# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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_CL2550
_database_code_depnum_ccdc_archive 'CCDC 1940732'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;
_cell_length_a                   9.59870(4)
_cell_length_b                   11.36410(4)
_cell_length_c                   22.08550(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.217(4)
_cell_angle_gamma                90
_cell_volume                     2405.303(17)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C32 H24 Cl1 N1 
# Dc =      1.26 Fooo =    960.00 Mu =      1.80 M =    458.00
# Found Formula = C32 H26 Cl1 N1 
# Dc =      1.27 FOOO =    968.00 Mu =      1.80 M =    460.02

_chemical_formula_sum            'C32 H26 Cl1 N1'
_chemical_formula_moiety         'C32 H26 Cl1 N1'
_chemical_compound_source        .
_chemical_formula_weight         460.02


_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2
_cell_measurement_theta_max      33
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.270
# Non-dispersive F(000): 
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.180

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            85480
_reflns_number_total             9710
_diffrn_reflns_av_R_equivalents  0.052
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 9710 
# Theoretical number of reflections is about 20252 


_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         34.406
_diffrn_measured_fraction_theta_max 0.958

_diffrn_reflns_theta_full        31.309
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              -15
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              35



_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.49


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 

_refine_ls_number_restraints     6
_refine_ls_number_parameters     315
_refine_ls_number_reflns         7598
_refine_ls_wR_factor_ref         0.0452
_refine_ls_goodness_of_fit_ref   0.9656
_refine_ls_shift/su_max          0.0030610
_refine_ls_shift/su_mean         0.0000914


# The values computed with all filters except I/sigma 
_refine_ls_R_factor_all          0.0379
_refine_ls_wR_factor_all         0.0452

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7598
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_gt          0.0452


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.847 0.693 0.494 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.79761(2) 0.694254(18) 0.614261(10) 0.0185 1.0000 Uani . . . . . .
N1 N 0.54700(8) 0.24838(7) 0.69322(4) 0.0174 1.0000 Uani D . . . . .
C11 C 0.12173(11) 0.68360(9) 0.54401(5) 0.0259 1.0000 Uani . . . . . .
C10 C 0.17797(12) 0.68531(10) 0.60358(6) 0.0286 1.0000 Uani . . . . . .
C9 C 0.26177(10) 0.59301(9) 0.62550(5) 0.0235 1.0000 Uani . . . . . .
C8 C 0.29170(8) 0.49803(7) 0.58795(4) 0.0148 1.0000 Uani . . . . . .
C7 C 0.37977(8) 0.39579(7) 0.61390(3) 0.0135 1.0000 Uani . . . . . .
C6 C 0.52833(8) 0.42983(7) 0.63482(3) 0.0127 1.0000 Uani . . . . . .
C1 C 0.60833(8) 0.35081(7) 0.67210(3) 0.0132 1.0000 Uani D . . . . .
C2 C 0.74859(8) 0.37762(7) 0.68984(3) 0.0129 1.0000 Uani . . . . . .
C20 C 0.83605(8) 0.28776(7) 0.72648(3) 0.0137 1.0000 Uani . . . . . .
C27 C 0.96225(8) 0.34419(7) 0.75998(4) 0.0142 1.0000 Uani . . . . . .
C32 C 0.94212(9) 0.40840(8) 0.81276(4) 0.0161 1.0000 Uani . . . . . .
C31 C 1.05269(9) 0.46724(8) 0.84307(4) 0.0175 1.0000 Uani . . . . . .
C30 C 1.18552(9) 0.46265(9) 0.82086(4) 0.0214 1.0000 Uani . . . . . .
C28 C 1.09583(9) 0.33839(10) 0.73870(4) 0.0229 1.0000 Uani . . . . . .
C29 C 1.20664(10) 0.39766(12) 0.76897(5) 0.0279 1.0000 Uani . . . . . .
C21 C 0.87311(8) 0.18259(7) 0.68727(3) 0.0137 1.0000 Uani . . . . . .
C26 C 0.86580(10) 0.18782(8) 0.62398(4) 0.0186 1.0000 Uani . . . . . .
C25 C 0.89698(10) 0.08917(8) 0.58960(4) 0.0204 1.0000 Uani . . . . . .
C24 C 0.93518(9) -0.01617(8) 0.61773(4) 0.0184 1.0000 Uani . . . . . .
C23 C 0.94266(9) -0.02231(8) 0.68089(4) 0.0179 1.0000 Uani . . . . . .
C22 C 0.91338(9) 0.07629(8) 0.71524(4) 0.0158 1.0000 Uani . . . . . .
C14 C 0.37787(8) 0.29100(7) 0.57078(3) 0.0136 1.0000 Uani . . . . . .
C15 C 0.48405(9) 0.27305(8) 0.53084(4) 0.0169 1.0000 Uani . . . . . .
C16 C 0.47716(10) 0.17906(8) 0.49019(4) 0.0195 1.0000 Uani . . . . . .
C17 C 0.36458(10) 0.10177(8) 0.48897(4) 0.0191 1.0000 Uani . . . . . .
C18 C 0.25886(10) 0.11864(8) 0.52863(4) 0.0187 1.0000 Uani . . . . . .
C19 C 0.26524(9) 0.21281(8) 0.56925(4) 0.0164 1.0000 Uani . . . . . .
C12 C 0.15074(10) 0.59022(9) 0.50658(4) 0.0226 1.0000 Uani . . . . . .
C13 C 0.23584(9) 0.49796(8) 0.52830(4) 0.0181 1.0000 Uani . . . . . .
C5 C 0.58883(8) 0.53483(7) 0.61657(3) 0.0136 1.0000 Uani . . . . . .
C4 C 0.72588(8) 0.56066(7) 0.63542(4) 0.0136 1.0000 Uani . . . . . .
C3 C 0.80636(8) 0.48344(7) 0.67121(3) 0.0138 1.0000 Uani . . . . . .
H111 H 0.0638 0.7467 0.5292 0.0305 1.0000 Uiso . . . . . .
H101 H 0.1595 0.7499 0.6294 0.0342 1.0000 Uiso . . . . . .
H91 H 0.2994 0.5944 0.6663 0.0279 1.0000 Uiso . . . . . .
H71 H 0.3358 0.3701 0.6491 0.0159 1.0000 Uiso . . . . . .
H201 H 0.7783 0.2582 0.7566 0.0159 1.0000 Uiso . . . . . .
H321 H 0.8515 0.4121 0.8281 0.0190 1.0000 Uiso . . . . . .
H311 H 1.0374 0.5105 0.8790 0.0206 1.0000 Uiso . . . . . .
H301 H 1.2609 0.5038 0.8410 0.0256 1.0000 Uiso . . . . . .
H281 H 1.1120 0.2934 0.7034 0.0275 1.0000 Uiso . . . . . .
H291 H 1.2975 0.3932 0.7539 0.0331 1.0000 Uiso . . . . . .
H261 H 0.8394 0.2594 0.6041 0.0219 1.0000 Uiso . . . . . .
H251 H 0.8923 0.0941 0.5466 0.0242 1.0000 Uiso . . . . . .
H241 H 0.9556 -0.0833 0.5942 0.0217 1.0000 Uiso . . . . . .
H231 H 0.9682 -0.0942 0.7007 0.0213 1.0000 Uiso . . . . . .
H221 H 0.9209 0.0716 0.7583 0.0186 1.0000 Uiso . . . . . .
H151 H 0.5613 0.3253 0.5314 0.0200 1.0000 Uiso . . . . . .
H161 H 0.5497 0.1680 0.4632 0.0232 1.0000 Uiso . . . . . .
H171 H 0.3599 0.0378 0.4612 0.0225 1.0000 Uiso . . . . . .
H181 H 0.1822 0.0655 0.5282 0.0222 1.0000 Uiso . . . . . .
H191 H 0.1921 0.2241 0.5961 0.0195 1.0000 Uiso . . . . . .
H121 H 0.1126 0.5884 0.4657 0.0267 1.0000 Uiso . . . . . .
H131 H 0.2557 0.4341 0.5023 0.0213 1.0000 Uiso . . . . . .
H51 H 0.5365 0.5886 0.5913 0.0159 1.0000 Uiso . . . . . .
H31 H 0.9006 0.5025 0.6831 0.0162 1.0000 Uiso . . . . . .
H1 H 0.6023(15) 0.1923(12) 0.7043(7) 0.0262(18) 1.0000 Uiso D . . . . .
H2 H 0.4798(15) 0.2183(13) 0.6706(7) 0.0266(18) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C4 . 1.7417(8) yes
N1 . C1 . 1.3964(11) yes
N1 . H1 . 0.857(13) no
N1 . H2 . 0.864(13) no
C11 . C10 . 1.3939(16) yes
C11 . C12 . 1.3831(15) yes
C11 . H111 . 0.954 no
C10 . C9 . 1.3921(14) yes
C10 . H101 . 0.952 no
C9 . C8 . 1.4007(12) yes
C9 . H91 . 0.953 no
C8 . C7 . 1.5293(12) yes
C8 . C13 . 1.3941(12) yes
C7 . C6 . 1.5240(11) yes
C7 . C14 . 1.5244(11) yes
C7 . H71 . 0.952 no
C6 . C1 . 1.4152(11) yes
C6 . C5 . 1.3963(11) yes
C1 . C2 . 1.4141(11) yes
C2 . C20 . 1.5252(11) yes
C2 . C3 . 1.3959(11) yes
C20 . C27 . 1.5250(11) yes
C20 . C21 . 1.5295(11) yes
C20 . H201 . 0.951 no
C27 . C32 . 1.3978(11) yes
C27 . C28 . 1.3917(12) yes
C32 . C31 . 1.3935(12) yes
C32 . H321 . 0.952 no
C31 . C30 . 1.3926(13) yes
C31 . H311 . 0.952 no
C30 . C29 . 1.3876(14) yes
C30 . H301 . 0.951 no
C28 . C29 . 1.3973(13) yes
C28 . H281 . 0.953 no
C29 . H291 . 0.952 no
C21 . C26 . 1.3968(11) yes
C21 . C22 . 1.4012(11) yes
C26 . C25 . 1.3958(12) yes
C26 . H261 . 0.952 no
C25 . C24 . 1.3885(13) yes
C25 . H251 . 0.949 no
C24 . C23 . 1.3946(13) yes
C24 . H241 . 0.950 no
C23 . C22 . 1.3906(12) yes
C23 . H231 . 0.952 no
C22 . H221 . 0.951 no
C14 . C15 . 1.3996(11) yes
C14 . C19 . 1.3983(11) yes
C15 . C16 . 1.3945(12) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.3916(13) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.3906(13) yes
C17 . H171 . 0.951 no
C18 . C19 . 1.3955(12) yes
C18 . H181 . 0.951 no
C19 . H191 . 0.952 no
C12 . C13 . 1.3974(13) yes
C12 . H121 . 0.954 no
C13 . H131 . 0.951 no
C5 . C4 . 1.3888(11) yes
C5 . H51 . 0.952 no
C4 . C3 . 1.3868(11) yes
C3 . H31 . 0.952 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . H1 . 116.7(10) no
C1 . N1 . H2 . 116.9(10) no
H1 . N1 . H2 . 107.5(14) no
C10 . C11 . C12 . 119.64(9) yes
C10 . C11 . H111 . 120.0 no
C12 . C11 . H111 . 120.3 no
C11 . C10 . C9 . 120.22(9) yes
C11 . C10 . H101 . 120.0 no
C9 . C10 . H101 . 119.7 no
C10 . C9 . C8 . 120.56(9) yes
C10 . C9 . H91 . 119.8 no
C8 . C9 . H91 . 119.6 no
C9 . C8 . C7 . 119.40(8) yes
C9 . C8 . C13 . 118.63(8) yes
C7 . C8 . C13 . 121.93(7) yes
C8 . C7 . C6 . 114.13(7) yes
C8 . C7 . C14 . 111.86(6) yes
C6 . C7 . C14 . 111.46(6) yes
C8 . C7 . H71 . 106.1 no
C6 . C7 . H71 . 106.3 no
C14 . C7 . H71 . 106.3 no
C7 . C6 . C1 . 118.89(7) yes
C7 . C6 . C5 . 121.78(7) yes
C1 . C6 . C5 . 119.29(7) yes
C6 . C1 . N1 . 119.88(7) yes
C6 . C1 . C2 . 120.10(7) yes
N1 . C1 . C2 . 119.98(7) yes
C1 . C2 . C20 . 119.34(7) yes
C1 . C2 . C3 . 119.45(7) yes
C20 . C2 . C3 . 121.15(7) yes
C2 . C20 . C27 . 111.99(7) yes
C2 . C20 . C21 . 111.18(6) yes
C27 . C20 . C21 . 113.56(7) yes
C2 . C20 . H201 . 106.5 no
C27 . C20 . H201 . 106.7 no
C21 . C20 . H201 . 106.5 no
C20 . C27 . C32 . 118.75(7) yes
C20 . C27 . C28 . 122.55(7) yes
C32 . C27 . C28 . 118.65(8) yes
C27 . C32 . C31 . 120.92(8) yes
C27 . C32 . H321 . 119.5 no
C31 . C32 . H321 . 119.6 no
C32 . C31 . C30 . 120.03(8) yes
C32 . C31 . H311 . 120.0 no
C30 . C31 . H311 . 120.0 no
C31 . C30 . C29 . 119.34(8) yes
C31 . C30 . H301 . 120.3 no
C29 . C30 . H301 . 120.4 no
C27 . C28 . C29 . 120.44(8) yes
C27 . C28 . H281 . 119.8 no
C29 . C28 . H281 . 119.7 no
C28 . C29 . C30 . 120.61(9) yes
C28 . C29 . H291 . 119.7 no
C30 . C29 . H291 . 119.7 no
C20 . C21 . C26 . 122.21(7) yes
C20 . C21 . C22 . 119.42(7) yes
C26 . C21 . C22 . 118.36(8) yes
C21 . C26 . C25 . 120.65(8) yes
C21 . C26 . H261 . 119.7 no
C25 . C26 . H261 . 119.6 no
C26 . C25 . C24 . 120.57(8) yes
C26 . C25 . H251 . 119.8 no
C24 . C25 . H251 . 119.6 no
C25 . C24 . C23 . 119.21(8) yes
C25 . C24 . H241 . 120.3 no
C23 . C24 . H241 . 120.5 no
C24 . C23 . C22 . 120.31(8) yes
C24 . C23 . H231 . 120.0 no
C22 . C23 . H231 . 119.7 no
C21 . C22 . C23 . 120.88(8) yes
C21 . C22 . H221 . 119.5 no
C23 . C22 . H221 . 119.6 no
C7 . C14 . C15 . 121.60(7) yes
C7 . C14 . C19 . 119.58(7) yes
C15 . C14 . C19 . 118.78(7) yes
C14 . C15 . C16 . 120.49(8) yes
C14 . C15 . H151 . 119.8 no
C16 . C15 . H151 . 119.8 no
C15 . C16 . C17 . 120.31(8) yes
C15 . C16 . H161 . 119.7 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 119.60(8) yes
C16 . C17 . H171 . 120.2 no
C18 . C17 . H171 . 120.1 no
C17 . C18 . C19 . 120.23(8) yes
C17 . C18 . H181 . 119.8 no
C19 . C18 . H181 . 119.9 no
C14 . C19 . C18 . 120.58(8) yes
C14 . C19 . H191 . 119.7 no
C18 . C19 . H191 . 119.7 no
C11 . C12 . C13 . 120.26(9) yes
C11 . C12 . H121 . 120.1 no
C13 . C12 . H121 . 119.6 no
C12 . C13 . C8 . 120.69(8) yes
C12 . C13 . H131 . 119.8 no
C8 . C13 . H131 . 119.5 no
C6 . C5 . C4 . 119.76(7) yes
C6 . C5 . H51 . 120.3 no
C4 . C5 . H51 . 120.0 no
Cl1 . C4 . C5 . 119.07(6) yes
Cl1 . C4 . C3 . 119.25(6) yes
C5 . C4 . C3 . 121.68(7) yes
C2 . C3 . C4 . 119.69(7) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 120.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H2 . C14 . 128.4(12) 0.864 2.502 3.1129(12) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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_cl511
_database_code_depnum_ccdc_archive 'CCDC 1940733'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_date             2019-07-09T13:27:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H23 Cl2 N3 V'
_chemical_formula_moiety         'C8 H23 Cl2 N3 V'
_chemical_formula_weight         283.13
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.139(3)
_cell_length_b                   9.122(2)
_cell_length_c                   12.098(2)
_cell_angle_alpha                90
_cell_angle_beta                 126.55(3)
_cell_angle_gamma                90
_cell_volume                     1519.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#




_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.98
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_absorpt_correction_T_min  0.3140
_exptl_absorpt_correction_T_max  0.7490


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford-Diffraction XCALIBUR'
_diffrn_measurement_method       ω-φ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.059
_diffrn_reflns_number            7615
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.908
_diffrn_reflns_theta_max         32.189
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.928
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_coverage         0.998
_reflns_number_total             4408
_reflns_number_gt                2205
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2016/4
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4408
_refine_ls_number_parameters     136
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.62(8)
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
V1 V 0.7254(2) 0.02581(7) 0.8874(3) 0.0501(2) Uani 1 1 d . . . . .
CL1 Cl 0.82520(9) 0.1137(4) 1.11415(12) 0.0693(8) Uani 1 1 d . . . . .
CL2 Cl 0.62569(10) 0.1111(4) 0.66073(13) 0.0730(9) Uani 1 1 d . . . . .
N1 N 0.7281(9) -0.1535(4) 0.8892(11) 0.0758(12) Uani 1 1 d . . . . .
N2 N 0.6079(7) 0.0733(11) 0.9027(9) 0.063(3) Uani 1 1 d . . . . .
H2 H 0.630858 0.038074 0.995831 0.075 Uiso 1 1 calc R U . . .
N3 N 0.8428(7) 0.0681(12) 0.8764(9) 0.070(3) Uani 1 1 d . . . . .
H3 H 0.82096 0.032987 0.783698 0.084 Uiso 1 1 calc R U . . .
C1 C 0.7415(6) -0.3130(5) 0.8895(9) 0.081(2) Uani 1 1 d D U . . .
C2 C 0.6545(8) -0.3733(14) 0.7589(10) 0.162(5) Uani 1 1 d D U . . .
H2A H 0.650217 -0.331865 0.680719 0.242 Uiso 1 1 calc R U . . .
H2B H 0.59594 -0.347489 0.751305 0.242 Uiso 1 1 calc R U . . .
H2C H 0.659962 -0.48021 0.758683 0.242 Uiso 1 1 calc R U . . .
C3 C 0.7558(8) -0.3710(14) 1.0154(10) 0.113(3) Uani 1 1 d D U . . .
H3A H 0.702577 -0.337561 1.018025 0.169 Uiso 1 1 calc R U . . .
H3B H 0.81771 -0.33528 1.097098 0.169 Uiso 1 1 calc R U . . .
H3C H 0.756467 -0.478411 1.013915 0.169 Uiso 1 1 calc R U . . .
C4 C 0.8309(7) -0.3558(8) 0.8944(10) 0.119(2) Uani 1 1 d D U . . .
H4A H 0.890443 -0.327291 0.98353 0.178 Uiso 1 1 calc R U . . .
H4B H 0.827956 -0.305143 0.82053 0.178 Uiso 1 1 calc R U . . .
H4C H 0.831042 -0.461987 0.882294 0.178 Uiso 1 1 calc R U . . .
C5 C 0.5158(9) -0.0132(19) 0.8008(15) 0.116(5) Uani 1 1 d . . . . .
H5A H 0.494113 0.00766 0.706936 0.173 Uiso 1 1 calc R U . . .
H5B H 0.464952 0.015328 0.810253 0.173 Uiso 1 1 calc R U . . .
H5C H 0.529165 -0.118242 0.819544 0.173 Uiso 1 1 calc R U . . .
C6 C 0.5890(12) 0.2331(15) 0.9007(15) 0.107(5) Uani 1 1 d . . . . .
H6A H 0.537017 0.247477 0.911022 0.161 Uiso 1 1 calc R U . . .
H6B H 0.569377 0.27534 0.813022 0.161 Uiso 1 1 calc R U . . .
H6C H 0.648273 0.281711 0.976604 0.161 Uiso 1 1 calc R U . . .
C7 C 0.8616(9) 0.2302(16) 0.8799(11) 0.088(4) Uani 1 1 d . . . . .
H7A H 0.905773 0.246655 0.85487 0.132 Uiso 1 1 calc R U . . .
H7B H 0.891167 0.267987 0.972789 0.132 Uiso 1 1 calc R U . . .
H7C H 0.800117 0.281132 0.814348 0.132 Uiso 1 1 calc R U . . .
C8 C 0.9368(11) 0.0040(19) 0.9737(14) 0.104(4) Uani 1 1 d . . . . .
H8A H 0.968267 0.051987 1.063182 0.156 Uiso 1 1 calc R U . . .
H8B H 0.976844 0.017086 0.941149 0.156 Uiso 1 1 calc R U . . .
H8C H 0.929515 -0.100923 0.982947 0.156 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
V1 N1 1.636(4) . ?
V1 N3 2.129(10) . ?
V1 N2 2.173(9) . ?
V1 CL2 2.338(3) . ?
V1 CL1 2.346(3) . ?
N1 C1 1.473(6) . ?
N2 C6 1.491(14) . ?
N2 C5 1.521(13) . ?
N3 C8 1.437(15) . ?
N3 C7 1.509(16) . ?
C1 C3 1.489(8) . ?
C1 C2 1.489(8) . ?
C1 C4 1.548(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 V1 N3 99.3(5) . . ?
N1 V1 N2 102.6(5) . . ?
N3 V1 N2 158.05(16) . . ?
N1 V1 CL2 110.1(4) . . ?
N3 V1 CL2 85.6(3) . . ?
N2 V1 CL2 88.1(3) . . ?
N1 V1 CL1 109.4(4) . . ?
N3 V1 CL1 87.3(3) . . ?
N2 V1 CL1 84.3(3) . . ?
CL2 V1 CL1 140.56(5) . . ?
C1 N1 V1 172.3(10) . . ?
C6 N2 C5 112.6(12) . . ?
C6 N2 V1 113.4(9) . . ?
C5 N2 V1 113.2(8) . . ?
C8 N3 C7 105.0(12) . . ?
C8 N3 V1 121.1(8) . . ?
C7 N3 V1 111.7(8) . . ?
N1 C1 C3 106.5(8) . . ?
N1 C1 C2 107.8(9) . . ?
C3 C1 C2 113.9(6) . . ?
N1 C1 C4 113.5(7) . . ?
C3 C1 C4 108.4(6) . . ?
C2 C1 C4 106.9(6) . . ?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1940734'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;
#============================================================= 

_cell_length_a                   12.320(5)
_cell_angle_alpha                90
_cell_length_b                   23.643(5)
_cell_angle_beta                 108.331(5)
_cell_length_c                   19.162(5)
_cell_angle_gamma                90
_cell_volume                     5298(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

# choose from: rm (reference molecule of 
# known chirality), ad (anomolous 
# dispersion - ie. Flack param), rmad 
# (both rm and ad), syn (known from 
# synthetic pathway), unk (unknown) 
# or . (not applicable). 

_chemical_absolute_configuration .

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N   ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'Cl  ' 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 International_Tables_Vol_IV_Table_2.2B
'V   ' 0.3005 0.5294 10.2971 6.8657 7.3511 0.4385 2.0703 26.8938 2.0571
102.4780 1.2199 International_Tables_Vol_IV_Table_2.2B


_cell_formula_units_Z            4
_chemical_formula_sum            ' C53 H66 Cl4 N6 V2 '
_chemical_formula_moiety         ' 2(C23 H29 Cl2 N3 V), C7 H8 '
_chemical_compound_source        
;
?
;
_chemical_formula_weight         1030.84


_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2
_cell_measurement_theta_max      24
_cell_measurement_temperature    180

_exptl_crystal_description       ' stick '
_exptl_crystal_colour            ' orange '
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
# Non-dispersive F(000): 
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    0.595

_diffrn_measurement_device_type  
; 
Stoe IPDS 
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
; 
 IPDS (Stoe & Cie, 1996) 
;
_computing_data_reduction        
; 
 XRED (Stoe & Cie 1996) 
;
_computing_cell_refinement       
; 
 IPDS (Stoe & Cie, 1996) 
;
_computing_structure_solution    
; 
 SIR92 (Altomare et al, 1994) 
;

_diffrn_measurement_method       'φ scans'

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.94
# Sheldrick geometric definitions 0.91 0.94 


_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      180
_diffrn_reflns_number            42991
_reflns_number_total             7929
_diffrn_reflns_av_R_equivalents  0.09
# Number of reflections with Friedels Law is 7929 
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 8439 


_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         24.121
_diffrn_measured_fraction_theta_max 0.941

_diffrn_reflns_theta_full        24.121
_diffrn_measured_fraction_theta_full 0.968


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              21


_refine_diff_density_min         -0.45
_refine_diff_density_max         0.39


_refine_ls_number_reflns         4587
_refine_ls_number_restraints     0
_refine_ls_number_parameters     552

#_refine_ls_R_factor_ref 0.0466 
_refine_ls_wR_factor_ref         0.0446
_refine_ls_goodness_of_fit_ref   1.1336

#_reflns_number_all 7892 
_refine_ls_R_factor_all          0.0908
_refine_ls_wR_factor_all         0.0503

# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:
_reflns_threshold_expression     I>1.00u(I)
_reflns_number_gt                4587
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_gt          0.0446


_refine_ls_shift/su_max          0.001030
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.78 1.53 2.49 
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_disorder_assembly
_atom_site_refinement_disorder_group
_atom_site_attached_hydrogens
V1 V 0.27458(5) 0.62142(3) 0.47768(3) 0.0202 1.0000 Uani . . . . . .
V2 V 0.22462(5) 0.61989(3) 0.03988(3) 0.0193 1.0000 Uani . . . . . .
Cl1 Cl 0.35857(8) 0.70885(4) 0.46969(5) 0.0308 1.0000 Uani . . . . . .
Cl2 Cl 0.31915(9) 0.53770(4) 0.54313(5) 0.0365 1.0000 Uani . . . . . .
Cl3 Cl 0.14960(8) 0.70806(4) 0.05544(5) 0.0280 1.0000 Uani . . . . . .
Cl4 Cl 0.16992(10) 0.54058(4) -0.03320(6) 0.0405 1.0000 Uani . . . . . .
N1 N 0.1449(2) 0.62062(12) 0.41909(15) 0.0213 1.0000 Uani . . . . . .
N2 N 0.2348(3) 0.65675(13) 0.57155(16) 0.0243 1.0000 Uani . . . . . .
N3 N 0.3701(3) 0.59163(14) 0.41113(18) 0.0328 1.0000 Uani . . . . . .
N4 N 0.3571(2) 0.61534(12) 0.09439(15) 0.0200 1.0000 Uani . . . . . .
N5 N 0.1424(3) 0.58845(15) 0.10926(19) 0.0386 1.0000 Uani . . . . . .
N6 N 0.2532(3) 0.65977(13) -0.05550(17) 0.0307 1.0000 Uani . . . . . .
C1 C 0.0262(3) 0.62170(16) 0.36886(19) 0.0228 1.0000 Uani . . . . . .
C2 C 0.4731(3) 0.60650(15) 0.14451(19) 0.0207 1.0000 Uani . . . . . .
C11 C 0.1555(4) 0.62315(18) 0.5992(2) 0.0351 1.0000 Uani . . . . . .
C12 C 0.3364(4) 0.67328(19) 0.6338(2) 0.0381 1.0000 Uani . . . . . .
C13 C 0.3292(4) 0.5439(2) 0.3630(3) 0.0546 1.0000 Uani . . . . . .
C14 C 0.4937(4) 0.5871(2) 0.4499(3) 0.0459 1.0000 Uani . . . . . .
C21 C 0.1865(5) 0.5440(3) 0.1598(3) 0.0667 1.0000 Uani . . . . . .
C22 C 0.0177(4) 0.5869(2) 0.0790(3) 0.0489 1.0000 Uani . . . . . .
C23 C 0.3362(4) 0.6319(2) -0.0844(2) 0.0431 1.0000 Uani . . . . . .
C24 C 0.1481(4) 0.6720(2) -0.1161(2) 0.0463 1.0000 Uani . . . . . .
C31 C -0.0501(3) 0.63571(15) 0.41598(19) 0.0206 1.0000 Uani . . . . . .
C32 C -0.1226(3) 0.59603(15) 0.43324(19) 0.0232 1.0000 Uani . . . . . .
C33 C -0.1841(3) 0.61017(18) 0.4802(2) 0.0315 1.0000 Uani . . . . . .
C34 C -0.1722(3) 0.66364(18) 0.5127(2) 0.0331 1.0000 Uani . . . . . .
C35 C -0.1021(3) 0.70284(17) 0.4959(2) 0.0302 1.0000 Uani . . . . . .
C36 C -0.0403(3) 0.68911(16) 0.4490(2) 0.0267 1.0000 Uani . . . . . .
C41 C 0.0173(3) 0.66744(15) 0.31008(19) 0.0222 1.0000 Uani . . . . . .
C42 C -0.0823(3) 0.6977(2) 0.2793(2) 0.0362 1.0000 Uani . . . . . .
C43 C -0.0908(4) 0.7370(2) 0.2233(2) 0.0443 1.0000 Uani . . . . . .
C44 C 0.0011(4) 0.74641(19) 0.1981(2) 0.0369 1.0000 Uani . . . . . .
C45 C 0.1008(3) 0.71682(19) 0.2285(2) 0.0324 1.0000 Uani . . . . . .
C46 C 0.1095(3) 0.67758(18) 0.2840(2) 0.0289 1.0000 Uani . . . . . .
C51 C -0.0014(3) 0.56298(16) 0.3324(2) 0.0246 1.0000 Uani . . . . . .
C52 C -0.0785(4) 0.55701(18) 0.2622(2) 0.0340 1.0000 Uani . . . . . .
C53 C -0.1070(5) 0.5034(2) 0.2311(2) 0.0480 1.0000 Uani . . . . . .
C54 C -0.0587(4) 0.45617(19) 0.2702(3) 0.0449 1.0000 Uani . . . . . .
C55 C 0.0181(4) 0.46120(18) 0.3401(2) 0.0360 1.0000 Uani . . . . . .
C56 C 0.0457(3) 0.51476(16) 0.3713(2) 0.0291 1.0000 Uani . . . . . .
C61 C 0.4923(3) 0.64430(16) 0.21359(18) 0.0214 1.0000 Uani . . . . . .
C62 C 0.4036(3) 0.67174(16) 0.2297(2) 0.0268 1.0000 Uani . . . . . .
C63 C 0.4244(3) 0.70361(18) 0.2929(2) 0.0316 1.0000 Uani . . . . . .
C64 C 0.5333(4) 0.70853(18) 0.3412(2) 0.0337 1.0000 Uani . . . . . .
C65 C 0.6228(3) 0.68194(18) 0.3257(2) 0.0306 1.0000 Uani . . . . . .
C66 C 0.6035(3) 0.65018(17) 0.2621(2) 0.0296 1.0000 Uani . . . . . .
C71 C 0.4844(3) 0.54305(16) 0.1653(2) 0.0249 1.0000 Uani . . . . . .
C72 C 0.5280(4) 0.52378(18) 0.2363(2) 0.0367 1.0000 Uani . . . . . .
C73 C 0.5344(4) 0.4658(2) 0.2516(3) 0.0487 1.0000 Uani . . . . . .
C74 C 0.4976(4) 0.42716(18) 0.1954(3) 0.0419 1.0000 Uani . . . . . .
C75 C 0.4518(4) 0.44636(17) 0.1240(2) 0.0365 1.0000 Uani . . . . . .
C76 C 0.4470(3) 0.50392(16) 0.1087(2) 0.0294 1.0000 Uani . . . . . .
C81 C 0.5574(3) 0.62556(16) 0.10464(18) 0.0240 1.0000 Uani . . . . . .
C82 C 0.5518(3) 0.68132(17) 0.0792(2) 0.0310 1.0000 Uani . . . . . .
C83 C 0.6257(4) 0.70063(18) 0.0440(2) 0.0383 1.0000 Uani . . . . . .
C84 C 0.7091(4) 0.66469(19) 0.0340(2) 0.0399 1.0000 Uani . . . . . .
C85 C 0.7153(4) 0.60952(19) 0.0584(2) 0.0380 1.0000 Uani . . . . . .
C86 C 0.6401(3) 0.58975(17) 0.0932(2) 0.0301 1.0000 Uani . . . . . .
C90 C 0.8524(5) 0.6187(2) 0.8796(3) 0.0621(14) 1.0000 Uiso . . . . . .
C91 C 0.7798(4) 0.6338(2) 0.8038(3) 0.0466(11) 1.0000 Uiso . . . . . .
C92 C 0.7796(4) 0.6011(2) 0.7428(3) 0.0537(13) 1.0000 Uiso . . . . . .
C93 C 0.7107(5) 0.6162(2) 0.6727(3) 0.0577(13) 1.0000 Uiso . . . . . .
C94 C 0.6391(4) 0.6617(2) 0.6614(3) 0.0499(12) 1.0000 Uiso . . . . . .
C95 C 0.6378(4) 0.6942(2) 0.7214(3) 0.0524(12) 1.0000 Uiso . . . . . .
C96 C 0.7077(4) 0.6797(2) 0.7910(3) 0.0441(11) 1.0000 Uiso . . . . . .
H2 H 0.1931 0.6919 0.5493 0.067(2) 1.0000 Uiso . . . . . .
H3 H 0.3550 0.6236 0.3752 0.067(2) 1.0000 Uiso . . . . . .
H5 H 0.1686 0.6203 0.1449 0.067(2) 1.0000 Uiso . . . . . .
H6 H 0.2885 0.6965 -0.0336 0.067(2) 1.0000 Uiso . . . . . .
H111 H 0.0876 0.6121 0.5570 0.067(2) 1.0000 Uiso . . . . . .
H112 H 0.1305 0.6464 0.6349 0.067(2) 1.0000 Uiso . . . . . .
H113 H 0.1957 0.5885 0.6243 0.067(2) 1.0000 Uiso . . . . . .
H121 H 0.3897 0.6960 0.6151 0.067(2) 1.0000 Uiso . . . . . .
H122 H 0.3111 0.6966 0.6696 0.067(2) 1.0000 Uiso . . . . . .
H123 H 0.3763 0.6386 0.6591 0.067(2) 1.0000 Uiso . . . . . .
H131 H 0.2455 0.5480 0.3375 0.067(2) 1.0000 Uiso . . . . . .
H132 H 0.3707 0.5421 0.3258 0.067(2) 1.0000 Uiso . . . . . .
H133 H 0.3439 0.5082 0.3927 0.067(2) 1.0000 Uiso . . . . . .
H141 H 0.5195 0.6207 0.4826 0.067(2) 1.0000 Uiso . . . . . .
H142 H 0.5362 0.5858 0.4132 0.067(2) 1.0000 Uiso . . . . . .
H143 H 0.5094 0.5518 0.4801 0.067(2) 1.0000 Uiso . . . . . .
H211 H 0.2721 0.5470 0.1789 0.067(2) 1.0000 Uiso . . . . . .
H212 H 0.1551 0.5471 0.2018 0.067(2) 1.0000 Uiso . . . . . .
H213 H 0.1646 0.5069 0.1347 0.067(2) 1.0000 Uiso . . . . . .
H221 H -0.0091 0.6190 0.0436 0.067(2) 1.0000 Uiso . . . . . .
H222 H -0.0163 0.5906 0.1197 0.067(2) 1.0000 Uiso . . . . . .
H223 H -0.0068 0.5503 0.0526 0.067(2) 1.0000 Uiso . . . . . .
H231 H 0.4078 0.6238 -0.0431 0.067(2) 1.0000 Uiso . . . . . .
H232 H 0.3548 0.6575 -0.1209 0.067(2) 1.0000 Uiso . . . . . .
H233 H 0.3034 0.5958 -0.1091 0.067(2) 1.0000 Uiso . . . . . .
H241 H 0.0914 0.6909 -0.0963 0.067(2) 1.0000 Uiso . . . . . .
H242 H 0.1663 0.6974 -0.1526 0.067(2) 1.0000 Uiso . . . . . .
H243 H 0.1149 0.6358 -0.1408 0.067(2) 1.0000 Uiso . . . . . .
H321 H -0.1297 0.5573 0.4114 0.067(2) 1.0000 Uiso . . . . . .
H331 H -0.2367 0.5817 0.4912 0.067(2) 1.0000 Uiso . . . . . .
H341 H -0.2149 0.6732 0.5477 0.067(2) 1.0000 Uiso . . . . . .
H351 H -0.0957 0.7417 0.5177 0.067(2) 1.0000 Uiso . . . . . .
H361 H 0.0127 0.7178 0.4387 0.067(2) 1.0000 Uiso . . . . . .
H421 H -0.1494 0.6910 0.2970 0.067(2) 1.0000 Uiso . . . . . .
H431 H -0.1636 0.7587 0.2017 0.067(2) 1.0000 Uiso . . . . . .
H441 H -0.0046 0.7745 0.1579 0.067(2) 1.0000 Uiso . . . . . .
H451 H 0.1677 0.7236 0.2106 0.067(2) 1.0000 Uiso . . . . . .
H461 H 0.1825 0.6564 0.3057 0.067(2) 1.0000 Uiso . . . . . .
H521 H -0.1139 0.5913 0.2336 0.067(2) 1.0000 Uiso . . . . . .
H531 H -0.1624 0.4995 0.1802 0.067(2) 1.0000 Uiso . . . . . .
H541 H -0.0791 0.4179 0.2480 0.067(2) 1.0000 Uiso . . . . . .
H551 H 0.0539 0.4267 0.3682 0.067(2) 1.0000 Uiso . . . . . .
H561 H 0.0998 0.5183 0.4223 0.067(2) 1.0000 Uiso . . . . . .
H621 H 0.3239 0.6683 0.1951 0.067(2) 1.0000 Uiso . . . . . .
H631 H 0.3591 0.7230 0.3038 0.067(2) 1.0000 Uiso . . . . . .
H641 H 0.5474 0.7315 0.3872 0.067(2) 1.0000 Uiso . . . . . .
H651 H 0.7023 0.6856 0.3607 0.067(2) 1.0000 Uiso . . . . . .
H661 H 0.6690 0.6314 0.2510 0.067(2) 1.0000 Uiso . . . . . .
H721 H 0.5556 0.5515 0.2775 0.067(2) 1.0000 Uiso . . . . . .
H731 H 0.5659 0.4525 0.3036 0.067(2) 1.0000 Uiso . . . . . .
H741 H 0.5032 0.3857 0.2063 0.067(2) 1.0000 Uiso . . . . . .
H751 H 0.4224 0.4184 0.0830 0.067(2) 1.0000 Uiso . . . . . .
H761 H 0.4163 0.5174 0.0567 0.067(2) 1.0000 Uiso . . . . . .
H821 H 0.4930 0.7076 0.0872 0.067(2) 1.0000 Uiso . . . . . .
H831 H 0.6194 0.7405 0.0253 0.067(2) 1.0000 Uiso . . . . . .
H841 H 0.7648 0.6787 0.0095 0.067(2) 1.0000 Uiso . . . . . .
H851 H 0.7742 0.5835 0.0505 0.067(2) 1.0000 Uiso . . . . . .
H861 H 0.6455 0.5497 0.1104 0.067(2) 1.0000 Uiso . . . . . .
H901 H 0.8984 0.5841 0.8778 0.067(2) 1.0000 Uiso . . . . . .
H902 H 0.9051 0.6508 0.9011 0.067(2) 1.0000 Uiso . . . . . .
H903 H 0.8026 0.6109 0.9108 0.067(2) 1.0000 Uiso . . . . . .
H921 H 0.8291 0.5667 0.7497 0.067(2) 1.0000 Uiso . . . . . .
H931 H 0.7135 0.5929 0.6295 0.067(2) 1.0000 Uiso . . . . . .
H941 H 0.5882 0.6711 0.6110 0.067(2) 1.0000 Uiso . . . . . .
H951 H 0.5873 0.7283 0.7144 0.067(2) 1.0000 Uiso . . . . . .
H961 H 0.7057 0.7037 0.8336 0.067(2) 1.0000 Uiso . . . . . .
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 . N3 . 2.110(4) yes
V1 . N2 . 2.175(3) yes
V1 . N1 . 1.639(3) yes
V1 . Cl2 . 2.3150(12) yes
V1 . Cl1 . 2.3381(12) yes
V2 . N6 . 2.181(3) yes
V2 . N5 . 2.048(4) yes
V2 . N4 . 1.642(3) yes
V2 . Cl4 . 2.3102(12) yes
V2 . Cl3 . 2.3370(12) yes
N1 . C1 . 1.476(4) yes
N2 . H2 . 0.999 no
N2 . C12 . 1.485(5) yes
N2 . C11 . 1.480(5) yes
N3 . H3 . 1.000 no
N3 . C14 . 1.473(6) yes
N3 . C13 . 1.444(5) yes
N4 . C2 . 1.464(4) yes
N5 . H5 . 0.999 no
N5 . C22 . 1.462(6) yes
N5 . C21 . 1.416(6) yes
N6 . H6 . 1.001 no
N6 . C24 . 1.471(5) yes
N6 . C23 . 1.463(6) yes
C1 . C51 . 1.544(5) yes
C1 . C41 . 1.540(5) yes
C1 . C31 . 1.531(5) yes
C2 . C81 . 1.537(5) yes
C2 . C71 . 1.547(5) yes
C2 . C61 . 1.553(5) yes
C11 . H113 . 0.999 no
C11 . H112 . 0.999 no
C11 . H111 . 0.998 no
C12 . H123 . 0.999 no
C12 . H122 . 1.003 no
C12 . H121 . 0.999 no
C13 . H133 . 1.004 no
C13 . H132 . 1.000 no
C13 . H131 . 0.997 no
C14 . H143 . 0.999 no
C14 . H142 . 1.001 no
C14 . H141 . 1.001 no
C21 . H213 . 0.998 no
C21 . H212 . 0.999 no
C21 . H211 . 1.003 no
C22 . H223 . 1.000 no
C22 . H222 . 0.998 no
C22 . H221 . 1.003 no
C23 . H233 . 0.998 no
C23 . H232 . 1.002 no
C23 . H231 . 1.002 no
C24 . H243 . 1.002 no
C24 . H242 . 0.999 no
C24 . H241 . 1.000 no
C31 . C36 . 1.400(5) yes
C31 . C32 . 1.404(5) yes
C32 . H321 . 0.998 no
C32 . C33 . 1.387(6) yes
C33 . H331 . 1.002 no
C33 . C34 . 1.396(6) yes
C34 . H341 . 1.000 no
C34 . C35 . 1.372(6) yes
C35 . H351 . 1.002 no
C35 . C36 . 1.387(6) yes
C36 . H361 . 1.002 no
C41 . C46 . 1.397(5) yes
C41 . C42 . 1.383(5) yes
C42 . H421 . 1.001 no
C42 . C43 . 1.397(6) yes
C43 . H431 . 1.003 no
C43 . C44 . 1.382(6) yes
C44 . H441 . 1.003 no
C44 . C45 . 1.374(6) yes
C45 . H451 . 0.999 no
C45 . C46 . 1.391(6) yes
C46 . H461 . 0.999 no
C51 . C56 . 1.386(6) yes
C51 . C52 . 1.387(5) yes
C52 . H521 . 0.999 no
C52 . C53 . 1.398(6) yes
C53 . H531 . 1.003 no
C53 . C54 . 1.372(7) yes
C54 . H541 . 0.998 no
C54 . C55 . 1.381(6) yes
C55 . H551 . 1.001 no
C55 . C56 . 1.396(6) yes
C56 . H561 . 0.999 no
C61 . C66 . 1.399(5) yes
C61 . C62 . 1.387(5) yes
C62 . H621 . 1.000 no
C62 . C63 . 1.381(5) yes
C63 . H631 . 1.003 no
C63 . C64 . 1.374(6) yes
C64 . H641 . 1.001 no
C64 . C65 . 1.381(6) yes
C65 . H651 . 1.001 no
C65 . C66 . 1.387(5) yes
C66 . H661 . 1.000 no
C71 . C76 . 1.390(5) yes
C71 . C72 . 1.373(5) yes
C72 . H721 . 0.999 no
C72 . C73 . 1.398(6) yes
C73 . H731 . 0.999 no
C73 . C74 . 1.376(7) yes
C74 . H741 . 0.999 no
C74 . C75 . 1.383(6) yes
C75 . H751 . 1.002 no
C75 . C76 . 1.389(6) yes
C76 . H761 . 1.001 no
C81 . C86 . 1.394(5) yes
C81 . C82 . 1.399(5) yes
C82 . H821 . 1.002 no
C82 . C83 . 1.372(6) yes
C83 . H831 . 1.003 no
C83 . C84 . 1.392(6) yes
C84 . H841 . 1.002 no
C84 . C85 . 1.380(6) yes
C85 . H851 . 0.998 no
C85 . C86 . 1.382(6) yes
C86 . H861 . 0.999 no
C90 . H903 . 1.000 no
C90 . H902 . 0.999 no
C90 . H901 . 1.002 no
C90 . C91 . 1.490(7) yes
C91 . C96 . 1.375(7) yes
C91 . C92 . 1.400(7) yes
C92 . H921 . 1.000 no
C92 . C93 . 1.390(7) yes
C93 . H931 . 1.003 no
C93 . C94 . 1.364(7) yes
C94 . H941 . 0.998 no
C94 . C95 . 1.388(7) yes
C95 . H951 . 1.001 no
C95 . C96 . 1.384(7) yes
C96 . H961 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 . V1 . N2 . 160.39(12) yes
N3 . V1 . N1 . 101.02(14) yes
N2 . V1 . N1 . 98.41(13) yes
N3 . V1 . Cl2 . 87.68(10) yes
N2 . V1 . Cl2 . 87.54(8) yes
N1 . V1 . Cl2 . 112.04(11) yes
N3 . V1 . Cl1 . 85.01(10) yes
N2 . V1 . Cl1 . 86.22(9) yes
N1 . V1 . Cl1 . 108.76(11) yes
Cl2 . V1 . Cl1 . 139.19(5) yes
N6 . V2 . N5 . 160.74(13) yes
N6 . V2 . N4 . 99.85(14) yes
N5 . V2 . N4 . 99.16(14) yes
N6 . V2 . Cl4 . 86.34(9) yes
N5 . V2 . Cl4 . 89.38(11) yes
N4 . V2 . Cl4 . 111.99(11) yes
N6 . V2 . Cl3 . 84.03(9) yes
N5 . V2 . Cl3 . 86.83(11) yes
N4 . V2 . Cl3 . 109.35(11) yes
Cl4 . V2 . Cl3 . 138.56(5) yes
C1 . N1 . V1 . 177.1(3) yes
H2 . N2 . C12 . 108.338 no
H2 . N2 . C11 . 106.887 no
C12 . N2 . C11 . 109.7(3) yes
H2 . N2 . V1 . 100.725 no
C12 . N2 . V1 . 114.4(3) yes
C11 . N2 . V1 . 115.8(2) yes
H3 . N3 . C14 . 109.946 no
H3 . N3 . C13 . 101.482 no
C14 . N3 . C13 . 111.3(3) yes
H3 . N3 . V1 . 98.335 no
C14 . N3 . V1 . 113.8(3) yes
C13 . N3 . V1 . 119.9(3) yes
C2 . N4 . V2 . 175.2(3) yes
H5 . N5 . C22 . 111.340 no
H5 . N5 . C21 . 96.885 no
C22 . N5 . C21 . 112.5(4) yes
H5 . N5 . V2 . 92.833 no
C22 . N5 . V2 . 115.1(3) yes
C21 . N5 . V2 . 123.4(3) yes
H6 . N6 . C24 . 108.549 no
H6 . N6 . C23 . 106.578 no
C24 . N6 . C23 . 109.6(3) yes
H6 . N6 . V2 . 100.780 no
C24 . N6 . V2 . 114.4(3) yes
C23 . N6 . V2 . 116.1(3) yes
C51 . C1 . C41 . 110.2(3) yes
C51 . C1 . C31 . 111.9(3) yes
C41 . C1 . C31 . 111.3(3) yes
C51 . C1 . N1 . 108.2(3) yes
C41 . C1 . N1 . 108.5(3) yes
C31 . C1 . N1 . 106.6(3) yes
C81 . C2 . C71 . 113.1(3) yes
C81 . C2 . C61 . 108.0(3) yes
C71 . C2 . C61 . 111.2(3) yes
C81 . C2 . N4 . 107.7(3) yes
C71 . C2 . N4 . 107.3(3) yes
C61 . C2 . N4 . 109.4(3) yes
H113 . C11 . H112 . 109.636 no
H113 . C11 . H111 . 109.703 no
H112 . C11 . H111 . 109.705 no
H113 . C11 . N2 . 109.283 no
H112 . C11 . N2 . 109.207 no
H111 . C11 . N2 . 109.291 no
H123 . C12 . H122 . 109.357 no
H123 . C12 . H121 . 109.646 no
H122 . C12 . H121 . 109.356 no
H123 . C12 . N2 . 109.585 no
H122 . C12 . N2 . 109.290 no
H121 . C12 . N2 . 109.594 no
H133 . C13 . H132 . 109.182 no
H133 . C13 . H131 . 109.417 no
H132 . C13 . H131 . 109.742 no
H133 . C13 . N3 . 109.245 no
H132 . C13 . N3 . 109.568 no
H131 . C13 . N3 . 109.672 no
H143 . C14 . H142 . 109.479 no
H143 . C14 . H141 . 109.517 no
H142 . C14 . H141 . 109.337 no
H143 . C14 . N3 . 109.568 no
H142 . C14 . N3 . 109.504 no
H141 . C14 . N3 . 109.421 no
H213 . C21 . H212 . 109.744 no
H213 . C21 . H211 . 109.383 no
H212 . C21 . H211 . 109.271 no
H213 . C21 . N5 . 109.643 no
H212 . C21 . N5 . 109.479 no
H211 . C21 . N5 . 109.305 no
H223 . C22 . H222 . 109.657 no
H223 . C22 . H221 . 109.295 no
H222 . C22 . H221 . 109.404 no
H223 . C22 . N5 . 109.567 no
H222 . C22 . N5 . 109.577 no
H221 . C22 . N5 . 109.326 no
H233 . C23 . H232 . 109.449 no
H233 . C23 . H231 . 109.510 no
H232 . C23 . H231 . 109.165 no
H233 . C23 . N6 . 109.675 no
H232 . C23 . N6 . 109.491 no
H231 . C23 . N6 . 109.536 no
H243 . C24 . H242 . 109.406 no
H243 . C24 . H241 . 109.323 no
H242 . C24 . H241 . 109.540 no
H243 . C24 . N6 . 109.380 no
H242 . C24 . N6 . 109.624 no
H241 . C24 . N6 . 109.554 no
C36 . C31 . C32 . 117.9(4) yes
C36 . C31 . C1 . 118.6(3) yes
C32 . C31 . C1 . 123.3(3) yes
H321 . C32 . C33 . 119.925 no
H321 . C32 . C31 . 119.467 no
C33 . C32 . C31 . 120.6(4) yes
H331 . C33 . C34 . 119.977 no
H331 . C33 . C32 . 119.709 no
C34 . C33 . C32 . 120.3(4) yes
H341 . C34 . C35 . 120.456 no
H341 . C34 . C33 . 120.015 no
C35 . C34 . C33 . 119.5(4) yes
H351 . C35 . C36 . 119.838 no
H351 . C35 . C34 . 119.617 no
C36 . C35 . C34 . 120.5(4) yes
H361 . C36 . C35 . 119.538 no
H361 . C36 . C31 . 119.395 no
C35 . C36 . C31 . 121.1(4) yes
C46 . C41 . C42 . 118.1(3) yes
C46 . C41 . C1 . 120.2(3) yes
C42 . C41 . C1 . 121.7(3) yes
H421 . C42 . C43 . 119.731 no
H421 . C42 . C41 . 119.333 no
C43 . C42 . C41 . 120.9(4) yes
H431 . C43 . C44 . 119.846 no
H431 . C43 . C42 . 119.924 no
C44 . C43 . C42 . 120.2(4) yes
H441 . C44 . C45 . 119.996 no
H441 . C44 . C43 . 120.544 no
C45 . C44 . C43 . 119.5(4) yes
H451 . C45 . C46 . 119.747 no
H451 . C45 . C44 . 119.796 no
C46 . C45 . C44 . 120.5(4) yes
H461 . C46 . C45 . 119.660 no
H461 . C46 . C41 . 119.493 no
C45 . C46 . C41 . 120.8(4) yes
C56 . C51 . C52 . 118.7(4) yes
C56 . C51 . C1 . 120.1(3) yes
C52 . C51 . C1 . 121.1(3) yes
H521 . C52 . C53 . 119.588 no
H521 . C52 . C51 . 119.786 no
C53 . C52 . C51 . 120.6(4) yes
H531 . C53 . C54 . 120.048 no
H531 . C53 . C52 . 120.115 no
C54 . C53 . C52 . 119.8(4) yes
H541 . C54 . C55 . 119.613 no
H541 . C54 . C53 . 119.946 no
C55 . C54 . C53 . 120.4(4) yes
H551 . C55 . C56 . 120.131 no
H551 . C55 . C54 . 120.268 no
C56 . C55 . C54 . 119.6(4) yes
H561 . C56 . C51 . 119.662 no
H561 . C56 . C55 . 119.579 no
C51 . C56 . C55 . 120.8(4) yes
C66 . C61 . C62 . 118.8(3) yes
C66 . C61 . C2 . 118.6(3) yes
C62 . C61 . C2 . 122.7(3) yes
H621 . C62 . C63 . 119.935 no
H621 . C62 . C61 . 119.464 no
C63 . C62 . C61 . 120.6(3) yes
H631 . C63 . C64 . 119.837 no
H631 . C63 . C62 . 119.530 no
C64 . C63 . C62 . 120.6(4) yes
H641 . C64 . C65 . 120.368 no
H641 . C64 . C63 . 120.096 no
C65 . C64 . C63 . 119.5(3) yes
H651 . C65 . C66 . 119.721 no
H651 . C65 . C64 . 119.756 no
C66 . C65 . C64 . 120.5(3) yes
H661 . C66 . C65 . 119.971 no
H661 . C66 . C61 . 120.098 no
C65 . C66 . C61 . 119.9(4) yes
C76 . C71 . C72 . 118.9(4) yes
C76 . C71 . C2 . 117.6(3) yes
C72 . C71 . C2 . 123.6(3) yes
H721 . C72 . C73 . 119.598 no
H721 . C72 . C71 . 119.605 no
C73 . C72 . C71 . 120.8(4) yes
H731 . C73 . C74 . 119.942 no
H731 . C73 . C72 . 119.832 no
C74 . C73 . C72 . 120.2(4) yes
H741 . C74 . C75 . 120.499 no
H741 . C74 . C73 . 120.291 no
C75 . C74 . C73 . 119.2(4) yes
H751 . C75 . C76 . 119.961 no
H751 . C75 . C74 . 119.555 no
C76 . C75 . C74 . 120.5(4) yes
H761 . C76 . C75 . 119.942 no
H761 . C76 . C71 . 119.668 no
C75 . C76 . C71 . 120.4(4) yes
C86 . C81 . C82 . 118.4(4) yes
C86 . C81 . C2 . 122.7(3) yes
C82 . C81 . C2 . 118.8(3) yes
H821 . C82 . C83 . 119.489 no
H821 . C82 . C81 . 119.356 no
C83 . C82 . C81 . 121.2(4) yes
H831 . C83 . C84 . 120.169 no
H831 . C83 . C82 . 119.987 no
C84 . C83 . C82 . 119.8(4) yes
H841 . C84 . C85 . 119.950 no
H841 . C84 . C83 . 120.419 no
C85 . C84 . C83 . 119.6(4) yes
H851 . C85 . C86 . 119.707 no
H851 . C85 . C84 . 119.636 no
C86 . C85 . C84 . 120.7(4) yes
H861 . C86 . C85 . 119.632 no
H861 . C86 . C81 . 120.095 no
C85 . C86 . C81 . 120.3(4) yes
H903 . C90 . H902 . 109.542 no
H903 . C90 . H901 . 109.335 no
H902 . C90 . H901 . 109.400 no
H903 . C90 . C91 . 109.591 no
H902 . C90 . C91 . 109.427 no
H901 . C90 . C91 . 109.532 no
C96 . C91 . C92 . 117.1(4) yes
C96 . C91 . C90 . 121.2(5) yes
C92 . C91 . C90 . 121.6(5) yes
H921 . C92 . C93 . 119.841 no
H921 . C92 . C91 . 119.853 no
C93 . C92 . C91 . 120.3(5) yes
H931 . C93 . C94 . 119.336 no
H931 . C93 . C92 . 119.123 no
C94 . C93 . C92 . 121.5(5) yes
H941 . C94 . C95 . 120.668 no
H941 . C94 . C93 . 120.564 no
C95 . C94 . C93 . 118.8(5) yes
H951 . C95 . C96 . 120.008 no
H951 . C95 . C94 . 120.295 no
C96 . C95 . C94 . 119.7(5) yes
H961 . C96 . C91 . 118.846 no
H961 . C96 . C95 . 118.626 no
C91 . C96 . C95 . 122.5(5) yes
####################################################################### 
# 
# 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_CL2425
_database_code_depnum_ccdc_archive 'CCDC 1940735'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_date             2019-07-05T17:04:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C25 H27 Cl1.50 N1.50 V0.50'
_chemical_formula_weight         427.12

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   13.7831(5)
_cell_length_b                   12.4060(5)
_cell_length_c                   25.9963(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.2650(10)
_cell_angle_gamma                90
_cell_volume                     4418.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#




_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1796


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_number            43482
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             4516
_reflns_number_gt                4313
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2016/4
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+4.6825P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4516
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.074
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
V V 0.3005 0.5294 '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'

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 0.5 1.07593(13) 0.75 0.0122(3) Uani 1 2 d S T P . .
C2 C 0.48489(8) 1.01959(10) 0.70239(4) 0.0125(2) Uani 1 1 d . . . . .
C3 C 0.48405(8) 0.90749(10) 0.70299(5) 0.0138(2) Uani 1 1 d . . . . .
H3 H 0.472675 0.868166 0.671549 0.017 Uiso 1 1 calc R U . . .
C4 C 0.5 0.85355(13) 0.75 0.0140(3) Uani 1 2 d S T P . .
C5 C 0.47510(9) 1.08518(9) 0.65277(4) 0.0129(2) Uani 1 1 d . . . . .
H5 H 0.43828 1.15173 0.660365 0.016 Uiso 1 1 calc R U . . .
C6 C 0.57418(9) 1.12369(10) 0.63891(4) 0.0138(2) Uani 1 1 d . . . . .
C7 C 0.66254(9) 1.07777(11) 0.65859(5) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.662917 1.018176 0.681559 0.023 Uiso 1 1 calc R U . . .
C8 C 0.75070(10) 1.11831(12) 0.64495(6) 0.0238(3) Uani 1 1 d . . . . .
H8 H 0.810517 1.086155 0.65871 0.029 Uiso 1 1 calc R U . . .
C9 C 0.75152(10) 1.20499(11) 0.61152(5) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.811555 1.233154 0.602599 0.026 Uiso 1 1 calc R U . . .
C10 C 0.66338(10) 1.25038(11) 0.59116(5) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.663128 1.309257 0.567782 0.027 Uiso 1 1 calc R U . . .
C11 C 0.57581(10) 1.21018(11) 0.60478(5) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.516099 1.242043 0.590647 0.022 Uiso 1 1 calc R U . . .
C12 C 0.41525(9) 1.03094(9) 0.60730(5) 0.0131(2) Uani 1 1 d . . . . .
C13 C 0.31469(9) 1.04829(10) 0.60024(5) 0.0164(2) Uani 1 1 d . . . . .
H13 H 0.285017 1.091466 0.624333 0.02 Uiso 1 1 calc R U . . .
C14 C 0.25734(10) 1.00329(11) 0.55843(5) 0.0204(3) Uani 1 1 d . . . . .
H14 H 0.189002 1.01619 0.553944 0.024 Uiso 1 1 calc R U . . .
C15 C 0.29994(10) 0.93945(10) 0.52322(5) 0.0197(3) Uani 1 1 d . . . . .
H15 H 0.260943 0.908456 0.494617 0.024 Uiso 1 1 calc R U . . .
C16 C 0.39980(10) 0.92119(11) 0.53006(5) 0.0200(3) Uani 1 1 d . . . . .
H16 H 0.429169 0.877177 0.506171 0.024 Uiso 1 1 calc R U . . .
C17 C 0.45713(9) 0.96701(10) 0.57173(5) 0.0173(3) Uani 1 1 d . . . . .
H17 H 0.525543 0.954526 0.575936 0.021 Uiso 1 1 calc R U . . .
C18 C 0.72103(10) 1.27765(12) 0.75788(6) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.782271 1.280358 0.74198 0.039 Uiso 1 1 calc R U . . .
H18B H 0.700937 1.202402 0.761111 0.039 Uiso 1 1 calc R U . . .
H18C H 0.730646 1.310845 0.792263 0.039 Uiso 1 1 calc R U . . .
C19 C 0.67741(11) 1.44843(12) 0.71612(6) 0.0292(3) Uani 1 1 d . . . . .
H19A H 0.679869 1.489549 0.748424 0.044 Uiso 1 1 calc R U . . .
H19B H 0.631614 1.482967 0.689658 0.044 Uiso 1 1 calc R U . . .
H19C H 0.742546 1.446477 0.704342 0.044 Uiso 1 1 calc R U . . .
C20 C 0.63547(10) 0.75763(11) 0.56933(5) 0.0212(3) Uani 1 1 d . . . . .
C21 C 0.59795(10) 0.71442(11) 0.61268(5) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.624659 0.736448 0.646265 0.026 Uiso 1 1 calc R U . . .
C22 C 0.52252(10) 0.64004(12) 0.60760(6) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.497841 0.611762 0.637539 0.03 Uiso 1 1 calc R U . . .
C23 C 0.48300(11) 0.60682(12) 0.55875(6) 0.0286(3) Uani 1 1 d . . . . .
H23 H 0.431752 0.555263 0.555082 0.034 Uiso 1 1 calc R U . . .
C24 C 0.51907(11) 0.64964(12) 0.51536(6) 0.0295(3) Uani 1 1 d . . . . .
H24 H 0.492296 0.62741 0.481812 0.035 Uiso 1 1 calc R U . . .
C25 C 0.59410(11) 0.72482(12) 0.52072(5) 0.0259(3) Uani 1 1 d . . . . .
H25 H 0.617518 0.75428 0.490682 0.031 Uiso 1 1 calc R U . . .
C26 C 0.71901(11) 0.83616(13) 0.57555(7) 0.0309(3) Uani 1 1 d . . . . .
H26A H 0.778191 0.799111 0.590613 0.046 Uiso 1 1 calc R U . . .
H26B H 0.703548 0.895011 0.598444 0.046 Uiso 1 1 calc R U . . .
H26C H 0.729729 0.865552 0.541636 0.046 Uiso 1 1 calc R U . . .
CL1 Cl 0.43991(2) 1.39778(3) 0.67226(2) 0.02087(9) Uani 1 1 d . . . . .
CL2 Cl 0.5 0.71258(3) 0.75 0.01816(10) Uani 1 2 d S T P . .
V1 V 0.5 1.32172(2) 0.75 0.01253(8) Uani 1 2 d S T P . .
N1 N 0.5 1.18707(12) 0.75 0.0139(3) Uani 1 2 d S T P . .
N2 N 0.64445(8) 1.33704(9) 0.72509(5) 0.0188(2) Uani 1 1 d . . . . .
H2 H 0.6386(13) 1.3055(14) 0.6958(7) 0.027(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.379(2) . ?
C1 C2 1.4170(14) 2_656 ?
C1 C2 1.4170(14) . ?
C2 C3 1.3908(17) . ?
C2 C5 1.5187(16) . ?
C3 C4 1.3897(14) . ?
C4 C3 1.3896(14) 2_656 ?
C4 CL2 1.7488(17) . ?
C5 C12 1.5223(16) . ?
C5 C6 1.5266(16) . ?
C6 C7 1.3905(18) . ?
C6 C11 1.3940(17) . ?
C7 C8 1.3962(19) . ?
C8 C9 1.383(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.3872(19) . ?
C12 C17 1.3906(17) . ?
C12 C13 1.3948(17) . ?
C13 C14 1.3893(18) . ?
C14 C15 1.388(2) . ?
C15 C16 1.3870(19) . ?
C16 C17 1.3908(18) . ?
C18 N2 1.4789(17) . ?
C19 N2 1.4811(18) . ?
C20 C25 1.390(2) . ?
C20 C21 1.3970(19) . ?
C20 C26 1.503(2) . ?
C21 C22 1.386(2) . ?
C22 C23 1.389(2) . ?
C23 C24 1.387(2) . ?
C24 C25 1.388(2) . ?
CL1 V1 2.3012(3) . ?
V1 N1 1.6705(15) . ?
V1 N2 2.1681(11) 2_656 ?
V1 N2 2.1681(11) . ?
V1 CL1 2.3013(3) 2_656 ?

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
N1 C1 C2 119.56(8) . 2_656 ?
N1 C1 C2 119.56(8) . . ?
C2 C1 C2 120.88(15) 2_656 . ?
C3 C2 C1 118.95(11) . . ?
C3 C2 C5 123.04(11) . . ?
C1 C2 C5 117.94(11) . . ?
C4 C3 C2 119.38(11) . . ?
C3 C4 C3 122.43(16) 2_656 . ?
C3 C4 CL2 118.79(8) 2_656 . ?
C3 C4 CL2 118.79(8) . . ?
C2 C5 C12 114.39(10) . . ?
C2 C5 C6 111.67(10) . . ?
C12 C5 C6 112.21(10) . . ?
C7 C6 C11 118.38(12) . . ?
C7 C6 C5 123.71(11) . . ?
C11 C6 C5 117.91(11) . . ?
C6 C7 C8 120.70(12) . . ?
C9 C8 C7 120.43(12) . . ?
C8 C9 C10 119.16(12) . . ?
C11 C10 C9 120.38(12) . . ?
C10 C11 C6 120.93(12) . . ?
C17 C12 C13 118.62(11) . . ?
C17 C12 C5 122.63(11) . . ?
C13 C12 C5 118.72(11) . . ?
C14 C13 C12 120.89(12) . . ?
C15 C14 C13 119.97(12) . . ?
C16 C15 C14 119.60(12) . . ?
C15 C16 C17 120.30(12) . . ?
C12 C17 C16 120.61(12) . . ?
C25 C20 C21 118.02(13) . . ?
C25 C20 C26 121.41(13) . . ?
C21 C20 C26 120.57(13) . . ?
C22 C21 C20 121.24(13) . . ?
C21 C22 C23 120.01(14) . . ?
C24 C23 C22 119.37(14) . . ?
C23 C24 C25 120.32(14) . . ?
C24 C25 C20 121.02(14) . . ?
N1 V1 N2 95.03(3) . 2_656 ?
N1 V1 N2 95.03(3) . . ?
N2 V1 N2 169.95(6) 2_656 . ?
N1 V1 CL1 114.208(10) . . ?
N2 V1 CL1 88.40(3) 2_656 . ?
N2 V1 CL1 87.48(3) . . ?
N1 V1 CL1 114.207(10) . 2_656 ?
N2 V1 CL1 87.48(3) 2_656 2_656 ?
N2 V1 CL1 88.40(3) . 2_656 ?
CL1 V1 CL1 131.58(2) . 2_656 ?
C1 N1 V1 180 . . ?
C18 N2 C19 110.10(11) . . ?
C18 N2 V1 113.90(9) . . ?
C19 N2 V1 115.86(9) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_CL2482
_database_code_depnum_ccdc_archive 'CCDC 1940736'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_date             2019-07-05T16:52:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C47 H39 Cl3 N4 V'
_chemical_formula_sum            'C47 H39 Cl3 N4 V'
_chemical_formula_weight         817.11

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.343(3)
_cell_length_b                   12.699(3)
_cell_length_c                   18.845(5)
_cell_angle_alpha                94.699(9)
_cell_angle_beta                 97.476(7)
_cell_angle_gamma                94.983(8)
_cell_volume                     2198.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             846

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_number            51790
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.095
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             8947
_reflns_number_gt                7803
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2016/4
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0801P)²+1.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8947
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_all         0.0477
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.123

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.6274(2) 0.26871(15) 0.25653(10) 0.0109(4) Uani 1 1 d . . . . .
C2 C 0.6499(2) 0.20256(16) 0.31358(10) 0.0123(4) Uani 1 1 d . . . . .
C3 C 0.5765(2) 0.10151(16) 0.30616(11) 0.0148(4) Uani 1 1 d . . . . .
H3 H 0.589593 0.05698 0.344134 0.018 Uiso 1 1 calc R U . . .
C4 C 0.4847(2) 0.06549(16) 0.24388(12) 0.0165(4) Uani 1 1 d . . . . .
C5 C 0.4644(2) 0.12753(16) 0.18704(11) 0.0153(4) Uani 1 1 d . . . . .
H5 H 0.401928 0.100549 0.144383 0.018 Uiso 1 1 calc R U . . .
C6 C 0.5354(2) 0.22936(16) 0.19231(10) 0.0121(4) Uani 1 1 d . . . . .
C7 C 0.5222(2) 0.29610(15) 0.12851(10) 0.0120(4) Uani 1 1 d . . . . .
H7 H 0.586677 0.363401 0.143547 0.014 Uiso 1 1 calc R U . . .
C8 C 0.3713(2) 0.32805(16) 0.10515(11) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.3551(3) 0.3906(2) 0.04730(13) 0.0269(5) Uani 1 1 d . . . . .
H9 H 0.43672 0.410075 0.024268 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2224(3) 0.4243(2) 0.02322(16) 0.0382(7) Uani 1 1 d . . . . .
H10 H 0.21289 0.465892 -0.016493 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1029(3) 0.3975(2) 0.05700(15) 0.0340(6) Uani 1 1 d . . . . .
H11 H 0.011681 0.421363 0.040978 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1174(3) 0.3359(2) 0.11412(13) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.035682 0.317385 0.137362 0.03 Uiso 1 1 calc R U . . .
C13 C 0.2505(2) 0.30075(18) 0.13783(12) 0.0184(4) Uani 1 1 d . . . . .
H13 H 0.258828 0.257646 0.176767 0.022 Uiso 1 1 calc R U . . .
C14 C 0.5825(2) 0.24011(16) 0.06602(10) 0.0125(4) Uani 1 1 d . . . . .
C15 C 0.4984(2) 0.16224(16) 0.01852(11) 0.0172(4) Uani 1 1 d . . . . .
H15 H 0.399248 0.145177 0.023198 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5598(3) 0.10919(18) -0.03601(12) 0.0276(6) Uani 1 1 d . . . . .
H16 H 0.502235 0.055508 -0.068006 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7031(3) 0.1338(2) -0.04400(13) 0.0313(6) Uani 1 1 d . . . . .
H17 H 0.744656 0.09658 -0.080794 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7853(3) 0.2125(2) 0.00175(13) 0.0291(6) Uani 1 1 d . . . . .
H18 H 0.883493 0.230619 -0.004245 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7268(2) 0.26595(19) 0.05660(12) 0.0200(5) Uani 1 1 d . . . . .
H19 H 0.784954 0.320244 0.087832 0.024 Uiso 1 1 calc R U . . .
C20 C 0.7557(2) 0.23926(15) 0.38104(10) 0.0124(4) Uani 1 1 d . . . . .
H20 H 0.766331 0.318639 0.384811 0.015 Uiso 1 1 calc R U . . .
C21 C 0.6916(2) 0.20718(16) 0.44756(11) 0.0129(4) Uani 1 1 d . . . . .
C22 C 0.7209(2) 0.11438(16) 0.47941(11) 0.0160(4) Uani 1 1 d . . . . .
H22 H 0.784981 0.069123 0.460156 0.019 Uiso 1 1 calc R U . . .
C23 C 0.6572(2) 0.08773(18) 0.53898(12) 0.0205(5) Uani 1 1 d . . . . .
H23 H 0.676562 0.023781 0.559618 0.025 Uiso 1 1 calc R U . . .
C24 C 0.5657(2) 0.15371(19) 0.56840(12) 0.0210(5) Uani 1 1 d . . . . .
H24 H 0.524163 0.136163 0.609835 0.025 Uiso 1 1 calc R U . . .
C25 C 0.5349(2) 0.24611(18) 0.53689(12) 0.0200(5) Uani 1 1 d . . . . .
H25 H 0.471681 0.291594 0.55662 0.024 Uiso 1 1 calc R U . . .
C26 C 0.5966(2) 0.27158(16) 0.47685(11) 0.0163(4) Uani 1 1 d . . . . .
H26 H 0.573685 0.3341 0.455191 0.02 Uiso 1 1 calc R U . . .
C27 C 0.9070(2) 0.20424(16) 0.37686(11) 0.0146(4) Uani 1 1 d . . . . .
C28 C 0.9485(2) 0.16101(17) 0.31332(12) 0.0189(4) Uani 1 1 d . . . . .
H28 H 0.879486 0.148837 0.271077 0.023 Uiso 1 1 calc R U . . .
C29 C 1.0897(3) 0.13533(18) 0.31069(14) 0.0241(5) Uani 1 1 d . . . . .
H29 H 1.11605 0.105837 0.266826 0.029 Uiso 1 1 calc R U . . .
C30 C 1.1920(3) 0.15257(19) 0.37177(15) 0.0267(5) Uani 1 1 d . . . . .
H30 H 1.288632 0.135615 0.369932 0.032 Uiso 1 1 calc R U . . .
C31 C 1.1517(3) 0.1949(2) 0.43557(14) 0.0257(5) Uani 1 1 d . . . . .
H31 H 1.220642 0.20606 0.477852 0.031 Uiso 1 1 calc R U . . .
C32 C 1.0113(2) 0.22090(18) 0.43798(12) 0.0200(5) Uani 1 1 d . . . . .
H32 H 0.985541 0.250588 0.481925 0.024 Uiso 1 1 calc R U . . .
C33 C 0.4344(2) 0.53471(17) 0.24211(12) 0.0181(4) Uani 1 1 d . . . . .
H33 H 0.42715 0.490252 0.279909 0.022 Uiso 1 1 calc R U . . .
C34 C 0.3090(2) 0.56987(19) 0.20871(14) 0.0244(5) Uani 1 1 d . . . . .
H34 H 0.21787 0.549772 0.223441 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3179(3) 0.6345(2) 0.15370(14) 0.0283(5) Uani 1 1 d . . . . .
H35 H 0.233408 0.66003 0.130092 0.034 Uiso 1 1 calc R U . . .
C36 C 0.4528(3) 0.6613(2) 0.13376(14) 0.0266(5) Uani 1 1 d . . . . .
H36 H 0.462397 0.705555 0.096064 0.032 Uiso 1 1 calc R U . . .
C37 C 0.5730(2) 0.62287(17) 0.16928(12) 0.0196(4) Uani 1 1 d . . . . .
H37 H 0.664842 0.641232 0.154792 0.023 Uiso 1 1 calc R U . . .
C38 C 1.0081(2) 0.52992(17) 0.40655(11) 0.0160(4) Uani 1 1 d . . . . .
H38 H 0.943233 0.57102 0.428901 0.019 Uiso 1 1 calc R U . . .
C39 C 1.1452(2) 0.52522(18) 0.44258(12) 0.0202(5) Uani 1 1 d . . . . .
H39 H 1.1739 0.562839 0.488629 0.024 Uiso 1 1 calc R U . . .
C40 C 1.2406(2) 0.46522(19) 0.41104(13) 0.0221(5) Uani 1 1 d . . . . .
H40 H 1.336384 0.462043 0.43442 0.027 Uiso 1 1 calc R U . . .
C41 C 1.1935(2) 0.40999(17) 0.34472(12) 0.0187(4) Uani 1 1 d . . . . .
H41 H 1.255766 0.366735 0.322165 0.022 Uiso 1 1 calc R U . . .
C42 C 1.0545(2) 0.41845(16) 0.31154(11) 0.0151(4) Uani 1 1 d . . . . .
H42 H 1.022904 0.380003 0.265997 0.018 Uiso 1 1 calc R U . . .
C43 C 0.7513(2) 0.74815(17) 0.33350(12) 0.0178(4) Uani 1 1 d . . . . .
H43 H 0.651414 0.725685 0.332973 0.021 Uiso 1 1 calc R U . . .
C44 C 0.8019(3) 0.85119(18) 0.36069(13) 0.0243(5) Uani 1 1 d . . . . .
H44 H 0.737722 0.898146 0.378029 0.029 Uiso 1 1 calc R U . . .
C45 C 0.9469(3) 0.88464(18) 0.36220(14) 0.0274(5) Uani 1 1 d . . . . .
H45 H 0.985135 0.954239 0.38179 0.033 Uiso 1 1 calc R U . . .
C46 C 1.0345(3) 0.81488(19) 0.33470(14) 0.0259(5) Uani 1 1 d . . . . .
H46 H 1.134479 0.835969 0.334324 0.031 Uiso 1 1 calc R U . . .
C47 C 0.9761(2) 0.71394(17) 0.30764(12) 0.0185(4) Uani 1 1 d . . . . .
H47 H 1.037503 0.667028 0.287824 0.022 Uiso 1 1 calc R U . . .
N1 N 0.69400(17) 0.37088(13) 0.26391(9) 0.0115(3) Uani 1 1 d . . . . .
N2 N 0.56655(18) 0.56072(13) 0.22341(9) 0.0134(3) Uani 1 1 d . . . . .
N3 N 0.83615(19) 0.67871(13) 0.30795(9) 0.0141(3) Uani 1 1 d . . . . .
N4 N 0.96206(18) 0.47871(13) 0.34095(9) 0.0131(3) Uani 1 1 d . . . . .
CL1 Cl 0.87906(5) 0.51942(4) 0.17795(3) 0.01536(12) Uani 1 1 d . . . . .
CL2 Cl 0.65250(5) 0.52384(4) 0.39004(3) 0.01439(12) Uani 1 1 d . . . . .
CL3 Cl 0.39589(7) -0.06232(4) 0.23732(3) 0.02847(15) Uani 1 1 d . . . . .
V1 V 0.75576(3) 0.50041(2) 0.27997(2) 0.00989(10) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.378(3) . ?
C1 C6 1.417(3) . ?
C1 C2 1.423(3) . ?
C2 C3 1.389(3) . ?
C2 C20 1.519(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.95 . ?
C4 C5 1.384(3) . ?
C4 CL3 1.745(2) . ?
C5 C6 1.391(3) . ?
C5 H5 0.95 . ?
C6 C7 1.525(3) . ?
C7 C8 1.521(3) . ?
C7 C14 1.521(3) . ?
C7 H7 1 . ?
C8 C13 1.386(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.95 . ?
C10 C11 1.386(4) . ?
C10 H10 0.95 . ?
C11 C12 1.381(4) . ?
C11 H11 0.95 . ?
C12 C13 1.389(3) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 C15 1.390(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.95 . ?
C16 C17 1.378(4) . ?
C16 H16 0.95 . ?
C17 C18 1.373(4) . ?
C17 H17 0.95 . ?
C18 C19 1.387(3) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C27 1.527(3) . ?
C20 C21 1.528(3) . ?
C20 H20 1 . ?
C21 C26 1.393(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.95 . ?
C23 C24 1.382(3) . ?
C23 H23 0.95 . ?
C24 C25 1.393(3) . ?
C24 H24 0.95 . ?
C25 C26 1.383(3) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.392(3) . ?
C27 C32 1.398(3) . ?
C28 C29 1.392(3) . ?
C28 H28 0.95 . ?
C29 C30 1.387(4) . ?
C29 H29 0.95 . ?
C30 C31 1.387(4) . ?
C30 H30 0.95 . ?
C31 C32 1.385(3) . ?
C31 H31 0.95 . ?
C32 H32 0.95 . ?
C33 N2 1.349(3) . ?
C33 C34 1.383(3) . ?
C33 H33 0.95 . ?
C34 C35 1.380(3) . ?
C34 H34 0.95 . ?
C35 C36 1.383(3) . ?
C35 H35 0.95 . ?
C36 C37 1.378(3) . ?
C36 H36 0.95 . ?
C37 N2 1.344(3) . ?
C37 H37 0.95 . ?
C38 N4 1.348(3) . ?
C38 C39 1.378(3) . ?
C38 H38 0.95 . ?
C39 C40 1.382(3) . ?
C39 H39 0.95 . ?
C40 C41 1.381(3) . ?
C40 H40 0.95 . ?
C41 C42 1.383(3) . ?
C41 H41 0.95 . ?
C42 N4 1.345(3) . ?
C42 H42 0.95 . ?
C43 N3 1.338(3) . ?
C43 C44 1.385(3) . ?
C43 H43 0.95 . ?
C44 C45 1.380(4) . ?
C44 H44 0.95 . ?
C45 C46 1.373(4) . ?
C45 H45 0.95 . ?
C46 C47 1.379(3) . ?
C46 H46 0.95 . ?
C47 N3 1.345(3) . ?
C47 H47 0.95 . ?
N1 V1 1.6847(17) . ?
N2 V1 2.1740(18) . ?
N3 V1 2.3184(18) . ?
N4 V1 2.1631(18) . ?
CL1 V1 2.3844(8) . ?
CL2 V1 2.4066(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 120.12(17) . . ?
N1 C1 C2 120.11(17) . . ?
C6 C1 C2 119.76(17) . . ?
C3 C2 C1 119.07(18) . . ?
C3 C2 C20 119.70(18) . . ?
C1 C2 C20 121.20(17) . . ?
C4 C3 C2 120.30(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.50(19) . . ?
C3 C4 CL3 118.37(16) . . ?
C5 C4 CL3 120.12(16) . . ?
C4 C5 C6 120.06(19) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 119.26(18) . . ?
C5 C6 C7 120.77(18) . . ?
C1 C6 C7 119.88(17) . . ?
C8 C7 C14 111.33(16) . . ?
C8 C7 C6 115.50(17) . . ?
C14 C7 C6 109.52(16) . . ?
C8 C7 H7 106.7 . . ?
C14 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C13 C8 C9 118.3(2) . . ?
C13 C8 C7 124.43(19) . . ?
C9 C8 C7 117.22(19) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.5(2) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C19 118.87(19) . . ?
C15 C14 C7 121.72(18) . . ?
C19 C14 C7 119.40(18) . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C2 C20 C27 112.74(16) . . ?
C2 C20 C21 110.24(16) . . ?
C27 C20 C21 113.52(16) . . ?
C2 C20 H20 106.6 . . ?
C27 C20 H20 106.6 . . ?
C21 C20 H20 106.6 . . ?
C26 C21 C22 118.31(19) . . ?
C26 C21 C20 118.76(18) . . ?
C22 C21 C20 122.91(18) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120 . . ?
C24 C25 H25 120 . . ?
C25 C26 C21 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C28 C27 C32 117.9(2) . . ?
C28 C27 C20 122.65(19) . . ?
C32 C27 C20 119.34(19) . . ?
C27 C28 C29 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.2(2) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C27 121.1(2) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
N2 C33 C34 122.9(2) . . ?
N2 C33 H33 118.5 . . ?
C34 C33 H33 118.5 . . ?
C35 C34 C33 119.2(2) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 118.4(2) . . ?
C34 C35 H35 120.8 . . ?
C36 C35 H35 120.8 . . ?
C37 C36 C35 119.2(2) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
N2 C37 C36 123.2(2) . . ?
N2 C37 H37 118.4 . . ?
C36 C37 H37 118.4 . . ?
N4 C38 C39 122.8(2) . . ?
N4 C38 H38 118.6 . . ?
C39 C38 H38 118.6 . . ?
C38 C39 C40 119.3(2) . . ?
C38 C39 H39 120.3 . . ?
C40 C39 H39 120.3 . . ?
C41 C40 C39 118.4(2) . . ?
C41 C40 H40 120.8 . . ?
C39 C40 H40 120.8 . . ?
C40 C41 C42 119.2(2) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
N4 C42 C41 122.9(2) . . ?
N4 C42 H42 118.6 . . ?
C41 C42 H42 118.6 . . ?
N3 C43 C44 123.2(2) . . ?
N3 C43 H43 118.4 . . ?
C44 C43 H43 118.4 . . ?
C45 C44 C43 119.0(2) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C46 C45 C44 118.4(2) . . ?
C46 C45 H45 120.8 . . ?
C44 C45 H45 120.8 . . ?
C45 C46 C47 119.4(2) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
N3 C47 C46 123.1(2) . . ?
N3 C47 H47 118.4 . . ?
C46 C47 H47 118.4 . . ?
C1 N1 V1 171.54(15) . . ?
C37 N2 C33 117.07(18) . . ?
C37 N2 V1 123.43(14) . . ?
C33 N2 V1 119.50(14) . . ?
C43 N3 C47 116.89(18) . . ?
C43 N3 V1 121.78(14) . . ?
C47 N3 V1 120.82(14) . . ?
C42 N4 C38 117.33(18) . . ?
C42 N4 V1 120.05(14) . . ?
C38 N4 V1 122.44(14) . . ?
N1 V1 N4 96.86(7) . . ?
N1 V1 N2 96.36(7) . . ?
N4 V1 N2 166.78(6) . . ?
N1 V1 N3 176.93(7) . . ?
N4 V1 N3 82.86(6) . . ?
N2 V1 N3 83.94(6) . . ?
N1 V1 CL1 99.39(6) . . ?
N4 V1 CL1 88.05(5) . . ?
N2 V1 CL1 89.81(5) . . ?
N3 V1 CL1 83.66(5) . . ?
N1 V1 CL2 93.94(6) . . ?
N4 V1 CL2 89.86(5) . . ?
N2 V1 CL2 89.22(5) . . ?
N3 V1 CL2 83.01(5) . . ?
CL1 V1 CL2 166.66(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C50 H501 C5 0.96 2.52 3.383(3) 149 . . 1_655 yes
C15 H151 C56 0.96 2.46 3.328(3) 151 . . 2_655 yes

