# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1405386'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.1825(10)
_cell_length_b                   9.7365(13)
_cell_length_c                   27.817(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 94.452(10)
_cell_angle_gamma                90.0
_cell_volume                     3019.5(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
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

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'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C32 H39 B1 F2 N8 
# Dc =      1.29 Fooo =   1208.00 Mu =      0.87 M =    584.52
# Found Formula = C31 H37 B1 F2 N8 
# Dc =      1.25 FOOO =   1208.00 Mu =      0.86 M =    570.50

_chemical_formula_sum            'C31 H37 B1 F2 N8'
_chemical_formula_moiety         'C31 H37 B1 F2 N8'
_chemical_compound_source        ?
_chemical_formula_weight         570.50


_cell_measurement_reflns_used    3019
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.099
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_max          0.331

_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.086

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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      293
_diffrn_reflns_number            16283
_reflns_number_total             7122
_diffrn_reflns_av_R_equivalents  0.087
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7122 
# Theoretical number of reflections is about 15940 


_diffrn_reflns_theta_min         2.777
_diffrn_reflns_theta_max         29.417
_diffrn_measured_fraction_theta_max 0.951

_diffrn_reflns_theta_full        25.004
_diffrn_measured_fraction_theta_full 0.981


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.63


# 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 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     2
_refine_ls_number_parameters     379
_oxford_refine_ls_R_factor_ref   0.0782
_refine_ls_wR_factor_ref         0.0839
_refine_ls_goodness_of_fit_ref   1.0809
_refine_ls_shift/su_max          0.0002010
_refine_ls_shift/su_mean         0.0000166


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7105
_refine_ls_R_factor_all          0.1582
_refine_ls_wR_factor_all         0.1026

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3613
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_gt          0.0854

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #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: 
 8.04 5.58 6.16 1.55 
;

# 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
F1 F 0.2258(2) 0.3941(2) 0.69025(9) 0.0619 1.0000 Uani . . . . . .
B2 B 0.1832(4) 0.2756(5) 0.66786(17) 0.0459 1.0000 Uani . . . . . .
F3 F 0.27875(18) 0.2044(3) 0.64984(8) 0.0588 1.0000 Uani . . . . . .
N4 N 0.1235(3) 0.1844(4) 0.70522(11) 0.0489 1.0000 Uani . . . . . .
C5 C 0.0011(3) 0.1508(4) 0.70201(15) 0.0502 1.0000 Uani . . . . . .
C6 C -0.0736(3) 0.1880(4) 0.66208(16) 0.0518 1.0000 Uani . . . . . .
C7 C -0.0294(3) 0.2612(4) 0.62394(16) 0.0519 1.0000 Uani . . . . . .
N8 N 0.0897(3) 0.3073(3) 0.62656(12) 0.0500 1.0000 Uani . . . . . .
C9 C 0.1054(3) 0.3699(4) 0.58399(16) 0.0552 1.0000 Uani . . . . . .
C10 C 0.2135(3) 0.4401(5) 0.57101(15) 0.0550 1.0000 Uani . . . . . .
C11 C 0.3231(4) 0.4686(5) 0.59341(15) 0.0537 1.0000 Uani . . . . . .
N12 N 0.3799(3) 0.5421(4) 0.56138(13) 0.0613 1.0000 Uani . . . . . .
N13 N 0.3107(3) 0.5589(5) 0.52080(15) 0.0810 1.0000 Uani . . . . . .
N14 N 0.2086(3) 0.4979(5) 0.52614(14) 0.0781 1.0000 Uani . . . . . .
C15 C 0.5029(4) 0.5939(6) 0.56559(18) 0.0741 1.0000 Uani . . . . . .
C16 C 0.5164(5) 0.7254(7) 0.5381(3) 0.1049 1.0000 Uani . . . . . .
C17 C 0.6430(5) 0.7773(7) 0.5405(2) 0.1051 1.0000 Uani . . . . . .
C18 C 0.6639(7) 0.8925(9) 0.5048(4) 0.1588 1.0000 Uani . . . . . .
C19 C 0.7936(8) 0.9413(11) 0.5067(4) 0.1727 1.0000 Uani D . . . . .
C20 C 0.8133(11) 1.0447(13) 0.4681(4) 0.2245 1.0000 Uani D . . . . .
C21 C 0.0000(4) 0.3634(5) 0.55424(17) 0.0702 1.0000 Uani . . . . . .
C22 C -0.0834(4) 0.2958(5) 0.57866(17) 0.0663 1.0000 Uani . . . . . .
C23 C -0.2028(3) 0.1479(5) 0.65779(16) 0.0547 1.0000 Uani . . . . . .
C24 C -0.2383(4) 0.0128(5) 0.66509(17) 0.0608 1.0000 Uani . . . . . .
C25 C -0.3576(4) -0.0229(5) 0.65831(19) 0.0712 1.0000 Uani . . . . . .
C26 C -0.4430(4) 0.0730(6) 0.64534(19) 0.0723 1.0000 Uani . . . . . .
C27 C -0.4092(4) 0.2070(6) 0.6395(2) 0.0750 1.0000 Uani . . . . . .
C28 C -0.2903(4) 0.2458(5) 0.64586(18) 0.0649 1.0000 Uani . . . . . .
C29 C -0.0213(4) 0.0765(5) 0.74363(17) 0.0624 1.0000 Uani . . . . . .
C30 C 0.0847(4) 0.0623(6) 0.77085(17) 0.0700 1.0000 Uani . . . . . .
C31 C 0.1736(3) 0.1298(5) 0.74662(15) 0.0533 1.0000 Uani . . . . . .
C32 C 0.3002(3) 0.1303(5) 0.76261(15) 0.0556 1.0000 Uani . . . . . .
C33 C 0.3996(4) 0.1952(5) 0.74739(15) 0.0581 1.0000 Uani . . . . . .
N34 N 0.4922(3) 0.1477(4) 0.77557(13) 0.0642 1.0000 Uani . . . . . .
C35 C 0.6193(4) 0.1841(6) 0.77722(17) 0.0684 1.0000 Uani . . . . . .
C36 C 0.6465(5) 0.3031(7) 0.8115(2) 0.0935 1.0000 Uani . . . . . .
C37 C 0.7729(5) 0.3406(7) 0.8173(2) 0.1146 1.0000 Uani D . . . . .
C38 C 0.8449(5) 0.2457(7) 0.8537(3) 0.1155 1.0000 Uani D . . . . .
C39 C 0.9729(6) 0.2986(9) 0.8637(3) 0.1332 1.0000 Uani . . . . . .
C40 C 1.0383(7) 0.2024(10) 0.8955(3) 0.1419 1.0000 Uani . . . . . .
N41 N 0.4550(4) 0.0586(6) 0.80799(17) 0.0953 1.0000 Uani . . . . . .
N42 N 0.3374(4) 0.0498(6) 0.79981(16) 0.0950 1.0000 Uani . . . . . .
H111 H 0.3557 0.4412 0.6254 0.0733 1.0000 Uiso . . . . . .
H152 H 0.5301 0.6097 0.6003 0.0973 1.0000 Uiso . . . . . .
H151 H 0.5588 0.5247 0.5541 0.0973 1.0000 Uiso . . . . . .
H162 H 0.4642 0.7951 0.5511 0.1322 1.0000 Uiso . . . . . .
H161 H 0.4865 0.7083 0.5040 0.1323 1.0000 Uiso . . . . . .
H172 H 0.6651 0.8104 0.5738 0.1375 1.0000 Uiso . . . . . .
H171 H 0.6967 0.6988 0.5348 0.1372 1.0000 Uiso . . . . . .
H182 H 0.6123 0.9739 0.5107 0.1892 1.0000 Uiso . . . . . .
H181 H 0.6402 0.8637 0.4709 0.1891 1.0000 Uiso . . . . . .
H191 H 0.8138 0.9832 0.5395 0.2042 1.0000 Uiso . . . . . .
H192 H 0.8493 0.8633 0.5043 0.2043 1.0000 Uiso . . . . . .
H202 H 0.8985 1.0631 0.4691 0.3341 1.0000 Uiso . . . . . .
H203 H 0.7684 1.1251 0.4778 0.3342 1.0000 Uiso . . . . . .
H201 H 0.7801 1.0065 0.4389 0.3342 1.0000 Uiso . . . . . .
H211 H -0.0137 0.4031 0.5218 0.0923 1.0000 Uiso . . . . . .
H221 H -0.1639 0.2733 0.5663 0.0853 1.0000 Uiso . . . . . .
H241 H -0.1782 -0.0548 0.6759 0.0774 1.0000 Uiso . . . . . .
H251 H -0.3807 -0.1175 0.6636 0.0917 1.0000 Uiso . . . . . .
H261 H -0.5275 0.0471 0.6394 0.0953 1.0000 Uiso . . . . . .
H271 H -0.4698 0.2736 0.6299 0.0977 1.0000 Uiso . . . . . .
H281 H -0.2677 0.3418 0.6421 0.0865 1.0000 Uiso . . . . . .
H291 H -0.0979 0.0396 0.7513 0.0816 1.0000 Uiso . . . . . .
H301 H 0.1002 0.0138 0.8015 0.0908 1.0000 Uiso . . . . . .
H331 H 0.4026 0.2623 0.7207 0.0767 1.0000 Uiso . . . . . .
H351 H 0.6701 0.1032 0.7880 0.0923 1.0000 Uiso . . . . . .
H352 H 0.6387 0.2120 0.7445 0.0926 1.0000 Uiso . . . . . .
H361 H 0.6193 0.2786 0.8432 0.1212 1.0000 Uiso . . . . . .
H362 H 0.5985 0.3843 0.7989 0.1216 1.0000 Uiso . . . . . .
H372 H 0.7836 0.4348 0.8321 0.1505 1.0000 Uiso . . . . . .
H371 H 0.8123 0.3351 0.7876 0.1505 1.0000 Uiso . . . . . .
H382 H 0.8025 0.2537 0.8857 0.1592 1.0000 Uiso . . . . . .
H381 H 0.8431 0.1539 0.8431 0.1595 1.0000 Uiso . . . . . .
H392 H 0.9685 0.3920 0.8816 0.1802 1.0000 Uiso . . . . . .
H391 H 1.0082 0.3150 0.8344 0.1802 1.0000 Uiso . . . . . .
H402 H 1.1205 0.2274 0.9017 0.2160 1.0000 Uiso . . . . . .
H401 H 1.0006 0.1959 0.9264 0.2160 1.0000 Uiso . . . . . .
H403 H 1.0325 0.1117 0.8806 0.2162 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.003(7)
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
F1 . B2 . 1.378(5) yes
B2 . F3 . 1.399(5) yes
B2 . N4 . 1.556(6) yes
B2 . N8 . 1.524(6) yes
N4 . C5 . 1.403(5) yes
N4 . C31 . 1.350(5) yes
C5 . C6 . 1.385(6) yes
C5 . C29 . 1.404(6) yes
C6 . C7 . 1.400(6) yes
C6 . C23 . 1.492(5) yes
C7 . N8 . 1.402(5) yes
C7 . C22 . 1.395(6) yes
N8 . C9 . 1.355(5) yes
C9 . C10 . 1.459(6) yes
C9 . C21 . 1.388(6) yes
C10 . C11 . 1.360(6) yes
C10 . N14 . 1.366(5) yes
C11 . N12 . 1.341(5) yes
C11 . H111 . 0.972 no
N12 . N13 . 1.328(5) yes
N12 . C15 . 1.461(6) yes
N13 . N14 . 1.306(5) yes
C15 . C16 . 1.504(8) yes
C15 . H152 . 1.002 no
C15 . H151 . 0.989 no
C16 . C17 . 1.500(7) yes
C16 . H162 . 0.982 no
C16 . H161 . 0.996 no
C17 . C18 . 1.527(10) yes
C17 . H172 . 0.995 no
C17 . H171 . 0.992 no
C18 . C19 . 1.523(10) yes
C18 . H182 . 1.001 no
C18 . H181 . 1.000 no
C19 . C20 . 1.4999(11) yes
C19 . H191 . 1.007 no
C19 . H192 . 0.988 no
C20 . H202 . 0.967 no
C20 . H203 . 0.979 no
C20 . H201 . 0.943 no
C21 . C22 . 1.365(6) yes
C21 . H211 . 0.982 no
C22 . H221 . 0.963 no
C23 . C24 . 1.394(6) yes
C23 . C28 . 1.388(6) yes
C24 . C25 . 1.378(6) yes
C24 . H241 . 0.972 no
C25 . C26 . 1.364(7) yes
C25 . H251 . 0.971 no
C26 . C27 . 1.371(7) yes
C26 . H261 . 0.980 no
C27 . C28 . 1.380(6) yes
C27 . H271 . 0.962 no
C28 . H281 . 0.975 no
C29 . C30 . 1.363(6) yes
C29 . H291 . 0.969 no
C30 . C31 . 1.407(6) yes
C30 . H301 . 0.978 no
C31 . C32 . 1.451(6) yes
C32 . C33 . 1.373(6) yes
C32 . N42 . 1.338(6) yes
C33 . N34 . 1.333(5) yes
C33 . H331 . 0.991 no
N34 . C35 . 1.462(6) yes
N34 . N41 . 1.341(6) yes
C35 . C36 . 1.516(8) yes
C35 . H351 . 1.003 no
C35 . H352 . 0.989 no
C36 . C37 . 1.456(8) yes
C36 . H361 . 0.984 no
C36 . H362 . 1.004 no
C37 . C38 . 1.5488(11) yes
C37 . H372 . 1.009 no
C37 . H371 . 0.968 no
C38 . C39 . 1.526(8) yes
C38 . H382 . 1.044 no
C38 . H381 . 0.942 no
C39 . C40 . 1.446(11) yes
C39 . H392 . 1.040 no
C39 . H391 . 0.947 no
C40 . H402 . 0.953 no
C40 . H401 . 0.988 no
C40 . H403 . 0.975 no
N41 . N42 . 1.319(6) yes
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
F1 . B2 . F3 . 109.3(3) yes
F1 . B2 . N4 . 109.1(3) yes
F3 . B2 . N4 . 109.6(3) yes
F1 . B2 . N8 . 111.4(3) yes
F3 . B2 . N8 . 109.2(3) yes
N4 . B2 . N8 . 108.3(3) yes
B2 . N4 . C5 . 123.9(3) yes
B2 . N4 . C31 . 128.6(3) yes
C5 . N4 . C31 . 107.5(3) yes
N4 . C5 . C6 . 121.0(4) yes
N4 . C5 . C29 . 107.7(4) yes
C6 . C5 . C29 . 131.4(4) yes
C5 . C6 . C7 . 121.0(3) yes
C5 . C6 . C23 . 121.0(4) yes
C7 . C6 . C23 . 118.0(4) yes
C6 . C7 . N8 . 120.9(4) yes
C6 . C7 . C22 . 130.8(4) yes
N8 . C7 . C22 . 108.2(4) yes
C7 . N8 . B2 . 124.6(3) yes
C7 . N8 . C9 . 106.6(3) yes
B2 . N8 . C9 . 128.5(3) yes
N8 . C9 . C10 . 126.4(4) yes
N8 . C9 . C21 . 109.8(3) yes
C10 . C9 . C21 . 123.8(4) yes
C9 . C10 . C11 . 135.8(4) yes
C9 . C10 . N14 . 116.4(4) yes
C11 . C10 . N14 . 107.8(4) yes
C10 . C11 . N12 . 105.1(4) yes
C10 . C11 . H111 . 128.6 no
N12 . C11 . H111 . 126.3 no
C11 . N12 . N13 . 110.8(3) yes
C11 . N12 . C15 . 128.5(4) yes
N13 . N12 . C15 . 120.6(4) yes
N12 . N13 . N14 . 107.7(4) yes
C10 . N14 . N13 . 108.5(4) yes
N12 . C15 . C16 . 112.6(4) yes
N12 . C15 . H152 . 110.1 no
C16 . C15 . H152 . 108.9 no
N12 . C15 . H151 . 110.7 no
C16 . C15 . H151 . 109.0 no
H152 . C15 . H151 . 105.4 no
C15 . C16 . C17 . 113.3(5) yes
C15 . C16 . H162 . 108.4 no
C17 . C16 . H162 . 109.7 no
C15 . C16 . H161 . 107.6 no
C17 . C16 . H161 . 110.1 no
H162 . C16 . H161 . 107.5 no
C16 . C17 . C18 . 114.3(6) yes
C16 . C17 . H172 . 108.4 no
C18 . C17 . H172 . 109.2 no
C16 . C17 . H171 . 108.3 no
C18 . C17 . H171 . 109.7 no
H172 . C17 . H171 . 106.8 no
C17 . C18 . C19 . 113.6(7) yes
C17 . C18 . H182 . 110.9 no
C19 . C18 . H182 . 107.9 no
C17 . C18 . H181 . 111.3 no
C19 . C18 . H181 . 107.6 no
H182 . C18 . H181 . 105.1 no
C18 . C19 . C20 . 112.2(8) yes
C18 . C19 . H191 . 107.6 no
C20 . C19 . H191 . 109.9 no
C18 . C19 . H192 . 111.1 no
C20 . C19 . H192 . 109.8 no
H191 . C19 . H192 . 105.9 no
C19 . C20 . H202 . 107.6 no
C19 . C20 . H203 . 103.4 no
H202 . C20 . H203 . 111.7 no
C19 . C20 . H201 . 106.4 no
H202 . C20 . H201 . 114.7 no
H203 . C20 . H201 . 112.1 no
C9 . C21 . C22 . 107.9(4) yes
C9 . C21 . H211 . 126.5 no
C22 . C21 . H211 . 125.6 no
C7 . C22 . C21 . 107.5(4) yes
C7 . C22 . H221 . 126.5 no
C21 . C22 . H221 . 125.9 no
C6 . C23 . C24 . 121.4(4) yes
C6 . C23 . C28 . 120.0(4) yes
C24 . C23 . C28 . 118.6(4) yes
C23 . C24 . C25 . 120.1(4) yes
C23 . C24 . H241 . 119.1 no
C25 . C24 . H241 . 120.7 no
C24 . C25 . C26 . 121.0(4) yes
C24 . C25 . H251 . 119.0 no
C26 . C25 . H251 . 120.0 no
C25 . C26 . C27 . 119.2(4) yes
C25 . C26 . H261 . 121.0 no
C27 . C26 . H261 . 119.8 no
C26 . C27 . C28 . 121.2(4) yes
C26 . C27 . H271 . 118.6 no
C28 . C27 . H271 . 120.1 no
C23 . C28 . C27 . 119.8(4) yes
C23 . C28 . H281 . 120.0 no
C27 . C28 . H281 . 120.3 no
C5 . C29 . C30 . 107.9(4) yes
C5 . C29 . H291 . 126.2 no
C30 . C29 . H291 . 125.9 no
C29 . C30 . C31 . 107.6(4) yes
C29 . C30 . H301 . 128.4 no
C31 . C30 . H301 . 124.0 no
C30 . C31 . N4 . 109.3(3) yes
C30 . C31 . C32 . 124.3(4) yes
N4 . C31 . C32 . 126.2(3) yes
C31 . C32 . C33 . 134.5(4) yes
C31 . C32 . N42 . 118.2(4) yes
C33 . C32 . N42 . 107.3(4) yes
C32 . C33 . N34 . 105.7(4) yes
C32 . C33 . H331 . 127.6 no
N34 . C33 . H331 . 126.7 no
C33 . N34 . C35 . 130.1(4) yes
C33 . N34 . N41 . 110.6(4) yes
C35 . N34 . N41 . 119.2(4) yes
N34 . C35 . C36 . 110.6(4) yes
N34 . C35 . H351 . 110.2 no
C36 . C35 . H351 . 109.4 no
N34 . C35 . H352 . 108.6 no
C36 . C35 . H352 . 108.7 no
H351 . C35 . H352 . 109.3 no
C35 . C36 . C37 . 114.0(5) yes
C35 . C36 . H361 . 108.5 no
C37 . C36 . H361 . 109.0 no
C35 . C36 . H362 . 107.8 no
C37 . C36 . H362 . 109.2 no
H361 . C36 . H362 . 108.1 no
C36 . C37 . C38 . 112.0(5) yes
C36 . C37 . H372 . 110.9 no
C38 . C37 . H372 . 103.6 no
C36 . C37 . H371 . 113.2 no
C38 . C37 . H371 . 106.0 no
H372 . C37 . H371 . 110.6 no
C37 . C38 . C39 . 110.6(6) yes
C37 . C38 . H382 . 105.4 no
C39 . C38 . H382 . 107.5 no
C37 . C38 . H381 . 111.3 no
C39 . C38 . H381 . 112.0 no
H382 . C38 . H381 . 109.8 no
C38 . C39 . C40 . 108.5(6) yes
C38 . C39 . H392 . 107.7 no
C40 . C39 . H392 . 108.3 no
C38 . C39 . H391 . 110.3 no
C40 . C39 . H391 . 114.2 no
H392 . C39 . H391 . 107.6 no
C39 . C40 . H402 . 112.4 no
C39 . C40 . H401 . 110.1 no
H402 . C40 . H401 . 109.2 no
C39 . C40 . H403 . 108.2 no
H402 . C40 . H403 . 109.8 no
H401 . C40 . H403 . 107.0 no
N34 . N41 . N42 . 106.5(4) yes
C32 . N42 . N41 . 110.0(4) yes
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
C15 . H152 . N41 3_656 155.7 1.002 2.591 3.528(8) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 11/12/14 at 10:06:31
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 11/12/14 at 10:06:31
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.500000 , 0.001000 = C(19) TO C(20) 
DISTANCE 1.550000 , 0.001000 = C(37) TO C(38) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-6 1 3 x .
