
C24 C22 C23 120.1(2) . . ?
C24 C22 C21 120.0(2) . . ?
C23 C22 C21 120.0(2) . . ?
C24 C23 C22 117.2(2) 2_467 . ?
C24 C23 C25 121.5(2) 2_467 . ?
C22 C23 C25 121.3(2) . . ?
C23 C24 C22 122.7(2) 2_467 . ?
C23 C24 H24 118.6 2_467 . ?
C22 C24 H24 118.6 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C31 C36 119.3(7) . . ?
C32 C31 C37 121.5(13) . . ?
C36 C31 C37 119.1(12) . . ?
C31 C32 C33 120.4(7) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 120.5(7) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 118.5(7) . . ?
C35 C34 H34 120.8 . . ?
C33 C34 H34 120.8 . . ?
C34 C35 C36 120.9(7) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 120.2(7) . . ?
C31 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C32B C31B C36B 119.3(7) . . ?
C32B C31B C37B 121.1(12) . . ?
C36B C31B C37B 119.6(11) . . ?
C31B C32B C33B 120.0(7) . . ?
C31B C32B H32B 120.0 . . ?
C33B C32B H32B 120.0 . . ?
C32B C33B C34B 121.0(7) . . ?
C32B C33B H33B 119.5 . . ?
C34B C33B H33B 119.5 . . ?
C35B C34B C33B 118.6(7) . . ?
C35B C34B H34B 120.7 . . ?
C33B C34B H34B 120.7 . . ?
C34B C35B C36B 120.3(7) . . ?
C34B C35B H35B 119.9 . . ?
C36B C35B H35B 119.9 . . ?
C31B C36B C35B 120.5(7) . . ?
C31B C36B H36B 119.8 . . ?
C35B C36B H36B 119.8 . . ?
C31B C37B H37D 109.5 . . ?
C31B C37B H37E 109.5 . . ?
H37D C37B H37E 109.5 . . ?
C31B C37B H37F 109.5 . . ?
H37D C37B H37F 109.5 . . ?
H37E C37B H37F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.2(5) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C11 1.3(5) . . . . ?
C12 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C13 0.0(4) . . . . ?
C2 C1 C10 C11 2.1(4) . . . . ?
C2 C1 C10 N9 178.9(3) . . . . ?
C13 N9 C10 C1 -177.4(2) . . . . ?
C14 N9 C10 C1 17.3(4) . . . . ?
C13 N9 C10 C11 -0.3(2) . . . . ?
C14 N9 C10 C11 -165.62(19) . . . . ?
C3 C4 C11 C10 0.6(4) . . . . ?
C3 C4 C11 C12 -179.3(3) . . . . ?
C1 C10 C11 C4 -2.3(4) . . . . ?
N9 C10 C11 C4 -179.7(2) . . . . ?
C1 C10 C11 C12 177.6(2) . . . . ?
N9 C10 C11 C12 0.2(3) . . . . ?
C6 C5 C12 C13 -0.3(3) . . . . ?
C6 C5 C12 C11 -176.0(2) . . . . ?
C4 C11 C12 C5 -4.1(5) . . . . ?
C10 C11 C12 C5 176.1(2) . . . . ?
C4 C11 C12 C13 179.9(3) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C7 C8 C13 N9 176.5(2) . . . . ?
C7 C8 C13 C12 -0.5(3) . . . . ?
C10 N9 C13 C8 -177.0(2) . . . . ?
C14 N9 C13 C8 -11.6(4) . . . . ?
C10 N9 C13 C12 0.3(2) . . . . ?
C14 N9 C13 C12 165.72(19) . . . . ?
C5 C12 C13 C8 0.6(3) . . . . ?
C11 C12 C13 C8 177.4(2) . . . . ?
C5 C12 C13 N9 -176.89(19) . . . . ?
C11 C12 C13 N9 -0.2(2) . . . . ?
C13 N9 C14 C15 55.7(3) . . . . ?
C10 N9 C14 C15 -141.4(2) . . . . ?
C13 N9 C14 C19 -122.9(2) . . . . ?
C10 N9 C14 C19 40.0(3) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
N9 C14 C15 C16 -178.46(18) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C16 C17 C20 179.96(19) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C20 C17 C18 C19 -179.6(2) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
N9 C14 C19 C18 178.85(19) . . . . ?
C24 C22 C23 C24 -0.1(4) . . . 2_467 ?
C21 C22 C23 C24 178.8(2) . . . 2_467 ?
C24 C22 C23 C25 -179.6(2) . . . . ?
C21 C22 C23 C25 -0.7(4) . . . . ?
C23 C22 C24 C23 0.1(4) . . . 2_467 ?
C21 C22 C24 C23 -178.8(2) . . . 2_467 ?
C36 C31 C32 C33 -3(6) . . . . ?
C37 C31 C32 C33 -179(3) . . . . ?
C31 C32 C33 C34 -2(5) . . . . ?
C32 C33 C34 C35 5(4) . . . . ?
C33 C34 C35 C36 -2(4) . . . . ?
C32 C31 C36 C35 5(5) . . . . ?
C37 C31 C36 C35 -178(3) . . . . ?
C34 C35 C36 C31 -3(4) . . . . ?
C36B C31B C32B C33B -2(3) . . . . ?
C37B C31B C32B C33B 178.8(18) . . . . ?
C31B C32B C33B C34B 0(3) . . . . ?
C32B C33B C34B C35B -2(4) . . . . ?
C33B C34B C35B C36B 5(4) . . . . ?
C32B C31B C36B C35B 6(4) . . . . ?
C37B C31B C36B C35B -175.1(19) . . . . ?
C34B C35B C36B C31B -8(3) . . . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_2-THF
_database_code_depnum_ccdc_archive 'CCDC 1940318'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C48H32N2,C4H8O
_chemical_formula_sum            'C52 H40 N2 O'
_chemical_formula_weight         708.86

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   32.439(7)
_cell_length_b                   5.7640(12)
_cell_length_c                   22.026(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.054(5)
_cell_angle_gamma                90
_cell_volume                     3843.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      0.981
_cell_measurement_theta_max      0.985

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.215
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8791
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3594
_reflns_number_gt                2746
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0883P)²+1.3139P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3594
_refine_ls_number_parameters     318
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.25284(7) 1.0067(4) 0.56240(10) 0.0498(5) Uani 1 1 d . . . . .
H1 H 0.261999 0.898210 0.537317 0.060 Uiso 1 1 calc R U . . .
C2 C 0.21290(7) 1.1218(4) 0.53654(11) 0.0556(6) Uani 1 1 d . . . . .
H2 H 0.194340 1.091699 0.492844 0.067 Uiso 1 1 calc R U . . .
C3 C 0.19930(7) 1.2802(4) 0.57291(11) 0.0570(6) Uani 1 1 d . . . . .
H3 H 0.171652 1.356197 0.553726 0.068 Uiso 1 1 calc R U . . .
C4 C 0.22509(7) 1.3290(4) 0.63607(11) 0.0498(5) Uani 1 1 d . . . . .
H4 H 0.215557 1.438532 0.660455 0.060 Uiso 1 1 calc R U . . .
C5 C 0.30569(7) 1.3420(3) 0.78518(10) 0.0470(5) Uani 1 1 d . . . . .
H5 H 0.283991 1.450074 0.786771 0.056 Uiso 1 1 calc R U . . .
C6 C 0.34324(7) 1.3064(4) 0.83886(11) 0.0528(6) Uani 1 1 d . . . . .
H6 H 0.347511 1.391229 0.877625 0.063 Uiso 1 1 calc R U . . .
C7 C 0.37528(7) 1.1463(4) 0.83702(10) 0.0509(5) Uani 1 1 d . . . . .
H7 H 0.400964 1.124562 0.874728 0.061 Uiso 1 1 calc R U . . .
C8 C 0.37036(6) 1.0190(3) 0.78144(9) 0.0441(5) Uani 1 1 d . . . . .
H8 H 0.392178 0.910935 0.780288 0.053 Uiso 1 1 calc R U . . .
N9 N 0.31950(5) 0.9587(3) 0.66502(8) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.27906(6) 1.0556(3) 0.62639(9) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.26575(6) 1.2151(3) 0.66425(9) 0.0396(5) Uani 1 1 d . . . . .
C12 C 0.29977(6) 1.2173(3) 0.72821(9) 0.0382(4) Uani 1 1 d . . . . .
C13 C 0.33216(6) 1.0560(3) 0.72737(9) 0.0372(4) Uani 1 1 d . . . . .
C14 C 0.34542(6) 0.8095(3) 0.64188(9) 0.0357(4) Uani 1 1 d . . . . .
C15 C 0.36099(6) 0.5994(3) 0.67289(9) 0.0377(4) Uani 1 1 d . . . . .
H15 H 0.354385 0.555078 0.709929 0.045 Uiso 1 1 calc R U . . .
C16 C 0.38601(6) 0.4561(3) 0.64972(9) 0.0380(4) Uani 1 1 d . . . . .
H16 H 0.396389 0.312547 0.670892 0.046 Uiso 1 1 calc R U . . .
C17 C 0.39632(6) 0.5186(3) 0.59560(9) 0.0368(4) Uani 1 1 d . . . . .
C18 C 0.38055(6) 0.7307(3) 0.56510(9) 0.0410(5) Uani 1 1 d . . . . .
H18 H 0.387117 0.775658 0.528075 0.049 Uiso 1 1 calc R U . . .
C19 C 0.35568(6) 0.8744(3) 0.58809(9) 0.0405(5) Uani 1 1 d . . . . .
H19 H 0.345461 1.018633 0.567228 0.049 Uiso 1 1 calc R U . . .
C20 C 0.42295(6) 0.3699(3) 0.57055(9) 0.0395(5) Uani 1 1 d . . . . .
C21 C 0.44417(6) 0.2560(3) 0.54974(9) 0.0414(5) Uani 1 1 d . . . . .
C22 C 0.47196(6) 0.1241(3) 0.52328(9) 0.0369(4) Uani 1 1 d . . . . .
C23 C 0.47497(6) 0.1885(3) 0.46365(9) 0.0395(4) Uani 1 1 d . . . . .
C24 C 0.49677(6) -0.0624(3) 0.55841(9) 0.0417(5) Uani 1 1 d . . . . .
H24 H 0.494200 -0.104005 0.598634 0.050 Uiso 1 1 calc R U . . .
C25 C 0.44784(8) 0.3866(4) 0.42408(10) 0.0549(6) Uani 1 1 d . . . . .
H25A H 0.416491 0.344230 0.407998 0.082 Uiso 1 1 calc R U . . .
H25B H 0.457046 0.418777 0.387131 0.082 Uiso 1 1 calc R U . . .
H25C H 0.452391 0.525321 0.451455 0.082 Uiso 1 1 calc R U . . .
O31 O 0.5336(4) 0.222(2) 0.2172(7) 0.069(2) Uani 0.25 1 d D U P A -1
C32 C 0.5186(7) 0.027(2) 0.2444(10) 0.075(2) Uani 0.25 1 d D U P A -1
H32A H 0.540776 -0.013567 0.287408 0.090 Uiso 0.25 1 calc R U P A -1
H32B H 0.514289 -0.109639 0.215451 0.090 Uiso 0.25 1 calc R U P A -1
C33 C 0.4763(6) 0.090(3) 0.2513(12) 0.073(2) Uani 0.25 1 d D U P A -1
H33A H 0.470768 -0.002440 0.285452 0.088 Uiso 0.25 1 calc R U P A -1
H33B H 0.451030 0.074640 0.209768 0.088 Uiso 0.25 1 calc R U P A -1
C34 C 0.4867(6) 0.350(3) 0.2719(10) 0.070(2) Uani 0.25 1 d D U P A -1
H34A H 0.459380 0.441492 0.263607 0.084 Uiso 0.25 1 calc R U P A -1
H34B H 0.505888 0.364889 0.318256 0.084 Uiso 0.25 1 calc R U P A -1
C35 C 0.5099(6) 0.418(3) 0.2283(11) 0.068(2) Uani 0.25 1 d D U P A -1
H35A H 0.488287 0.473618 0.186388 0.081 Uiso 0.25 1 calc R U P A -1
H35B H 0.530737 0.545999 0.248131 0.081 Uiso 0.25 1 calc R U P A -1
O41 O 0.4663(4) 0.220(2) 0.2839(7) 0.073(2) Uani 0.25 1 d D U P B -2
C42 C 0.4838(6) 0.026(3) 0.2601(10) 0.074(2) Uani 0.25 1 d D U P B -2
H42A H 0.461508 -0.030349 0.218917 0.089 Uiso 0.25 1 calc R U P B -2
H42B H 0.490811 -0.101448 0.292190 0.089 Uiso 0.25 1 calc R U P B -2
C43 C 0.5239(5) 0.098(3) 0.2489(9) 0.069(2) Uani 0.25 1 d D U P B -2
H43A H 0.528229 0.008082 0.213364 0.083 Uiso 0.25 1 calc R U P B -2
H43B H 0.550527 0.084087 0.288830 0.083 Uiso 0.25 1 calc R U P B -2
C44 C 0.5124(7) 0.357(3) 0.2292(10) 0.068(2) Uani 0.25 1 d D U P B -2
H44A H 0.539210 0.451728 0.236715 0.082 Uiso 0.25 1 calc R U P B -2
H44B H 0.492421 0.372260 0.183292 0.082 Uiso 0.25 1 calc R U P B -2
C45 C 0.4900(6) 0.420(2) 0.2745(9) 0.070(2) Uani 0.25 1 d D U P B -2
H45A H 0.512062 0.469660 0.316622 0.084 Uiso 0.25 1 calc R U P B -2
H45B H 0.469273 0.549443 0.256350 0.084 Uiso 0.25 1 calc R U P B -2


_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
C1 C2 1.383(3) . ?
C1 C10 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9500 . ?
C4 C11 1.402(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 C12 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.393(3) . ?
C8 H8 0.9500 . ?
N9 C10 1.398(2) . ?
N9 C13 1.401(2) . ?
N9 C14 1.420(2) . ?
C10 C11 1.409(3) . ?
C11 C12 1.444(3) . ?
C12 C13 1.408(2) . ?
C14 C19 1.392(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(3) . ?
C17 C20 1.458(2) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.159(3) . ?
C21 C22 1.452(3) . ?
C22 C24 1.398(3) . ?
C22 C23 1.402(3) . ?
C23 C24 1.388(3) 5_656 ?
C23 C25 1.512(3) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O31 C35 1.437(10) . ?
O31 C32 1.438(9) . ?
C32 C33 1.477(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.567(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.470(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
O41 C42 1.435(10) . ?
O41 C45 1.437(9) . ?
C42 C43 1.469(8) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.562(17) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.471(8) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?

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 C1 C10 117.5(2) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C11 119.18(19) . . ?
C3 C4 H4 120.4 . . ?
C11 C4 H4 120.4 . . ?
C6 C5 C12 119.26(19) . . ?
C6 C5 H5 120.4 . . ?
C12 C5 H5 120.4 . . ?
C5 C6 C7 120.72(19) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.51(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C13 117.31(18) . . ?
C7 C8 H8 121.3 . . ?
C13 C8 H8 121.3 . . ?
C10 N9 C13 108.49(15) . . ?
C10 N9 C14 124.81(16) . . ?
C13 N9 C14 126.27(15) . . ?
C1 C10 N9 129.43(17) . . ?
C1 C10 C11 121.80(18) . . ?
N9 C10 C11 108.69(16) . . ?
C4 C11 C10 118.86(19) . . ?
C4 C11 C12 134.05(18) . . ?
C10 C11 C12 107.08(16) . . ?
C5 C12 C13 119.25(18) . . ?
C5 C12 C11 133.66(17) . . ?
C13 C12 C11 107.09(16) . . ?
C8 C13 N9 129.36(17) . . ?
C8 C13 C12 121.93(17) . . ?
N9 C13 C12 108.65(16) . . ?
C19 C14 C15 119.72(16) . . ?
C19 C14 N9 119.75(16) . . ?
C15 C14 N9 120.54(16) . . ?
C16 C15 C14 119.85(17) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.01(17) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 118.46(16) . . ?
C16 C17 C20 121.85(17) . . ?
C18 C17 C20 119.70(16) . . ?
C19 C18 C17 120.76(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.20(17) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C21 C20 C17 178.4(2) . . ?
C20 C21 C22 177.0(2) . . ?
C24 C22 C23 120.15(17) . . ?
C24 C22 C21 119.84(17) . . ?
C23 C22 C21 119.98(17) . . ?
C24 C23 C22 117.80(17) 5_656 . ?
C24 C23 C25 120.99(18) 5_656 . ?
C22 C23 C25 121.21(17) . . ?
C23 C24 C22 122.05(18) 5_656 . ?
C23 C24 H24 119.0 5_656 . ?
C22 C24 H24 119.0 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C35 O31 C32 105.3(8) . . ?
O31 C32 C33 108.3(10) . . ?
O31 C32 H32A 110.0 . . ?
C33 C32 H32A 110.0 . . ?
O31 C32 H32B 110.0 . . ?
C33 C32 H32B 110.0 . . ?
H32A C32 H32B 108.4 . . ?
C32 C33 C34 99.0(7) . . ?
C32 C33 H33A 112.0 . . ?
C34 C33 H33A 112.0 . . ?
C32 C33 H33B 112.0 . . ?
C34 C33 H33B 112.0 . . ?
H33A C33 H33B 109.7 . . ?
C35 C34 C33 99.9(7) . . ?
C35 C34 H34A 111.8 . . ?
C33 C34 H34A 111.8 . . ?
C35 C34 H34B 111.8 . . ?
C33 C34 H34B 111.8 . . ?
H34A C34 H34B 109.5 . . ?
O31 C35 C34 109.3(10) . . ?
O31 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
O31 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.3 . . ?
C42 O41 C45 105.5(8) . . ?
O41 C42 C43 109.4(10) . . ?
O41 C42 H42A 109.8 . . ?
C43 C42 H42A 109.8 . . ?
O41 C42 H42B 109.8 . . ?
C43 C42 H42B 109.8 . . ?
H42A C42 H42B 108.2 . . ?
C42 C43 C44 100.2(7) . . ?
C42 C43 H43A 111.7 . . ?
C44 C43 H43A 111.7 . . ?
C42 C43 H43B 111.7 . . ?
C44 C43 H43B 111.7 . . ?
H43A C43 H43B 109.5 . . ?
C45 C44 C43 100.0(8) . . ?
C45 C44 H44A 111.8 . . ?
C43 C44 H44A 111.8 . . ?
C45 C44 H44B 111.8 . . ?
C43 C44 H44B 111.8 . . ?
H44A C44 H44B 109.5 . . ?
O41 C45 C44 108.8(9) . . ?
O41 C45 H45A 109.9 . . ?
C44 C45 H45A 109.9 . . ?
O41 C45 H45B 109.9 . . ?
C44 C45 H45B 109.9 . . ?
H45A C45 H45B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C11 -0.4(3) . . . . ?
C12 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C13 -0.2(3) . . . . ?
C2 C1 C10 N9 177.00(19) . . . . ?
C2 C1 C10 C11 0.4(3) . . . . ?
C13 N9 C10 C1 -177.12(19) . . . . ?
C14 N9 C10 C1 10.0(3) . . . . ?
C13 N9 C10 C11 -0.2(2) . . . . ?
C14 N9 C10 C11 -173.01(16) . . . . ?
C3 C4 C11 C10 0.7(3) . . . . ?
C3 C4 C11 C12 -177.6(2) . . . . ?
C1 C10 C11 C4 -0.7(3) . . . . ?
N9 C10 C11 C4 -177.95(16) . . . . ?
C1 C10 C11 C12 177.99(17) . . . . ?
N9 C10 C11 C12 0.8(2) . . . . ?
C6 C5 C12 C13 0.8(3) . . . . ?
C6 C5 C12 C11 -178.46(19) . . . . ?
C4 C11 C12 C5 -3.3(4) . . . . ?
C10 C11 C12 C5 178.2(2) . . . . ?
C4 C11 C12 C13 177.4(2) . . . . ?
C10 C11 C12 C13 -1.08(19) . . . . ?
C7 C8 C13 N9 177.56(18) . . . . ?
C7 C8 C13 C12 0.6(3) . . . . ?
C10 N9 C13 C8 -177.78(18) . . . . ?
C14 N9 C13 C8 -5.1(3) . . . . ?
C10 N9 C13 C12 -0.5(2) . . . . ?
C14 N9 C13 C12 172.19(16) . . . . ?
C5 C12 C13 C8 -0.9(3) . . . . ?
C11 C12 C13 C8 178.49(17) . . . . ?
C5 C12 C13 N9 -178.44(16) . . . . ?
C11 C12 C13 N9 0.98(19) . . . . ?
C10 N9 C14 C19 50.9(2) . . . . ?
C13 N9 C14 C19 -120.7(2) . . . . ?
C10 N9 C14 C15 -129.67(19) . . . . ?
C13 N9 C14 C15 58.8(2) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
N9 C14 C15 C16 179.80(16) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C15 C16 C17 C20 179.65(16) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C20 C17 C18 C19 -179.50(17) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 0.9(3) . . . . ?
N9 C14 C19 C18 -179.65(16) . . . . ?
C24 C22 C23 C24 -0.3(3) . . . 5_656 ?
C21 C22 C23 C24 177.63(16) . . . 5_656 ?
C24 C22 C23 C25 178.83(18) . . . . ?
C21 C22 C23 C25 -3.3(3) . . . . ?
C23 C22 C24 C23 0.3(3) . . . 5_656 ?
C21 C22 C24 C23 -177.62(17) . . . 5_656 ?
C35 O31 C32 C33 18.7(17) . . . . ?
O31 C32 C33 C34 -37.3(14) . . . . ?
C32 C33 C34 C35 40.6(13) . . . . ?
C32 O31 C35 C34 9.9(17) . . . . ?
C33 C34 C35 O31 -32.1(15) . . . . ?
C45 O41 C42 C43 11.7(18) . . . . ?
O41 C42 C43 C44 -31.8(15) . . . . ?
C42 C43 C44 C45 38.6(12) . . . . ?
C42 O41 C45 C44 15.5(19) . . . . ?
C43 C44 C45 O41 -34.2(15) . . . . ?

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
C8 H8 O31 0.95 2.51 3.402(13) 156.6 5_666

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_2-Cl_Benzene
_database_code_depnum_ccdc_archive 'CCDC 1940316'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C54H37ClN2
_chemical_formula_sum            'C54 H37 Cl N2'
_chemical_formula_weight         749.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.44130(10)
_cell_length_b                   14.0103(3)
_cell_length_c                   15.0265(3)
_cell_angle_alpha                114.8020(10)
_cell_angle_beta                 90.263(2)
_cell_angle_gamma                101.034(2)
_cell_volume                     1016.01(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      0.792
_cell_measurement_theta_max      0.947

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    1.128
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8766
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.255
_diffrn_reflns_theta_max         70.065
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3835
_reflns_number_gt                2000
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+0.0226P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0025(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3835
_refine_ls_number_parameters     354
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.020
_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
C1 C 0.5780(5) 0.1238(2) 0.6266(2) 0.0763(8) Uani 1 1 d . . . . .
H1 H 0.436757 0.083960 0.582296 0.092 Uiso 1 1 calc R U . . .
C2 C 0.6941(6) 0.0803(3) 0.6780(2) 0.0893(9) Uani 1 1 d . . . . .
H2 H 0.627728 0.010045 0.668476 0.107 Uiso 1 1 calc R U . . .
C3 C 0.9061(7) 0.1380(3) 0.7431(2) 0.0938(10) Uani 1 1 d . . . . .
H3 H 0.981533 0.105954 0.775787 0.113 Uiso 1 1 calc R U . . .
C4 C 1.0056(6) 0.2424(3) 0.75982(19) 0.0892(10) Uani 1 1 d . . . . .
H4 H 1.147867 0.281255 0.803827 0.107 Uiso 1 1 calc R U . . .
C5 C 1.1414(7) 0.4829(3) 0.7545(3) 0.1027(11) Uani 1 1 d . . . . .
H5 H 1.261662 0.484473 0.799569 0.123 Uiso 1 1 calc R U . . .
C6 C 1.1478(8) 0.5709(3) 0.7349(3) 0.1190(13) Uani 1 1 d . . . . .
H6 H 1.274680 0.632035 0.766527 0.143 Uiso 1 1 calc R U . . .
C7 C 0.9688(8) 0.5695(3) 0.6690(3) 0.1163(13) Uani 1 1 d . . . . .
H7 H 0.975998 0.630416 0.657838 0.140 Uiso 1 1 calc R U . . .
C8 C 0.7783(7) 0.4799(3) 0.6189(3) 0.1040(11) Uani 1 1 d . . . . .
H8 H 0.657103 0.479625 0.574919 0.125 Uiso 1 1 calc R U . . .
N9 N 0.6064(4) 0.29060(18) 0.59881(15) 0.0736(6) Uani 1 1 d . . . . .
C10 C 0.6794(5) 0.2288(2) 0.64338(17) 0.0663(7) Uani 1 1 d . . . . .
C11 C 0.8916(5) 0.2897(2) 0.71019(18) 0.0720(7) Uani 1 1 d . . . . .
C12 C 0.9528(6) 0.3922(2) 0.7061(2) 0.0778(8) Uani 1 1 d . . . . .
C13 C 0.7760(6) 0.3901(2) 0.6374(2) 0.0794(8) Uani 1 1 d . . . . .
C14 C 0.4339(5) 0.2496(2) 0.51345(19) 0.0702(7) Uani 1 1 d . . . . .
C15 C 0.5116(5) 0.2650(2) 0.4313(2) 0.0814(8) Uani 1 1 d . . . . .
H15 H 0.672621 0.303468 0.433100 0.098 Uiso 1 1 calc R U . . .
C16 C 0.3468(6) 0.2226(3) 0.3468(2) 0.0830(9) Uani 1 1 d . . . . .
H16 H 0.398105 0.233868 0.292381 0.100 Uiso 1 1 calc R U . . .
C17 C 0.1074(5) 0.1637(2) 0.3417(2) 0.0731(8) Uani 1 1 d . . . . .
C18 C 0.0343(5) 0.1481(2) 0.42468(19) 0.0726(7) Uani 1 1 d . . . . .
H18 H -0.125376 0.108597 0.422959 0.087 Uiso 1 1 calc R U . . .
C19 C 0.1975(5) 0.1908(2) 0.50879(19) 0.0709(7) Uani 1 1 d . . . . .
H19 H 0.146810 0.179668 0.563313 0.085 Uiso 1 1 calc R U . . .
C20 C -0.0591(5) 0.1197(2) 0.2529(2) 0.0773(8) Uani 1 1 d . . . . .
C21 C -0.1922(6) 0.0856(2) 0.1792(2) 0.0792(8) Uani 1 1 d . . . . .
C22 C -0.3467(6) 0.0434(2) 0.08835(19) 0.0742(7) Uani 1 1 d . . . . .
C23 C -0.2764(6) 0.0780(2) 0.0153(2) 0.0759(8) Uani 1 1 d . . . . .
C24 C -0.4327(6) 0.0332(2) -0.0713(2) 0.0795(8) Uani 1 1 d . . . . .
H24 H -0.388180 0.055279 -0.120451 0.095 Uiso 1 1 calc R U . . .
C25 C -0.0407(6) 0.1603(3) 0.0307(2) 0.0991(10) Uani 1 1 d . . . . .
H25A H -0.015093 0.169149 -0.028774 0.149 Uiso 1 1 calc R U . . .
H25B H 0.099650 0.137030 0.047949 0.149 Uiso 1 1 calc R U . . .
H25C H -0.055477 0.227723 0.082972 0.149 Uiso 1 1 calc R U . . .
Cl1 Cl 0.523(2) 0.6694(8) -0.0001(8) 0.116(3) Uani 0.25 1 d . U P A -1
C31 C 0.510(6) 0.549(2) 0.002(2) 0.098(3) Uani 0.25 1 d . U P A -1
C32 C 0.370(7) 0.523(5) 0.061(3) 0.102(3) Uani 0.25 1 d . U P A -1
H32 H 0.317312 0.576172 0.114327 0.122 Uiso 0.25 1 calc R U P A -1
C33 C 0.307(6) 0.427(3) 0.045(2) 0.103(3) Uani 0.25 1 d . U P A -1
H33 H 0.162613 0.393477 0.061121 0.123 Uiso 0.25 1 calc R U P A -1
C34 C 0.513(6) 0.380(3) -0.007(2) 0.103(3) Uani 0.25 1 d . U P A -1
H34 H 0.524697 0.313094 -0.009959 0.124 Uiso 0.25 1 calc R U P A -1
C35 C 0.669(5) 0.421(3) -0.045(2) 0.106(3) Uani 0.25 1 d . U P A -1
H35 H 0.793750 0.383913 -0.073636 0.127 Uiso 0.25 1 calc R U P A -1
C36 C 0.673(11) 0.483(6) -0.047(5) 0.103(3) Uani 0.25 1 d . U P A -1
H36 H 0.789035 0.505127 -0.083975 0.124 Uiso 0.25 1 calc R U P A -1
Cl1B Cl 0.460(2) 0.6997(9) 0.0266(10) 0.130(3) Uani 0.25 1 d . U P B -2
C31B C 0.471(7) 0.569(3) 0.017(3) 0.100(3) Uani 0.25 1 d . U P B -2
C32B C 0.293(8) 0.531(4) 0.059(3) 0.103(3) Uani 0.25 1 d . U P B -2
H32B H 0.162234 0.565879 0.083547 0.123 Uiso 0.25 1 calc R U P B -2
C33B C 0.314(6) 0.421(2) 0.0681(19) 0.104(3) Uani 0.25 1 d . U P B -2
H33B H 0.233053 0.407851 0.117585 0.124 Uiso 0.25 1 calc R U P B -2
C34B C 0.409(5) 0.364(3) 0.024(2) 0.104(3) Uani 0.25 1 d . U P B -2
H34B H 0.366984 0.297156 0.024615 0.124 Uiso 0.25 1 calc R U P B -2
C35B C 0.615(5) 0.377(2) -0.045(2) 0.103(3) Uani 0.25 1 d . U P B -2
H35B H 0.700577 0.324249 -0.082647 0.124 Uiso 0.25 1 calc R U P B -2
C36B C 0.664(8) 0.518(2) -0.038(3) 0.102(3) Uani 0.25 1 d . U P B -2
H36B H 0.789426 0.549049 -0.065733 0.122 Uiso 0.25 1 calc R U P B -2


_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
C1 C2 1.380(4) . ?
C1 C10 1.382(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C11 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 C12 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(5) . ?
C7 H7 0.9300 . ?
C8 C13 1.395(4) . ?
C8 H8 0.9300 . ?
N9 C13 1.398(3) . ?
N9 C10 1.404(3) . ?
N9 C14 1.422(3) . ?
C10 C11 1.401(3) . ?
C11 C12 1.437(4) . ?
C12 C13 1.396(4) . ?
C14 C19 1.372(4) . ?
C14 C15 1.395(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(3) . ?
C17 C20 1.437(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.182(4) . ?
C21 C22 1.429(3) . ?
C22 C24 1.390(4) 2_455 ?
C22 C23 1.402(4) . ?
C23 C24 1.382(4) . ?
C23 C25 1.495(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
Cl1 C31 1.69(3) . ?
C31 C32 1.28(6) . ?
C31 C36 1.39(7) . ?
C31 C35 2.00(5) . ?
C32 C33 1.24(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.47(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.22(4) . ?
C34 C36 1.87(8) . ?
C34 H34 0.9300 . ?
C35 C36 0.89(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
Cl1B C31B 1.79(4) . ?
C31B C32B 1.31(6) . ?
C31B C36B 1.44(5) . ?
C32B C33B 1.63(6) . ?
C32B H32B 0.9300 . ?
C33B C34B 1.03(5) . ?
C33B H33B 0.9300 . ?
C34B C35B 1.56(4) . ?
C34B H34B 0.9300 . ?
C35B C36B 1.90(4) . ?
C35B H35B 0.9300 . ?
C36B H36B 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 C1 C10 117.6(3) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 121.9(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C11 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C11 C4 H4 120.3 . . ?
C6 C5 C12 118.9(4) . . ?
C6 C5 H5 120.6 . . ?
C12 C5 H5 120.6 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 121.8(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C13 117.1(4) . . ?
C7 C8 H8 121.4 . . ?
C13 C8 H8 121.4 . . ?
C13 N9 C10 107.5(2) . . ?
C13 N9 C14 125.7(2) . . ?
C10 N9 C14 125.1(2) . . ?
C1 C10 C11 121.7(3) . . ?
C1 C10 N9 129.3(2) . . ?
C11 C10 N9 109.0(2) . . ?
C4 C11 C10 119.1(3) . . ?
C4 C11 C12 133.7(3) . . ?
C10 C11 C12 107.1(2) . . ?
C5 C12 C13 120.1(3) . . ?
C5 C12 C11 132.8(3) . . ?
C13 C12 C11 107.1(3) . . ?
C8 C13 C12 121.2(3) . . ?
C8 C13 N9 129.4(3) . . ?
C12 C13 N9 109.3(3) . . ?
C19 C14 C15 119.5(3) . . ?
C19 C14 N9 121.3(2) . . ?
C15 C14 N9 119.1(3) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 C20 120.3(3) . . ?
C18 C17 C20 121.5(3) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C14 C19 C18 121.1(3) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C17 178.2(3) . . ?
C20 C21 C22 178.2(3) . . ?
C24 C22 C23 119.4(2) 2_455 . ?
C24 C22 C21 120.1(3) 2_455 . ?
C23 C22 C21 120.5(3) . . ?
C24 C23 C22 117.6(3) . . ?
C24 C23 C25 121.4(3) . . ?
C22 C23 C25 121.0(3) . . ?
C23 C24 C22 123.0(3) . 2_455 ?
C23 C24 H24 118.5 . . ?
C22 C24 H24 118.5 2_455 . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C31 C36 119(6) . . ?
C32 C31 Cl1 119(4) . . ?
C36 C31 Cl1 121(4) . . ?
C32 C31 C35 97(4) . . ?
C36 C31 C35 22(3) . . ?
Cl1 C31 C35 143(2) . . ?
C33 C32 C31 119(5) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 104(3) . . ?
C32 C33 H33 128.0 . . ?
C34 C33 H33 128.0 . . ?
C35 C34 C33 125(4) . . ?
C35 C34 C36 23(3) . . ?
C33 C34 C36 102(3) . . ?
C35 C34 H34 117.4 . . ?
C33 C34 H34 117.4 . . ?
C36 C34 H34 140.2 . . ?
C36 C35 C34 125(7) . . ?
C36 C35 C31 36(5) . . ?
C34 C35 C31 89(3) . . ?
C36 C35 H35 117.5 . . ?
C34 C35 H35 117.5 . . ?
C31 C35 H35 153.5 . . ?
C35 C36 C31 121(8) . . ?
C35 C36 C34 32(4) . . ?
C31 C36 C34 89(4) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
C34 C36 H36 151.1 . . ?
C32B C31B C36B 129(4) . . ?
C32B C31B Cl1B 113(3) . . ?
C36B C31B Cl1B 117(4) . . ?
C31B C32B C33B 117(3) . . ?
C31B C32B H32B 121.7 . . ?
C33B C32B H32B 121.7 . . ?
C34B C33B C32B 126(3) . . ?
C34B C33B H33B 117.2 . . ?
C32B C33B H33B 117.2 . . ?
C33B C34B C35B 128(4) . . ?
C33B C34B H34B 115.9 . . ?
C35B C34B H34B 115.9 . . ?
C34B C35B C36B 109(3) . . ?
C34B C35B H35B 125.6 . . ?
C36B C35B H35B 125.6 . . ?
C31B C36B C35B 108(4) . . ?
C31B C36B H36B 126.0 . . ?
C35B C36B H36B 126.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C11 -0.2(5) . . . . ?
C12 C5 C6 C7 0.7(6) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
C6 C7 C8 C13 -0.5(6) . . . . ?
C2 C1 C10 C11 -0.2(4) . . . . ?
C2 C1 C10 N9 177.1(3) . . . . ?
C13 N9 C10 C1 -176.9(3) . . . . ?
C14 N9 C10 C1 -11.3(4) . . . . ?
C13 N9 C10 C11 0.6(3) . . . . ?
C14 N9 C10 C11 166.3(2) . . . . ?
C3 C4 C11 C10 -0.8(4) . . . . ?
C3 C4 C11 C12 -175.9(3) . . . . ?
C1 C10 C11 C4 1.0(4) . . . . ?
N9 C10 C11 C4 -176.8(2) . . . . ?
C1 C10 C11 C12 177.3(2) . . . . ?
N9 C10 C11 C12 -0.5(3) . . . . ?
C6 C5 C12 C13 1.1(5) . . . . ?
C6 C5 C12 C11 -179.2(3) . . . . ?
C4 C11 C12 C5 -4.1(6) . . . . ?
C10 C11 C12 C5 -179.6(3) . . . . ?
C4 C11 C12 C13 175.7(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C7 C8 C13 C12 2.3(5) . . . . ?
C7 C8 C13 N9 179.1(3) . . . . ?
C5 C12 C13 C8 -2.7(5) . . . . ?
C11 C12 C13 C8 177.6(3) . . . . ?
C5 C12 C13 N9 180.0(3) . . . . ?
C11 C12 C13 N9 0.2(3) . . . . ?
C10 N9 C13 C8 -177.6(3) . . . . ?
C14 N9 C13 C8 16.9(5) . . . . ?
C10 N9 C13 C12 -0.5(3) . . . . ?
C14 N9 C13 C12 -166.1(2) . . . . ?
C13 N9 C14 C19 -142.8(3) . . . . ?
C10 N9 C14 C19 54.1(4) . . . . ?
C13 N9 C14 C15 40.5(4) . . . . ?
C10 N9 C14 C15 -122.6(3) . . . . ?
C19 C14 C15 C16 1.4(4) . . . . ?
N9 C14 C15 C16 178.1(2) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C15 C16 C17 C20 -179.4(3) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C20 C17 C18 C19 179.8(2) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?
N9 C14 C19 C18 -177.7(2) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C24 C22 C23 C24 -0.1(5) 2_455 . . . ?
C21 C22 C23 C24 179.3(2) . . . . ?
C24 C22 C23 C25 179.9(3) 2_455 . . . ?
C21 C22 C23 C25 -0.7(5) . . . . ?
C22 C23 C24 C22 0.1(5) . . . 2_455 ?
C25 C23 C24 C22 -179.9(3) . . . 2_455 ?
C36 C31 C32 C33 -28(6) . . . . ?
Cl1 C31 C32 C33 161(3) . . . . ?
C35 C31 C32 C33 -25(4) . . . . ?
C31 C32 C33 C34 28(4) . . . . ?
C32 C33 C34 C35 -17(4) . . . . ?
C32 C33 C34 C36 -17(3) . . . . ?
C33 C34 C35 C36 -2(7) . . . . ?
C33 C34 C35 C31 2(3) . . . . ?
C36 C34 C35 C31 4(5) . . . . ?
C34 C35 C36 C31 7(9) . . . . ?
C31 C35 C36 C34 -7(9) . . . . ?
C32 C31 C36 C35 7(9) . . . . ?
Cl1 C31 C36 C35 178(5) . . . . ?
C32 C31 C36 C34 11(5) . . . . ?
Cl1 C31 C36 C34 -178(2) . . . . ?
C35 C31 C36 C34 3(5) . . . . ?
C33 C34 C36 C35 179(6) . . . . ?
C35 C34 C36 C31 -174(8) . . . . ?
C33 C34 C36 C31 4(3) . . . . ?
C36B C31B C32B C33B 11(6) . . . . ?
Cl1B C31B C32B C33B -171(2) . . . . ?
C31B C32B C33B C34B -23(6) . . . . ?
C32B C33B C34B C35B 18(6) . . . . ?
C33B C34B C35B C36B -2(5) . . . . ?
C32B C31B C36B C35B 2(5) . . . . ?
Cl1B C31B C36B C35B -176(2) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chlorobenzene'
####################################################################### 
# 
# 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_2-p_Xylene
_database_code_depnum_ccdc_archive 'CCDC 1940317'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C28H21N
_chemical_formula_sum            'C28 H21 N'
_chemical_formula_weight         371.46

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.5357(5)
_cell_length_b                   13.9222(14)
_cell_length_c                   15.0956(15)
_cell_angle_alpha                115.448(2)
_cell_angle_beta                 90.572(2)
_cell_angle_gamma                97.252(2)
_cell_volume                     1039.44(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      0.984
_cell_measurement_theta_max      0.995

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20975
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         29.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5594
_reflns_number_gt                2748
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.1358P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5594
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C1 C 0.4701(3) 0.37331(15) -0.12377(13) 0.0582(5) Uani 1 1 d . . . . .
H1 H 0.370961 0.417189 -0.079280 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6314(4) 0.41239(17) -0.17355(14) 0.0686(6) Uani 1 1 d . . . . .
H2 H 0.640395 0.483852 -0.162502 0.082 Uiso 1 1 calc R U . . .
C3 C 0.7805(4) 0.3477(2) -0.23964(15) 0.0745(6) Uani 1 1 d . . . . .
H3 H 0.888671 0.376516 -0.271690 0.089 Uiso 1 1 calc R U . . .
C4 C 0.7705(4) 0.24192(19) -0.25829(13) 0.0687(6) Uani 1 1 d . . . . .
H4 H 0.870106 0.198784 -0.303165 0.082 Uiso 1 1 calc R U . . .
C5 C 0.6467(5) -0.00150(19) -0.25921(16) 0.0820(7) Uani 1 1 d . . . . .
H5 H 0.764638 -0.007849 -0.304091 0.098 Uiso 1 1 calc R U . . .
C6 C 0.5566(5) -0.0877(2) -0.24289(19) 0.0991(8) Uani 1 1 d . . . . .
H6 H 0.614787 -0.152850 -0.276493 0.119 Uiso 1 1 calc R U . . .
C7 C 0.3793(5) -0.07972(19) -0.1769(2) 0.0960(8) Uani 1 1 d . . . . .
H7 H 0.318561 -0.140058 -0.167921 0.115 Uiso 1 1 calc R U . . .
C8 C 0.2907(4) 0.01614(17) -0.12407(17) 0.0818(7) Uani 1 1 d . . . . .
H8 H 0.172555 0.021523 -0.079437 0.098 Uiso 1 1 calc R U . . .
N9 N 0.3244(3) 0.20829(12) -0.09945(10) 0.0552(4) Uani 1 1 d . . . . .
C10 C 0.4608(3) 0.26650(14) -0.14233(11) 0.0497(4) Uani 1 1 d . . . . .
C11 C 0.6097(3) 0.19953(15) -0.20941(12) 0.0548(5) Uani 1 1 d . . . . .
C12 C 0.5609(3) 0.09624(16) -0.20815(13) 0.0592(5) Uani 1 1 d . . . . .
C13 C 0.3851(4) 0.10381(15) -0.14037(13) 0.0595(5) Uani 1 1 d . . . . .
C14 C 0.1956(3) 0.25383(14) -0.01340(12) 0.0505(4) Uani 1 1 d . . . . .
C15 C 0.2560(4) 0.23781(17) 0.06819(14) 0.0652(5) Uani 1 1 d . . . . .
H15 H 0.379168 0.197405 0.066132 0.078 Uiso 1 1 calc R U . . .
C16 C 0.1338(4) 0.28159(17) 0.15203(14) 0.0659(5) Uani 1 1 d . . . . .
H16 H 0.176025 0.270726 0.206474 0.079 Uiso 1 1 calc R U . . .
C17 C -0.0517(3) 0.34184(14) 0.15674(13) 0.0532(5) Uani 1 1 d . . . . .
C18 C -0.1082(3) 0.35809(14) 0.07483(12) 0.0544(5) Uani 1 1 d . . . . .
H18 H -0.230407 0.398952 0.076781 0.065 Uiso 1 1 calc R U . . .
C19 C 0.0142(3) 0.31449(14) -0.00931(12) 0.0529(4) Uani 1 1 d . . . . .
H19 H -0.025809 0.326102 -0.063552 0.064 Uiso 1 1 calc R U . . .
C20 C -0.1793(3) 0.38548(15) 0.24535(13) 0.0568(5) Uani 1 1 d . . . . .
C21 C -0.2797(3) 0.41807(14) 0.31883(13) 0.0564(5) Uani 1 1 d . . . . .
C22 C -0.3938(3) 0.45815(13) 0.41073(12) 0.0500(4) Uani 1 1 d . . . . .
C23 C -0.3329(3) 0.42573(13) 0.48324(13) 0.0502(4) Uani 1 1 d . . . . .
C24 C -0.5583(3) 0.53083(14) 0.42866(12) 0.0536(5) Uani 1 1 d . . . . .
H24 H -0.596745 0.551066 0.379582 0.064 Uiso 1 1 calc R U . . .
C25 C -0.1553(4) 0.34769(16) 0.46645(15) 0.0691(6) Uani 1 1 d . . . . .
H25A H -0.217072 0.280460 0.411957 0.104 Uiso 1 1 calc R U . . .
H25B H -0.134084 0.336626 0.524422 0.104 Uiso 1 1 calc R U . . .
H25C H -0.001131 0.376027 0.452240 0.104 Uiso 1 1 calc R U . . .
C31 C 0.1433(3) 0.09779(16) 0.51761(14) 0.0605(5) Uani 1 1 d . . . . .
C32 C -0.0743(4) 0.06419(17) 0.46092(15) 0.0678(5) Uani 1 1 d . . . . .
H32 H -0.127062 0.106992 0.433512 0.081 Uiso 1 1 calc R U . . .
C33 C -0.2154(4) -0.03164(17) 0.44410(14) 0.0672(5) Uani 1 1 d . . . . .
H33 H -0.362356 -0.051988 0.406045 0.081 Uiso 1 1 calc R U . . .
C34 C 0.2975(4) 0.20272(19) 0.5367(2) 0.0959(8) Uani 1 1 d . . . . .
H34A H 0.467070 0.195091 0.539185 0.144 Uiso 1 1 calc R U . . .
H34B H 0.261087 0.257627 0.598286 0.144 Uiso 1 1 calc R U . . .
H34C H 0.262750 0.222387 0.484738 0.144 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
C1 C2 1.379(2) . ?
C1 C10 1.384(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C11 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(3) . ?
C5 C12 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.387(3) . ?
C8 H8 0.9300 . ?
N9 C10 1.397(2) . ?
N9 C13 1.402(2) . ?
N9 C14 1.422(2) . ?
C10 C11 1.405(2) . ?
C11 C12 1.438(3) . ?
C12 C13 1.399(2) . ?
C14 C19 1.377(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.374(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(2) . ?
C17 C20 1.444(2) . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.178(2) . ?
C21 C22 1.441(2) . ?
C22 C24 1.389(2) . ?
C22 C23 1.404(2) . ?
C23 C24 1.384(2) 2_466 ?
C23 C25 1.500(2) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C31 C33 1.374(3) 2_556 ?
C31 C32 1.377(3) . ?
C31 C34 1.505(3) . ?
C32 C33 1.377(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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 C1 C10 117.67(18) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.75(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C11 119.35(19) . . ?
C3 C4 H4 120.3 . . ?
C11 C4 H4 120.3 . . ?
C6 C5 C12 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C12 C5 H5 120.3 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C13 117.3(2) . . ?
C7 C8 H8 121.3 . . ?
C13 C8 H8 121.3 . . ?
C10 N9 C13 107.93(14) . . ?
C10 N9 C14 125.13(14) . . ?
C13 N9 C14 125.26(15) . . ?
C1 C10 N9 129.50(16) . . ?
C1 C10 C11 121.61(16) . . ?
N9 C10 C11 108.82(15) . . ?
C4 C11 C10 119.06(18) . . ?
C4 C11 C12 133.73(18) . . ?
C10 C11 C12 107.16(15) . . ?
C5 C12 C13 119.1(2) . . ?
C5 C12 C11 133.82(19) . . ?
C13 C12 C11 107.10(16) . . ?
C8 C13 C12 121.78(19) . . ?
C8 C13 N9 129.20(18) . . ?
C12 C13 N9 108.98(16) . . ?
C19 C14 C15 119.50(16) . . ?
C19 C14 N9 121.16(16) . . ?
C15 C14 N9 119.33(16) . . ?
C16 C15 C14 120.05(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.05(18) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.21(16) . . ?
C18 C17 C20 122.00(17) . . ?
C16 C17 C20 119.79(17) . . ?
C19 C18 C17 120.89(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C14 C19 C18 120.29(16) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C17 177.2(2) . . ?
C20 C21 C22 177.8(2) . . ?
C24 C22 C23 120.06(15) . . ?
C24 C22 C21 120.19(16) . . ?
C23 C22 C21 119.73(16) . . ?
C24 C23 C22 117.44(16) 2_466 . ?
C24 C23 C25 121.10(17) 2_466 . ?
C22 C23 C25 121.45(16) . . ?
C23 C24 C22 122.49(16) 2_466 . ?
C23 C24 H24 118.8 2_466 . ?
C22 C24 H24 118.8 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C33 C31 C32 117.48(18) 2_556 . ?
C33 C31 C34 121.1(2) 2_556 . ?
C32 C31 C34 121.4(2) . . ?
C33 C32 C31 121.19(19) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C31 C33 C32 121.33(19) 2_556 . ?
C31 C33 H33 119.3 2_556 . ?
C32 C33 H33 119.3 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C11 -0.6(3) . . . . ?
C12 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C13 0.5(4) . . . . ?
C2 C1 C10 N9 176.73(17) . . . . ?
C2 C1 C10 C11 0.0(3) . . . . ?
C13 N9 C10 C1 -177.73(18) . . . . ?
C14 N9 C10 C1 -11.9(3) . . . . ?
C13 N9 C10 C11 -0.65(19) . . . . ?
C14 N9 C10 C11 165.14(16) . . . . ?
C3 C4 C11 C10 0.2(3) . . . . ?
C3 C4 C11 C12 -176.9(2) . . . . ?
C1 C10 C11 C4 0.0(3) . . . . ?
N9 C10 C11 C4 -177.31(16) . . . . ?
C1 C10 C11 C12 177.86(16) . . . . ?
N9 C10 C11 C12 0.51(19) . . . . ?
C6 C5 C12 C13 0.6(3) . . . . ?
C6 C5 C12 C11 -178.0(2) . . . . ?
C4 C11 C12 C5 -4.1(4) . . . . ?
C10 C11 C12 C5 178.5(2) . . . . ?
C4 C11 C12 C13 177.2(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C7 C8 C13 C12 0.7(3) . . . . ?
C7 C8 C13 N9 178.1(2) . . . . ?
C5 C12 C13 C8 -1.3(3) . . . . ?
C11 C12 C13 C8 177.64(18) . . . . ?
C5 C12 C13 N9 -179.13(17) . . . . ?
C11 C12 C13 N9 -0.2(2) . . . . ?
C10 N9 C13 C8 -177.1(2) . . . . ?
C14 N9 C13 C8 17.1(3) . . . . ?
C10 N9 C13 C12 0.5(2) . . . . ?
C14 N9 C13 C12 -165.22(16) . . . . ?
C10 N9 C14 C19 59.3(2) . . . . ?
C13 N9 C14 C19 -137.32(19) . . . . ?
C10 N9 C14 C15 -119.9(2) . . . . ?
C13 N9 C14 C15 43.4(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
N9 C14 C15 C16 179.77(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C15 C16 C17 C20 179.07(18) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C20 C17 C18 C19 -179.21(16) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
N9 C14 C19 C18 -179.90(15) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C24 C22 C23 C24 -0.3(3) . . . 2_466 ?
C21 C22 C23 C24 178.00(16) . . . 2_466 ?
C24 C22 C23 C25 -179.79(16) . . . . ?
C21 C22 C23 C25 -1.5(3) . . . . ?
C23 C22 C24 C23 0.3(3) . . . 2_466 ?
C21 C22 C24 C23 -177.98(16) . . . 2_466 ?
C33 C31 C32 C33 0.6(3) 2_556 . . . ?
C34 C31 C32 C33 -179.67(19) . . . . ?
C31 C32 C33 C31 -0.6(3) . . . 2_556 ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: p-xylene'
####################################################################### 
# 
# 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_cu_118RMB17_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1940320'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C48H32N2
_chemical_formula_sum            'C48 H32 N2'
_chemical_formula_weight         636.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   34.4065(11)
_cell_length_b                   5.4036(2)
_cell_length_c                   19.9747(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.0100(10)
_cell_angle_gamma                90
_cell_volume                     3418.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      71.74

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.183
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_max          0.457
_exptl_absorpt_coefficient_mu    0.548
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   ' SADABS-2016/2, Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54175
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Incoatec ImuS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17285
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         70.060
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3244
_reflns_number_gt                2943
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0740P)²+0.7891P] 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         3244
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33043(3) 0.02404(18) 0.69025(5) 0.0472(2) Uani 1 1 d . . . . .
C1 C 0.29049(3) -0.0730(2) 0.64814(6) 0.0463(3) Uani 1 1 d . . . . .
C3 C 0.22396(4) -0.1267(3) 0.55113(7) 0.0651(4) Uani 1 1 d . . . . .
H3 H 0.204053 -0.079339 0.505993 0.078 Uiso 1 1 calc R U . . .
C2 C 0.26166(4) 0.0014(3) 0.58063(7) 0.0590(3) Uani 1 1 d . . . . .
H2 H 0.267464 0.133076 0.555997 0.071 Uiso 1 1 calc R U . . .
C4 C 0.21510(4) -0.3250(3) 0.58741(8) 0.0652(4) Uani 1 1 d . . . . .
H4 H 0.189870 -0.411202 0.565521 0.078 Uiso 1 1 calc R U . . .
C5 C 0.24317(4) -0.3947(2) 0.65505(7) 0.0579(3) Uani 1 1 d . . . . .
H5 H 0.237040 -0.526082 0.679375 0.069 Uiso 1 1 calc R U . . .
C6 C 0.28120(4) -0.2648(2) 0.68690(6) 0.0468(3) Uani 1 1 d . . . . .
C7 C 0.31631(4) -0.2824(2) 0.75604(6) 0.0465(3) Uani 1 1 d . . . . .
C8 C 0.32512(4) -0.4382(2) 0.81555(7) 0.0593(3) Uani 1 1 d . . . . .
H8 H 0.305442 -0.555324 0.816103 0.071 Uiso 1 1 calc R U . . .
C9 C 0.36319(5) -0.4170(3) 0.87346(7) 0.0655(4) Uani 1 1 d . . . . .
H9 H 0.369307 -0.521018 0.913380 0.079 Uiso 1 1 calc R U . . .
C10 C 0.39270(5) -0.2420(3) 0.87316(7) 0.0616(3) Uani 1 1 d . . . . .
H10 H 0.418356 -0.231308 0.912903 0.074 Uiso 1 1 calc R U . . .
C11 C 0.38465(4) -0.0828(2) 0.81477(6) 0.0527(3) Uani 1 1 d . . . . .
H11 H 0.404440 0.034589 0.814841 0.063 Uiso 1 1 calc R U . . .
C12 C 0.34616(4) -0.1042(2) 0.75630(6) 0.0440(3) Uani 1 1 d . . . . .
C13 C 0.35514(3) 0.1691(2) 0.66218(6) 0.0446(3) Uani 1 1 d . . . . .
C14 C 0.35656(4) 0.1076(2) 0.59559(6) 0.0534(3) Uani 1 1 d . . . . .
H14 H 0.341330 -0.027844 0.569775 0.064 Uiso 1 1 calc R U . . .
C15 C 0.38034(4) 0.2456(3) 0.56752(7) 0.0570(3) Uani 1 1 d . . . . .
H15 H 0.380803 0.203408 0.522709 0.068 Uiso 1 1 calc R U . . .
C16 C 0.40369(4) 0.4480(2) 0.60566(7) 0.0519(3) Uani 1 1 d . . . . .
C17 C 0.40266(4) 0.5054(2) 0.67306(7) 0.0556(3) Uani 1 1 d . . . . .
H17 H 0.418383 0.638341 0.699522 0.067 Uiso 1 1 calc R U . . .
C18 C 0.37868(4) 0.3680(2) 0.70116(7) 0.0513(3) Uani 1 1 d . . . . .
H18 H 0.378314 0.408806 0.746137 0.062 Uiso 1 1 calc R U . . .
C19 C 0.42897(4) 0.5911(2) 0.57693(8) 0.0584(3) Uani 1 1 d . . . . .
C20 C 0.45030(4) 0.7073(3) 0.55419(7) 0.0591(3) Uani 1 1 d . . . . .
C21 C 0.47614(4) 0.8556(2) 0.52758(7) 0.0547(3) Uani 1 1 d . . . . .
C22 C 0.47629(4) 0.8073(2) 0.45900(7) 0.0566(3) Uani 1 1 d . . . . .
H22 H 0.460292 0.676122 0.431941 0.068 Uiso 1 1 calc R U . . .
C23 C 0.49961(4) 0.9491(2) 0.42989(7) 0.0549(3) Uani 1 1 d . . . . .
C24 C 0.49803(5) 0.8989(3) 0.35477(8) 0.0713(4) Uani 1 1 d . . . . .
H24A H 0.483266 0.746547 0.336888 0.107 Uiso 1 1 calc R U . . .
H24B H 0.526255 0.886277 0.356595 0.107 Uiso 1 1 calc R U . . .
H24C H 0.483554 1.031893 0.322914 0.107 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 C12 1.3985(14) . ?
N1 C1 1.4028(14) . ?
N1 C13 1.4227(13) . ?
C1 C2 1.3851(17) . ?
C1 C6 1.4029(16) . ?
C3 C2 1.3825(19) . ?
C3 C4 1.393(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3996(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.4392(17) . ?
C7 C8 1.3899(16) . ?
C7 C12 1.4062(15) . ?
C8 C9 1.372(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3874(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.3863(17) . ?
C11 H11 0.9300 . ?
C13 C18 1.3871(16) . ?
C13 C14 1.3901(16) . ?
C14 C15 1.3779(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.3939(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.3956(17) . ?
C16 C19 1.4402(16) . ?
C17 C18 1.3816(16) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.1827(17) . ?
C20 C21 1.4441(16) . ?
C21 C22 1.3966(19) . ?
C21 C23 1.406(2) 5_676 ?
C22 C23 1.3905(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.5046(19) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C12 N1 C1 107.91(9) . . ?
C12 N1 C13 125.05(9) . . ?
C1 N1 C13 124.47(9) . . ?
C2 C1 N1 129.50(11) . . ?
C2 C1 C6 121.39(11) . . ?
N1 C1 C6 109.05(10) . . ?
C2 C3 C4 121.56(13) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C2 C1 117.71(13) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C5 C4 C3 120.72(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.92(12) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.58(12) . . ?
C5 C6 C7 133.47(11) . . ?
C1 C6 C7 106.95(9) . . ?
C8 C7 C12 119.78(11) . . ?
C8 C7 C6 132.94(11) . . ?
C12 C7 C6 107.23(9) . . ?
C9 C8 C7 119.18(11) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.78(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.31(12) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 117.86(11) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 N1 130.03(10) . . ?
C11 C12 C7 121.08(10) . . ?
N1 C12 C7 108.85(10) . . ?
C18 C13 C14 119.41(10) . . ?
C18 C13 N1 120.88(10) . . ?
C14 C13 N1 119.69(10) . . ?
C15 C14 C13 120.56(11) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.63(11) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 118.34(10) . . ?
C15 C16 C19 120.84(12) . . ?
C17 C16 C19 120.81(12) . . ?
C18 C17 C16 121.13(11) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 119.91(11) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C16 178.95(15) . . ?
C19 C20 C21 178.24(16) . . ?
C22 C21 C23 120.28(11) . 5_676 ?
C22 C21 C20 119.74(13) . . ?
C23 C21 C20 119.97(12) 5_676 . ?
C23 C22 C21 122.08(13) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C21 117.64(12) . 5_676 ?
C22 C23 C24 121.05(13) . . ?
C21 C23 C24 121.29(11) 5_676 . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_2-Free_2
_database_code_depnum_ccdc_archive 'CCDC 1940321'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C48H32N2
_chemical_formula_sum            'C48 H32 N2'
_chemical_formula_weight         636.75

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

_cell_length_a                   9.6185(5)
_cell_length_b                   11.6931(7)
_cell_length_c                   30.7216(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3455.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2728
_cell_measurement_theta_min      0.993
_cell_measurement_theta_max      0.996

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47430
_diffrn_reflns_av_unetI/netI     0.1812
_diffrn_reflns_av_R_equivalents  0.1678
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7981
_reflns_number_gt                2728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+1.4118P] 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_abs_structure_details 
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7981
_refine_ls_number_parameters     906
_refine_ls_number_restraints     2106
_refine_ls_R_factor_all          0.2871
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.928
_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
C1 C 0.4210(12) 0.794(2) 0.0827(5) 0.081(3) Uani 0.512(3) 1 d D U P A 1
H1 H 0.495198 0.773085 0.100358 0.097 Uiso 0.512(3) 1 calc R U P A 1
C2 C 0.4423(14) 0.829(2) 0.0403(5) 0.090(3) Uani 0.512(3) 1 d D U P A 1
H2 H 0.531797 0.838724 0.029509 0.108 Uiso 0.512(3) 1 calc R U P A 1
C3 C 0.3259(15) 0.849(2) 0.0138(5) 0.089(3) Uani 0.512(3) 1 d D U P A 1
H3 H 0.340646 0.866455 -0.015311 0.107 Uiso 0.512(3) 1 calc R U P A 1
C4 C 0.1925(14) 0.844(2) 0.0286(4) 0.082(3) Uani 0.512(3) 1 d D U P A 1
H4 H 0.117963 0.860366 0.010395 0.098 Uiso 0.512(3) 1 calc R U P A 1
C5 C -0.0951(12) 0.8152(14) 0.0935(4) 0.087(3) Uani 0.512(3) 1 d D U P A 1
H5 H -0.131257 0.837232 0.066654 0.105 Uiso 0.512(3) 1 calc R U P A 1
C6 C -0.1802(13) 0.7998(15) 0.1282(5) 0.098(3) Uani 0.512(3) 1 d D U P A 1
H6 H -0.275591 0.806264 0.123911 0.117 Uiso 0.512(3) 1 calc R U P A 1
C7 C -0.1334(14) 0.7755(14) 0.1688(4) 0.092(3) Uani 0.512(3) 1 d D U P A 1
H7 H -0.196261 0.766859 0.191504 0.110 Uiso 0.512(3) 1 calc R U P A 1
C8 C 0.0074(13) 0.7636(13) 0.1764(4) 0.080(3) Uani 0.512(3) 1 d D U P A 1
H8 H 0.041174 0.748704 0.204238 0.096 Uiso 0.512(3) 1 calc R U P A 1
N9 N 0.2415(10) 0.7652(15) 0.1399(3) 0.067(2) Uani 0.512(3) 1 d D U P A 1
C10 C 0.2867(11) 0.793(3) 0.0983(5) 0.070(2) Uani 0.512(3) 1 d D U P A 1
C11 C 0.1711(12) 0.812(3) 0.0725(4) 0.072(2) Uani 0.512(3) 1 d D U P A 1
C12 C 0.0497(11) 0.797(2) 0.0986(4) 0.073(3) Uani 0.512(3) 1 d D U P A 1
C13 C 0.0960(12) 0.775(2) 0.1414(4) 0.069(3) Uani 0.512(3) 1 d D U P A 1
C14 C 0.3271(16) 0.7479(11) 0.1772(4) 0.062(2) Uani 0.512(3) 1 d D U P A 1
C15 C 0.4138(12) 0.8330(10) 0.1886(3) 0.067(2) Uani 0.512(3) 1 d D U P A 1
H15 H 0.408974 0.903349 0.174582 0.081 Uiso 0.512(3) 1 calc R U P A 1
C16 C 0.5107(11) 0.8154(10) 0.2215(3) 0.065(2) Uani 0.512(3) 1 d D U P A 1
H16 H 0.576081 0.871780 0.227611 0.078 Uiso 0.512(3) 1 calc R U P A 1
C17 C 0.511(3) 0.7153(11) 0.2452(8) 0.063(2) Uani 0.512(3) 1 d D U P A 1
C18 C 0.4102(11) 0.6334(10) 0.2366(3) 0.065(2) Uani 0.512(3) 1 d D U P A 1
H18 H 0.405247 0.567890 0.253727 0.078 Uiso 0.512(3) 1 calc R U P A 1
C19 C 0.3170(10) 0.6483(10) 0.2027(3) 0.063(2) Uani 0.512(3) 1 d D U P A 1
H19 H 0.249132 0.593713 0.196969 0.076 Uiso 0.512(3) 1 calc R U P A 1
C20 C 0.614(3) 0.6936(14) 0.2784(7) 0.070(3) Uani 0.512(3) 1 d D U P A 1
C21 C 0.6984(14) 0.6750(18) 0.3050(5) 0.071(3) Uani 0.512(3) 1 d D U P A 1
C22 C 0.8015(11) 0.648(2) 0.3374(4) 0.068(3) Uani 0.512(3) 1 d D U P A 1
C23 C 0.7623(13) 0.613(7) 0.3785(6) 0.071(3) Uani 0.512(3) 1 d D U P A 1
C24 C 0.8683(12) 0.609(2) 0.4093(4) 0.071(3) Uani 0.512(3) 1 d D U P A 1
H24 H 0.844583 0.608731 0.438698 0.086 Uiso 0.512(3) 1 calc R U P A 1
C25 C 1.0052(12) 0.606(2) 0.3982(4) 0.072(3) Uani 0.512(3) 1 d D U P A 1
C26 C 1.0441(11) 0.6421(13) 0.3568(4) 0.074(3) Uani 0.512(3) 1 d D U P A 1
C27 C 0.9417(11) 0.6633(12) 0.3272(3) 0.070(3) Uani 0.512(3) 1 d D U P A 1
H26 H 0.965858 0.688325 0.299470 0.084 Uiso 0.512(3) 1 calc R U P A 1
C28 C 0.6147(12) 0.6492(14) 0.3939(6) 0.091(5) Uani 0.512(3) 1 d D U P A 1
H28A H 0.616989 0.727219 0.403642 0.136 Uiso 0.512(3) 1 calc R U P A 1
H28B H 0.585674 0.600752 0.417454 0.136 Uiso 0.512(3) 1 calc R U P A 1
H28C H 0.550349 0.642102 0.370190 0.136 Uiso 0.512(3) 1 calc R U P A 1
C29 C 1.179(2) 0.5510(18) 0.4619(7) 0.070(3) Uani 0.512(3) 1 d D U P A 1
C30 C 1.1075(16) 0.590(2) 0.4315(5) 0.074(4) Uani 0.512(3) 1 d D U P A 1
C31 C 1.4142(11) 0.6057(12) 0.6621(3) 0.075(3) Uani 0.512(3) 1 d D U P A 1
H31 H 1.331211 0.602190 0.646612 0.090 Uiso 0.512(3) 1 calc R U P A 1
C32 C 1.4164(13) 0.6118(13) 0.7072(4) 0.084(3) Uani 0.512(3) 1 d D U P A 1
H32 H 1.333129 0.610870 0.722616 0.101 Uiso 0.512(3) 1 calc R U P A 1
C33 C 1.5401(15) 0.6191(13) 0.7296(4) 0.090(3) Uani 0.512(3) 1 d D U P A 1
H33 H 1.537103 0.623594 0.759764 0.108 Uiso 0.512(3) 1 calc R U P A 1
C34 C 1.6650(14) 0.6201(13) 0.7099(3) 0.087(3) Uani 0.512(3) 1 d D U P A 1
H34 H 1.746436 0.625503 0.726131 0.104 Uiso 0.512(3) 1 calc R U P A 1
C35 C 1.9241(11) 0.6174(12) 0.6358(4) 0.081(3) Uani 0.512(3) 1 d D U P A 1
H35 H 1.967715 0.626602 0.662597 0.098 Uiso 0.512(3) 1 calc R U P A 1
C36 C 2.0003(12) 0.6101(13) 0.5985(4) 0.088(3) Uani 0.512(3) 1 d D U P A 1
H36 H 2.096596 0.615407 0.600155 0.106 Uiso 0.512(3) 1 calc R U P A 1
C37 C 1.9382(12) 0.5949(12) 0.5584(4) 0.079(3) Uani 0.512(3) 1 d D U P A 1
H37 H 1.993151 0.586429 0.533733 0.095 Uiso 0.512(3) 1 calc R U P A 1
C38 C 1.7949(11) 0.5923(16) 0.5547(3) 0.073(3) Uani 0.512(3) 1 d D U P A 1
H38 H 1.752502 0.584719 0.527656 0.087 Uiso 0.512(3) 1 calc R U P A 1
N39 N 1.5725(9) 0.5980(11) 0.5972(3) 0.064(2) Uani 0.512(3) 1 d D U P A 1
C40 C 1.5420(10) 0.6051(12) 0.6414(3) 0.067(2) Uani 0.512(3) 1 d D U P A 1
C41 C 1.6692(12) 0.6129(13) 0.6641(3) 0.074(2) Uani 0.512(3) 1 d D U P A 1
C42 C 1.7780(11) 0.6108(13) 0.6331(3) 0.074(2) Uani 0.512(3) 1 d D U P A 1
C43 C 1.7174(10) 0.6010(13) 0.5918(3) 0.067(3) Uani 0.512(3) 1 d D U P A 1
C44 C 1.4736(13) 0.5857(15) 0.5633(4) 0.060(3) Uani 0.512(3) 1 d D U P A 1
C45 C 1.377(2) 0.499(2) 0.5651(6) 0.060(3) Uani 0.512(3) 1 d D U P A 1
H45 H 1.378038 0.447579 0.588060 0.072 Uiso 0.512(3) 1 calc R U P A 1
C46 C 1.277(2) 0.4892(19) 0.5324(5) 0.060(3) Uani 0.512(3) 1 d D U P A 1
H46 H 1.206104 0.435173 0.534970 0.072 Uiso 0.512(3) 1 calc R U P A 1
C47 C 1.282(4) 0.559(3) 0.4966(10) 0.064(2) Uani 0.512(3) 1 d D U P A 1
C48 C 1.3745(19) 0.650(2) 0.4966(5) 0.068(3) Uani 0.512(3) 1 d D U P A 1
H48 H 1.369356 0.705280 0.474672 0.082 Uiso 0.512(3) 1 calc R U P A 1
C49 C 1.474(2) 0.6605(19) 0.5290(6) 0.066(3) Uani 0.512(3) 1 d D U P A 1
H49 H 1.540408 0.717955 0.527410 0.079 Uiso 0.512(3) 1 calc R U P A 1
C50 C 1.1964(12) 0.6542(15) 0.3445(5) 0.096(4) Uani 0.512(3) 1 d D U P A 1
H50A H 1.204756 0.659415 0.313427 0.144 Uiso 0.512(3) 1 calc R U P A 1
H50B H 1.246999 0.588691 0.354712 0.144 Uiso 0.512(3) 1 calc R U P A 1
H50C H 1.233740 0.722097 0.357613 0.144 Uiso 0.512(3) 1 calc R U P A 1
C1B C 0.3841(13) 0.817(2) 0.0789(5) 0.081(3) Uani 0.488(3) 1 d D U P A 2
H1B H 0.465369 0.813959 0.095276 0.097 Uiso 0.488(3) 1 calc R U P A 2
C2B C 0.3879(14) 0.841(2) 0.0346(5) 0.088(3) Uani 0.488(3) 1 d D U P A 2
H2B H 0.472267 0.853405 0.020597 0.106 Uiso 0.488(3) 1 calc R U P A 2
C3B C 0.2630(16) 0.846(2) 0.0115(5) 0.087(3) Uani 0.488(3) 1 d D U P A 2
H3B H 0.266519 0.862422 -0.018121 0.104 Uiso 0.488(3) 1 calc R U P A 2
C4B C 0.1362(14) 0.829(2) 0.0303(4) 0.079(3) Uani 0.488(3) 1 d D U P A 2
H4B H 0.054811 0.833592 0.013972 0.094 Uiso 0.488(3) 1 calc R U P A 2
C5B C -0.1221(13) 0.7548(15) 0.0984(4) 0.086(3) Uani 0.488(3) 1 d D U P A 2
H5B H -0.164824 0.766046 0.071530 0.103 Uiso 0.488(3) 1 calc R U P A 2
C6B C -0.1957(13) 0.7176(16) 0.1330(5) 0.097(3) Uani 0.488(3) 1 d D U P A 2
H6B H -0.291272 0.708453 0.129916 0.116 Uiso 0.488(3) 1 calc R U P A 2
C7B C -0.1371(14) 0.6931(15) 0.1718(4) 0.091(3) Uani 0.488(3) 1 d D U P A 2
H7B H -0.192656 0.666221 0.194408 0.109 Uiso 0.488(3) 1 calc R U P A 2
C8B C 0.0043(14) 0.7074(14) 0.1787(4) 0.078(3) Uani 0.488(3) 1 d D U P A 2
H8B H 0.044920 0.690121 0.205340 0.093 Uiso 0.488(3) 1 calc R U P A 2
N9B N 0.2263(11) 0.7707(16) 0.1412(3) 0.068(2) Uani 0.488(3) 1 d D U P A 2
C10B C 0.2569(11) 0.797(3) 0.0979(5) 0.069(2) Uani 0.488(3) 1 d D U P A 2
C11B C 0.1329(12) 0.805(3) 0.0752(4) 0.071(3) Uani 0.488(3) 1 d D U P A 2
C12B C 0.0220(11) 0.776(3) 0.1039(4) 0.072(3) Uani 0.488(3) 1 d D U P A 2
C13B C 0.0824(12) 0.748(2) 0.1443(4) 0.070(3) Uani 0.488(3) 1 d D U P A 2
C14B C 0.3246(17) 0.7421(11) 0.1744(5) 0.063(2) Uani 0.488(3) 1 d D U P A 2
C15B C 0.3295(13) 0.8084(12) 0.2101(4) 0.071(3) Uani 0.488(3) 1 d D U P A 2
H15B H 0.273345 0.872905 0.212061 0.085 Uiso 0.488(3) 1 calc R U P A 2
C16B C 0.4192(13) 0.7803(11) 0.2443(3) 0.072(3) Uani 0.488(3) 1 d D U P A 2
H16B H 0.418405 0.824549 0.269422 0.087 Uiso 0.488(3) 1 calc R U P A 2
C17B C 0.508(3) 0.6887(12) 0.2415(8) 0.062(3) Uani 0.488(3) 1 d D U P A 2
C18B C 0.5092(11) 0.6252(10) 0.2034(3) 0.063(2) Uani 0.488(3) 1 d D U P A 2
H18B H 0.570140 0.563854 0.200705 0.076 Uiso 0.488(3) 1 calc R U P A 2
C19B C 0.4205(11) 0.6518(11) 0.1693(3) 0.063(3) Uani 0.488(3) 1 d D U P A 2
H19B H 0.424121 0.610581 0.143424 0.075 Uiso 0.488(3) 1 calc R U P A 2
C20B C 0.604(3) 0.6596(14) 0.2763(8) 0.069(3) Uani 0.488(3) 1 d D U P A 2
C21B C 0.6884(16) 0.6391(18) 0.3030(5) 0.071(3) Uani 0.488(3) 1 d D U P A 2
C22B C 0.7919(12) 0.620(2) 0.3363(4) 0.068(3) Uani 0.488(3) 1 d D U P A 2
C23B C 0.7549(14) 0.619(7) 0.3798(6) 0.069(3) Uani 0.488(3) 1 d D U P A 2
C24B C 0.8574(13) 0.584(2) 0.4089(4) 0.072(3) Uani 0.488(3) 1 d D U P A 2
H24B H 0.831078 0.561471 0.436795 0.086 Uiso 0.488(3) 1 calc R U P A 2
C25B C 0.9943(12) 0.581(3) 0.3980(4) 0.071(3) Uani 0.488(3) 1 d D U P A 2
C26B C 1.0292(12) 0.5713(13) 0.3542(4) 0.070(3) Uani 0.488(3) 1 d D U P A 2
C27B C 0.9265(12) 0.5905(13) 0.3242(4) 0.068(3) Uani 0.488(3) 1 d D U P A 2
H27B H 0.947568 0.583777 0.294771 0.082 Uiso 0.488(3) 1 calc R U P A 2
C28B C 0.6027(13) 0.5837(15) 0.3897(6) 0.084(5) Uani 0.488(3) 1 d D U P A 2
H28D H 0.561386 0.551793 0.364006 0.125 Uiso 0.488(3) 1 calc R U P A 2
H28E H 0.550624 0.649547 0.398765 0.125 Uiso 0.488(3) 1 calc R U P A 2
H28F H 0.602050 0.527595 0.412555 0.125 Uiso 0.488(3) 1 calc R U P A 2
C29B C 1.191(2) 0.5848(18) 0.4581(7) 0.070(3) Uani 0.488(3) 1 d D U P A 2
C30B C 1.0962(16) 0.562(2) 0.4316(5) 0.073(4) Uani 0.488(3) 1 d D U P A 2
C31B C 1.3840(12) 0.5434(13) 0.6615(4) 0.074(3) Uani 0.488(3) 1 d D U P A 2
H31B H 1.305738 0.550662 0.643910 0.089 Uiso 0.488(3) 1 calc R U P A 2
C32B C 1.3736(14) 0.5331(13) 0.7063(4) 0.084(3) Uani 0.488(3) 1 d D U P A 2
H32B H 1.286905 0.538680 0.719592 0.101 Uiso 0.488(3) 1 calc R U P A 2
C33B C 1.4905(16) 0.5145(14) 0.7316(4) 0.089(3) Uani 0.488(3) 1 d D U P A 2
H33B H 1.479427 0.505173 0.761491 0.107 Uiso 0.488(3) 1 calc R U P A 2
C34B C 1.6194(14) 0.5094(13) 0.7149(3) 0.082(3) Uani 0.488(3) 1 d D U P A 2
H34B H 1.695766 0.497157 0.732852 0.099 Uiso 0.488(3) 1 calc R U P A 2
C35B C 1.8967(11) 0.5090(13) 0.6469(4) 0.081(3) Uani 0.488(3) 1 d D U P A 2
H35B H 1.932768 0.494237 0.674386 0.097 Uiso 0.488(3) 1 calc R U P A 2
C36B C 1.9829(13) 0.5162(15) 0.6117(4) 0.088(3) Uani 0.488(3) 1 d D U P A 2
H36B H 2.078234 0.507974 0.615590 0.105 Uiso 0.488(3) 1 calc R U P A 2
C37B C 1.9314(12) 0.5355(14) 0.5705(4) 0.084(3) Uani 0.488(3) 1 d D U P A 2
H37B H 1.991551 0.535201 0.546803 0.101 Uiso 0.488(3) 1 calc R U P A 2
C38B C 1.7912(12) 0.5554(17) 0.5640(4) 0.074(3) Uani 0.488(3) 1 d D U P A 2
H38B H 1.757119 0.573835 0.536579 0.089 Uiso 0.488(3) 1 calc R U P A 2
N39B N 1.5587(9) 0.5536(12) 0.6008(3) 0.063(3) Uani 0.488(3) 1 d D U P A 2
C40B C 1.5169(11) 0.5424(13) 0.6441(3) 0.068(3) Uani 0.488(3) 1 d D U P A 2
C41B C 1.6367(12) 0.5231(14) 0.6696(3) 0.074(2) Uani 0.488(3) 1 d D U P A 2
C42B C 1.7531(11) 0.5241(14) 0.6411(3) 0.073(2) Uani 0.488(3) 1 d D U P A 2
C43B C 1.7040(11) 0.5472(13) 0.5989(3) 0.068(3) Uani 0.488(3) 1 d D U P A 2
C44B C 1.4674(14) 0.5600(16) 0.5647(4) 0.060(3) Uani 0.488(3) 1 d D U P A 2
C45B C 1.363(2) 0.481(2) 0.5598(6) 0.060(3) Uani 0.488(3) 1 d D U P A 2
H45B H 1.348961 0.425381 0.581023 0.072 Uiso 0.488(3) 1 calc R U P A 2
C46B C 1.277(2) 0.484(2) 0.5232(6) 0.061(3) Uani 0.488(3) 1 d D U P A 2
H46B H 1.212480 0.425689 0.518661 0.074 Uiso 0.488(3) 1 calc R U P A 2
C47B C 1.288(4) 0.572(3) 0.4939(11) 0.064(3) Uani 0.488(3) 1 d D U P A 2
C48B C 1.404(2) 0.643(2) 0.4965(6) 0.068(3) Uani 0.488(3) 1 d D U P A 2
H48B H 1.422511 0.693900 0.473950 0.081 Uiso 0.488(3) 1 calc R U P A 2
C49B C 1.491(2) 0.6387(19) 0.5322(6) 0.065(3) Uani 0.488(3) 1 d D U P A 2
H49B H 1.565614 0.688974 0.534328 0.078 Uiso 0.488(3) 1 calc R U P A 2
C50B C 1.1769(12) 0.5477(14) 0.3397(4) 0.084(4) Uani 0.488(3) 1 d D U P A 2
H50D H 1.177962 0.532545 0.309024 0.126 Uiso 0.488(3) 1 calc R U P A 2
H50E H 1.212342 0.482503 0.355125 0.126 Uiso 0.488(3) 1 calc R U P A 2
H50F H 1.233921 0.613137 0.345849 0.126 Uiso 0.488(3) 1 calc R U P A 2


_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
C1 C10 1.377(10) . ?
C1 C2 1.379(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(13) . ?
C3 H3 0.9300 . ?
C4 C11 1.413(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.356(13) . ?
C5 C12 1.417(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(12) . ?
C7 H7 0.9300 . ?
C8 C13 1.379(11) . ?
C8 H8 0.9300 . ?
N9 C10 1.389(9) . ?
N9 C13 1.404(9) . ?
N9 C14 1.424(8) . ?
C10 C11 1.384(10) . ?
C11 C12 1.428(10) . ?
C12 C13 1.413(10) . ?
C14 C15 1.345(13) . ?
C14 C19 1.408(14) . ?
C15 C16 1.390(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.39(2) . ?
C17 C20 1.446(10) . ?
C18 C19 1.385(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.171(9) . ?
C21 C22 1.440(10) . ?
C22 C23 1.381(17) . ?
C22 C27 1.395(11) . ?
C23 C24 1.392(16) . ?
C23 C28 1.56(3) . ?
C24 C25 1.362(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(12) . ?
C25 C30 1.431(10) . ?
C26 C27 1.363(10) . ?
C26 C50 1.520(12) . ?
C27 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.249(13) . ?
C29 C47 1.457(10) . ?
C31 C40 1.384(12) . ?
C31 C32 1.389(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.344(14) . ?
C33 H33 0.9300 . ?
C34 C41 1.411(11) . ?
C34 H34 0.9300 . ?
C35 C36 1.362(13) . ?
C35 C42 1.410(12) . ?
C35 H35 0.9300 . ?
C36 C37 1.381(12) . ?
C36 H36 0.9300 . ?
C37 C38 1.383(10) . ?
C37 H37 0.9300 . ?
C38 C43 1.365(11) . ?
C38 H38 0.9300 . ?
N39 C40 1.393(10) . ?
N39 C43 1.404(10) . ?
N39 C44 1.416(9) . ?
C40 C41 1.411(11) . ?
C41 C42 1.416(12) . ?
C42 C43 1.401(11) . ?
C44 C49 1.372(10) . ?
C44 C45 1.375(10) . ?
C45 C46 1.396(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.371(11) . ?
C46 H46 0.9300 . ?
C47 C48 1.389(12) . ?
C48 C49 1.384(10) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C1B C10B 1.373(11) . ?
C1B C2B 1.391(11) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.397(13) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.363(13) . ?
C3B H3B 0.9300 . ?
C4B C11B 1.410(10) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.349(13) . ?
C5B C12B 1.420(12) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.351(12) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.386(12) . ?
C7B H7B 0.9300 . ?
C8B C13B 1.383(11) . ?
C8B H8B 0.9300 . ?
N9B C10B 1.398(9) . ?
N9B C13B 1.412(10) . ?
N9B C14B 1.430(8) . ?
C10B C11B 1.385(11) . ?
C11B C12B 1.424(11) . ?
C12B C13B 1.409(10) . ?
C14B C15B 1.344(13) . ?
C14B C19B 1.411(14) . ?
C15B C16B 1.398(11) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.38(2) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.39(2) . ?
C17B C20B 1.452(10) . ?
C18B C19B 1.387(11) . ?
C18B H18B 0.9300 . ?
C19B H19B 0.9300 . ?
C20B C21B 1.176(9) . ?
C21B C22B 1.446(10) . ?
C22B C23B 1.383(17) . ?
C22B C27B 1.390(11) . ?
C23B C24B 1.395(16) . ?
C23B C28B 1.55(3) . ?
C24B C25B 1.360(11) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.391(12) . ?
C25B C30B 1.440(10) . ?
C26B C27B 1.370(11) . ?
C26B C50B 1.514(12) . ?
C27B H27B 0.9300 . ?
C28B H28D 0.9600 . ?
C28B H28E 0.9600 . ?
C28B H28F 0.9600 . ?
C29B C30B 1.254(13) . ?
C29B C47B 1.446(10) . ?
C31B C40B 1.385(12) . ?
C31B C32B 1.388(11) . ?
C31B H31B 0.9300 . ?
C32B C33B 1.384(13) . ?
C32B H32B 0.9300 . ?
C33B C34B 1.343(14) . ?
C33B H33B 0.9300 . ?
C34B C41B 1.412(11) . ?
C34B H34B 0.9300 . ?
C35B C36B 1.365(13) . ?
C35B C42B 1.404(12) . ?
C35B H35B 0.9300 . ?
C36B C37B 1.377(12) . ?
C36B H36B 0.9300 . ?
C37B C38B 1.383(11) . ?
C37B H37B 0.9300 . ?
C38B C43B 1.364(11) . ?
C38B H38B 0.9300 . ?
N39B C40B 1.397(10) . ?
N39B C43B 1.401(10) . ?
N39B C44B 1.416(9) . ?
C40B C41B 1.411(12) . ?
C41B C42B 1.420(13) . ?
C42B C43B 1.405(11) . ?
C44B C49B 1.375(11) . ?
C44B C45B 1.375(10) . ?
C45B C46B 1.394(10) . ?
C45B H45B 0.9300 . ?
C46B C47B 1.375(11) . ?
C46B H46B 0.9300 . ?
C47B C48B 1.391(11) . ?
C48B C49B 1.384(10) . ?
C48B H48B 0.9300 . ?
C49B H49B 0.9300 . ?
C50B H50D 0.9600 . ?
C50B H50E 0.9600 . ?
C50B H50F 0.9600 . ?

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
C10 C1 C2 118.1(10) . . ?
C10 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C1 C2 C3 118.5(10) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 123.4(10) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C11 117.8(10) . . ?
C3 C4 H4 121.1 . . ?
C11 C4 H4 121.1 . . ?
C6 C5 C12 119.0(10) . . ?
C6 C5 H5 120.5 . . ?
C12 C5 H5 120.5 . . ?
C7 C6 C5 123.4(10) . . ?
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C6 C7 C8 120.3(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C13 C8 C7 117.6(9) . . ?
C13 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C10 N9 C13 108.9(7) . . ?
C10 N9 C14 126.3(8) . . ?
C13 N9 C14 124.1(8) . . ?
C1 C10 C11 123.5(8) . . ?
C1 C10 N9 128.0(8) . . ?
C11 C10 N9 108.3(7) . . ?
C10 C11 C4 118.2(9) . . ?
C10 C11 C12 108.4(7) . . ?
C4 C11 C12 133.4(9) . . ?
C13 C12 C5 116.2(9) . . ?
C13 C12 C11 106.7(7) . . ?
C5 C12 C11 136.3(9) . . ?
C8 C13 N9 129.3(8) . . ?
C8 C13 C12 123.3(8) . . ?
N9 C13 C12 107.4(8) . . ?
C15 C14 C19 120.6(8) . . ?
C15 C14 N9 117.6(10) . . ?
C19 C14 N9 121.7(9) . . ?
C14 C15 C16 119.8(10) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.7(10) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.0(8) . . ?
C16 C17 C20 121.4(15) . . ?
C18 C17 C20 119.6(14) . . ?
C19 C18 C17 120.5(10) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 118.6(9) . . ?
C18 C19 H19 120.7 . . ?
C14 C19 H19 120.7 . . ?
C21 C20 C17 179(2) . . ?
C20 C21 C22 178(2) . . ?
C23 C22 C27 120.5(8) . . ?
C23 C22 C21 120.6(9) . . ?
C27 C22 C21 118.9(9) . . ?
C22 C23 C24 116(2) . . ?
C22 C23 C28 116(2) . . ?
C24 C23 C28 118(3) . . ?
C25 C24 C23 122.5(9) . . ?
C25 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C24 C25 C26 118.8(8) . . ?
C24 C25 C30 119.3(8) . . ?
C26 C25 C30 120.5(10) . . ?
C27 C26 C25 118.1(9) . . ?
C27 C26 C50 120.9(9) . . ?
C25 C26 C50 120.9(9) . . ?
C26 C27 C22 121.7(9) . . ?
C26 C27 H26 119.2 . . ?
C22 C27 H26 119.2 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C47 154(2) . . ?
C29 C30 C25 164(2) . . ?
C40 C31 C32 116.4(9) . . ?
C40 C31 H31 121.8 . . ?
C32 C31 H31 121.8 . . ?
C33 C32 C31 121.0(11) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C32 123.4(10) . . ?
C34 C33 H33 118.3 . . ?
C32 C33 H33 118.3 . . ?
C33 C34 C41 118.2(10) . . ?
C33 C34 H34 120.9 . . ?
C41 C34 H34 120.9 . . ?
C36 C35 C42 118.9(10) . . ?
C36 C35 H35 120.6 . . ?
C42 C35 H35 120.6 . . ?
C35 C36 C37 121.7(10) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C38 120.5(10) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C43 C38 C37 118.3(10) . . ?
C43 C38 H38 120.9 . . ?
C37 C38 H38 120.9 . . ?
C40 N39 C43 108.8(7) . . ?
C40 N39 C44 125.6(8) . . ?
C43 N39 C44 125.6(8) . . ?
C31 C40 N39 129.4(8) . . ?
C31 C40 C41 122.9(9) . . ?
N39 C40 C41 107.7(8) . . ?
C34 C41 C40 118.2(10) . . ?
C34 C41 C42 134.0(10) . . ?
C40 C41 C42 107.9(8) . . ?
C43 C42 C35 118.2(10) . . ?
C43 C42 C41 107.7(8) . . ?
C35 C42 C41 134.1(10) . . ?
C38 C43 C42 122.3(9) . . ?
C38 C43 N39 129.7(8) . . ?
C42 C43 N39 107.9(8) . . ?
C49 C44 C45 119.9(7) . . ?
C49 C44 N39 120.0(9) . . ?
C45 C44 N39 120.0(9) . . ?
C44 C45 C46 120.1(8) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C47 C46 C45 119.9(9) . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C46 C47 C48 119.0(10) . . ?
C46 C47 C29 121.5(10) . . ?
C48 C47 C29 118.8(9) . . ?
C49 C48 C47 120.3(9) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C44 C49 C48 120.0(8) . . ?
C44 C49 H49 120.0 . . ?
C48 C49 H49 120.0 . . ?
C26 C50 H50A 109.5 . . ?
C26 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C26 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C10B C1B C2B 118.2(10) . . ?
C10B C1B H1B 120.9 . . ?
C2B C1B H1B 120.9 . . ?
C1B C2B C3B 118.9(10) . . ?
C1B C2B H2B 120.5 . . ?
C3B C2B H2B 120.5 . . ?
C4B C3B C2B 123.3(10) . . ?
C4B C3B H3B 118.4 . . ?
C2B C3B H3B 118.4 . . ?
C3B C4B C11B 117.6(10) . . ?
C3B C4B H4B 121.2 . . ?
C11B C4B H4B 121.2 . . ?
C6B C5B C12B 118.4(10) . . ?
C6B C5B H5B 120.8 . . ?
C12B C5B H5B 120.8 . . ?
C5B C6B C7B 123.1(10) . . ?
C5B C6B H6B 118.5 . . ?
C7B C6B H6B 118.5 . . ?
C6B C7B C8B 121.2(11) . . ?
C6B C7B H7B 119.4 . . ?
C8B C7B H7B 119.4 . . ?
C13B C8B C7B 117.4(9) . . ?
C13B C8B H8B 121.3 . . ?
C7B C8B H8B 121.3 . . ?
C10B N9B C13B 108.2(7) . . ?
C10B N9B C14B 126.3(8) . . ?
C13B N9B C14B 123.8(9) . . ?
C1B C10B C11B 122.9(8) . . ?
C1B C10B N9B 128.9(8) . . ?
C11B C10B N9B 108.2(7) . . ?
C10B C11B C4B 119.1(9) . . ?
C10B C11B C12B 108.5(7) . . ?
C4B C11B C12B 132.1(10) . . ?
C13B C12B C5B 117.8(10) . . ?
C13B C12B C11B 107.0(7) . . ?
C5B C12B C11B 134.4(9) . . ?
C8B C13B C12B 122.0(8) . . ?
C8B C13B N9B 130.5(8) . . ?
C12B C13B N9B 107.6(8) . . ?
C15B C14B C19B 119.9(8) . . ?
C15B C14B N9B 118.1(10) . . ?
C19B C14B N9B 121.9(10) . . ?
C14B C15B C16B 120.0(10) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C17B C16B C15B 121.5(10) . . ?
C17B C16B H16B 119.3 . . ?
C15B C16B H16B 119.3 . . ?
C16B C17B C18B 118.2(8) . . ?
C16B C17B C20B 122.3(15) . . ?
C18B C17B C20B 119.5(15) . . ?
C17B C18B C19B 121.0(10) . . ?
C17B C18B H18B 119.5 . . ?
C19B C18B H18B 119.5 . . ?
C18B C19B C14B 119.1(9) . . ?
C18B C19B H19B 120.5 . . ?
C14B C19B H19B 120.5 . . ?
C21B C20B C17B 176(3) . . ?
C20B C21B C22B 177(2) . . ?
C23B C22B C27B 119.8(10) . . ?
C23B C22B C21B 120.5(9) . . ?
C27B C22B C21B 119.4(9) . . ?
C22B C23B C24B 116.0(19) . . ?
C22B C23B C28B 116(3) . . ?
C24B C23B C28B 117(3) . . ?
C25B C24B C23B 122.4(10) . . ?
C25B C24B H24B 118.8 . . ?
C23B C24B H24B 118.8 . . ?
C24B C25B C26B 118.3(8) . . ?
C24B C25B C30B 119.2(9) . . ?
C26B C25B C30B 121.2(10) . . ?
C27B C26B C25B 117.7(9) . . ?
C27B C26B C50B 120.5(9) . . ?
C25B C26B C50B 121.7(9) . . ?
C26B C27B C22B 122.1(9) . . ?
C26B C27B H27B 118.9 . . ?
C22B C27B H27B 118.9 . . ?
C23B C28B H28D 109.5 . . ?
C23B C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C23B C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
C30B C29B C47B 160(2) . . ?
C29B C30B C25B 158(2) . . ?
C40B C31B C32B 116.6(10) . . ?
C40B C31B H31B 121.7 . . ?
C32B C31B H31B 121.7 . . ?
C33B C32B C31B 120.8(11) . . ?
C33B C32B H32B 119.6 . . ?
C31B C32B H32B 119.6 . . ?
C34B C33B C32B 122.8(10) . . ?
C34B C33B H33B 118.6 . . ?
C32B C33B H33B 118.6 . . ?
C33B C34B C41B 118.8(11) . . ?
C33B C34B H34B 120.6 . . ?
C41B C34B H34B 120.6 . . ?
C36B C35B C42B 119.4(10) . . ?
C36B C35B H35B 120.3 . . ?
C42B C35B H35B 120.3 . . ?
C35B C36B C37B 121.3(10) . . ?
C35B C36B H36B 119.4 . . ?
C37B C36B H36B 119.4 . . ?
C36B C37B C38B 120.7(11) . . ?
C36B C37B H37B 119.7 . . ?
C38B C37B H37B 119.7 . . ?
C43B C38B C37B 118.3(10) . . ?
C43B C38B H38B 120.8 . . ?
C37B C38B H38B 120.8 . . ?
C40B N39B C43B 108.7(7) . . ?
C40B N39B C44B 125.0(8) . . ?
C43B N39B C44B 126.2(8) . . ?
C31B C40B N39B 129.1(8) . . ?
C31B C40B C41B 122.8(9) . . ?
N39B C40B C41B 108.0(8) . . ?
C40B C41B C34B 117.9(10) . . ?
C40B C41B C42B 107.5(8) . . ?
C34B C41B C42B 134.5(10) . . ?
C35B C42B C43B 118.1(10) . . ?
C35B C42B C41B 134.2(10) . . ?
C43B C42B C41B 107.7(8) . . ?
C38B C43B N39B 129.8(8) . . ?
C38B C43B C42B 122.1(9) . . ?
N39B C43B C42B 108.0(8) . . ?
C49B C44B C45B 119.5(8) . . ?
C49B C44B N39B 120.0(9) . . ?
C45B C44B N39B 120.2(9) . . ?
C44B C45B C46B 120.4(8) . . ?
C44B C45B H45B 119.8 . . ?
C46B C45B H45B 119.8 . . ?
C47B C46B C45B 120.0(9) . . ?
C47B C46B H46B 120.0 . . ?
C45B C46B H46B 120.0 . . ?
C46B C47B C48B 118.2(10) . . ?
C46B C47B C29B 121.8(9) . . ?
C48B C47B C29B 119.7(9) . . ?
C49B C48B C47B 120.6(9) . . ?
C49B C48B H48B 119.7 . . ?
C47B C48B H48B 119.7 . . ?
C44B C49B C48B 120.0(9) . . ?
C44B C49B H49B 120.0 . . ?
C48B C49B H49B 120.0 . . ?
C26B C50B H50D 109.5 . . ?
C26B C50B H50E 109.5 . . ?
H50D C50B H50E 109.5 . . ?
C26B C50B H50F 109.5 . . ?
H50D C50B H50F 109.5 . . ?
H50E C50B H50F 109.5 . . ?

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_2-CHCl3
_database_code_depnum_ccdc_archive 'CCDC 1940319'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H33 Cl3 N2'
_chemical_formula_weight         756.12

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   33.601(2)
_cell_length_b                   5.7693(3)
_cell_length_c                   20.7237(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.430(5)
_cell_angle_gamma                90
_cell_volume                     3788.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1438
_cell_measurement_theta_min      0.953
_cell_measurement_theta_max      0.958

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.281
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10463
_diffrn_reflns_av_unetI/netI     0.2423
_diffrn_reflns_av_R_equivalents  0.02959
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.285
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3440
_reflns_number_gt                1438
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     300
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.2328
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.977
_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
C1 C 0.12929(16) 0.5148(8) 0.2094(2) 0.0339(14) Uani 1 1 d . . . . .
H1 H 0.109523 0.400266 0.211804 0.041 Uiso 1 1 calc R U . . .
C2 C 0.12266(18) 0.6468(9) 0.1511(3) 0.0408(15) Uani 1 1 d . . . . .
H2 H 0.097922 0.621793 0.112828 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1515(2) 0.8166(9) 0.1472(3) 0.0430(15) Uani 1 1 d . . . . .
H3 H 0.146205 0.905047 0.106534 0.052 Uiso 1 1 calc R U . . .
C4 C 0.18768(17) 0.8562(8) 0.2020(3) 0.0360(14) Uani 1 1 d . . . . .
H4 H 0.207212 0.971833 0.199445 0.043 Uiso 1 1 calc R U . . .
C5 C 0.26576(17) 0.8482(8) 0.3531(3) 0.0367(14) Uani 1 1 d . . . . .
H5 H 0.272790 0.966766 0.326991 0.044 Uiso 1 1 calc R U . . .
C6 C 0.29274(17) 0.7951(9) 0.4188(3) 0.0425(15) Uani 1 1 d . . . . .
H6 H 0.318505 0.877489 0.437516 0.051 Uiso 1 1 calc R U . . .
C7 C 0.28220(17) 0.6226(9) 0.4569(3) 0.0442(15) Uani 1 1 d . . . . .
H7 H 0.301290 0.586814 0.501086 0.053 Uiso 1 1 calc R U . . .
C8 C 0.24502(16) 0.5026(8) 0.4325(3) 0.0364(14) Uani 1 1 d . . . . .
H8 H 0.237755 0.387057 0.459331 0.044 Uiso 1 1 calc R U . . .
N9 N 0.17961(12) 0.4526(6) 0.32903(19) 0.0266(10) Uani 1 1 d . . . . .
C10 C 0.16566(15) 0.5551(8) 0.2640(2) 0.0247(12) Uani 1 1 d . . . . .
C11 C 0.19525(16) 0.7250(8) 0.2612(3) 0.0271(12) Uani 1 1 d . . . . .
C12 C 0.22850(16) 0.7245(8) 0.3269(3) 0.0259(12) Uani 1 1 d . . . . .
C13 C 0.21809(15) 0.5568(8) 0.3665(2) 0.0253(12) Uani 1 1 d . . . . .
C14 C 0.15512(15) 0.3069(8) 0.3565(2) 0.0244(12) Uani 1 1 d . . . . .
C15 C 0.14736(15) 0.3713(8) 0.4157(2) 0.0306(13) Uani 1 1 d . . . . .
H15 H 0.158471 0.513129 0.437633 0.037 Uiso 1 1 calc R U . . .
C16 C 0.12379(15) 0.2324(8) 0.4429(2) 0.0307(13) Uani 1 1 d . . . . .
H16 H 0.118786 0.278724 0.483543 0.037 Uiso 1 1 calc R U . . .
C17 C 0.10702(15) 0.0222(8) 0.4112(3) 0.0279(13) Uani 1 1 d . . . . .
C18 C 0.11503(15) -0.0405(8) 0.3517(3) 0.0301(13) Uani 1 1 d . . . . .
H18 H 0.103913 -0.181818 0.329501 0.036 Uiso 1 1 calc R U . . .
C19 C 0.13863(15) 0.0980(7) 0.3248(2) 0.0265(12) Uani 1 1 d . . . . .
H19 H 0.143823 0.051771 0.284323 0.032 Uiso 1 1 calc R U . . .
C20 C 0.08153(16) -0.1206(8) 0.4392(3) 0.0315(13) Uani 1 1 d . . . . .
C21 C 0.05981(16) -0.2391(9) 0.4603(3) 0.0366(14) Uani 1 1 d . . . . .
C22 C 0.03015(16) -0.3724(9) 0.4820(3) 0.0327(14) Uani 1 1 d . . . . .
C23 C -0.02101(16) -0.6889(8) 0.4595(3) 0.0357(14) Uani 1 1 d . . . . .
C24 C 0.00928(16) -0.5606(9) 0.4431(3) 0.0360(14) Uani 1 1 d . . . . .
H24 H 0.016058 -0.602923 0.403661 0.043 Uiso 1 1 calc R U . . .
C25 C -0.04357(17) -0.8886(9) 0.4144(3) 0.0497(17) Uani 1 1 d . . . . .
H25A H -0.037323 -1.033194 0.440650 0.075 Uiso 1 1 calc R U . . .
H25B H -0.033886 -0.900849 0.374841 0.075 Uiso 1 1 calc R U . . .
H25C H -0.074074 -0.860553 0.398568 0.075 Uiso 1 1 calc R U . . .
C31 C 0.0000(3) 0.5927(12) 0.2311(6) 0.059(3) Uani 0.426(3) 1 d D U P A -1
H31 H 0.001661 0.642838 0.185806 0.070 Uiso 0.426(3) 1 calc R U P A -1
Cl1 Cl 0.0463(4) 0.4375(17) 0.2756(7) 0.081(4) Uani 0.426(3) 1 d D U P A -1
Cl2 Cl -0.0043(2) 0.8386(9) 0.2777(4) 0.085(3) Uani 0.426(3) 1 d D U P A -1
Cl3 Cl -0.0441(3) 0.4110(13) 0.2171(4) 0.0323(15) Uani 0.426(3) 1 d D U P A -1
C31B C 0.0087(7) 0.564(4) 0.2715(14) 0.068(4) Uani 0.074(3) 1 d D U P A -2
H31B H 0.027922 0.509040 0.316897 0.082 Uiso 0.074(3) 1 calc R U P A -2
Cl1B Cl 0.0393(7) 0.651(4) 0.2214(14) 0.080(5) Uani 0.074(3) 1 d D U P A -2
Cl2B Cl -0.0210(9) 0.799(5) 0.285(2) 0.061(6) Uani 0.074(3) 1 d D U P A -2
Cl3B Cl -0.0251(9) 0.336(4) 0.2308(17) 0.080(6) Uani 0.074(3) 1 d D U P A -2


_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
C1 C2 1.381(6) . ?
C1 C10 1.381(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9500 . ?
C4 C11 1.390(6) . ?
C4 H4 0.9500 . ?
C5 C12 1.386(6) . ?
C5 C6 1.395(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(7) . ?
C7 H7 0.9500 . ?
C8 C13 1.402(6) . ?
C8 H8 0.9500 . ?
N9 C10 1.402(6) . ?
N9 C13 1.403(6) . ?
N9 C14 1.422(6) . ?
C10 C11 1.411(6) . ?
C11 C12 1.445(6) . ?
C12 C13 1.387(6) . ?
C14 C15 1.386(6) . ?
C14 C19 1.396(6) . ?
C15 C16 1.373(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(7) . ?
C17 C20 1.443(7) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.184(6) . ?
C21 C22 1.445(7) . ?
C22 C23 1.392(7) 5_546 ?
C22 C24 1.395(7) . ?
C23 C24 1.389(7) . ?
C23 C25 1.518(6) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C31 Cl2 1.751(7) . ?
C31 Cl3 1.760(7) . ?
C31 Cl1 1.764(7) . ?
C31 H31 1.0000 . ?
C31B Cl2B 1.757(9) . ?
C31B Cl1B 1.758(9) . ?
C31B Cl3B 1.760(9) . ?
C31B H31B 1.0000 . ?

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 C1 C10 117.7(5) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 121.5(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C11 119.3(5) . . ?
C3 C4 H4 120.3 . . ?
C11 C4 H4 120.3 . . ?
C12 C5 C6 118.6(5) . . ?
C12 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.4(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 121.8(5) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C13 117.4(5) . . ?
C7 C8 H8 121.3 . . ?
C13 C8 H8 121.3 . . ?
C10 N9 C13 107.6(4) . . ?
C10 N9 C14 125.6(4) . . ?
C13 N9 C14 125.6(4) . . ?
C1 C10 N9 129.7(4) . . ?
C1 C10 C11 121.8(4) . . ?
N9 C10 C11 108.5(4) . . ?
C4 C11 C10 119.3(5) . . ?
C4 C11 C12 133.5(5) . . ?
C10 C11 C12 107.1(4) . . ?
C5 C12 C13 120.0(5) . . ?
C5 C12 C11 133.1(5) . . ?
C13 C12 C11 106.9(4) . . ?
C12 C13 C8 121.7(4) . . ?
C12 C13 N9 109.8(4) . . ?
C8 C13 N9 128.4(4) . . ?
C15 C14 C19 119.1(4) . . ?
C15 C14 N9 120.0(4) . . ?
C19 C14 N9 120.9(5) . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.5(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 118.2(5) . . ?
C18 C17 C20 121.5(4) . . ?
C16 C17 C20 120.2(5) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 120.3(5) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C21 C20 C17 178.0(6) . . ?
C20 C21 C22 174.9(5) . . ?
C23 C22 C24 119.2(5) 5_546 . ?
C23 C22 C21 120.8(5) 5_546 . ?
C24 C22 C21 120.0(5) . . ?
C24 C23 C22 118.0(5) . 5_546 ?
C24 C23 C25 120.6(5) . . ?
C22 C23 C25 121.3(5) 5_546 . ?
C23 C24 C22 122.8(5) . . ?
C23 C24 H24 118.6 . . ?
C22 C24 H24 118.6 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Cl2 C31 Cl3 110.6(6) . . ?
Cl2 C31 Cl1 110.1(6) . . ?
Cl3 C31 Cl1 109.3(5) . . ?
Cl2 C31 H31 108.9 . . ?
Cl3 C31 H31 108.9 . . ?
Cl1 C31 H31 108.9 . . ?
Cl2B C31B Cl1B 110.3(9) . . ?
Cl2B C31B Cl3B 110.0(8) . . ?
Cl1B C31B Cl3B 109.8(8) . . ?
Cl2B C31B H31B 108.9 . . ?
Cl1B C31B H31B 108.9 . . ?
Cl3B C31B H31B 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C2 C3 C4 C11 0.3(8) . . . . ?
C12 C5 C6 C7 -0.4(8) . . . . ?
C5 C6 C7 C8 -1.3(8) . . . . ?
C6 C7 C8 C13 1.4(8) . . . . ?
C2 C1 C10 N9 178.0(5) . . . . ?
C2 C1 C10 C11 0.2(7) . . . . ?
C13 N9 C10 C1 -178.8(5) . . . . ?
C14 N9 C10 C1 -10.8(8) . . . . ?
C13 N9 C10 C11 -0.7(5) . . . . ?
C14 N9 C10 C11 167.3(4) . . . . ?
C3 C4 C11 C10 -0.3(7) . . . . ?
C3 C4 C11 C12 -178.4(5) . . . . ?
C1 C10 C11 C4 0.1(7) . . . . ?
N9 C10 C11 C4 -178.1(4) . . . . ?
C1 C10 C11 C12 178.6(4) . . . . ?
N9 C10 C11 C12 0.4(5) . . . . ?
C6 C5 C12 C13 1.9(7) . . . . ?
C6 C5 C12 C11 -176.1(5) . . . . ?
C4 C11 C12 C5 -3.5(9) . . . . ?
C10 C11 C12 C5 178.3(5) . . . . ?
C4 C11 C12 C13 178.3(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C5 C12 C13 C8 -1.9(7) . . . . ?
C11 C12 C13 C8 176.6(4) . . . . ?
C5 C12 C13 N9 -179.0(4) . . . . ?
C11 C12 C13 N9 -0.5(5) . . . . ?
C7 C8 C13 C12 0.2(7) . . . . ?
C7 C8 C13 N9 176.8(5) . . . . ?
C10 N9 C13 C12 0.7(5) . . . . ?
C14 N9 C13 C12 -167.2(4) . . . . ?
C10 N9 C13 C8 -176.1(5) . . . . ?
C14 N9 C13 C8 15.9(8) . . . . ?
C10 N9 C14 C15 -119.3(5) . . . . ?
C13 N9 C14 C15 46.5(6) . . . . ?
C10 N9 C14 C19 60.7(6) . . . . ?
C13 N9 C14 C19 -133.4(5) . . . . ?
C19 C14 C15 C16 0.0(7) . . . . ?
N9 C14 C15 C16 -180.0(4) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C15 C16 C17 C20 -178.7(5) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C20 C17 C18 C19 178.8(4) . . . . ?
C17 C18 C19 C14 -0.3(7) . . . . ?
C15 C14 C19 C18 0.2(7) . . . . ?
N9 C14 C19 C18 -179.9(4) . . . . ?
C22 C23 C24 C22 -1.0(8) 5_546 . . . ?
C25 C23 C24 C22 178.5(4) . . . . ?
C23 C22 C24 C23 1.1(8) 5_546 . . . ?
C21 C22 C24 C23 -176.9(5) . . . . ?

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
C1 H1 Cl1 0.95 2.86 3.523(15) 127.8 .

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
