# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_ambient
_audit_creation_date             12-09-01
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_ambient in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.8581(2)
_cell_length_b                   14.7849(4)
_cell_length_c                   17.3015(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.966(2)
_cell_angle_gamma                90
_cell_volume                     1754.06(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      1.71 Fooo =    888.00 Mu =     18.46 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      1.72 FOOO =    888.00 Mu =     18.47 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      2
_cell_measurement_theta_max      24
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.847

# Sheldrick geometric approximatio 0.69 0.69 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.69
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_reflns_number            34795
_reflns_number_total             5362
_diffrn_reflns_av_R_equivalents  0.065
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5362 
# Theoretical number of reflections is about 10675 


_diffrn_reflns_theta_min         1.812
_diffrn_reflns_theta_max         30.531
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        30.531
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_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     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.78
_refine_diff_density_max         0.70


# 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         2650
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0510
_refine_ls_wR_factor_ref         0.0512
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0004389
_refine_ls_shift/su_mean         0.0000230


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5362
_refine_ls_R_factor_all          0.1196
_refine_ls_wR_factor_all         0.1015

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2650
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_gt          0.0512

# 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    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: 
 0.432 0.419 0.252 
;

# 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
H1 H 0.4910 0.3720 0.4143 0.0536 1.0000 Uiso R . . . . .
H2 H 0.5536 0.3739 0.2804 0.0652 1.0000 Uiso R . . . . .
H3 H 0.3439 0.3016 0.1940 0.0654 1.0000 Uiso R . . . . .
H5 H 0.0091 0.2120 0.1752 0.0691 1.0000 Uiso R . . . . .
H6 H -0.2542 0.1510 0.2371 0.0684 1.0000 Uiso R . . . . .
H7 H -0.2888 0.1557 0.3728 0.0583 1.0000 Uiso R . . . . .
H12 H -0.1682 0.3501 0.5533 0.0554 1.0000 Uiso R . . . . .
H13 H -0.2136 0.4728 0.6370 0.0725 1.0000 Uiso R . . . . .
H14 H 0.0492 0.5587 0.6763 0.0713 1.0000 Uiso R . . . . .
H16 H 0.0862 0.1443 0.5913 0.0564 1.0000 Uiso R . . . . .
H17 H 0.2716 0.0313 0.6524 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7511 0.1237 0.5438 0.0491 1.0000 Uiso R . . . . .
H20 H 0.5656 0.2385 0.4862 0.0487 1.0000 Uiso R . . . . .
C1 C 0.4028(7) 0.3429(3) 0.3786(3) 0.0423(10) 1.0000 Uiso . . . . . .
C2 C 0.4405(8) 0.3448(4) 0.2990(3) 0.0538(13) 1.0000 Uiso . . . . . .
C3 C 0.3160(8) 0.3030(4) 0.2480(3) 0.0558(13) 1.0000 Uiso . . . . . .
C4 C 0.1486(8) 0.2613(3) 0.2747(3) 0.0459(11) 1.0000 Uiso . . . . . .
C5 C -0.0009(9) 0.2162(4) 0.2307(4) 0.0595(14) 1.0000 Uiso . . . . . .
C6 C -0.1553(8) 0.1793(4) 0.2677(3) 0.0552(13) 1.0000 Uiso . . . . . .
C7 C -0.1774(7) 0.1819(3) 0.3481(3) 0.0453(11) 1.0000 Uiso . . . . . .
C8 C -0.0371(6) 0.2241(3) 0.3918(3) 0.0366(10) 1.0000 Uiso . . . . . .
C9 C 0.1210(6) 0.2621(3) 0.3538(3) 0.0339(9) 1.0000 Uiso . . . . . .
C10 C 0.2679(7) 0.4258(3) 0.5709(3) 0.0399(10) 1.0000 Uiso . . . . . .
C11 C 0.1256(6) 0.3670(3) 0.5437(3) 0.0367(10) 1.0000 Uiso . . . . . .
C12 C -0.0583(8) 0.3865(3) 0.5694(3) 0.0465(11) 1.0000 Uiso . . . . . .
C13 C -0.0877(9) 0.4596(4) 0.6193(3) 0.0587(13) 1.0000 Uiso . . . . . .
C14 C 0.0674(9) 0.5107(4) 0.6411(4) 0.0608(15) 1.0000 Uiso . . . . . .
C15 C 0.3044(6) 0.2040(3) 0.5313(3) 0.0348(9) 1.0000 Uiso . . . . . .
C16 C 0.2223(8) 0.1409(3) 0.5813(3) 0.0465(11) 1.0000 Uiso . . . . . .
C17 C 0.3316(8) 0.0728(4) 0.6173(3) 0.0499(12) 1.0000 Uiso . . . . . .
C18 C 0.5279(7) 0.0677(3) 0.6026(3) 0.0402(10) 1.0000 Uiso . . . . . .
C19 C 0.6152(7) 0.1283(3) 0.5537(3) 0.0411(10) 1.0000 Uiso . . . . . .
C20 C 0.5033(7) 0.1956(3) 0.5197(3) 0.0382(10) 1.0000 Uiso . . . . . .
I1 I 0.69826(6) -0.03438(2) 0.65380(2) 0.0624 1.0000 Uani . . . . . .
B1 B 0.1663(7) 0.2790(3) 0.4910(3) 0.0353(10) 1.0000 Uiso . . . . . .
O1 O -0.0268(5) 0.2364(2) 0.46835(18) 0.0405(7) 1.0000 Uiso . . . . . .
N1 N 0.2469(5) 0.3021(2) 0.4050(2) 0.0357(8) 1.0000 Uiso . . . . . .
F1 F 0.4547(4) 0.4106(2) 0.54843(18) 0.0579(8) 1.0000 Uiso . . . . . .
N2 N 0.2504(7) 0.4954(3) 0.6166(3) 0.0514(10) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0686(3) 0.04010(17) 0.0781(3) 0.0026(2) -0.01448(18) 0.01247(18)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1047(2)
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
H1 . C1 . 0.960 no
H2 . C2 . 0.948 no
H3 . C3 . 0.957 no
H5 . C5 . 0.965 no
H6 . C6 . 0.951 no
H7 . C7 . 0.963 no
H12 . C12 . 0.963 no
H13 . C13 . 0.942 no
H14 . C14 . 0.946 no
H16 . C16 . 0.953 no
H17 . C17 . 0.960 no
H19 . C19 . 0.953 no
H20 . C20 . 0.965 no
C1 . C2 . 1.406(7) yes
C1 . N1 . 1.317(6) yes
C2 . C3 . 1.364(8) yes
C3 . C4 . 1.389(8) yes
C4 . C5 . 1.431(8) yes
C4 . C9 . 1.386(7) yes
C5 . C6 . 1.361(8) yes
C6 . C7 . 1.401(7) yes
C7 . C8 . 1.365(7) yes
C8 . C9 . 1.396(6) yes
C8 . O1 . 1.337(5) yes
C9 . N1 . 1.362(6) yes
C10 . C11 . 1.384(6) yes
C10 . F1 . 1.364(6) yes
C10 . N2 . 1.303(6) yes
C11 . C12 . 1.375(7) yes
C11 . B1 . 1.615(7) yes
C12 . C13 . 1.400(8) yes
C13 . C14 . 1.353(8) yes
C14 . N2 . 1.351(8) yes
C15 . C16 . 1.397(7) yes
C15 . C20 . 1.387(6) yes
C15 . B1 . 1.610(6) yes
C16 . C17 . 1.396(7) yes
C17 . C18 . 1.377(7) yes
C18 . C19 . 1.376(7) yes
C18 . I1 . 2.096(5) yes
C19 . C20 . 1.382(6) yes
B1 . O1 . 1.513(6) yes
B1 . N1 . 1.632(7) 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
H1 . C1 . C2 . 119.9 no
H1 . C1 . N1 . 119.2 no
C2 . C1 . N1 . 120.9(5) yes
C1 . C2 . H2 . 120.4 no
C1 . C2 . C3 . 120.0(5) yes
H2 . C2 . C3 . 119.6 no
H3 . C3 . C2 . 120.5 no
H3 . C3 . C4 . 119.6 no
C2 . C3 . C4 . 119.9(5) yes
C3 . C4 . C5 . 128.3(5) yes
C3 . C4 . C9 . 116.8(5) yes
C5 . C4 . C9 . 114.9(5) yes
C4 . C5 . H5 . 119.8 no
C4 . C5 . C6 . 119.5(5) yes
H5 . C5 . C6 . 120.7 no
H6 . C6 . C5 . 117.8 no
H6 . C6 . C7 . 118.5 no
C5 . C6 . C7 . 123.6(5) yes
H7 . C7 . C6 . 121.9 no
H7 . C7 . C8 . 119.6 no
C6 . C7 . C8 . 118.4(5) yes
C7 . C8 . C9 . 117.9(4) yes
C7 . C8 . O1 . 129.5(4) yes
C9 . C8 . O1 . 112.5(4) yes
C8 . C9 . C4 . 125.6(4) yes
C8 . C9 . N1 . 110.9(4) yes
C4 . C9 . N1 . 123.5(4) yes
C11 . C10 . F1 . 117.3(4) yes
C11 . C10 . N2 . 129.1(5) yes
F1 . C10 . N2 . 113.5(4) yes
C10 . C11 . C12 . 113.8(4) yes
C10 . C11 . B1 . 124.8(4) yes
C12 . C11 . B1 . 121.3(4) yes
H12 . C12 . C11 . 120.5 no
H12 . C12 . C13 . 119.3 no
C11 . C12 . C13 . 120.2(5) yes
C12 . C13 . H13 . 120.2 no
C12 . C13 . C14 . 118.9(6) yes
H13 . C13 . C14 . 120.9 no
H14 . C14 . C13 . 119.2 no
H14 . C14 . N2 . 117.5 no
C13 . C14 . N2 . 123.3(6) yes
C16 . C15 . C20 . 115.9(4) yes
C16 . C15 . B1 . 119.2(4) yes
C20 . C15 . B1 . 124.9(4) yes
H16 . C16 . C15 . 118.9 no
H16 . C16 . C17 . 118.4 no
C15 . C16 . C17 . 122.7(5) yes
H17 . C17 . C16 . 120.7 no
H17 . C17 . C18 . 120.8 no
C16 . C17 . C18 . 118.4(5) yes
C17 . C18 . C19 . 121.0(5) yes
C17 . C18 . I1 . 120.1(4) yes
C19 . C18 . I1 . 118.9(3) yes
H19 . C19 . C18 . 120.1 no
H19 . C19 . C20 . 120.8 no
C18 . C19 . C20 . 119.1(5) yes
H20 . C20 . C15 . 118.3 no
H20 . C20 . C19 . 118.7 no
C15 . C20 . C19 . 122.9(4) yes
C11 . B1 . C15 . 114.6(4) yes
C11 . B1 . O1 . 108.8(4) yes
C15 . B1 . O1 . 109.4(4) yes
C11 . B1 . N1 . 114.3(4) yes
C15 . B1 . N1 . 109.4(4) yes
O1 . B1 . N1 . 99.1(3) yes
B1 . O1 . C8 . 110.2(3) yes
B1 . N1 . C9 . 106.4(3) yes
B1 . N1 . C1 . 134.6(4) yes
C9 . N1 . C1 . 118.8(4) yes
C14 . N2 . C10 . 114.7(5) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/09/12 at 14:28:16
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/09/12 at 14:28:16
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 993575'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=0.16GPa
_audit_creation_date             12-09-11
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=0.16GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.8234(4)
_cell_length_b                   14.7074(7)
_cell_length_c                   17.200(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.814(7)
_cell_angle_gamma                90
_cell_volume                     1725.9(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      1.74 Fooo =    888.00 Mu =     18.76 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      1.75 FOOO =    888.00 Mu =     18.77 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    2630
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.877

# Sheldrick geometric approximatio 0.69 0.69 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.69
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         164630
_diffrn_reflns_number            9268
_reflns_number_total             1184
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1184 
# Theoretical number of reflections is about 6318 


_diffrn_reflns_theta_min         2.770
_diffrn_reflns_theta_max         25.375
_diffrn_measured_fraction_theta_max 0.372

_diffrn_reflns_theta_full        25.375
_diffrn_measured_fraction_theta_full 0.372


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.39
_refine_diff_density_max         0.37


# 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         933
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0501
_refine_ls_wR_factor_ref         0.0396
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0003291
_refine_ls_shift/su_mean         0.0000181


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1178
_refine_ls_R_factor_all          0.0732
_refine_ls_wR_factor_all         0.0671

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                933
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_gt          0.0396

# 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    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: 
 0.858E-01 0.485E-01 0.320E-01 
;

# 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
H1 H 0.4919 0.8739 0.4095 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5496 0.8708 0.2804 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3444 0.8014 0.1902 0.0653 1.0000 Uiso R . . . . .
H5 H 0.0090 0.7112 0.1733 0.0681 1.0000 Uiso R . . . . .
H6 H -0.2521 0.6502 0.2371 0.0663 1.0000 Uiso R . . . . .
H7 H -0.2907 0.6554 0.3691 0.0562 1.0000 Uiso R . . . . .
H12 H -0.1657 0.8521 0.5536 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2120 0.9736 0.6382 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0492 1.0587 0.6783 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0863 0.6439 0.5922 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2725 0.5320 0.6502 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7480 0.6228 0.5423 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5658 0.7375 0.4852 0.0475 1.0000 Uiso R . . . . .
F1 F 0.4545(7) 0.9120(3) 0.5482(7) 0.0516(16) 1.0000 Uiso . . . . . .
B1 B 0.1672(15) 0.7791(6) 0.4871(16) 0.030(3) 1.0000 Uiso . . . . . .
O1 O -0.0296(9) 0.7369(4) 0.4675(9) 0.040(2) 1.0000 Uiso . . . . . .
N2 N 0.2483(12) 0.9967(5) 0.6176(10) 0.046(2) 1.0000 Uiso . . . . . .
N1 N 0.2450(11) 0.8021(4) 0.4016(10) 0.0326(19) 1.0000 Uiso . . . . . .
C1 C 0.4058(16) 0.8453(6) 0.3748(16) 0.043(3) 1.0000 Uiso . . . . . .
C2 C 0.4383(17) 0.8417(6) 0.2988(17) 0.051(3) 1.0000 Uiso . . . . . .
C3 C 0.3168(15) 0.8021(6) 0.2428(14) 0.059(3) 1.0000 Uiso . . . . . .
C4 C 0.1479(15) 0.7595(6) 0.2735(15) 0.040(3) 1.0000 Uiso . . . . . .
C5 C 0.0001(15) 0.7152(6) 0.2275(15) 0.062(4) 1.0000 Uiso . . . . . .
C6 C -0.1550(17) 0.6783(7) 0.2672(17) 0.056(4) 1.0000 Uiso . . . . . .
C7 C -0.1824(16) 0.6809(5) 0.3453(16) 0.040(3) 1.0000 Uiso . . . . . .
C8 C -0.0397(13) 0.7245(5) 0.3905(15) 0.029(3) 1.0000 Uiso . . . . . .
C9 C 0.1185(14) 0.7617(5) 0.3489(15) 0.032(3) 1.0000 Uiso . . . . . .
C10 C 0.2666(13) 0.9259(5) 0.5699(12) 0.036(2) 1.0000 Uiso . . . . . .
C11 C 0.1260(12) 0.8672(5) 0.5432(12) 0.033(2) 1.0000 Uiso . . . . . .
C12 C -0.0590(14) 0.8879(6) 0.5694(12) 0.043(3) 1.0000 Uiso . . . . . .
C13 C -0.0881(15) 0.9602(6) 0.6205(13) 0.052(3) 1.0000 Uiso . . . . . .
C14 C 0.0679(15) 1.0114(6) 0.6441(14) 0.055(3) 1.0000 Uiso . . . . . .
C15 C 0.3034(12) 0.7034(5) 0.5323(12) 0.033(2) 1.0000 Uiso . . . . . .
C16 C 0.2196(13) 0.6405(5) 0.5823(12) 0.040(3) 1.0000 Uiso . . . . . .
C17 C 0.3312(13) 0.5730(6) 0.6162(12) 0.042(3) 1.0000 Uiso . . . . . .
C18 C 0.5288(12) 0.5666(5) 0.6006(12) 0.033(2) 1.0000 Uiso . . . . . .
C19 C 0.6141(14) 0.6275(5) 0.5524(12) 0.042(3) 1.0000 Uiso . . . . . .
C20 C 0.5032(12) 0.6961(5) 0.5180(11) 0.036(2) 1.0000 Uiso . . . . . .
I1 I 0.70088(11) 0.46506(4) 0.65383(10) 0.0649 1.0000 Uani . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0637(5) 0.0367(3) 0.094(2) 0.0033(6) -0.0108(6) 0.0117(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.03287(9)
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
H1 . C1 . 0.932 no
H2 . C2 . 0.931 no
H3 . C3 . 0.927 no
H5 . C5 . 0.936 no
H6 . C6 . 0.932 no
H7 . C7 . 0.929 no
H12 . C12 . 0.935 no
H13 . C13 . 0.924 no
H14 . C14 . 0.920 no
H16 . C16 . 0.929 no
H17 . C17 . 0.934 no
H19 . C19 . 0.935 no
H20 . C20 . 0.938 no
F1 . C10 . 1.356(11) yes
B1 . O1 . 1.513(14) yes
B1 . N1 . 1.61(3) yes
B1 . C11 . 1.64(2) yes
B1 . C15 . 1.639(18) yes
O1 . C8 . 1.34(3) yes
N2 . C10 . 1.333(18) yes
N2 . C14 . 1.337(15) yes
N1 . C1 . 1.355(16) yes
N1 . C9 . 1.38(2) yes
C1 . C2 . 1.33(3) yes
C2 . C3 . 1.39(3) yes
C3 . C4 . 1.420(19) yes
C4 . C5 . 1.43(2) yes
C4 . C9 . 1.32(3) yes
C5 . C6 . 1.38(2) yes
C6 . C7 . 1.36(3) yes
C7 . C8 . 1.39(2) yes
C8 . C9 . 1.41(2) yes
C10 . C11 . 1.366(14) yes
C11 . C12 . 1.380(14) yes
C12 . C13 . 1.40(2) yes
C13 . C14 . 1.361(15) yes
C15 . C16 . 1.39(2) yes
C15 . C20 . 1.393(13) yes
C16 . C17 . 1.376(16) yes
C17 . C18 . 1.382(13) yes
C18 . C19 . 1.36(2) yes
C18 . I1 . 2.102(11) yes
C19 . C20 . 1.387(16) 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
O1 . B1 . N1 . 100.7(16) yes
O1 . B1 . C11 . 107.2(9) yes
N1 . B1 . C11 . 115.7(9) yes
O1 . B1 . C15 . 108.8(7) yes
N1 . B1 . C15 . 112.6(10) yes
C11 . B1 . C15 . 111.0(16) yes
B1 . O1 . C8 . 108.1(13) yes
C10 . N2 . C14 . 115.6(10) yes
B1 . N1 . C1 . 133.7(16) yes
B1 . N1 . C9 . 107.4(11) yes
C1 . N1 . C9 . 118.8(18) yes
H1 . C1 . N1 . 119.9 no
H1 . C1 . C2 . 122.4 no
N1 . C1 . C2 . 117.6(16) yes
H2 . C2 . C1 . 117.6 no
H2 . C2 . C3 . 116.0 no
C1 . C2 . C3 . 126.3(15) yes
C2 . C3 . H3 . 123.6 no
C2 . C3 . C4 . 114(2) yes
H3 . C3 . C4 . 122.4 no
C3 . C4 . C5 . 124(2) yes
C3 . C4 . C9 . 119.5(16) yes
C5 . C4 . C9 . 116.1(14) yes
C4 . C5 . H5 . 121.6 no
C4 . C5 . C6 . 116(2) yes
H5 . C5 . C6 . 122.0 no
H6 . C6 . C5 . 116.3 no
H6 . C6 . C7 . 117.1 no
C5 . C6 . C7 . 126.5(17) yes
H7 . C7 . C6 . 123.0 no
H7 . C7 . C8 . 119.6 no
C6 . C7 . C8 . 117.4(15) yes
C7 . C8 . O1 . 129.9(16) yes
C7 . C8 . C9 . 115(2) yes
O1 . C8 . C9 . 114.8(14) yes
C8 . C9 . N1 . 108(2) yes
C8 . C9 . C4 . 128.2(17) yes
N1 . C9 . C4 . 123.8(12) yes
F1 . C10 . N2 . 112.7(9) yes
F1 . C10 . C11 . 118.3(11) yes
N2 . C10 . C11 . 129.0(10) yes
B1 . C11 . C10 . 124.8(9) yes
B1 . C11 . C12 . 122.1(9) yes
C10 . C11 . C12 . 113.1(11) yes
H12 . C12 . C11 . 119.5 no
H12 . C12 . C13 . 119.6 no
C11 . C12 . C13 . 120.8(10) yes
C12 . C13 . H13 . 120.6 no
C12 . C13 . C14 . 119.5(12) yes
H13 . C13 . C14 . 119.9 no
H14 . C14 . C13 . 119.6 no
H14 . C14 . N2 . 118.5 no
C13 . C14 . N2 . 121.9(15) yes
B1 . C15 . C16 . 120.6(9) yes
B1 . C15 . C20 . 121.2(12) yes
C16 . C15 . C20 . 118.0(10) yes
C15 . C16 . H16 . 119.4 no
C15 . C16 . C17 . 120.8(9) yes
H16 . C16 . C17 . 119.8 no
H17 . C17 . C16 . 119.5 no
H17 . C17 . C18 . 120.4 no
C16 . C17 . C18 . 120.1(12) yes
C17 . C18 . C19 . 120.1(10) yes
C17 . C18 . I1 . 120.3(10) yes
C19 . C18 . I1 . 119.6(7) yes
H19 . C19 . C18 . 119.5 no
H19 . C19 . C20 . 120.2 no
C18 . C19 . C20 . 120.3(9) yes
C15 . C20 . H20 . 120.7 no
C15 . C20 . C19 . 120.7(12) yes
H20 . C20 . C19 . 118.6 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 11/09/12 at 10:56:38
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT F    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 11/09/12 at 10:56:38
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
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
-2 16 7 x .
2 7 1 x .
-1 4 4 x .
-3 3 4 x .
-3 13 7 x .
7 6 1 x .
_database_code_depnum_ccdc_archive 'CCDC 993576'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=1.09GPa
_audit_creation_date             12-09-11
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=1.09GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.6545(2)
_cell_length_b                   14.3261(5)
_cell_length_c                   16.7183(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.460(5)
_cell_angle_gamma                90
_cell_volume                     1593.75(15)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      1.88 Fooo =    888.00 Mu =     20.32 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      1.89 FOOO =    888.00 Mu =     20.32 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    3429
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.032

# Sheldrick geometric approximatio 0.67 0.67 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.67
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         1085565
_diffrn_reflns_number            8787
_reflns_number_total             1141
_diffrn_reflns_av_R_equivalents  0.043
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1141 
# Theoretical number of reflections is about 5858 


_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         25.382
_diffrn_measured_fraction_theta_max 0.391

_diffrn_reflns_theta_full        25.382
_diffrn_measured_fraction_theta_full 0.391


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.39


# 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         878
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0354
_refine_ls_wR_factor_ref         0.0385
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0003439
_refine_ls_shift/su_mean         0.0000259


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1132
_refine_ls_R_factor_all          0.0642
_refine_ls_wR_factor_all         0.0571

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                878
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_gt          0.0385

# 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    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: 
 0.381 0.145 0.203 
;

# 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
H1 H 0.4916 0.8720 0.4014 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5597 0.8696 0.2718 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3494 0.7966 0.1809 0.0653 1.0000 Uiso R . . . . .
H5 H -0.0025 0.7069 0.1599 0.0681 1.0000 Uiso R . . . . .
H6 H -0.2690 0.6482 0.2266 0.0663 1.0000 Uiso R . . . . .
H7 H -0.3085 0.6545 0.3605 0.0562 1.0000 Uiso R . . . . .
H12 H -0.1788 0.8536 0.5547 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2226 0.9757 0.6410 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0419 1.0621 0.6830 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0813 0.6401 0.5916 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2682 0.5274 0.6518 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7513 0.6210 0.5370 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5650 0.7353 0.4814 0.0475 1.0000 Uiso R . . . . .
C1 C 0.4055(11) 0.8434(4) 0.3667(12) 0.0274(17) 1.0000 Uiso . . . . . .
C2 C 0.4484(12) 0.8405(5) 0.2902(13) 0.035(2) 1.0000 Uiso . . . . . .
C3 C 0.3218(12) 0.7974(5) 0.2336(12) 0.042(2) 1.0000 Uiso . . . . . .
C4 C 0.1448(12) 0.7564(5) 0.2645(13) 0.0303(18) 1.0000 Uiso . . . . . .
C5 C -0.0114(12) 0.7109(5) 0.2141(13) 0.047(2) 1.0000 Uiso . . . . . .
C6 C -0.1719(13) 0.6763(5) 0.2567(15) 0.039(2) 1.0000 Uiso . . . . . .
C7 C -0.2003(11) 0.6801(4) 0.3367(13) 0.0269(18) 1.0000 Uiso . . . . . .
C8 C -0.0521(9) 0.7243(4) 0.3894(12) 0.0176(16) 1.0000 Uiso . . . . . .
C9 C 0.1098(10) 0.7612(4) 0.3415(12) 0.0226(17) 1.0000 Uiso . . . . . .
C10 C 0.2652(10) 0.9308(5) 0.5705(11) 0.0288(17) 1.0000 Uiso . . . . . .
C11 C 0.1179(9) 0.8700(4) 0.5407(10) 0.0227(15) 1.0000 Uiso . . . . . .
C12 C -0.0722(10) 0.8894(5) 0.5705(11) 0.0285(17) 1.0000 Uiso . . . . . .
C13 C -0.0987(11) 0.9623(5) 0.6233(12) 0.0373(19) 1.0000 Uiso . . . . . .
C14 C 0.0606(11) 1.0149(5) 0.6489(12) 0.040(2) 1.0000 Uiso . . . . . .
C15 C 0.2977(9) 0.7021(4) 0.5284(10) 0.0251(16) 1.0000 Uiso . . . . . .
C16 C 0.2146(10) 0.6367(4) 0.5817(10) 0.0267(16) 1.0000 Uiso . . . . . .
C17 C 0.3269(10) 0.5684(5) 0.6178(11) 0.0308(17) 1.0000 Uiso . . . . . .
C18 C 0.5317(10) 0.5633(4) 0.6016(10) 0.0254(16) 1.0000 Uiso . . . . . .
C19 C 0.6174(10) 0.6257(4) 0.5470(10) 0.0275(17) 1.0000 Uiso . . . . . .
C20 C 0.5024(10) 0.6938(4) 0.5143(10) 0.0267(16) 1.0000 Uiso . . . . . .
I1 I 0.71461(7) 0.46249(3) 0.65431(7) 0.0425 1.0000 Uani . . . . . .
B1 B 0.1551(11) 0.7807(5) 0.4825(13) 0.0226(18) 1.0000 Uiso . . . . . .
O1 O -0.0435(7) 0.7379(3) 0.4666(9) 0.0306(15) 1.0000 Uiso . . . . . .
N1 N 0.2407(8) 0.8020(3) 0.3961(8) 0.0220(13) 1.0000 Uiso . . . . . .
F1 F 0.4561(6) 0.9163(3) 0.5421(6) 0.0355(11) 1.0000 Uiso . . . . . .
N2 N 0.2462(8) 1.0005(4) 0.6179(9) 0.0356(15) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0413(3) 0.0248(2) 0.061(2) 0.0028(4) -0.0100(4) 0.0070(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1427(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
H1 . C1 . 0.910 no
H2 . C2 . 0.906 no
H3 . C3 . 0.900 no
H5 . C5 . 0.910 no
H6 . C6 . 0.910 no
H7 . C7 . 0.903 no
H12 . C12 . 0.913 no
H13 . C13 . 0.899 no
H14 . C14 . 0.894 no
H16 . C16 . 0.905 no
H17 . C17 . 0.908 no
H19 . C19 . 0.911 no
H20 . C20 . 0.912 no
C1 . C2 . 1.31(2) yes
C1 . N1 . 1.344(12) yes
C2 . C3 . 1.41(2) yes
C3 . C4 . 1.417(15) yes
C4 . C5 . 1.48(2) yes
C4 . C9 . 1.31(2) yes
C5 . C6 . 1.381(19) yes
C6 . C7 . 1.35(3) yes
C7 . C8 . 1.46(2) yes
C8 . C9 . 1.447(18) yes
C8 . O1 . 1.31(2) yes
C9 . N1 . 1.387(18) yes
C10 . C11 . 1.401(13) yes
C10 . F1 . 1.376(10) yes
C10 . N2 . 1.281(16) yes
C11 . C12 . 1.391(11) yes
C11 . B1 . 1.626(17) yes
C12 . C13 . 1.381(19) yes
C13 . C14 . 1.365(14) yes
C14 . N2 . 1.359(12) yes
C15 . C16 . 1.409(17) yes
C15 . C20 . 1.390(9) yes
C15 . B1 . 1.657(15) yes
C16 . C17 . 1.368(15) yes
C17 . C18 . 1.393(10) yes
C18 . C19 . 1.403(17) yes
C18 . I1 . 2.080(10) yes
C19 . C20 . 1.353(13) yes
B1 . O1 . 1.479(10) yes
B1 . N1 . 1.59(2) 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
H1 . C1 . C2 . 119.7 no
H1 . C1 . N1 . 118.5 no
C2 . C1 . N1 . 121.8(13) yes
H2 . C2 . C1 . 120.0 no
H2 . C2 . C3 . 117.4 no
C1 . C2 . C3 . 122.4(10) yes
C2 . C3 . H3 . 122.5 no
C2 . C3 . C4 . 115.6(17) yes
H3 . C3 . C4 . 121.9 no
C3 . C4 . C5 . 123.8(18) yes
C3 . C4 . C9 . 119.4(14) yes
C5 . C4 . C9 . 116.8(11) yes
C4 . C5 . H5 . 122.8 no
C4 . C5 . C6 . 114.0(18) yes
H5 . C5 . C6 . 123.2 no
C5 . C6 . H6 . 114.9 no
C5 . C6 . C7 . 127.6(14) yes
H6 . C6 . C7 . 117.4 no
H7 . C7 . C6 . 122.5 no
H7 . C7 . C8 . 116.6 no
C6 . C7 . C8 . 121.0(11) yes
C7 . C8 . C9 . 109.0(17) yes
C7 . C8 . O1 . 133.2(11) yes
C9 . C8 . O1 . 117.7(11) yes
C8 . C9 . C4 . 131.5(13) yes
C8 . C9 . N1 . 104.8(16) yes
C4 . C9 . N1 . 123.6(9) yes
C11 . C10 . F1 . 115.3(10) yes
C11 . C10 . N2 . 129.3(8) yes
F1 . C10 . N2 . 115.3(7) yes
C10 . C11 . C12 . 112.5(10) yes
C10 . C11 . B1 . 126.4(7) yes
C12 . C11 . B1 . 121.0(7) yes
C11 . C12 . H12 . 119.4 no
C11 . C12 . C13 . 120.1(8) yes
H12 . C12 . C13 . 120.5 no
C12 . C13 . H13 . 119.7 no
C12 . C13 . C14 . 121.0(9) yes
H13 . C13 . C14 . 119.4 no
C13 . C14 . H14 . 120.3 no
C13 . C14 . N2 . 120.2(13) yes
H14 . C14 . N2 . 119.3 no
C16 . C15 . C20 . 116.1(9) yes
C16 . C15 . B1 . 121.2(6) yes
C20 . C15 . B1 . 122.5(11) yes
C15 . C16 . H16 . 118.1 no
C15 . C16 . C17 . 122.6(7) yes
H16 . C16 . C17 . 119.3 no
C16 . C17 . H17 . 120.2 no
C16 . C17 . C18 . 118.9(11) yes
H17 . C17 . C18 . 120.9 no
C17 . C18 . C19 . 119.7(10) yes
C17 . C18 . I1 . 121.6(9) yes
C19 . C18 . I1 . 118.6(5) yes
C18 . C19 . H19 . 118.5 no
C18 . C19 . C20 . 119.4(7) yes
H19 . C19 . C20 . 122.0 no
C15 . C20 . H20 . 120.0 no
C15 . C20 . C19 . 123.0(11) yes
H20 . C20 . C19 . 117.0 no
C15 . B1 . C11 . 110.3(13) yes
C15 . B1 . O1 . 108.0(6) yes
C11 . B1 . O1 . 107.1(7) yes
C15 . B1 . N1 . 110.1(7) yes
C11 . B1 . N1 . 116.8(7) yes
O1 . B1 . N1 . 104.0(13) yes
B1 . O1 . C8 . 105.8(11) yes
B1 . N1 . C9 . 106.9(8) yes
B1 . N1 . C1 . 135.9(12) yes
C9 . N1 . C1 . 117.1(14) yes
C14 . N2 . C10 . 116.6(8) 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
C1 . H1 . N2 2_676 132.1(5) 0.910 2.548 3.229(16) yes
C19 . H19 . O1 1_655 125.8(2) 0.911 2.465 3.088(16) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 11/09/12 at 13:18:12
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 11/09/12 at 13:18:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
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 2 6 x .
-3 6 6 x .
2 1 3 x .
-1 8 4 x .
-3 10 7 x .
-1 11 7 x .
1 14 7 x .
1 12 7 x .
6 2 5 x .
_database_code_depnum_ccdc_archive 'CCDC 993577'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=2.04GPa
_audit_creation_date             12-09-11
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=2.04GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.5502(4)
_cell_length_b                   14.1051(7)
_cell_length_c                   16.497(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.396(8)
_cell_angle_gamma                90
_cell_volume                     1524.1(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      1.97 Fooo =    888.00 Mu =     21.25 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      1.98 FOOO =    888.00 Mu =     21.25 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    2750
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.125

# Sheldrick geometric approximatio 0.65 0.65 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.65
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         2037080
_diffrn_reflns_number            7648
_reflns_number_total             1067
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1067 
# Theoretical number of reflections is about 5583 


_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         25.359
_diffrn_measured_fraction_theta_max 0.382

_diffrn_reflns_theta_full        25.359
_diffrn_measured_fraction_theta_full 0.382


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.36


# 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         869
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0326
_refine_ls_wR_factor_ref         0.0348
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0003926
_refine_ls_shift/su_mean         0.0000231


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1065
_refine_ls_R_factor_all          0.0467
_refine_ls_wR_factor_all         0.0438

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                869
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0348

# 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    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: 
 0.321 0.171 0.175 
;

# 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
H1 H 0.4944 0.8718 0.4009 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5590 0.8684 0.2657 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3482 0.7945 0.1763 0.0653 1.0000 Uiso R . . . . .
H5 H -0.0082 0.7061 0.1562 0.0681 1.0000 Uiso R . . . . .
H6 H -0.2809 0.6477 0.2237 0.0663 1.0000 Uiso R . . . . .
H7 H -0.3206 0.6551 0.3584 0.0562 1.0000 Uiso R . . . . .
H12 H -0.1860 0.8550 0.5533 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2314 0.9766 0.6424 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0400 1.0643 0.6837 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0779 0.6371 0.5899 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2709 0.5241 0.6519 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7533 0.6188 0.5379 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5643 0.7350 0.4804 0.0475 1.0000 Uiso R . . . . .
C1 C 0.4083(11) 0.8432(4) 0.3662(11) 0.0224(16) 1.0000 Uiso . . . . . .
C2 C 0.4477(11) 0.8393(4) 0.2841(11) 0.0275(18) 1.0000 Uiso . . . . . .
C3 C 0.3206(11) 0.7952(4) 0.2290(10) 0.0339(18) 1.0000 Uiso . . . . . .
C4 C 0.1381(11) 0.7556(4) 0.2569(11) 0.0242(17) 1.0000 Uiso . . . . . .
C5 C -0.0170(12) 0.7100(5) 0.2103(11) 0.040(2) 1.0000 Uiso . . . . . .
C6 C -0.1838(12) 0.6759(4) 0.2538(12) 0.0298(19) 1.0000 Uiso . . . . . .
C7 C -0.2124(12) 0.6807(4) 0.3346(12) 0.0266(17) 1.0000 Uiso . . . . . .
C8 C -0.0606(9) 0.7250(4) 0.3820(10) 0.0161(14) 1.0000 Uiso . . . . . .
C9 C 0.1084(10) 0.7608(4) 0.3389(10) 0.0154(14) 1.0000 Uiso . . . . . .
C10 C 0.2596(10) 0.9328(4) 0.5684(9) 0.0202(15) 1.0000 Uiso . . . . . .
C11 C 0.1120(9) 0.8712(4) 0.5385(8) 0.0187(15) 1.0000 Uiso . . . . . .
C12 C -0.0793(11) 0.8908(4) 0.5691(10) 0.0293(17) 1.0000 Uiso . . . . . .
C13 C -0.1075(11) 0.9631(4) 0.6247(10) 0.0311(16) 1.0000 Uiso . . . . . .
C14 C 0.0587(12) 1.0171(4) 0.6496(11) 0.036(2) 1.0000 Uiso . . . . . .
C15 C 0.2926(10) 0.7005(4) 0.5269(9) 0.0195(15) 1.0000 Uiso . . . . . .
C16 C 0.2112(10) 0.6337(4) 0.5799(9) 0.0216(15) 1.0000 Uiso . . . . . .
C17 C 0.3295(11) 0.5652(4) 0.6179(10) 0.0270(17) 1.0000 Uiso . . . . . .
C18 C 0.5330(10) 0.5616(4) 0.5989(9) 0.0199(15) 1.0000 Uiso . . . . . .
C19 C 0.6193(10) 0.6235(4) 0.5480(9) 0.0238(16) 1.0000 Uiso . . . . . .
C20 C 0.5017(10) 0.6936(4) 0.5133(9) 0.0240(15) 1.0000 Uiso . . . . . .
I1 I 0.72455(7) 0.46094(3) 0.65466(6) 0.0355 1.0000 Uani . . . . . .
B1 B 0.1521(12) 0.7796(4) 0.4828(11) 0.0218(17) 1.0000 Uiso . . . . . .
O1 O -0.0519(7) 0.7378(3) 0.4617(7) 0.0236(12) 1.0000 Uiso . . . . . .
N1 N 0.2383(8) 0.8020(3) 0.3948(7) 0.0202(12) 1.0000 Uiso . . . . . .
F1 F 0.4554(6) 0.9177(3) 0.5410(5) 0.0337(10) 1.0000 Uiso . . . . . .
N2 N 0.2436(8) 1.0031(4) 0.6198(7) 0.0266(13) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0334(3) 0.0208(2) 0.0523(15) 0.0023(3) -0.0069(4) 0.00522(17)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1127(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
H1 . C1 . 0.897 no
H2 . C2 . 0.891 no
H3 . C3 . 0.888 no
H5 . C5 . 0.897 no
H6 . C6 . 0.897 no
H7 . C7 . 0.889 no
H12 . C12 . 0.899 no
H13 . C13 . 0.885 no
H14 . C14 . 0.881 no
H16 . C16 . 0.891 no
H17 . C17 . 0.895 no
H19 . C19 . 0.896 no
H20 . C20 . 0.898 no
C1 . C2 . 1.381(19) yes
C1 . N1 . 1.344(11) yes
C2 . C3 . 1.378(17) yes
C3 . C4 . 1.401(13) yes
C4 . C5 . 1.423(16) yes
C4 . C9 . 1.369(19) yes
C5 . C6 . 1.397(16) yes
C6 . C7 . 1.35(2) yes
C7 . C8 . 1.407(17) yes
C8 . C9 . 1.414(15) yes
C8 . O1 . 1.329(16) yes
C9 . N1 . 1.379(15) yes
C10 . C11 . 1.388(10) yes
C10 . F1 . 1.380(9) yes
C10 . N2 . 1.310(14) yes
C11 . C12 . 1.382(12) yes
C11 . B1 . 1.608(15) yes
C12 . C13 . 1.386(17) yes
C13 . C14 . 1.388(12) yes
C14 . N2 . 1.324(12) yes
C15 . C16 . 1.394(15) yes
C15 . C20 . 1.393(10) yes
C15 . B1 . 1.617(12) yes
C16 . C17 . 1.386(13) yes
C17 . C18 . 1.372(11) yes
C18 . C19 . 1.340(15) yes
C18 . I1 . 2.102(9) yes
C19 . C20 . 1.376(11) yes
B1 . O1 . 1.499(10) yes
B1 . N1 . 1.59(2) 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
H1 . C1 . C2 . 121.6 no
H1 . C1 . N1 . 119.2 no
C2 . C1 . N1 . 119.2(11) yes
C1 . C2 . H2 . 118.3 no
C1 . C2 . C3 . 123.3(9) yes
H2 . C2 . C3 . 118.4 no
C2 . C3 . H3 . 121.6 no
C2 . C3 . C4 . 118.5(15) yes
H3 . C3 . C4 . 119.8 no
C3 . C4 . C5 . 127.6(16) yes
C3 . C4 . C9 . 115.5(11) yes
C5 . C4 . C9 . 116.9(10) yes
C4 . C5 . H5 . 121.0 no
C4 . C5 . C6 . 115.9(15) yes
H5 . C5 . C6 . 123.1 no
C5 . C6 . H6 . 114.9 no
C5 . C6 . C7 . 127.2(12) yes
H6 . C6 . C7 . 117.9 no
C6 . C7 . H7 . 122.1 no
C6 . C7 . C8 . 118.0(10) yes
H7 . C7 . C8 . 119.8 no
C7 . C8 . C9 . 115.6(16) yes
C7 . C8 . O1 . 129.5(11) yes
C9 . C8 . O1 . 114.9(9) yes
C8 . C9 . C4 . 126.5(11) yes
C8 . C9 . N1 . 107.2(14) yes
C4 . C9 . N1 . 126.3(8) yes
C11 . C10 . F1 . 115.7(9) yes
C11 . C10 . N2 . 130.2(8) yes
F1 . C10 . N2 . 114.1(6) yes
C10 . C11 . C12 . 112.1(9) yes
C10 . C11 . B1 . 126.2(6) yes
C12 . C11 . B1 . 121.4(6) yes
C11 . C12 . H12 . 119.2 no
C11 . C12 . C13 . 120.9(7) yes
H12 . C12 . C13 . 119.9 no
C12 . C13 . H13 . 120.2 no
C12 . C13 . C14 . 119.5(9) yes
H13 . C13 . C14 . 120.3 no
C13 . C14 . H14 . 119.4 no
C13 . C14 . N2 . 121.7(11) yes
H14 . C14 . N2 . 118.7 no
C16 . C15 . C20 . 115.8(8) yes
C16 . C15 . B1 . 122.0(7) yes
C20 . C15 . B1 . 122.2(9) yes
C15 . C16 . H16 . 117.3 no
C15 . C16 . C17 . 122.7(7) yes
H16 . C16 . C17 . 120.0 no
C16 . C17 . H17 . 119.5 no
C16 . C17 . C18 . 117.6(10) yes
H17 . C17 . C18 . 122.8 no
C17 . C18 . C19 . 122.2(8) yes
C17 . C18 . I1 . 120.2(8) yes
C19 . C18 . I1 . 117.5(5) yes
H19 . C19 . C18 . 119.1 no
H19 . C19 . C20 . 121.5 no
C18 . C19 . C20 . 119.5(7) yes
C15 . C20 . C19 . 122.1(10) yes
C15 . C20 . H20 . 120.4 no
C19 . C20 . H20 . 117.5 no
C15 . B1 . C11 . 113.0(12) yes
C15 . B1 . O1 . 109.6(5) yes
C11 . B1 . O1 . 107.5(6) yes
C15 . B1 . N1 . 110.1(7) yes
C11 . B1 . N1 . 115.0(7) yes
O1 . B1 . N1 . 100.9(11) yes
B1 . O1 . C8 . 108.3(9) yes
B1 . N1 . C9 . 107.7(8) yes
B1 . N1 . C1 . 134.9(11) yes
C9 . N1 . C1 . 117.2(13) yes
C14 . N2 . C10 . 115.5(7) 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
C1 . H1 . N2 2_676 131.5(5) 0.897 2.487 3.153(14) yes
C19 . H19 . O1 1_655 123.80(18) 0.896 2.459 3.050(14) yes
C20 . H20 . O1 1_655 122.7(3) 0.898 2.535 3.114(14) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 11/09/12 at 11:35:13
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 11/09/12 at 11:35:13
#
#LIST     16                                                                    
NO 
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
-5 2 5 x .
2 14 7 x .
_database_code_depnum_ccdc_archive 'CCDC 993578'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=3.02GPa
_audit_creation_date             12-09-01
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=3.02GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.4636(2)
_cell_length_b                   13.8775(5)
_cell_length_c                   16.3094(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.317(5)
_cell_angle_gamma                90
_cell_volume                     1462.91(16)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      2.05 Fooo =    888.00 Mu =     22.14 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      2.06 FOOO =    888.00 Mu =     22.14 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    2806
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    2.061
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.214

# Sheldrick geometric approximatio 0.64 0.64 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.64
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         3019480
_diffrn_reflns_number            8296
_reflns_number_total             1138
_diffrn_reflns_av_R_equivalents  0.043
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1138 
# Theoretical number of reflections is about 5348 


_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         25.333
_diffrn_measured_fraction_theta_max 0.424

_diffrn_reflns_theta_full        25.333
_diffrn_measured_fraction_theta_full 0.424


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.46


# 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         949
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0339
_refine_ls_wR_factor_ref         0.0355
_refine_ls_goodness_of_fit_ref   0.9998
_refine_ls_shift/su_max          0.0002960
_refine_ls_shift/su_mean         0.0000276


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1138
_refine_ls_R_factor_all          0.0477
_refine_ls_wR_factor_all         0.0413

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                949
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_gt          0.0355

# 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    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: 
 0.471 0.308 0.337 
;

# 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
H1 H 0.4952 0.8723 0.3972 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5601 0.8685 0.2623 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3512 0.7941 0.1717 0.0653 1.0000 Uiso R . . . . .
H5 H -0.0132 0.7064 0.1519 0.0681 1.0000 Uiso R . . . . .
H6 H -0.2886 0.6485 0.2149 0.0663 1.0000 Uiso R . . . . .
H7 H -0.3279 0.6546 0.3538 0.0562 1.0000 Uiso R . . . . .
H12 H -0.1951 0.8546 0.5538 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2409 0.9760 0.6450 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0337 1.0645 0.6858 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0759 0.6350 0.5898 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2707 0.5218 0.6524 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7557 0.6164 0.5327 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5626 0.7339 0.4788 0.0475 1.0000 Uiso R . . . . .
C1 C 0.4092(9) 0.8437(3) 0.3625(9) 0.0186(13) 1.0000 Uiso . . . . . .
C2 C 0.4488(10) 0.8395(4) 0.2807(9) 0.0245(15) 1.0000 Uiso . . . . . .
C3 C 0.3236(10) 0.7948(4) 0.2244(9) 0.0322(16) 1.0000 Uiso . . . . . .
C4 C 0.1330(9) 0.7560(3) 0.2540(8) 0.0187(13) 1.0000 Uiso . . . . . .
C5 C -0.0220(10) 0.7103(4) 0.2061(9) 0.0308(15) 1.0000 Uiso . . . . . .
C6 C -0.1915(11) 0.6766(4) 0.2450(11) 0.0325(17) 1.0000 Uiso . . . . . .
C7 C -0.2197(9) 0.6802(3) 0.3301(9) 0.0190(13) 1.0000 Uiso . . . . . .
C8 C -0.0690(8) 0.7242(3) 0.3781(8) 0.0130(12) 1.0000 Uiso . . . . . .
C9 C 0.1043(9) 0.7620(3) 0.3365(8) 0.0158(12) 1.0000 Uiso . . . . . .
C10 C 0.2562(9) 0.9343(3) 0.5669(8) 0.0189(13) 1.0000 Uiso . . . . . .
C11 C 0.1060(9) 0.8718(3) 0.5389(7) 0.0200(14) 1.0000 Uiso . . . . . .
C12 C -0.0884(10) 0.8904(4) 0.5695(8) 0.0254(14) 1.0000 Uiso . . . . . .
C13 C -0.1169(10) 0.9626(4) 0.6273(9) 0.0266(14) 1.0000 Uiso . . . . . .
C14 C 0.0524(11) 1.0172(4) 0.6517(9) 0.0333(17) 1.0000 Uiso . . . . . .
C15 C 0.2893(9) 0.6996(3) 0.5257(8) 0.0176(12) 1.0000 Uiso . . . . . .
C16 C 0.2092(10) 0.6316(4) 0.5798(8) 0.0214(14) 1.0000 Uiso . . . . . .
C17 C 0.3294(10) 0.5629(4) 0.6184(8) 0.0232(15) 1.0000 Uiso . . . . . .
C18 C 0.5348(9) 0.5592(3) 0.5990(8) 0.0194(14) 1.0000 Uiso . . . . . .
C19 C 0.6218(10) 0.6211(4) 0.5428(8) 0.0216(14) 1.0000 Uiso . . . . . .
C20 C 0.5000(9) 0.6925(3) 0.5117(8) 0.0194(13) 1.0000 Uiso . . . . . .
I1 I 0.73427(6) 0.45958(2) 0.65494(5) 0.0306 1.0000 Uani . . . . . .
B1 B 0.1476(10) 0.7795(4) 0.4796(9) 0.0182(15) 1.0000 Uiso . . . . . .
O1 O -0.0592(6) 0.7373(2) 0.4587(6) 0.0211(10) 1.0000 Uiso . . . . . .
N1 N 0.2353(8) 0.8023(3) 0.3916(6) 0.0181(11) 1.0000 Uiso . . . . . .
F1 F 0.4527(6) 0.9199(2) 0.5402(5) 0.0304(9) 1.0000 Uiso . . . . . .
N2 N 0.2395(8) 1.0042(3) 0.6212(6) 0.0261(12) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0281(3) 0.0182(2) 0.0454(12) 0.0019(3) -0.0048(3) 0.00387(14)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1153(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
H1 . C1 . 0.885 no
H2 . C2 . 0.879 no
H3 . C3 . 0.878 no
H5 . C5 . 0.887 no
H6 . C6 . 0.885 no
H7 . C7 . 0.877 no
H12 . C12 . 0.887 no
H13 . C13 . 0.873 no
H14 . C14 . 0.869 no
H16 . C16 . 0.879 no
H17 . C17 . 0.882 no
H19 . C19 . 0.884 no
H20 . C20 . 0.885 no
C1 . C2 . 1.362(16) yes
C1 . N1 . 1.350(9) yes
C2 . C3 . 1.369(15) yes
C3 . C4 . 1.431(11) yes
C4 . C5 . 1.417(13) yes
C4 . C9 . 1.362(14) yes
C5 . C6 . 1.353(13) yes
C6 . C7 . 1.401(17) yes
C7 . C8 . 1.388(14) yes
C8 . C9 . 1.413(11) yes
C8 . O1 . 1.329(13) yes
C9 . N1 . 1.352(13) yes
C10 . C11 . 1.378(9) yes
C10 . F1 . 1.360(8) yes
C10 . N2 . 1.319(13) yes
C11 . C12 . 1.379(11) yes
C11 . B1 . 1.628(12) yes
C12 . C13 . 1.388(15) yes
C13 . C14 . 1.388(11) yes
C14 . N2 . 1.323(11) yes
C15 . C16 . 1.393(13) yes
C15 . C20 . 1.385(9) yes
C15 . B1 . 1.621(11) yes
C16 . C17 . 1.380(11) yes
C17 . C18 . 1.368(10) yes
C18 . C19 . 1.379(14) yes
C18 . I1 . 2.096(8) yes
C19 . C20 . 1.362(10) yes
B1 . O1 . 1.497(8) yes
B1 . N1 . 1.578(16) 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
H1 . C1 . C2 . 121.7 no
H1 . C1 . N1 . 119.1 no
C2 . C1 . N1 . 119.2(9) yes
C1 . C2 . H2 . 118.3 no
C1 . C2 . C3 . 124.3(8) yes
H2 . C2 . C3 . 117.4 no
C2 . C3 . H3 . 122.6 no
C2 . C3 . C4 . 116.8(12) yes
H3 . C3 . C4 . 120.4 no
C3 . C4 . C5 . 126.1(12) yes
C3 . C4 . C9 . 115.7(9) yes
C5 . C4 . C9 . 118.2(8) yes
C4 . C5 . H5 . 121.8 no
C4 . C5 . C6 . 117.9(13) yes
H5 . C5 . C6 . 120.2 no
C5 . C6 . H6 . 117.7 no
C5 . C6 . C7 . 124.2(11) yes
H6 . C6 . C7 . 118.0 no
C6 . C7 . H7 . 122.1 no
C6 . C7 . C8 . 118.7(8) yes
H7 . C7 . C8 . 119.2 no
C7 . C8 . C9 . 116.6(12) yes
C7 . C8 . O1 . 130.4(9) yes
C9 . C8 . O1 . 113.0(8) yes
C8 . C9 . C4 . 124.3(9) yes
C8 . C9 . N1 . 109.3(11) yes
C4 . C9 . N1 . 126.4(7) yes
C11 . C10 . F1 . 117.3(8) yes
C11 . C10 . N2 . 128.7(7) yes
F1 . C10 . N2 . 113.8(6) yes
C10 . C11 . C12 . 113.8(8) yes
C10 . C11 . B1 . 125.0(6) yes
C12 . C11 . B1 . 121.1(6) yes
C11 . C12 . H12 . 119.9 no
C11 . C12 . C13 . 120.4(7) yes
H12 . C12 . C13 . 119.7 no
C12 . C13 . H13 . 120.3 no
C12 . C13 . C14 . 118.8(8) yes
H13 . C13 . C14 . 120.8 no
C13 . C14 . H14 . 118.9 no
C13 . C14 . N2 . 122.6(10) yes
H14 . C14 . N2 . 118.3 no
C16 . C15 . C20 . 115.2(7) yes
C16 . C15 . B1 . 123.1(6) yes
C20 . C15 . B1 . 121.7(8) yes
C15 . C16 . H16 . 116.7 no
C15 . C16 . C17 . 123.1(6) yes
H16 . C16 . C17 . 120.2 no
C16 . C17 . H17 . 119.3 no
C16 . C17 . C18 . 117.7(9) yes
H17 . C17 . C18 . 122.9 no
C17 . C18 . C19 . 122.0(7) yes
C17 . C18 . I1 . 121.3(7) yes
C19 . C18 . I1 . 116.7(5) yes
C18 . C19 . H19 . 118.7 no
C18 . C19 . C20 . 117.7(7) yes
H19 . C19 . C20 . 123.3 no
C15 . C20 . C19 . 123.8(8) yes
C15 . C20 . H20 . 120.5 no
C19 . C20 . H20 . 115.6 no
C11 . B1 . C15 . 110.9(9) yes
C11 . B1 . O1 . 107.0(5) yes
C15 . B1 . O1 . 109.8(5) yes
C11 . B1 . N1 . 116.4(5) yes
C15 . B1 . N1 . 110.7(6) yes
O1 . B1 . N1 . 101.3(9) yes
B1 . O1 . C8 . 108.4(7) yes
B1 . N1 . C9 . 107.1(6) yes
B1 . N1 . C1 . 135.1(9) yes
C9 . N1 . C1 . 117.5(10) yes
C14 . N2 . C10 . 115.6(6) 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
C1 . H1 . N2 2_676 132.4(4) 0.885 2.444 3.111(12) yes
C14 . H14 . C9 2_576 131.3(4) 0.869 2.594 3.234(12) yes
C19 . H19 . O1 1_655 122.35(17) 0.884 2.391 2.960(12) yes
C20 . H20 . O1 1_655 123.3(3) 0.885 2.469 3.046(12) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/09/12 at 18:34:48
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/09/12 at 18:34:48
#
#LIST     16                                                                    
NO 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 993579'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=3.96GPa
_audit_creation_date             12-09-11
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=3.96GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.4012(4)
_cell_length_b                   13.7152(9)
_cell_length_c                   16.187(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.438(8)
_cell_angle_gamma                90
_cell_volume                     1421.1(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      2.11 Fooo =    888.00 Mu =     22.79 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      2.12 FOOO =    888.00 Mu =     22.79 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    2302
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    2.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.279

# Sheldrick geometric approximatio 0.63 0.63 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.63
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         3963495
_diffrn_reflns_number            6840
_reflns_number_total             1142
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1142 
# Theoretical number of reflections is about 5206 


_diffrn_reflns_theta_min         2.970
_diffrn_reflns_theta_max         25.352
_diffrn_measured_fraction_theta_max 0.438

_diffrn_reflns_theta_full        25.352
_diffrn_measured_fraction_theta_full 0.438


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.34
_refine_diff_density_max         0.50


# 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         916
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0340
_refine_ls_wR_factor_ref         0.0367
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0002962
_refine_ls_shift/su_mean         0.0000275


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1138
_refine_ls_R_factor_all          0.0506
_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                916
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_gt          0.0367

# 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    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: 
 0.487 0.277 0.341 
;

# 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
H5 H -0.0179 0.7058 0.1476 0.0681 1.0000 Uiso R . . . . .
H6 H -0.2961 0.6486 0.2139 0.0663 1.0000 Uiso R . . . . .
H7 H -0.3364 0.6550 0.3531 0.0562 1.0000 Uiso R . . . . .
H12 H -0.2016 0.8540 0.5544 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2479 0.9751 0.6496 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0235 1.0632 0.6887 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0743 0.6338 0.5900 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2731 0.5203 0.6529 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7578 0.6145 0.5316 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5618 0.7330 0.4721 0.0475 1.0000 Uiso R . . . . .
H1 H 0.4934 0.8730 0.3965 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5671 0.8696 0.2599 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3498 0.7947 0.1683 0.0653 1.0000 Uiso R . . . . .
C1 C 0.4073(10) 0.8444(4) 0.3617(8) 0.0157(14) 1.0000 Uiso . . . . . .
C2 C 0.4558(11) 0.8405(4) 0.2783(9) 0.0245(16) 1.0000 Uiso . . . . . .
C3 C 0.3222(10) 0.7954(4) 0.2209(9) 0.0252(16) 1.0000 Uiso . . . . . .
C4 C 0.1334(10) 0.7561(4) 0.2508(9) 0.0178(14) 1.0000 Uiso . . . . . .
C5 C -0.0267(10) 0.7097(4) 0.2018(9) 0.0282(17) 1.0000 Uiso . . . . . .
C6 C -0.1990(11) 0.6767(4) 0.2440(10) 0.0207(15) 1.0000 Uiso . . . . . .
C7 C -0.2282(10) 0.6805(4) 0.3294(9) 0.0180(14) 1.0000 Uiso . . . . . .
C8 C -0.0749(9) 0.7254(4) 0.3764(9) 0.0140(14) 1.0000 Uiso . . . . . .
C9 C 0.1015(10) 0.7627(4) 0.3326(9) 0.0165(14) 1.0000 Uiso . . . . . .
C10 C 0.2509(10) 0.9358(4) 0.5694(9) 0.0177(14) 1.0000 Uiso . . . . . .
C11 C 0.1009(9) 0.8720(4) 0.5374(7) 0.0143(13) 1.0000 Uiso . . . . . .
C12 C -0.0949(11) 0.8898(4) 0.5702(8) 0.0214(15) 1.0000 Uiso . . . . . .
C13 C -0.1240(11) 0.9617(4) 0.6319(9) 0.0269(16) 1.0000 Uiso . . . . . .
C14 C 0.0422(11) 1.0160(4) 0.6546(9) 0.0279(17) 1.0000 Uiso . . . . . .
C15 C 0.2879(10) 0.6987(4) 0.5223(8) 0.0166(13) 1.0000 Uiso . . . . . .
C16 C 0.2077(10) 0.6304(4) 0.5800(8) 0.0186(14) 1.0000 Uiso . . . . . .
C17 C 0.3318(10) 0.5613(4) 0.6189(8) 0.0169(15) 1.0000 Uiso . . . . . .
C18 C 0.5358(10) 0.5575(3) 0.5983(8) 0.0150(14) 1.0000 Uiso . . . . . .
C19 C 0.6238(10) 0.6192(4) 0.5416(8) 0.0193(15) 1.0000 Uiso . . . . . .
C20 C 0.4992(10) 0.6916(4) 0.5050(8) 0.0201(14) 1.0000 Uiso . . . . . .
I1 I 0.74192(6) 0.45849(2) 0.65495(5) 0.0279 1.0000 Uani . . . . . .
B1 B 0.1430(12) 0.7790(5) 0.4770(10) 0.0211(17) 1.0000 Uiso . . . . . .
O1 O -0.0633(7) 0.7369(3) 0.4570(6) 0.0191(11) 1.0000 Uiso . . . . . .
N1 N 0.2343(8) 0.8031(3) 0.3920(6) 0.0136(11) 1.0000 Uiso . . . . . .
F1 F 0.4509(6) 0.9214(3) 0.5391(5) 0.0302(10) 1.0000 Uiso . . . . . .
N2 N 0.2365(8) 1.0043(4) 0.6220(6) 0.0211(13) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0256(3) 0.0162(2) 0.0418(11) 0.0016(2) -0.0044(3) 0.00332(16)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1193(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
H5 . C5 . 0.881 no
H6 . C6 . 0.876 no
H7 . C7 . 0.869 no
H12 . C12 . 0.877 no
H13 . C13 . 0.865 no
H14 . C14 . 0.860 no
H16 . C16 . 0.871 no
H17 . C17 . 0.874 no
H19 . C19 . 0.876 no
H20 . C20 . 0.877 no
H1 . C1 . 0.877 no
H2 . C2 . 0.871 no
H3 . C3 . 0.871 no
C1 . C2 . 1.389(17) yes
C1 . N1 . 1.340(9) yes
C2 . C3 . 1.402(15) yes
C3 . C4 . 1.412(11) yes
C4 . C5 . 1.439(14) yes
C4 . C9 . 1.345(16) yes
C5 . C6 . 1.378(13) yes
C6 . C7 . 1.397(15) yes
C7 . C8 . 1.382(14) yes
C8 . C9 . 1.432(12) yes
C8 . O1 . 1.316(13) yes
C9 . N1 . 1.394(14) yes
C10 . C11 . 1.396(10) yes
C10 . F1 . 1.389(9) yes
C10 . N2 . 1.271(13) yes
C11 . C12 . 1.386(11) yes
C11 . B1 . 1.632(13) yes
C12 . C13 . 1.417(15) yes
C13 . C14 . 1.347(11) yes
C14 . N2 . 1.364(10) yes
C15 . C16 . 1.422(13) yes
C15 . C20 . 1.387(9) yes
C15 . B1 . 1.612(12) yes
C16 . C17 . 1.385(11) yes
C17 . C18 . 1.351(11) yes
C18 . C19 . 1.373(14) yes
C18 . I1 . 2.099(8) yes
C19 . C20 . 1.403(11) yes
B1 . O1 . 1.475(9) yes
B1 . N1 . 1.534(17) 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
H1 . C1 . C2 . 119.8 no
H1 . C1 . N1 . 118.1 no
C2 . C1 . N1 . 122.1(9) yes
C1 . C2 . H2 . 120.3 no
C1 . C2 . C3 . 121.4(8) yes
H2 . C2 . C3 . 118.2 no
C2 . C3 . H3 . 121.7 no
C2 . C3 . C4 . 117.5(12) yes
H3 . C3 . C4 . 120.7 no
C3 . C4 . C5 . 126.0(12) yes
C3 . C4 . C9 . 116.6(9) yes
C5 . C4 . C9 . 117.3(8) yes
C4 . C5 . H5 . 121.6 no
C4 . C5 . C6 . 116.2(12) yes
H5 . C5 . C6 . 122.1 no
C5 . C6 . H6 . 115.8 no
C5 . C6 . C7 . 126.3(10) yes
H6 . C6 . C7 . 117.9 no
C6 . C7 . H7 . 122.4 no
C6 . C7 . C8 . 117.5(8) yes
H7 . C7 . C8 . 120.1 no
C7 . C8 . C9 . 116.5(13) yes
C7 . C8 . O1 . 129.3(9) yes
C9 . C8 . O1 . 114.2(8) yes
C8 . C9 . C4 . 126.1(9) yes
C8 . C9 . N1 . 106.2(11) yes
C4 . C9 . N1 . 127.6(7) yes
C11 . C10 . F1 . 114.4(8) yes
C11 . C10 . N2 . 131.2(7) yes
F1 . C10 . N2 . 114.5(6) yes
C10 . C11 . C12 . 111.7(8) yes
C10 . C11 . B1 . 126.6(6) yes
C12 . C11 . B1 . 121.4(6) yes
C11 . C12 . H12 . 119.6 no
C11 . C12 . C13 . 121.1(7) yes
H12 . C12 . C13 . 119.2 no
C12 . C13 . H13 . 120.5 no
C12 . C13 . C14 . 118.0(8) yes
H13 . C13 . C14 . 121.1 no
C13 . C14 . H14 . 118.5 no
C13 . C14 . N2 . 123.4(9) yes
H14 . C14 . N2 . 117.9 no
C16 . C15 . C20 . 116.4(7) yes
C16 . C15 . B1 . 122.6(6) yes
C20 . C15 . B1 . 121.0(8) yes
C15 . C16 . H16 . 116.5 no
C15 . C16 . C17 . 122.7(6) yes
H16 . C16 . C17 . 120.8 no
C16 . C17 . H17 . 118.6 no
C16 . C17 . C18 . 117.8(9) yes
H17 . C17 . C18 . 123.4 no
C17 . C18 . C19 . 122.9(7) yes
C17 . C18 . I1 . 121.6(7) yes
C19 . C18 . I1 . 115.5(5) yes
C18 . C19 . H19 . 119.1 no
C18 . C19 . C20 . 119.0(7) yes
H19 . C19 . C20 . 121.8 no
C19 . C20 . C15 . 121.1(8) yes
C19 . C20 . H20 . 117.0 no
C15 . C20 . H20 . 121.9 no
C11 . B1 . C15 . 111.0(10) yes
C11 . B1 . O1 . 106.6(6) yes
C15 . B1 . O1 . 110.1(5) yes
C11 . B1 . N1 . 115.7(6) yes
C15 . B1 . N1 . 109.5(7) yes
O1 . B1 . N1 . 103.6(10) yes
B1 . O1 . C8 . 107.9(8) yes
C9 . N1 . B1 . 107.3(6) yes
C9 . N1 . C1 . 114.7(10) yes
B1 . N1 . C1 . 137.8(10) yes
C14 . N2 . C10 . 114.6(7) 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
C6 . H6 . N2 4_464 128.2(2) 0.876 2.580 3.197(12) yes
C14 . H14 . C9 2_576 131.8(4) 0.860 2.541 3.179(12) yes
C19 . H19 . O1 1_655 121.36(18) 0.876 2.368 2.921(12) yes
C20 . H20 . C1 . 129.6(2) 0.877 2.545 3.177(12) yes
C20 . H20 . O1 1_655 122.3(3) 0.877 2.414 2.977(12) yes
C1 . H1 . N2 2_676 132.4(4) 0.877 2.433 3.093(12) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 11/09/12 at 16:10:47
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 11/09/12 at 16:10:47
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
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
-1 11 2 x .
-3 14 6 x .
-3 14 6 x .
-3 15 1 x .
-5 9 8 x .
_database_code_depnum_ccdc_archive 'CCDC 993580'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1_P=4.88GPa
_audit_creation_date             12-09-10
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title '1_P=4.88GPa in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

#end of refcif 
_cell_length_a                   6.3469(5)
_cell_length_b                   13.6039(10)
_cell_length_c                   16.105(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.549(10)
_cell_angle_gamma                90
_cell_volume                     1390.5(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H10 B1 F1 I1 N2 O1 
# Dc =      2.15 Fooo =    888.00 Mu =     23.29 M =    451.03
# Found Formula = C20 H13 B1 F1 I1 N2 O1 
# Dc =      2.17 FOOO =    888.00 Mu =     23.30 M =    454.05

_chemical_formula_sum            'C20 H13 B1 F1 I1 N2 O1'
_chemical_formula_moiety         'C20 H13 B1 F1 I1 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         454.05


_cell_measurement_reflns_used    1943
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    296

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.350

_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.330

# Sheldrick geometric approximatio 0.50 0.63 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.63
_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       ω

# 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    'Superflip (Palatinus & Chapuis, 2007)'
_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      296
_diffrn_ambient_pressure         4882700
_diffrn_reflns_number            6772
_reflns_number_total             1187
_diffrn_reflns_av_R_equivalents  0.057
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1187 
# Theoretical number of reflections is about 5202 


_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.543
_diffrn_measured_fraction_theta_max 0.455

_diffrn_reflns_theta_full        25.032
_diffrn_measured_fraction_theta_full 0.456


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.66
_refine_diff_density_max         0.52


# 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         910
_refine_ls_number_restraints     0
_refine_ls_number_parameters     110
_oxford_refine_ls_R_factor_ref   0.0392
_refine_ls_wR_factor_ref         0.0417
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0002065
_refine_ls_shift/su_mean         0.0000195


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1187
_refine_ls_R_factor_all          0.0615
_refine_ls_wR_factor_all         0.0553

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                910
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.0417

# 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    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: 
 0.559 0.245 0.378 
;

# 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
H1 H 0.4944 0.8747 0.3942 0.0545 1.0000 Uiso R . . . . .
H2 H 0.5677 0.8699 0.2579 0.0643 1.0000 Uiso R . . . . .
H3 H 0.3513 0.7955 0.1667 0.0653 1.0000 Uiso R . . . . .
H5 H -0.0192 0.7077 0.1460 0.0681 1.0000 Uiso R . . . . .
H6 H -0.3032 0.6484 0.2107 0.0663 1.0000 Uiso R . . . . .
H7 H -0.3393 0.6554 0.3507 0.0562 1.0000 Uiso R . . . . .
H12 H -0.2073 0.8539 0.5546 0.0552 1.0000 Uiso R . . . . .
H13 H -0.2566 0.9751 0.6461 0.0713 1.0000 Uiso R . . . . .
H14 H 0.0195 1.0642 0.6898 0.0683 1.0000 Uiso R . . . . .
H16 H 0.0744 0.6320 0.5887 0.0552 1.0000 Uiso R . . . . .
H17 H 0.2713 0.5192 0.6524 0.0605 1.0000 Uiso R . . . . .
H19 H 0.7583 0.6143 0.5302 0.0471 1.0000 Uiso R . . . . .
H20 H 0.5618 0.7319 0.4737 0.0475 1.0000 Uiso R . . . . .
C1 C 0.4083(12) 0.8461(4) 0.3595(10) 0.0181(17) 1.0000 Uiso . . . . . .
C2 C 0.4564(13) 0.8409(5) 0.2763(10) 0.0193(17) 1.0000 Uiso . . . . . .
C3 C 0.3237(12) 0.7962(5) 0.2193(9) 0.0228(19) 1.0000 Uiso . . . . . .
C4 C 0.1314(12) 0.7572(4) 0.2520(9) 0.0151(16) 1.0000 Uiso . . . . . .
C5 C -0.0281(12) 0.7117(5) 0.2001(10) 0.0261(19) 1.0000 Uiso . . . . . .
C6 C -0.2061(13) 0.6765(5) 0.2408(11) 0.0218(18) 1.0000 Uiso . . . . . .
C7 C -0.2310(12) 0.6809(5) 0.3269(10) 0.0187(18) 1.0000 Uiso . . . . . .
C8 C -0.0779(12) 0.7250(4) 0.3744(10) 0.0167(17) 1.0000 Uiso . . . . . .
C9 C 0.0957(12) 0.7637(4) 0.3340(9) 0.0177(17) 1.0000 Uiso . . . . . .
C10 C 0.2480(14) 0.9370(5) 0.5670(11) 0.0234(19) 1.0000 Uiso . . . . . .
C11 C 0.0984(12) 0.8713(5) 0.5378(9) 0.0194(18) 1.0000 Uiso . . . . . .
C12 C -0.1007(13) 0.8897(5) 0.5703(9) 0.0213(18) 1.0000 Uiso . . . . . .
C13 C -0.1327(14) 0.9617(5) 0.6283(10) 0.0274(19) 1.0000 Uiso . . . . . .
C14 C 0.0382(14) 1.0170(5) 0.6557(10) 0.031(2) 1.0000 Uiso . . . . . .
C15 C 0.2849(11) 0.6975(4) 0.5245(9) 0.0154(16) 1.0000 Uiso . . . . . .
C16 C 0.2077(13) 0.6286(5) 0.5787(9) 0.0198(17) 1.0000 Uiso . . . . . .
C17 C 0.3300(13) 0.5602(4) 0.6184(10) 0.0195(18) 1.0000 Uiso . . . . . .
C18 C 0.5418(13) 0.5558(5) 0.5989(9) 0.0218(19) 1.0000 Uiso . . . . . .
C19 C 0.6243(12) 0.6190(5) 0.5402(9) 0.0179(17) 1.0000 Uiso . . . . . .
C20 C 0.4992(12) 0.6905(4) 0.5066(9) 0.0170(16) 1.0000 Uiso . . . . . .
I1 I 0.74804(8) 0.45774(3) 0.65514(6) 0.0269 1.0000 Uani . . . . . .
B1 B 0.1419(14) 0.7793(5) 0.4788(10) 0.019(2) 1.0000 Uiso . . . . . .
O1 O -0.0675(8) 0.7368(3) 0.4559(6) 0.0179(12) 1.0000 Uiso . . . . . .
N1 N 0.2331(10) 0.8032(4) 0.3902(7) 0.0170(14) 1.0000 Uiso . . . . . .
F1 F 0.4490(7) 0.9224(3) 0.5398(5) 0.0268(11) 1.0000 Uiso . . . . . .
N2 N 0.2295(11) 1.0051(5) 0.6234(8) 0.0283(17) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0239(3) 0.0169(3) 0.0397(11) 0.0018(3) -0.0046(3) 0.0030(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1226(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
H1 . C1 . 0.870 no
H2 . C2 . 0.864 no
H3 . C3 . 0.867 no
H5 . C5 . 0.876 no
H6 . C6 . 0.869 no
H7 . C7 . 0.863 no
H12 . C12 . 0.870 no
H13 . C13 . 0.859 no
H14 . C14 . 0.855 no
H16 . C16 . 0.864 no
H17 . C17 . 0.868 no
H19 . C19 . 0.869 no
H20 . C20 . 0.872 no
C1 . C2 . 1.379(18) yes
C1 . N1 . 1.353(11) yes
C2 . C3 . 1.381(16) yes
C3 . C4 . 1.436(12) yes
C4 . C5 . 1.446(15) yes
C4 . C9 . 1.344(17) yes
C5 . C6 . 1.396(14) yes
C6 . C7 . 1.399(17) yes
C7 . C8 . 1.368(15) yes
C8 . C9 . 1.389(13) yes
C8 . O1 . 1.325(14) yes
C9 . N1 . 1.362(14) yes
C10 . C11 . 1.384(13) yes
C10 . F1 . 1.367(11) yes
C10 . N2 . 1.303(18) yes
C11 . C12 . 1.394(13) yes
C11 . B1 . 1.598(14) yes
C12 . C13 . 1.371(17) yes
C13 . C14 . 1.388(13) yes
C14 . N2 . 1.335(12) yes
C15 . C16 . 1.375(15) yes
C15 . C20 . 1.397(11) yes
C15 . B1 . 1.609(13) yes
C16 . C17 . 1.366(13) yes
C17 . C18 . 1.385(13) yes
C18 . C19 . 1.385(16) yes
C18 . I1 . 2.071(9) yes
C19 . C20 . 1.364(12) yes
B1 . O1 . 1.492(11) yes
B1 . N1 . 1.579(18) 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
H1 . C1 . C2 . 120.3 no
H1 . C1 . N1 . 118.1 no
C2 . C1 . N1 . 121.5(10) yes
C1 . C2 . H2 . 119.9 no
C1 . C2 . C3 . 121.9(9) yes
H2 . C2 . C3 . 118.0 no
C2 . C3 . H3 . 121.8 no
C2 . C3 . C4 . 115.7(12) yes
H3 . C3 . C4 . 122.4 no
C3 . C4 . C5 . 122.6(13) yes
C3 . C4 . C9 . 119.2(10) yes
C5 . C4 . C9 . 118.2(9) yes
C4 . C5 . H5 . 123.4 no
C4 . C5 . C6 . 116.1(14) yes
H5 . C5 . C6 . 120.4 no
C5 . C6 . H6 . 117.5 no
C5 . C6 . C7 . 123.4(11) yes
H6 . C6 . C7 . 119.1 no
C6 . C7 . H7 . 121.4 no
C6 . C7 . C8 . 119.1(9) yes
H7 . C7 . C8 . 119.5 no
C7 . C8 . C9 . 117.8(13) yes
C7 . C8 . O1 . 129.4(10) yes
C9 . C8 . O1 . 112.7(9) yes
C8 . C9 . C4 . 125.2(10) yes
C8 . C9 . N1 . 110.1(13) yes
C4 . C9 . N1 . 124.5(9) yes
C11 . C10 . F1 . 115.9(10) yes
C11 . C10 . N2 . 129.0(10) yes
F1 . C10 . N2 . 114.7(9) yes
C10 . C11 . C12 . 112.2(9) yes
C10 . C11 . B1 . 125.9(8) yes
C12 . C11 . B1 . 121.8(7) yes
C11 . C12 . H12 . 119.7 no
C11 . C12 . C13 . 121.6(8) yes
H12 . C12 . C13 . 118.6 no
C12 . C13 . H13 . 121.4 no
C12 . C13 . C14 . 118.9(9) yes
H13 . C13 . C14 . 119.6 no
C13 . C14 . H14 . 119.9 no
C13 . C14 . N2 . 121.5(11) yes
H14 . C14 . N2 . 118.3 no
C16 . C15 . C20 . 116.0(8) yes
C16 . C15 . B1 . 124.0(7) yes
C20 . C15 . B1 . 119.9(9) yes
C15 . C16 . H16 . 115.9 no
C15 . C16 . C17 . 123.9(8) yes
H16 . C16 . C17 . 120.2 no
C16 . C17 . H17 . 119.2 no
C16 . C17 . C18 . 118.2(10) yes
H17 . C17 . C18 . 122.6 no
C17 . C18 . C19 . 120.1(9) yes
C17 . C18 . I1 . 122.7(8) yes
C19 . C18 . I1 . 117.2(6) yes
C18 . C19 . H19 . 117.3 no
C18 . C19 . C20 . 119.4(8) yes
H19 . C19 . C20 . 123.0 no
C15 . C20 . C19 . 122.1(9) yes
C15 . C20 . H20 . 122.1 no
C19 . C20 . H20 . 115.8 no
C15 . B1 . C11 . 111.7(11) yes
C15 . B1 . O1 . 110.0(6) yes
C11 . B1 . O1 . 106.9(7) yes
C15 . B1 . N1 . 110.2(8) yes
C11 . B1 . N1 . 116.3(7) yes
O1 . B1 . N1 . 101.0(10) yes
B1 . O1 . C8 . 109.1(9) yes
B1 . N1 . C9 . 106.4(8) yes
B1 . N1 . C1 . 136.8(10) yes
C9 . N1 . C1 . 116.7(11) yes
C14 . N2 . C10 . 116.5(9) 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
C1 . H1 . N2 2_676 132.7(5) 0.870 2.416 3.073(14) yes
C6 . H6 . N2 4_464 127.8(3) 0.869 2.526 3.135(14) yes
C14 . H14 . C9 2_576 130.8(5) 0.855 2.481 3.107(14) yes
C19 . H19 . O1 1_655 120.8(2) 0.869 2.335 2.878(14) yes
C20 . H20 . C1 . 130.4(2) 0.872 2.591 3.225(14) yes
C20 . H20 . O1 1_655 123.3(3) 0.872 2.373 2.944(14) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 10/09/12 at 16:29:58
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U[ISO])  UNTIL C    (   20 ) 
CONT I    (    1 ,X'S,U'S) 
CONT B    (    1 ,X'S,U[ISO])  UNTIL N    (    2 ) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 10/09/12 at 16:29:58
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 993581'
