# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_46
_database_code_depnum_ccdc_archive 'CCDC 1455157'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_publcif_datablock.id            {70db1702-5fa0-41f6-aea6-2633e7588848}

_cell_length_a                   12.1284(4)
_cell_length_b                   15.8117(6)
_cell_length_c                   17.2351(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.641(2)
_cell_angle_gamma                90
_cell_volume                     3237.2(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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 C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C37 H40 F2 N4 O2 
# Dc =      1.25 Fooo =   1296.00 Mu =      0.86 M =    610.75
# Found Formula = C37 H40 F2 N4 O2 
# Dc =      1.25 FOOO =   1296.00 Mu =      0.86 M =    610.75

_chemical_formula_sum            'C37 H40 F2 N4 O2'
_chemical_formula_moiety         'C37 H40 F2 N4 O2'
_chemical_compound_source        ?
_chemical_formula_weight         610.73


_cell_measurement_reflns_used    1524
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    298

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.160

_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.086

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      298
_diffrn_reflns_number            10280
_reflns_number_total             9953
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 9953 
# Theoretical number of reflections is about 26909 


_diffrn_reflns_theta_min         2.959
_diffrn_reflns_theta_max         34.932
_diffrn_measured_fraction_theta_max 0.702

_diffrn_reflns_theta_full        25.151
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -17
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.24


# 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>2.0\s(I)
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_number_parameters     406
_oxford_refine_ls_R_factor_ref   0.0519
_refine_ls_wR_factor_ref         0.0931
_refine_ls_goodness_of_fit_ref   1.0970
_refine_ls_shift/su_max          0.0002078
_refine_ls_shift/su_mean         0.0000311


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        9953
_refine_ls_R_factor_all          0.4053
_refine_ls_wR_factor_all         0.1331

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4135
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_gt          0.0931

# 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 Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #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: 
 233. -115. 98.2 -22.2 -119. 
;

# 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
C1 C -0.1322(4) -0.0776(3) -0.7018(3) 0.0414 1.0000 Uani . . . . . .
C2 C -0.1175(4) -0.1461(3) -0.7607(3) 0.0468 1.0000 Uani . . . . . .
C3 C -0.1812(4) -0.2140(3) -0.7894(3) 0.0541 1.0000 Uani . . . . . .
C4 C -0.1433(5) -0.2710(3) -0.8403(3) 0.0667 1.0000 Uani . . . . . .
C5 C -0.0410(5) -0.2582(4) -0.8596(3) 0.0820 1.0000 Uani . . . . . .
C6 C 0.0277(5) -0.1926(4) -0.8289(4) 0.0840 1.0000 Uani . . . . . .
C7 C -0.0115(4) -0.1370(3) -0.7789(3) 0.0547 1.0000 Uani . . . . . .
C8 C 0.1561(5) -0.0358(4) -0.7486(4) 0.0889 1.0000 Uani . . . . . .
C9 C 0.2833(6) -0.1515(5) -0.7062(4) 0.1002 1.0000 Uani . . . . . .
C10 C 0.4003(6) -0.1749(6) -0.6649(5) 0.1173 1.0000 Uani . . . . . .
C11 C 0.4237(7) -0.1474(7) -0.5791(5) 0.1454 1.0000 Uani . . . . . .
C12 C 0.3906(6) -0.0562(7) -0.5738(4) 0.1385 1.0000 Uani . . . . . .
C13 C 0.2730(6) -0.0399(5) -0.6162(4) 0.1115 1.0000 Uani . . . . . .
C14 C -0.0166(4) -0.0316(3) -0.6882(3) 0.0528 1.0000 Uani . . . . . .
C15 C -0.0674(6) -0.1667(4) -0.5846(3) 0.0859 1.0000 Uani . . . . . .
C16 C -0.1979(5) -0.0488(3) -0.5857(3) 0.0693 1.0000 Uani . . . . . .
C17 C -0.2772(4) 0.0025(3) -0.6489(3) 0.0512 1.0000 Uani . . . . . .
C18 C -0.2952(4) 0.0932(3) -0.6274(3) 0.0557 1.0000 Uani . . . . . .
C19 C -0.2112(4) 0.1415(3) -0.5824(3) 0.0605 1.0000 Uani . . . . . .
C20 C -0.2310(5) 0.2246(4) -0.5626(3) 0.0705 1.0000 Uani . . . . . .
C21 C -0.3339(6) 0.2596(4) -0.5927(4) 0.0848 1.0000 Uani . . . . . .
C22 C -0.4168(6) 0.2162(4) -0.6390(4) 0.0863 1.0000 Uani . . . . . .
C23 C -0.3989(5) 0.1308(4) -0.6557(3) 0.0721 1.0000 Uani . . . . . .
C24 C -0.2320(4) -0.0122(3) -0.7274(2) 0.0395 1.0000 Uani . . . . . .
C25 C -0.3233(4) -0.0541(3) -0.7905(3) 0.0482 1.0000 Uani . . . . . .
C26 C -0.3133(4) -0.0441(3) -0.8749(3) 0.0434 1.0000 Uani . . . . . .
C27 C -0.3615(4) -0.1026(3) -0.9264(3) 0.0530 1.0000 Uani . . . . . .
C28 C -0.3593(4) -0.1093(3) -1.0115(3) 0.0502 1.0000 Uani . . . . . .
C29 C -0.3789(4) -0.0419(3) -1.0635(3) 0.0560 1.0000 Uani . . . . . .
C30 C -0.3722(4) -0.0506(3) -1.1432(3) 0.0599 1.0000 Uani . . . . . .
C31 C -0.3479(4) -0.1280(3) -1.1681(3) 0.0558 1.0000 Uani . . . . . .
C32 C -0.3292(5) -0.1969(3) -1.1214(3) 0.0691 1.0000 Uani . . . . . .
C33 C -0.3363(5) -0.1880(3) -1.0426(3) 0.0655 1.0000 Uani . . . . . .
C34 C -0.2432(4) 0.0271(3) -0.8980(3) 0.0590 1.0000 Uani . . . . . .
C35 C -0.1964(4) 0.0692(3) -0.7635(3) 0.0454 1.0000 Uani . . . . . .
C36 C -0.0803(5) 0.1173(3) -0.8561(3) 0.0659 1.0000 Uani . . . . . .
C37 C -0.0181(5) 0.0922(4) -0.9197(3) 0.0811 1.0000 Uani . . . . . .
F1 F -0.3502(4) 0.3422(2) -0.5746(3) 0.1319 1.0000 Uani . . . . . .
F2 F -0.3416(3) -0.1365(2) -1.24649(17) 0.0857 1.0000 Uani . . . . . .
O1 O 0.0134(3) 0.0261(2) -0.6424(2) 0.0772 1.0000 Uani . . . . . .
O2 O -0.3981(3) -0.0964(3) -0.77379(19) 0.0675 1.0000 Uani . . . . . .
N1 N -0.1587(4) -0.1171(2) -0.6305(2) 0.0540 1.0000 Uani . . . . . .
N2 N -0.1493(3) 0.0490(2) -0.8331(2) 0.0507 1.0000 Uani . . . . . .
N3 N 0.0474(3) -0.0708(3) -0.7348(2) 0.0632 1.0000 Uani . . . . . .
N4 N 0.2606(4) -0.0646(3) -0.6985(3) 0.0773 1.0000 Uani . . . . . .
H271 H -0.4014 -0.1443 -0.9029 0.0660 1.0000 Uiso . . . . . .
H171 H -0.3483 -0.0265 -0.6571 0.0660 1.0000 Uiso . . . . . .
H341 H -0.2132 0.0096 -0.9429 0.0740 1.0000 Uiso . . . . . .
H342 H -0.2907 0.0760 -0.9126 0.0740 1.0000 Uiso . . . . . .
H352 H -0.2598 0.1064 -0.7786 0.0600 1.0000 Uiso . . . . . .
H351 H -0.1390 0.0969 -0.7258 0.0600 1.0000 Uiso . . . . . .
H231 H -0.4592 0.0975 -0.6854 0.0890 1.0000 Uiso . . . . . .
H362 H -0.0276 0.1361 -0.8109 0.0780 1.0000 Uiso . . . . . .
H361 H -0.1297 0.1636 -0.8772 0.0780 1.0000 Uiso . . . . . .
H61 H 0.1024 -0.1843 -0.8382 0.1000 1.0000 Uiso . . . . . .
H291 H -0.3972 0.0120 -1.0434 0.0740 1.0000 Uiso . . . . . .
H191 H -0.1391 0.1169 -0.5626 0.0720 1.0000 Uiso . . . . . .
H373 H 0.0255 0.1388 -0.9340 0.1030 1.0000 Uiso . . . . . .
H372 H 0.0315 0.0465 -0.9001 0.1030 1.0000 Uiso . . . . . .
H371 H -0.0706 0.0740 -0.9665 0.1030 1.0000 Uiso . . . . . .
H91 H 0.2749 -0.1635 -0.7613 0.1260 1.0000 Uiso . . . . . .
H92 H 0.2319 -0.1848 -0.6837 0.1260 1.0000 Uiso . . . . . .
H301 H -0.3841 -0.0028 -1.1775 0.0760 1.0000 Uiso . . . . . .
H41 H -0.1912 -0.3177 -0.8610 0.0870 1.0000 Uiso . . . . . .
H31 H -0.2517 -0.2205 -0.7745 0.0690 1.0000 Uiso . . . . . .
H161 H -0.1344 -0.0148 -0.5608 0.0880 1.0000 Uiso . . . . . .
H162 H -0.2328 -0.0725 -0.5454 0.0880 1.0000 Uiso . . . . . .
H82 H 0.1557 0.0245 -0.7412 0.1110 1.0000 Uiso . . . . . .
H81 H 0.1634 -0.0471 -0.8027 0.1110 1.0000 Uiso . . . . . .
H101 H 0.4531 -0.1446 -0.6898 0.1460 1.0000 Uiso . . . . . .
H102 H 0.4140 -0.2344 -0.6678 0.1460 1.0000 Uiso . . . . . .
H151 H -0.0923 -0.1898 -0.5390 0.1050 1.0000 Uiso . . . . . .
H152 H -0.0500 -0.2120 -0.6167 0.1050 1.0000 Uiso . . . . . .
H153 H -0.0041 -0.1314 -0.5677 0.1050 1.0000 Uiso . . . . . .
H221 H -0.4886 0.2418 -0.6598 0.1090 1.0000 Uiso . . . . . .
H201 H -0.1711 0.2556 -0.5295 0.0860 1.0000 Uiso . . . . . .
H331 H -0.3277 -0.2356 -1.0072 0.0820 1.0000 Uiso . . . . . .
H51 H -0.0189 -0.2975 -0.8961 0.1010 1.0000 Uiso . . . . . .
H321 H -0.3109 -0.2498 -1.1428 0.0860 1.0000 Uiso . . . . . .
H122 H 0.4008 -0.0438 -0.5191 0.1610 1.0000 Uiso . . . . . .
H121 H 0.4417 -0.0223 -0.5975 0.1610 1.0000 Uiso . . . . . .
H131 H 0.2200 -0.0723 -0.5923 0.1340 1.0000 Uiso . . . . . .
H132 H 0.2550 0.0186 -0.6145 0.1340 1.0000 Uiso . . . . . .
H111 H 0.5018 -0.1560 -0.5544 0.1780 1.0000 Uiso . . . . . .
H112 H 0.3779 -0.1824 -0.5522 0.1780 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.995(3)
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
C1 . C2 . 1.519(6) yes
C1 . C14 . 1.554(6) yes
C1 . C24 . 1.585(6) yes
C1 . N1 . 1.472(6) yes
C2 . C3 . 1.356(6) yes
C2 . C7 . 1.391(7) yes
C3 . C4 . 1.398(7) yes
C3 . H31 . 0.947 no
C4 . C5 . 1.362(8) yes
C4 . H41 . 0.963 no
C5 . C6 . 1.369(8) yes
C5 . H51 . 0.960 no
C6 . C7 . 1.381(7) yes
C6 . H61 . 0.961 no
C7 . N3 . 1.402(6) yes
C8 . N3 . 1.492(7) yes
C8 . N4 . 1.455(7) yes
C8 . H82 . 0.962 no
C8 . H81 . 0.971 no
C9 . C10 . 1.500(9) yes
C9 . N4 . 1.413(8) yes
C9 . H91 . 0.954 no
C9 . H92 . 0.956 no
C10 . C11 . 1.512(11) yes
C10 . H101 . 0.967 no
C10 . H102 . 0.958 no
C11 . C12 . 1.504(13) yes
C11 . H111 . 0.967 no
C11 . H112 . 0.966 no
C12 . C13 . 1.489(9) yes
C12 . H122 . 0.947 no
C12 . H121 . 0.969 no
C13 . N4 . 1.450(8) yes
C13 . H131 . 0.976 no
C13 . H132 . 0.952 no
C14 . O1 . 1.213(5) yes
C14 . N3 . 1.372(6) yes
C15 . N1 . 1.454(7) yes
C15 . H151 . 0.969 no
C15 . H152 . 0.953 no
C15 . H153 . 0.947 no
C16 . C17 . 1.532(7) yes
C16 . N1 . 1.462(6) yes
C16 . H161 . 0.965 no
C16 . H162 . 0.960 no
C17 . C18 . 1.508(7) yes
C17 . C24 . 1.575(6) yes
C17 . H171 . 0.960 no
C18 . C19 . 1.380(7) yes
C18 . C23 . 1.388(7) yes
C19 . C20 . 1.390(7) yes
C19 . H191 . 0.956 no
C20 . C21 . 1.368(8) yes
C20 . H201 . 0.963 no
C21 . C22 . 1.340(9) yes
C21 . F1 . 1.366(6) yes
C22 . C23 . 1.406(8) yes
C22 . H221 . 0.962 no
C23 . H231 . 0.961 no
C24 . C25 . 1.537(6) yes
C24 . C35 . 1.530(6) yes
C25 . C26 . 1.492(6) yes
C25 . O2 . 1.207(5) yes
C26 . C27 . 1.332(6) yes
C26 . C34 . 1.512(6) yes
C27 . C28 . 1.477(6) yes
C27 . H271 . 0.955 no
C28 . C29 . 1.383(6) yes
C28 . C33 . 1.406(7) yes
C29 . C30 . 1.399(7) yes
C29 . H291 . 0.962 no
C30 . C31 . 1.350(7) yes
C30 . H301 . 0.952 no
C31 . C32 . 1.345(7) yes
C31 . F2 . 1.376(5) yes
C32 . C33 . 1.384(7) yes
C32 . H321 . 0.959 no
C33 . H331 . 0.961 no
C34 . N2 . 1.467(6) yes
C34 . H341 . 0.961 no
C34 . H342 . 0.966 no
C35 . N2 . 1.465(6) yes
C35 . H352 . 0.961 no
C35 . H351 . 0.957 no
C36 . C37 . 1.504(7) yes
C36 . N2 . 1.469(6) yes
C36 . H362 . 0.949 no
C36 . H361 . 0.969 no
C37 . H373 . 0.967 no
C37 . H372 . 0.957 no
C37 . H371 . 0.966 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
C2 . C1 . C14 . 102.2(4) yes
C2 . C1 . C24 . 117.8(4) yes
C14 . C1 . C24 . 110.6(3) yes
C2 . C1 . N1 . 109.2(3) yes
C14 . C1 . N1 . 114.5(4) yes
C24 . C1 . N1 . 103.0(3) yes
C1 . C2 . C3 . 132.4(5) yes
C1 . C2 . C7 . 108.3(4) yes
C3 . C2 . C7 . 118.9(5) yes
C2 . C3 . C4 . 120.3(5) yes
C2 . C3 . H31 . 117.7 no
C4 . C3 . H31 . 122.0 no
C3 . C4 . C5 . 119.2(5) yes
C3 . C4 . H41 . 118.4 no
C5 . C4 . H41 . 122.4 no
C4 . C5 . C6 . 122.1(5) yes
C4 . C5 . H51 . 116.9 no
C6 . C5 . H51 . 121.0 no
C5 . C6 . C7 . 117.7(6) yes
C5 . C6 . H61 . 124.1 no
C7 . C6 . H61 . 118.2 no
C2 . C7 . C6 . 121.7(5) yes
C2 . C7 . N3 . 110.4(4) yes
C6 . C7 . N3 . 127.7(5) yes
N3 . C8 . N4 . 118.7(5) yes
N3 . C8 . H82 . 108.5 no
N4 . C8 . H82 . 105.0 no
N3 . C8 . H81 . 109.8 no
N4 . C8 . H81 . 106.0 no
H82 . C8 . H81 . 108.3 no
C10 . C9 . N4 . 112.3(6) yes
C10 . C9 . H91 . 108.9 no
N4 . C9 . H91 . 107.6 no
C10 . C9 . H92 . 107.7 no
N4 . C9 . H92 . 110.0 no
H91 . C9 . H92 . 110.3 no
C9 . C10 . C11 . 111.5(6) yes
C9 . C10 . H101 . 108.3 no
C11 . C10 . H101 . 106.4 no
C9 . C10 . H102 . 112.0 no
C11 . C10 . H102 . 109.5 no
H101 . C10 . H102 . 109.0 no
C10 . C11 . C12 . 109.6(7) yes
C10 . C11 . H111 . 111.3 no
C12 . C11 . H111 . 111.0 no
C10 . C11 . H112 . 106.9 no
C12 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 108.4 no
C11 . C12 . C13 . 112.2(8) yes
C11 . C12 . H122 . 106.0 no
C13 . C12 . H122 . 111.9 no
C11 . C12 . H121 . 107.7 no
C13 . C12 . H121 . 109.2 no
H122 . C12 . H121 . 109.8 no
C12 . C13 . N4 . 109.5(6) yes
C12 . C13 . H131 . 110.4 no
N4 . C13 . H131 . 109.0 no
C12 . C13 . H132 . 110.8 no
N4 . C13 . H132 . 108.3 no
H131 . C13 . H132 . 108.9 no
C1 . C14 . O1 . 126.4(5) yes
C1 . C14 . N3 . 107.5(4) yes
O1 . C14 . N3 . 126.1(5) yes
N1 . C15 . H151 . 108.5 no
N1 . C15 . H152 . 108.9 no
H151 . C15 . H152 . 109.3 no
N1 . C15 . H153 . 109.3 no
H151 . C15 . H153 . 109.7 no
H152 . C15 . H153 . 111.2 no
C17 . C16 . N1 . 103.9(4) yes
C17 . C16 . H161 . 110.6 no
N1 . C16 . H161 . 109.3 no
C17 . C16 . H162 . 114.6 no
N1 . C16 . H162 . 109.3 no
H161 . C16 . H162 . 109.0 no
C16 . C17 . C18 . 115.4(4) yes
C16 . C17 . C24 . 104.8(4) yes
C18 . C17 . C24 . 116.3(4) yes
C16 . C17 . H171 . 105.6 no
C18 . C17 . H171 . 108.6 no
C24 . C17 . H171 . 105.2 no
C17 . C18 . C19 . 122.5(5) yes
C17 . C18 . C23 . 119.2(5) yes
C19 . C18 . C23 . 118.3(5) yes
C18 . C19 . C20 . 121.1(5) yes
C18 . C19 . H191 . 119.6 no
C20 . C19 . H191 . 119.3 no
C19 . C20 . C21 . 118.6(5) yes
C19 . C20 . H201 . 118.6 no
C21 . C20 . H201 . 122.7 no
C20 . C21 . C22 . 122.4(6) yes
C20 . C21 . F1 . 117.6(6) yes
C22 . C21 . F1 . 120.0(6) yes
C21 . C22 . C23 . 119.1(6) yes
C21 . C22 . H221 . 121.3 no
C23 . C22 . H221 . 119.6 no
C22 . C23 . C18 . 120.4(5) yes
C22 . C23 . H231 . 120.2 no
C18 . C23 . H231 . 119.4 no
C17 . C24 . C1 . 103.7(3) yes
C17 . C24 . C25 . 110.2(4) yes
C1 . C24 . C25 . 108.4(3) yes
C17 . C24 . C35 . 113.6(4) yes
C1 . C24 . C35 . 113.5(3) yes
C25 . C24 . C35 . 107.3(3) yes
C24 . C25 . C26 . 117.1(4) yes
C24 . C25 . O2 . 122.6(4) yes
C26 . C25 . O2 . 120.3(4) yes
C25 . C26 . C27 . 117.7(4) yes
C25 . C26 . C34 . 119.8(4) yes
C27 . C26 . C34 . 122.4(4) yes
C26 . C27 . C28 . 128.2(4) yes
C26 . C27 . H271 . 112.9 no
C28 . C27 . H271 . 118.9 no
C27 . C28 . C29 . 123.6(4) yes
C27 . C28 . C33 . 119.2(5) yes
C29 . C28 . C33 . 117.2(4) yes
C28 . C29 . C30 . 121.6(4) yes
C28 . C29 . H291 . 118.0 no
C30 . C29 . H291 . 120.3 no
C29 . C30 . C31 . 117.4(5) yes
C29 . C30 . H301 . 120.0 no
C31 . C30 . H301 . 122.6 no
C30 . C31 . C32 . 124.4(5) yes
C30 . C31 . F2 . 117.3(5) yes
C32 . C31 . F2 . 118.2(4) yes
C31 . C32 . C33 . 117.9(4) yes
C31 . C32 . H321 . 120.0 no
C33 . C32 . H321 . 122.1 no
C28 . C33 . C32 . 121.3(5) yes
C28 . C33 . H331 . 117.0 no
C32 . C33 . H331 . 121.6 no
C26 . C34 . N2 . 111.5(4) yes
C26 . C34 . H341 . 108.8 no
N2 . C34 . H341 . 108.7 no
C26 . C34 . H342 . 109.1 no
N2 . C34 . H342 . 109.9 no
H341 . C34 . H342 . 108.9 no
C24 . C35 . N2 . 109.8(4) yes
C24 . C35 . H352 . 110.4 no
N2 . C35 . H352 . 109.5 no
C24 . C35 . H351 . 109.6 no
N2 . C35 . H351 . 107.8 no
H352 . C35 . H351 . 109.7 no
C37 . C36 . N2 . 113.5(4) yes
C37 . C36 . H362 . 109.1 no
N2 . C36 . H362 . 109.5 no
C37 . C36 . H361 . 106.8 no
N2 . C36 . H361 . 108.2 no
H362 . C36 . H361 . 109.6 no
C36 . C37 . H373 . 111.4 no
C36 . C37 . H372 . 108.3 no
H373 . C37 . H372 . 109.2 no
C36 . C37 . H371 . 110.1 no
H373 . C37 . H371 . 108.5 no
H372 . C37 . H371 . 109.3 no
C1 . N1 . C16 . 106.0(4) yes
C1 . N1 . C15 . 114.4(4) yes
C16 . N1 . C15 . 113.9(4) yes
C36 . N2 . C34 . 111.4(4) yes
C36 . N2 . C35 . 113.4(4) yes
C34 . N2 . C35 . 107.8(4) yes
C8 . N3 . C7 . 124.1(5) yes
C8 . N3 . C14 . 123.3(5) yes
C7 . N3 . C14 . 111.5(4) yes
C8 . N4 . C13 . 113.7(5) yes
C8 . N4 . C9 . 114.3(5) yes
C13 . N4 . C9 . 111.7(6) 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_48
_database_code_depnum_ccdc_archive 'CCDC 1455158'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_publcif_datablock.id            {45371479-17b6-4498-a490-0931a3e9fb4c}

_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                   12.3371(4)
_cell_length_b                   16.2079(7)
_cell_length_c                   17.0271(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.522(2)
_cell_angle_gamma                90
_cell_volume                     3347.5(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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 C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C38 H42 F2 N4 O2 
# Dc =      1.24 Fooo =   1328.00 Mu =      0.85 M =    624.77
# Found Formula = C38 H42 F2 N4 O2 
# Dc =      1.24 FOOO =   1328.00 Mu =      0.85 M =    624.77

_chemical_formula_sum            'C38 H42 F2 N4 O2'
_chemical_formula_moiety         'C38 H42 F2 N4 O2'
_chemical_compound_source        ?
_chemical_formula_weight         624.76


_cell_measurement_reflns_used    1412
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    298

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.085

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      298
_diffrn_reflns_number            14424
_reflns_number_total             8040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 8040 
# Theoretical number of reflections is about 18063 


_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         29.508
_diffrn_measured_fraction_theta_max 0.862

_diffrn_reflns_theta_full        25.082
_diffrn_measured_fraction_theta_full 0.986


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.24


# 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>2.0\s(I)
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_number_parameters     415
_oxford_refine_ls_R_factor_ref   0.0683
_refine_ls_wR_factor_ref         0.1314
_refine_ls_goodness_of_fit_ref   1.0144
_refine_ls_shift/su_max          0.0001182
_refine_ls_shift/su_mean         0.0000269


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8040
_refine_ls_R_factor_all          0.4516
_refine_ls_wR_factor_all         0.2577

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4203
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_gt          0.1314

# 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 Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #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: 
 477. 468. 455. 175. 
;

# 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 -0.8508(6) -0.1481(3) -0.0834(4) 0.1513 1.0000 Uani . . . . . .
F2 F -0.8628(4) -0.6540(3) -0.7388(3) 0.1099 1.0000 Uani . . . . . .
C1 C -0.6372(6) -0.5643(4) -0.1963(4) 0.0555 1.0000 Uani . . . . . .
C2 C -0.6206(6) -0.6351(4) -0.2511(4) 0.0518 1.0000 Uani . . . . . .
O1 O -0.4900(5) -0.4615(3) -0.1476(4) 0.1088 1.0000 Uani . . . . . .
O2 O -0.8965(4) -0.5839(4) -0.2593(3) 0.0872 1.0000 Uani . . . . . .
C3 C -0.6862(6) -0.7031(5) -0.2746(4) 0.0658 1.0000 Uani . . . . . .
C4 C -0.6474(8) -0.7626(4) -0.3234(5) 0.0791 1.0000 Uani . . . . . .
N1 N -0.6573(6) -0.5950(4) -0.1206(4) 0.0927 1.0000 Uani . . . . . .
N2 N -0.6580(4) -0.4508(3) -0.3363(3) 0.0512 1.0000 Uani . . . . . .
N3 N -0.4589(5) -0.5633(4) -0.2340(4) 0.0714 1.0000 Uani . . . . . .
N4 N -0.2497(5) -0.5612(5) -0.2040(4) 0.0987 1.0000 Uani . . . . . .
C5 C -0.5495(8) -0.7547(6) -0.3442(4) 0.0977 1.0000 Uani . . . . . .
C6 C -0.4803(6) -0.6880(5) -0.3178(5) 0.0837 1.0000 Uani . . . . . .
C7 C -0.5168(6) -0.6299(5) -0.2716(4) 0.0665 1.0000 Uani . . . . . .
C8 C -0.3504(7) -0.5324(5) -0.2546(6) 0.1057 1.0000 Uani . . . . . .
C9 C -0.2278(9) -0.6505(6) -0.2026(6) 0.1244 1.0000 Uani . . . . . .
C10 C -0.1116(8) -0.6687(7) -0.1605(8) 0.1503 1.0000 Uani . . . . . .
C11 C -0.0843(10) -0.6290(8) -0.0824(6) 0.1434 1.0000 Uani . . . . . .
C12 C -0.1186(9) -0.5417(7) -0.0838(7) 0.1328 1.0000 Uani . . . . . .
C13 C -0.2343(8) -0.5274(7) -0.1256(6) 0.1335 1.0000 Uani . . . . . .
C14 C -0.5230(6) -0.5211(5) -0.1893(4) 0.0639 1.0000 Uani . . . . . .
C15 C -0.5663(10) -0.6419(6) -0.0726(5) 0.1315 1.0000 Uani . . . . . .
C16 C -0.6950(10) -0.5272(5) -0.0805(5) 0.1163 1.0000 Uani . . . . . .
C17 C -0.7763(7) -0.4815(5) -0.1432(4) 0.0710 1.0000 Uani . . . . . .
C18 C -0.7911(6) -0.3924(5) -0.1246(4) 0.0641 1.0000 Uani . . . . . .
C19 C -0.7097(6) -0.3426(5) -0.0816(4) 0.0709 1.0000 Uani . . . . . .
C20 C -0.7301(7) -0.2602(6) -0.0681(5) 0.0858 1.0000 Uani . . . . . .
C21 C -0.8323(8) -0.2312(5) -0.0956(5) 0.0809 1.0000 Uani . . . . . .
C22 C -0.9122(8) -0.2767(6) -0.1393(5) 0.1010 1.0000 Uani . . . . . .
C23 C -0.8929(7) -0.3579(5) -0.1514(5) 0.0820 1.0000 Uani . . . . . .
C24 C -0.7351(6) -0.5021(4) -0.2226(4) 0.0549 1.0000 Uani . . . . . .
C25 C -0.8246(6) -0.5450(4) -0.2827(4) 0.0628 1.0000 Uani . . . . . .
C26 C -0.8181(6) -0.5420(4) -0.3687(4) 0.0593 1.0000 Uani . . . . . .
C27 C -0.8694(6) -0.6009(5) -0.4151(4) 0.0665 1.0000 Uani . . . . . .
C28 C -0.8713(5) -0.6111(5) -0.5006(4) 0.0606 1.0000 Uani . . . . . .
C29 C -0.8843(7) -0.5479(5) -0.5563(4) 0.0790 1.0000 Uani . . . . . .
C30 C -0.8836(6) -0.5618(5) -0.6354(4) 0.0694 1.0000 Uani . . . . . .
C31 C -0.8700(6) -0.6414(5) -0.6601(5) 0.0787 1.0000 Uani . . . . . .
C32 C -0.8559(8) -0.7062(6) -0.6102(6) 0.0998 1.0000 Uani . . . . . .
C33 C -0.8566(6) -0.6916(5) -0.5298(5) 0.0802 1.0000 Uani . . . . . .
C34 C -0.7527(5) -0.4746(4) -0.3969(4) 0.0499 1.0000 Uani . . . . . .
C35 C -0.6992(5) -0.4249(4) -0.2647(4) 0.0520 1.0000 Uani . . . . . .
C36 C -0.5892(6) -0.3865(5) -0.3641(4) 0.0693 1.0000 Uani . . . . . .
C37 C -0.5311(7) -0.4210(6) -0.4287(5) 0.0851 1.0000 Uani . . . . . .
C38 C -0.4362(9) -0.3719(7) -0.4405(7) 0.1346 1.0000 Uani . . . . . .
H301 H -0.8934 -0.5185 -0.6715 0.0911 1.0000 Uiso . . . . . .
H291 H -0.8924 -0.4956 -0.5380 0.0973 1.0000 Uiso . . . . . .
H271 H -0.9053 -0.6405 -0.3907 0.0924 1.0000 Uiso . . . . . .
H341 H -0.7253 -0.4939 -0.4439 0.0705 1.0000 Uiso . . . . . .
H342 H -0.7995 -0.4272 -0.4120 0.0705 1.0000 Uiso . . . . . .
H352 H -0.7626 -0.3879 -0.2791 0.0718 1.0000 Uiso . . . . . .
H351 H -0.6411 -0.3979 -0.2284 0.0718 1.0000 Uiso . . . . . .
H171 H -0.8485 -0.5094 -0.1463 0.1010 1.0000 Uiso . . . . . .
H231 H -0.9492 -0.3919 -0.1786 0.1056 1.0000 Uiso . . . . . .
H221 H -0.9810 -0.2550 -0.1596 0.1310 1.0000 Uiso . . . . . .
H201 H -0.6753 -0.2265 -0.0404 0.1235 1.0000 Uiso . . . . . .
H191 H -0.6409 -0.3644 -0.0629 0.0958 1.0000 Uiso . . . . . .
H162 H -0.7283 -0.5452 -0.0356 0.1588 1.0000 Uiso . . . . . .
H161 H -0.6322 -0.4911 -0.0587 0.1588 1.0000 Uiso . . . . . .
H31 H -0.7527 -0.7087 -0.2570 0.0920 1.0000 Uiso . . . . . .
H41 H -0.6930 -0.8084 -0.3406 0.1058 1.0000 Uiso . . . . . .
H51 H -0.5256 -0.7932 -0.3770 0.1443 1.0000 Uiso . . . . . .
H61 H -0.4117 -0.6821 -0.3331 0.1323 1.0000 Uiso . . . . . .
H81 H -0.3500 -0.5518 -0.3088 0.1461 1.0000 Uiso . . . . . .
H82 H -0.3526 -0.4737 -0.2515 0.1461 1.0000 Uiso . . . . . .
H91 H -0.2392 -0.6703 -0.2579 0.1687 1.0000 Uiso . . . . . .
H92 H -0.2797 -0.6776 -0.1745 0.1687 1.0000 Uiso . . . . . .
H101 H -0.1045 -0.7278 -0.1549 0.1998 1.0000 Uiso . . . . . .
H102 H -0.0630 -0.6471 -0.1935 0.1998 1.0000 Uiso . . . . . .
H111 H -0.1265 -0.6593 -0.0466 0.1823 1.0000 Uiso . . . . . .
H112 H -0.0078 -0.6342 -0.0617 0.1823 1.0000 Uiso . . . . . .
H122 H -0.1092 -0.5210 -0.0290 0.1779 1.0000 Uiso . . . . . .
H121 H -0.0685 -0.5104 -0.1116 0.1779 1.0000 Uiso . . . . . .
H132 H -0.2844 -0.5532 -0.0963 0.1770 1.0000 Uiso . . . . . .
H131 H -0.2476 -0.4687 -0.1300 0.1770 1.0000 Uiso . . . . . .
H151 H -0.5419 -0.6841 -0.1062 0.1544 1.0000 Uiso . . . . . .
H153 H -0.5916 -0.6676 -0.0288 0.1544 1.0000 Uiso . . . . . .
H152 H -0.5069 -0.6052 -0.0539 0.1544 1.0000 Uiso . . . . . .
H362 H -0.6348 -0.3395 -0.3833 0.0909 1.0000 Uiso . . . . . .
H361 H -0.5349 -0.3690 -0.3176 0.0909 1.0000 Uiso . . . . . .
H371 H -0.5832 -0.4248 -0.4774 0.1287 1.0000 Uiso . . . . . .
H372 H -0.5033 -0.4771 -0.4112 0.1287 1.0000 Uiso . . . . . .
H382 H -0.3968 -0.4009 -0.4762 0.1523 1.0000 Uiso . . . . . .
H383 H -0.4629 -0.3202 -0.4649 0.1523 1.0000 Uiso . . . . . .
H381 H -0.3896 -0.3621 -0.3909 0.1523 1.0000 Uiso . . . . . .
H331 H -0.8480 -0.7353 -0.4943 0.1055 1.0000 Uiso . . . . . .
H321 H -0.8458 -0.7596 -0.6278 0.1238 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.994(4)
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 . C21 . 1.388(8) yes
F2 . C31 . 1.374(8) yes
C1 . C2 . 1.517(9) yes
C1 . N1 . 1.445(8) yes
C1 . C14 . 1.559(10) yes
C1 . C24 . 1.575(9) yes
C2 . C3 . 1.384(9) yes
C2 . C7 . 1.389(9) yes
O1 . C14 . 1.223(7) yes
O2 . C25 . 1.213(7) yes
C3 . C4 . 1.411(10) yes
C3 . H31 . 0.928 no
C4 . C5 . 1.326(11) yes
C4 . H41 . 0.945 no
N1 . C15 . 1.474(11) yes
N1 . C16 . 1.416(10) yes
N2 . C34 . 1.462(7) yes
N2 . C35 . 1.466(8) yes
N2 . C36 . 1.476(8) yes
N3 . C7 . 1.386(9) yes
N3 . C8 . 1.528(10) yes
N3 . C14 . 1.377(8) yes
N4 . C8 . 1.454(10) yes
N4 . C9 . 1.472(11) yes
N4 . C13 . 1.423(12) yes
C5 . C6 . 1.400(11) yes
C5 . H51 . 0.920 no
C6 . C7 . 1.355(10) yes
C6 . H61 . 0.935 no
C8 . H81 . 0.975 no
C8 . H82 . 0.954 no
C9 . C10 . 1.511(12) yes
C9 . H91 . 0.980 no
C9 . H92 . 0.972 no
C10 . C11 . 1.459(14) yes
C10 . H101 . 0.965 no
C10 . H102 . 0.960 no
C11 . C12 . 1.476(14) yes
C11 . H111 . 1.000 no
C11 . H112 . 0.949 no
C12 . C13 . 1.492(12) yes
C12 . H122 . 0.979 no
C12 . H121 . 0.985 no
C13 . H132 . 0.958 no
C13 . H131 . 0.966 no
C15 . H151 . 0.974 no
C15 . H153 . 0.955 no
C15 . H152 . 0.953 no
C16 . C17 . 1.517(11) yes
C16 . H162 . 0.976 no
C16 . H161 . 0.987 no
C17 . C18 . 1.497(10) yes
C17 . C24 . 1.565(9) yes
C17 . H171 . 0.992 no
C18 . C19 . 1.389(10) yes
C18 . C23 . 1.374(9) yes
C19 . C20 . 1.385(10) yes
C19 . H191 . 0.921 no
C20 . C21 . 1.347(11) yes
C20 . H201 . 0.928 no
C21 . C22 . 1.343(11) yes
C22 . C23 . 1.360(10) yes
C22 . H221 . 0.926 no
C23 . H231 . 0.940 no
C24 . C25 . 1.528(9) yes
C24 . C35 . 1.546(9) yes
C25 . C26 . 1.482(10) yes
C26 . C27 . 1.324(9) yes
C26 . C34 . 1.489(9) yes
C27 . C28 . 1.461(10) yes
C27 . H271 . 0.921 no
C28 . C29 . 1.385(10) yes
C28 . C33 . 1.419(10) yes
C29 . C30 . 1.367(10) yes
C29 . H291 . 0.915 no
C30 . C31 . 1.377(10) yes
C30 . H301 . 0.926 no
C31 . C32 . 1.343(11) yes
C32 . C33 . 1.391(11) yes
C32 . H321 . 0.931 no
C33 . H331 . 0.925 no
C34 . H341 . 0.975 no
C34 . H342 . 0.968 no
C35 . H352 . 0.980 no
C35 . H351 . 0.962 no
C36 . C37 . 1.524(11) yes
C36 . H362 . 0.967 no
C36 . H361 . 0.981 no
C37 . C38 . 1.460(12) yes
C37 . H371 . 0.955 no
C37 . H372 . 0.998 no
C38 . H382 . 0.966 no
C38 . H383 . 0.965 no
C38 . H381 . 0.945 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
C2 . C1 . N1 . 110.7(5) yes
C2 . C1 . C14 . 99.5(6) yes
N1 . C1 . C14 . 112.7(6) yes
C2 . C1 . C24 . 119.5(6) yes
N1 . C1 . C24 . 103.1(6) yes
C14 . C1 . C24 . 111.7(5) yes
C1 . C2 . C3 . 130.0(7) yes
C1 . C2 . C7 . 110.1(6) yes
C3 . C2 . C7 . 119.5(6) yes
C2 . C3 . C4 . 118.1(7) yes
C2 . C3 . H31 . 119.3 no
C4 . C3 . H31 . 122.6 no
C3 . C4 . C5 . 121.0(8) yes
C3 . C4 . H41 . 118.2 no
C5 . C4 . H41 . 120.8 no
C1 . N1 . C15 . 115.7(7) yes
C1 . N1 . C16 . 106.7(6) yes
C15 . N1 . C16 . 114.7(7) yes
C34 . N2 . C35 . 108.0(5) yes
C34 . N2 . C36 . 113.1(5) yes
C35 . N2 . C36 . 111.8(5) yes
C7 . N3 . C8 . 123.3(7) yes
C7 . N3 . C14 . 110.1(6) yes
C8 . N3 . C14 . 125.4(7) yes
C8 . N4 . C9 . 117.3(8) yes
C8 . N4 . C13 . 112.7(8) yes
C9 . N4 . C13 . 111.8(8) yes
C4 . C5 . C6 . 121.3(7) yes
C4 . C5 . H51 . 120.4 no
C6 . C5 . H51 . 118.3 no
C5 . C6 . C7 . 118.4(8) yes
C5 . C6 . H61 . 121.3 no
C7 . C6 . H61 . 120.3 no
C2 . C7 . N3 . 110.6(6) yes
C2 . C7 . C6 . 121.6(8) yes
N3 . C7 . C6 . 127.7(8) yes
N3 . C8 . N4 . 116.6(7) yes
N3 . C8 . H81 . 105.5 no
N4 . C8 . H81 . 107.8 no
N3 . C8 . H82 . 106.2 no
N4 . C8 . H82 . 108.4 no
H81 . C8 . H82 . 112.4 no
N4 . C9 . C10 . 110.8(9) yes
N4 . C9 . H91 . 108.3 no
C10 . C9 . H91 . 110.5 no
N4 . C9 . H92 . 108.5 no
C10 . C9 . H92 . 109.3 no
H91 . C9 . H92 . 109.4 no
C9 . C10 . C11 . 112.8(9) yes
C9 . C10 . H101 . 107.6 no
C11 . C10 . H101 . 110.2 no
C9 . C10 . H102 . 106.9 no
C11 . C10 . H102 . 107.9 no
H101 . C10 . H102 . 111.4 no
C10 . C11 . C12 . 112.9(9) yes
C10 . C11 . H111 . 106.2 no
C12 . C11 . H111 . 107.5 no
C10 . C11 . H112 . 110.4 no
C12 . C11 . H112 . 110.8 no
H111 . C11 . H112 . 108.9 no
C11 . C12 . C13 . 113.8(10) yes
C11 . C12 . H122 . 109.2 no
C13 . C12 . H122 . 109.8 no
C11 . C12 . H121 . 107.3 no
C13 . C12 . H121 . 108.8 no
H122 . C12 . H121 . 107.8 no
C12 . C13 . N4 . 109.8(9) yes
C12 . C13 . H132 . 109.7 no
N4 . C13 . H132 . 109.3 no
C12 . C13 . H131 . 109.0 no
N4 . C13 . H131 . 108.3 no
H132 . C13 . H131 . 110.8 no
C1 . C14 . N3 . 109.7(6) yes
C1 . C14 . O1 . 126.9(7) yes
N3 . C14 . O1 . 123.4(7) yes
N1 . C15 . H151 . 108.9 no
N1 . C15 . H153 . 109.4 no
H151 . C15 . H153 . 109.5 no
N1 . C15 . H152 . 108.9 no
H151 . C15 . H152 . 109.5 no
H153 . C15 . H152 . 110.6 no
N1 . C16 . C17 . 105.8(7) yes
N1 . C16 . H162 . 111.5 no
C17 . C16 . H162 . 112.3 no
N1 . C16 . H161 . 109.6 no
C17 . C16 . H161 . 110.4 no
H162 . C16 . H161 . 107.2 no
C16 . C17 . C18 . 114.4(6) yes
C16 . C17 . C24 . 103.2(6) yes
C18 . C17 . C24 . 117.3(6) yes
C16 . C17 . H171 . 106.7 no
C18 . C17 . H171 . 108.0 no
C24 . C17 . H171 . 106.6 no
C17 . C18 . C19 . 124.6(7) yes
C17 . C18 . C23 . 117.5(7) yes
C19 . C18 . C23 . 117.9(7) yes
C18 . C19 . C20 . 120.8(7) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 119.8 no
C19 . C20 . C21 . 117.8(8) yes
C19 . C20 . H201 . 120.9 no
C21 . C20 . H201 . 121.3 no
F1 . C21 . C20 . 117.1(9) yes
F1 . C21 . C22 . 119.5(9) yes
C20 . C21 . C22 . 123.1(8) yes
C21 . C22 . C23 . 119.0(8) yes
C21 . C22 . H221 . 121.9 no
C23 . C22 . H221 . 119.0 no
C18 . C23 . C22 . 121.2(8) yes
C18 . C23 . H231 . 118.2 no
C22 . C23 . H231 . 120.6 no
C17 . C24 . C1 . 104.1(5) yes
C17 . C24 . C25 . 111.5(6) yes
C1 . C24 . C25 . 108.7(5) yes
C17 . C24 . C35 . 113.2(6) yes
C1 . C24 . C35 . 112.3(6) yes
C25 . C24 . C35 . 107.0(5) yes
C24 . C25 . O2 . 120.0(7) yes
C24 . C25 . C26 . 118.9(6) yes
O2 . C25 . C26 . 121.0(6) yes
C25 . C26 . C27 . 117.4(6) yes
C25 . C26 . C34 . 118.2(6) yes
C27 . C26 . C34 . 124.4(7) yes
C26 . C27 . C28 . 126.5(7) yes
C26 . C27 . H271 . 116.7 no
C28 . C27 . H271 . 116.7 no
C27 . C28 . C29 . 125.3(7) yes
C27 . C28 . C33 . 118.2(7) yes
C29 . C28 . C33 . 116.5(7) yes
C28 . C29 . C30 . 122.2(8) yes
C28 . C29 . H291 . 117.3 no
C30 . C29 . H291 . 120.5 no
C29 . C30 . C31 . 118.6(7) yes
C29 . C30 . H301 . 120.3 no
C31 . C30 . H301 . 121.1 no
F2 . C31 . C30 . 118.1(8) yes
F2 . C31 . C32 . 118.5(8) yes
C30 . C31 . C32 . 123.3(8) yes
C31 . C32 . C33 . 117.8(8) yes
C31 . C32 . H321 . 122.2 no
C33 . C32 . H321 . 120.0 no
C28 . C33 . C32 . 121.7(8) yes
C28 . C33 . H331 . 118.9 no
C32 . C33 . H331 . 119.4 no
C26 . C34 . N2 . 112.2(5) yes
C26 . C34 . H341 . 108.6 no
N2 . C34 . H341 . 108.1 no
C26 . C34 . H342 . 109.7 no
N2 . C34 . H342 . 109.8 no
H341 . C34 . H342 . 108.4 no
C24 . C35 . N2 . 109.0(5) yes
C24 . C35 . H352 . 109.1 no
N2 . C35 . H352 . 110.4 no
C24 . C35 . H351 . 108.3 no
N2 . C35 . H351 . 109.5 no
H352 . C35 . H351 . 110.5 no
N2 . C36 . C37 . 110.3(6) yes
N2 . C36 . H362 . 109.3 no
C37 . C36 . H362 . 111.6 no
N2 . C36 . H361 . 107.0 no
C37 . C36 . H361 . 110.3 no
H362 . C36 . H361 . 108.3 no
C36 . C37 . C38 . 113.3(7) yes
C36 . C37 . H371 . 108.6 no
C38 . C37 . H371 . 110.2 no
C36 . C37 . H372 . 107.5 no
C38 . C37 . H372 . 107.3 no
H371 . C37 . H372 . 109.9 no
C37 . C38 . H382 . 109.3 no
C37 . C38 . H383 . 108.2 no
H382 . C38 . H383 . 108.9 no
C37 . C38 . H381 . 109.8 no
H382 . C38 . H381 . 110.5 no
H383 . C38 . H381 . 110.1 no

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
