# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_amc365_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 B F20), 2(C5 H17 B N O), C H2 Cl2'
_chemical_formula_sum            'C59 H36 B4 Cl2 F40 N2 O2'
_chemical_formula_weight         1679.04
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  P2yb

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

_cell_length_a                   8.8098(2)
_cell_length_b                   21.0038(6)
_cell_length_c                   17.4138(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.837(2)
_cell_angle_gamma                90.00
_cell_volume                     3183.99(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5891
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.92

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1668
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4629
_exptl_absorpt_correction_T_max  0.4952
_exptl_absorpt_process_details   'SADABS V2008/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30403
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             14515
_reflns_number_gt                10973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1131P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(12)
_refine_ls_number_reflns         14515
_refine_ls_number_parameters     989
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6388(9) 0.7508(3) 0.8573(4) 0.0412(15) Uani 1 1 d . . .
H1A H 0.7458 0.7786 0.8679 0.049 Uiso 1 1 calc R . .
H1B H 0.6395 0.7218 0.8048 0.049 Uiso 1 1 calc R . .
N1 N 0.6239(5) 0.7063(2) 0.9305(2) 0.0321(10) Uani 1 1 d . . .
H1N H 0.7120 0.6891 0.9457 0.038 Uiso 1 1 calc R . .
H2N H 0.6034 0.7302 0.9677 0.038 Uiso 1 1 calc R . .
O1 O 0.5009(5) 0.79477(18) 0.8472(2) 0.0419(10) Uani 1 1 d . . .
C1 C 0.5255(9) 0.8630(3) 0.8715(4) 0.0527(17) Uani 1 1 d . . .
H1C H 0.6122 0.8810 0.8486 0.063 Uiso 1 1 calc R . .
H1D H 0.4322 0.8882 0.8525 0.063 Uiso 1 1 calc R . .
C2 C 0.5590(7) 0.8663(3) 0.9562(3) 0.0399(13) Uani 1 1 d . . .
H2A H 0.4850 0.8400 0.9787 0.060 Uiso 1 1 calc R . .
H2B H 0.5512 0.9105 0.9730 0.060 Uiso 1 1 calc R . .
H2C H 0.6632 0.8505 0.9738 0.060 Uiso 1 1 calc R . .
C3 C 0.3901(8) 0.7889(3) 0.7755(4) 0.0517(16) Uani 1 1 d . . .
H3A H 0.2932 0.8099 0.7837 0.062 Uiso 1 1 calc R . .
H3B H 0.3675 0.7432 0.7658 0.062 Uiso 1 1 calc R . .
C4 C 0.4408(10) 0.8169(4) 0.7044(4) 0.0598(19) Uani 1 1 d . . .
H4A H 0.4600 0.8626 0.7124 0.090 Uiso 1 1 calc R . .
H4B H 0.3603 0.8106 0.6596 0.090 Uiso 1 1 calc R . .
H4C H 0.5354 0.7959 0.6948 0.090 Uiso 1 1 calc R . .
C5 C 0.5062(7) 0.6545(3) 0.9182(4) 0.0421(14) Uani 1 1 d . . .
H5A H 0.4039 0.6733 0.9040 0.063 Uiso 1 1 calc R . .
H5B H 0.5095 0.6298 0.9662 0.063 Uiso 1 1 calc R . .
H5C H 0.5281 0.6264 0.8763 0.063 Uiso 1 1 calc R . .
B2 B 0.3773(8) 0.7920(5) 0.4533(4) 0.055(2) Uani 1 1 d . A 1
H2D H 0.3541 0.7878 0.5134 0.066 Uiso 1 1 calc R A 1
H2E H 0.3187 0.8348 0.4270 0.066 Uiso 1 1 calc R A 1
N2 N 0.5613(6) 0.7971(2) 0.4523(3) 0.0400(11) Uani 1 1 d . A 1
H3N H 0.5757 0.7971 0.4080 0.048 Uiso 1 1 calc R A 1
H4N H 0.5908 0.8305 0.4709 0.048 Uiso 1 1 calc R A 1
O2 O 0.3231(5) 0.73635(19) 0.4093(2) 0.0390(9) Uani 1 1 d . A 1
C6 C 0.2658(8) 0.6835(2) 0.4503(3) 0.0387(14) Uani 1 1 d . A 1
H6A H 0.3277 0.6800 0.5026 0.046 Uiso 1 1 calc R A 1
H6B H 0.2788 0.6435 0.4219 0.046 Uiso 1 1 calc R A 1
C7 C 0.0960(9) 0.6912(3) 0.4588(5) 0.0569(19) Uani 1 1 d . A 1
H7A H 0.0790 0.7341 0.4781 0.085 Uiso 1 1 calc R A 1
H7B H 0.0685 0.6595 0.4956 0.085 Uiso 1 1 calc R A 1
H7C H 0.0321 0.6851 0.4081 0.085 Uiso 1 1 calc R A 1
C8 C 0.2363(7) 0.7447(3) 0.3276(3) 0.0401(13) Uani 1 1 d . A 1
H8A H 0.1988 0.7028 0.3066 0.048 Uiso 1 1 calc R A 1
H8B H 0.1461 0.7725 0.3291 0.048 Uiso 1 1 calc R A 1
C9 C 0.3368(6) 0.7731(4) 0.2768(4) 0.059(2) Uani 1 1 d . A 1
H9A H 0.3591 0.8174 0.2922 0.089 Uiso 1 1 calc R A 1
H9B H 0.2853 0.7717 0.2227 0.089 Uiso 1 1 calc R A 1
H9C H 0.4331 0.7490 0.2815 0.089 Uiso 1 1 calc R A 1
C10 C 0.6530(7) 0.7472(3) 0.4931(3) 0.0389(13) Uani 1 1 d . A 1
H10A H 0.6426 0.7485 0.5483 0.058 Uiso 1 1 calc R A 1
H10B H 0.7610 0.7533 0.4874 0.058 Uiso 1 1 calc R A 1
H10C H 0.6177 0.7058 0.4713 0.058 Uiso 1 1 calc R A 1
B3 B 0.9759(6) 0.5401(2) 0.1671(3) 0.0169(9) Uani 1 1 d . B 1
C11 C 0.8360(5) 0.5651(2) 0.2132(2) 0.0181(8) Uani 1 1 d . B 1
C12 C 0.8198(5) 0.6261(2) 0.2439(2) 0.0184(9) Uani 1 1 d . B 1
C13 C 0.7102(5) 0.6423(2) 0.2894(2) 0.0211(9) Uani 1 1 d . B 1
C14 C 0.6095(5) 0.5967(2) 0.3077(3) 0.0235(9) Uani 1 1 d . B 1
C15 C 0.6203(5) 0.5355(2) 0.2807(2) 0.0203(9) Uani 1 1 d . B 1
C16 C 0.7307(5) 0.5217(2) 0.2352(2) 0.0176(8) Uani 1 1 d . B 1
C17 C 0.9145(5) 0.5003(2) 0.0855(2) 0.0186(9) Uani 1 1 d . B 1
C18 C 0.7659(5) 0.4993(2) 0.0437(2) 0.0198(9) Uani 1 1 d . B 1
C19 C 0.7293(6) 0.4694(2) -0.0284(3) 0.0243(10) Uani 1 1 d . B 1
C20 C 0.8409(6) 0.4391(2) -0.0610(3) 0.0249(10) Uani 1 1 d . B 1
C21 C 0.9887(6) 0.4394(2) -0.0229(3) 0.0237(10) Uani 1 1 d . B 1
C22 C 1.0214(5) 0.4702(2) 0.0480(3) 0.0216(9) Uani 1 1 d . B 1
C23 C 1.0732(5) 0.5990(2) 0.1349(2) 0.0178(8) Uani 1 1 d . B 1
C24 C 1.2304(5) 0.6060(2) 0.1440(2) 0.0188(9) Uani 1 1 d . B 1
C25 C 1.3048(5) 0.6530(2) 0.1093(3) 0.0256(10) Uani 1 1 d . B 1
C26 C 1.2219(5) 0.6965(2) 0.0611(3) 0.0241(10) Uani 1 1 d . B 1
C27 C 1.0625(5) 0.6921(2) 0.0496(2) 0.0203(9) Uani 1 1 d . B 1
C28 C 0.9935(5) 0.6442(2) 0.0850(2) 0.0185(9) Uani 1 1 d . B 1
C29 C 1.0764(5) 0.4953(2) 0.2346(2) 0.0198(9) Uani 1 1 d . B 1
C30 C 1.1456(5) 0.5233(2) 0.3019(2) 0.0203(9) Uani 1 1 d . B 1
C31 C 1.2254(5) 0.4908(3) 0.3663(2) 0.0270(11) Uani 1 1 d . B 1
C32 C 1.2357(6) 0.4265(3) 0.3630(3) 0.0319(12) Uani 1 1 d . B 1
C33 C 1.1679(7) 0.3953(3) 0.2974(3) 0.0346(12) Uani 1 1 d . B 1
C34 C 1.0875(6) 0.4291(2) 0.2363(3) 0.0249(10) Uani 1 1 d . B 1
F1 F 0.9157(3) 0.67410(12) 0.23056(15) 0.0217(5) Uani 1 1 d . B 1
F2 F 0.7035(3) 0.70212(13) 0.31660(17) 0.0299(6) Uani 1 1 d . B 1
F3 F 0.5041(3) 0.61198(15) 0.35290(18) 0.0328(7) Uani 1 1 d . B 1
F4 F 0.5254(3) 0.49031(14) 0.29935(16) 0.0280(6) Uani 1 1 d . B 1
F5 F 0.7377(3) 0.46021(12) 0.21156(15) 0.0224(5) Uani 1 1 d . B 1
F6 F 0.6478(3) 0.52834(13) 0.07080(14) 0.0234(6) Uani 1 1 d . B 1
F7 F 0.5823(3) 0.47152(14) -0.06561(15) 0.0282(6) Uani 1 1 d . B 1
F8 F 0.8081(4) 0.41103(15) -0.13096(16) 0.0345(7) Uani 1 1 d . B 1
F9 F 1.1005(3) 0.41116(15) -0.05512(17) 0.0336(7) Uani 1 1 d . B 1
F10 F 1.1720(3) 0.47027(13) 0.08142(15) 0.0250(6) Uani 1 1 d . B 1
F11 F 1.3243(3) 0.56436(14) 0.18834(15) 0.0270(6) Uani 1 1 d . B 1
F12 F 1.4603(3) 0.65687(16) 0.12027(17) 0.0352(7) Uani 1 1 d . B 1
F13 F 1.2906(3) 0.74225(14) 0.02445(17) 0.0340(7) Uani 1 1 d . B 1
F14 F 0.9771(3) 0.73395(12) 0.00165(15) 0.0265(6) Uani 1 1 d . B 1
F15 F 0.8384(3) 0.64149(12) 0.06979(14) 0.0201(5) Uani 1 1 d . B 1
F16 F 1.1412(3) 0.58804(13) 0.30959(15) 0.0266(6) Uani 1 1 d . B 1
F17 F 1.2902(3) 0.52336(17) 0.42979(16) 0.0371(7) Uani 1 1 d . B 1
F18 F 1.3136(4) 0.39348(18) 0.42316(18) 0.0466(9) Uani 1 1 d . B 1
F19 F 1.1766(5) 0.33120(17) 0.2942(2) 0.0548(10) Uani 1 1 d . B 1
F20 F 1.0191(4) 0.39317(14) 0.17611(18) 0.0368(7) Uani 1 1 d . B 1
B4 B 0.1774(5) 0.4741(2) 0.6882(3) 0.0145(9) Uani 1 1 d . C 1
C35 C 0.0833(5) 0.5146(2) 0.7472(2) 0.0184(8) Uani 1 1 d . C 1
C36 C 0.1654(5) 0.5357(2) 0.8183(2) 0.0170(8) Uani 1 1 d . C 1
C37 C 0.0972(5) 0.5659(2) 0.8755(3) 0.0224(9) Uani 1 1 d . C 1
C38 C -0.0607(5) 0.5731(2) 0.8642(3) 0.0225(9) Uani 1 1 d . C 1
C39 C -0.1465(5) 0.5518(2) 0.7973(3) 0.0233(9) Uani 1 1 d . C 1
C40 C -0.0741(5) 0.5228(2) 0.7414(3) 0.0206(9) Uani 1 1 d . C 1
C41 C 0.0718(5) 0.4590(2) 0.6025(2) 0.0162(8) Uani 1 1 d . C 1
C42 C 0.0069(5) 0.5102(2) 0.5574(2) 0.0168(8) Uani 1 1 d . C 1
C43 C -0.0711(5) 0.5053(2) 0.4836(2) 0.0177(8) Uani 1 1 d . C 1
C44 C -0.0897(5) 0.4455(2) 0.4489(2) 0.0198(9) Uani 1 1 d . C 1
C45 C -0.0264(5) 0.3933(2) 0.4900(2) 0.0199(9) Uani 1 1 d . C 1
C46 C 0.0514(5) 0.4011(2) 0.5647(2) 0.0181(8) Uani 1 1 d . C 1
C47 C 0.3234(5) 0.5123(2) 0.6617(2) 0.0159(8) Uani 1 1 d . C 1
C48 C 0.4171(5) 0.4807(2) 0.6160(2) 0.0191(9) Uani 1 1 d . C 1
C49 C 0.5290(5) 0.5087(2) 0.5803(2) 0.0216(9) Uani 1 1 d . C 1
C50 C 0.5592(5) 0.5725(2) 0.5917(3) 0.0252(10) Uani 1 1 d . C 1
C51 C 0.4719(5) 0.6068(2) 0.6371(3) 0.0217(9) Uani 1 1 d . C 1
C52 C 0.3572(5) 0.5770(2) 0.6708(3) 0.0194(9) Uani 1 1 d . C 1
C53 C 0.2255(5) 0.40905(19) 0.7404(2) 0.0151(8) Uani 1 1 d . C 1
C54 C 0.3694(5) 0.3931(2) 0.7783(2) 0.0175(8) Uani 1 1 d . C 1
C55 C 0.3972(5) 0.3431(2) 0.8312(2) 0.0197(9) Uani 1 1 d . C 1
C56 C 0.2754(6) 0.3069(2) 0.8489(2) 0.0208(9) Uani 1 1 d . C 1
C57 C 0.1305(5) 0.3211(2) 0.8134(2) 0.0199(9) Uani 1 1 d . C 1
C58 C 0.1075(5) 0.3704(2) 0.7600(2) 0.0165(8) Uani 1 1 d . C 1
F21 F 0.3186(3) 0.52867(12) 0.83267(14) 0.0214(5) Uani 1 1 d . C 1
F22 F 0.1826(3) 0.58563(14) 0.94165(15) 0.0290(6) Uani 1 1 d . C 1
F23 F -0.1273(3) 0.60267(15) 0.91907(15) 0.0299(6) Uani 1 1 d . C 1
F24 F -0.3009(3) 0.55888(15) 0.78659(16) 0.0278(6) Uani 1 1 d . C 1
F25 F -0.1696(3) 0.50150(13) 0.67830(14) 0.0219(5) Uani 1 1 d . C 1
F26 F 0.0222(3) 0.56999(12) 0.58796(15) 0.0215(5) Uani 1 1 d . C 1
F27 F -0.1292(3) 0.55665(13) 0.44328(15) 0.0281(6) Uani 1 1 d . C 1
F28 F -0.1650(3) 0.43835(14) 0.37631(15) 0.0287(6) Uani 1 1 d . C 1
F29 F -0.0390(3) 0.33539(14) 0.45656(16) 0.0301(6) Uani 1 1 d . C 1
F30 F 0.1123(3) 0.34656(12) 0.59910(15) 0.0247(6) Uani 1 1 d . C 1
F31 F 0.3939(3) 0.41739(12) 0.60347(15) 0.0223(5) Uani 1 1 d . C 1
F32 F 0.6109(3) 0.47403(14) 0.53635(16) 0.0292(6) Uani 1 1 d . C 1
F33 F 0.6695(3) 0.60111(15) 0.55916(19) 0.0367(7) Uani 1 1 d . C 1
F34 F 0.4994(3) 0.66956(13) 0.64791(18) 0.0325(7) Uani 1 1 d . C 1
F35 F 0.2792(3) 0.61601(12) 0.71146(16) 0.0257(6) Uani 1 1 d . C 1
F36 F 0.4958(3) 0.42597(12) 0.76602(14) 0.0210(5) Uani 1 1 d . C 1
F37 F 0.5407(3) 0.33014(13) 0.86729(15) 0.0261(6) Uani 1 1 d . C 1
F38 F 0.3014(3) 0.25917(12) 0.90050(16) 0.0274(6) Uani 1 1 d . C 1
F39 F 0.0091(3) 0.28773(12) 0.83089(15) 0.0240(6) Uani 1 1 d . C 1
F40 F -0.0403(3) 0.38240(12) 0.72781(14) 0.0194(5) Uani 1 1 d . C 1
C59 C 0.9705(11) 0.6909(4) 0.7298(5) 0.075(2) Uani 1 1 d . D 1
H59A H 0.9971 0.6453 0.7264 0.090 Uiso 1 1 calc R D 1
H59B H 0.8571 0.6947 0.7214 0.090 Uiso 1 1 calc R D 1
Cl1 Cl 1.0482(3) 0.72138(10) 0.82537(11) 0.0699(5) Uani 1 1 d . D 1
Cl2 Cl 1.0465(3) 0.73423(11) 0.65778(12) 0.0740(6) Uani 1 1 d . D 1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.514(8) . ?
B1 N1 1.602(8) . ?
B1 H1A 1.1000 . ?
B1 H1B 1.1000 . ?
N1 C5 1.496(7) . ?
N1 H1N 0.8600 . ?
N1 H2N 0.8600 . ?
O1 C3 1.467(7) . ?
O1 C1 1.500(7) . ?
C1 C2 1.461(9) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.500(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
B2 O2 1.438(10) . ?
B2 N2 1.627(9) . ?
B2 H2D 1.1000 . ?
B2 H2E 1.1000 . ?
N2 C10 1.442(8) . ?
N2 H3N 0.8000 . ?
N2 H4N 0.8000 . ?
O2 C6 1.452(6) . ?
O2 C8 1.517(7) . ?
C6 C7 1.535(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.472(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
B3 C23 1.651(7) . ?
B3 C29 1.654(6) . ?
B3 C11 1.657(6) . ?
B3 C17 1.665(6) . ?
C11 C16 1.395(6) . ?
C11 C12 1.403(6) . ?
C12 F1 1.358(5) . ?
C12 C13 1.383(6) . ?
C13 F2 1.347(5) . ?
C13 C14 1.376(7) . ?
C14 F3 1.345(5) . ?
C14 C15 1.376(7) . ?
C15 F4 1.338(5) . ?
C15 C16 1.376(6) . ?
C16 F5 1.361(5) . ?
C17 C22 1.380(6) . ?
C17 C18 1.397(6) . ?
C18 F6 1.352(5) . ?
C18 C19 1.397(6) . ?
C19 F7 1.356(5) . ?
C19 C20 1.366(7) . ?
C20 F8 1.344(5) . ?
C20 C21 1.368(7) . ?
C21 F9 1.345(5) . ?
C21 C22 1.384(6) . ?
C22 F10 1.365(5) . ?
C23 C24 1.378(6) . ?
C23 C28 1.400(6) . ?
C24 F11 1.360(5) . ?
C24 C25 1.376(7) . ?
C25 F12 1.356(5) . ?
C25 C26 1.371(7) . ?
C26 F13 1.349(5) . ?
C26 C27 1.390(7) . ?
C27 F14 1.358(5) . ?
C27 C28 1.371(6) . ?
C28 F15 1.353(5) . ?
C29 C30 1.368(6) . ?
C29 C34 1.394(7) . ?
C30 F16 1.367(6) . ?
C30 C31 1.406(6) . ?
C31 F17 1.350(6) . ?
C31 C32 1.354(8) . ?
C32 F18 1.353(5) . ?
C32 C33 1.371(8) . ?
C33 F19 1.351(7) . ?
C33 C34 1.380(7) . ?
C34 F20 1.355(6) . ?
B4 C47 1.641(6) . ?
B4 C35 1.652(6) . ?
B4 C53 1.659(6) . ?
B4 C41 1.663(6) . ?
C35 C40 1.385(6) . ?
C35 C36 1.407(6) . ?
C36 F21 1.343(5) . ?
C36 C37 1.392(6) . ?
C37 F22 1.341(5) . ?
C37 C38 1.383(7) . ?
C38 F23 1.347(5) . ?
C38 C39 1.363(6) . ?
C39 F24 1.353(5) . ?
C39 C40 1.385(6) . ?
C40 F25 1.353(5) . ?
C41 C46 1.382(6) . ?
C41 C42 1.400(6) . ?
C42 F26 1.363(5) . ?
C42 C43 1.365(6) . ?
C43 F27 1.344(5) . ?
C43 C44 1.393(6) . ?
C44 F28 1.343(5) . ?
C44 C45 1.378(6) . ?
C45 F29 1.346(5) . ?
C45 C46 1.384(6) . ?
C46 F30 1.364(5) . ?
C47 C52 1.394(6) . ?
C47 C48 1.399(6) . ?
C48 F31 1.358(5) . ?
C48 C49 1.376(6) . ?
C49 F32 1.345(5) . ?
C49 C50 1.373(7) . ?
C50 F33 1.340(5) . ?
C50 C51 1.386(7) . ?
C51 F34 1.349(5) . ?
C51 C52 1.393(6) . ?
C52 F35 1.340(5) . ?
C53 C54 1.378(6) . ?
C53 C58 1.401(6) . ?
C54 F36 1.354(5) . ?
C54 C55 1.394(6) . ?
C55 F37 1.350(5) . ?
C55 C56 1.389(7) . ?
C56 F38 1.342(5) . ?
C56 C57 1.363(7) . ?
C57 F39 1.352(5) . ?
C57 C58 1.387(6) . ?
C58 F40 1.359(5) . ?
C59 Cl2 1.763(9) . ?
C59 Cl1 1.816(10) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 N1 106.6(5) . . ?
O1 B1 H1A 110.4 . . ?
N1 B1 H1A 110.4 . . ?
O1 B1 H1B 110.4 . . ?
N1 B1 H1B 110.4 . . ?
H1A B1 H1B 108.6 . . ?
C5 N1 B1 116.8(5) . . ?
C5 N1 H1N 108.1 . . ?
B1 N1 H1N 108.1 . . ?
C5 N1 H2N 108.1 . . ?
B1 N1 H2N 108.1 . . ?
H1N N1 H2N 107.3 . . ?
C3 O1 C1 111.6(4) . . ?
C3 O1 B1 117.7(5) . . ?
C1 O1 B1 118.1(5) . . ?
C2 C1 O1 109.1(5) . . ?
C2 C1 H1C 109.9 . . ?
O1 C1 H1C 109.9 . . ?
C2 C1 H1D 109.9 . . ?
O1 C1 H1D 109.9 . . ?
H1C C1 H1D 108.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 115.2(6) . . ?
O1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
O1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 B2 N2 107.3(6) . . ?
O2 B2 H2D 110.3 . . ?
N2 B2 H2D 110.3 . . ?
O2 B2 H2E 110.3 . . ?
N2 B2 H2E 110.3 . . ?
H2D B2 H2E 108.5 . . ?
C10 N2 B2 115.5(5) . . ?
C10 N2 H3N 108.4 . . ?
B2 N2 H3N 108.4 . . ?
C10 N2 H4N 108.4 . . ?
B2 N2 H4N 108.4 . . ?
H3N N2 H4N 107.5 . . ?
B2 O2 C6 118.1(5) . . ?
B2 O2 C8 118.9(5) . . ?
C6 O2 C8 112.7(4) . . ?
O2 C6 C7 112.6(5) . . ?
O2 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
O2 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C9 C8 O2 110.3(5) . . ?
C9 C8 H8A 109.6 . . ?
O2 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
O2 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C23 B3 C29 114.7(4) . . ?
C23 B3 C11 113.0(3) . . ?
C29 B3 C11 101.1(3) . . ?
C23 B3 C17 101.8(3) . . ?
C29 B3 C17 112.9(4) . . ?
C11 B3 C17 113.9(4) . . ?
C16 C11 C12 112.4(4) . . ?
C16 C11 B3 120.1(4) . . ?
C12 C11 B3 126.9(4) . . ?
F1 C12 C13 115.0(4) . . ?
F1 C12 C11 120.7(4) . . ?
C13 C12 C11 124.3(4) . . ?
F2 C13 C14 120.2(4) . . ?
F2 C13 C12 120.2(4) . . ?
C14 C13 C12 119.6(4) . . ?
F3 C14 C13 119.8(4) . . ?
F3 C14 C15 120.9(4) . . ?
C13 C14 C15 119.3(4) . . ?
F4 C15 C16 120.9(4) . . ?
F4 C15 C14 120.0(4) . . ?
C16 C15 C14 119.0(4) . . ?
F5 C16 C15 116.3(4) . . ?
F5 C16 C11 118.4(4) . . ?
C15 C16 C11 125.4(4) . . ?
C22 C17 C18 113.5(4) . . ?
C22 C17 B3 118.6(4) . . ?
C18 C17 B3 127.5(4) . . ?
F6 C18 C17 121.3(4) . . ?
F6 C18 C19 115.6(4) . . ?
C17 C18 C19 123.0(4) . . ?
F7 C19 C20 120.8(4) . . ?
F7 C19 C18 119.1(4) . . ?
C20 C19 C18 120.1(4) . . ?
F8 C20 C19 120.8(4) . . ?
F8 C20 C21 119.9(4) . . ?
C19 C20 C21 119.2(4) . . ?
F9 C21 C20 119.9(4) . . ?
F9 C21 C22 120.9(4) . . ?
C20 C21 C22 119.2(4) . . ?
F10 C22 C17 119.2(4) . . ?
F10 C22 C21 115.9(4) . . ?
C17 C22 C21 125.0(4) . . ?
C24 C23 C28 113.5(4) . . ?
C24 C23 B3 127.3(4) . . ?
C28 C23 B3 118.8(4) . . ?
F11 C24 C25 114.9(4) . . ?
F11 C24 C23 120.7(4) . . ?
C25 C24 C23 124.4(4) . . ?
F12 C25 C26 118.6(4) . . ?
F12 C25 C24 121.3(4) . . ?
C26 C25 C24 120.1(4) . . ?
F13 C26 C25 121.9(4) . . ?
F13 C26 C27 119.7(4) . . ?
C25 C26 C27 118.4(4) . . ?
F14 C27 C28 120.7(4) . . ?
F14 C27 C26 119.9(4) . . ?
C28 C27 C26 119.4(4) . . ?
F15 C28 C27 116.5(4) . . ?
F15 C28 C23 119.3(4) . . ?
C27 C28 C23 124.2(4) . . ?
C30 C29 C34 113.0(4) . . ?
C30 C29 B3 118.9(4) . . ?
C34 C29 B3 127.7(4) . . ?
F16 C30 C29 119.8(4) . . ?
F16 C30 C31 115.1(4) . . ?
C29 C30 C31 125.2(4) . . ?
F17 C31 C32 121.2(4) . . ?
F17 C31 C30 120.2(5) . . ?
C32 C31 C30 118.6(4) . . ?
F18 C32 C31 120.5(5) . . ?
F18 C32 C33 120.3(5) . . ?
C31 C32 C33 119.2(4) . . ?
F19 C33 C32 119.3(4) . . ?
F19 C33 C34 120.4(5) . . ?
C32 C33 C34 120.2(5) . . ?
F20 C34 C33 115.2(4) . . ?
F20 C34 C29 121.2(4) . . ?
C33 C34 C29 123.6(5) . . ?
C47 B4 C35 114.4(3) . . ?
C47 B4 C53 114.3(3) . . ?
C35 B4 C53 101.2(3) . . ?
C47 B4 C41 101.3(3) . . ?
C35 B4 C41 113.0(3) . . ?
C53 B4 C41 113.3(3) . . ?
C40 C35 C36 113.5(4) . . ?
C40 C35 B4 127.7(4) . . ?
C36 C35 B4 118.1(4) . . ?
F21 C36 C37 116.7(4) . . ?
F21 C36 C35 119.7(4) . . ?
C37 C36 C35 123.6(4) . . ?
F22 C37 C38 120.5(4) . . ?
F22 C37 C36 120.6(4) . . ?
C38 C37 C36 118.9(4) . . ?
F23 C38 C39 120.8(4) . . ?
F23 C38 C37 119.2(4) . . ?
C39 C38 C37 119.9(4) . . ?
F24 C39 C38 119.7(4) . . ?
F24 C39 C40 120.9(4) . . ?
C38 C39 C40 119.4(4) . . ?
F25 C40 C39 114.9(4) . . ?
F25 C40 C35 120.6(4) . . ?
C39 C40 C35 124.6(4) . . ?
C46 C41 C42 113.4(4) . . ?
C46 C41 B4 127.5(4) . . ?
C42 C41 B4 118.8(4) . . ?
F26 C42 C43 116.2(4) . . ?
F26 C42 C41 118.7(4) . . ?
C43 C42 C41 125.0(4) . . ?
F27 C43 C42 121.9(4) . . ?
F27 C43 C44 119.2(4) . . ?
C42 C43 C44 118.9(4) . . ?
F28 C44 C45 120.1(4) . . ?
F28 C44 C43 121.1(4) . . ?
C45 C44 C43 118.8(4) . . ?
F29 C45 C44 119.6(4) . . ?
F29 C45 C46 120.6(4) . . ?
C44 C45 C46 119.7(4) . . ?
F30 C46 C41 121.1(4) . . ?
F30 C46 C45 114.7(4) . . ?
C41 C46 C45 124.1(4) . . ?
C52 C47 C48 113.1(4) . . ?
C52 C47 B4 127.4(4) . . ?
C48 C47 B4 118.9(4) . . ?
F31 C48 C49 116.5(4) . . ?
F31 C48 C47 118.0(4) . . ?
C49 C48 C47 125.5(4) . . ?
F32 C49 C50 120.1(4) . . ?
F32 C49 C48 120.7(4) . . ?
C50 C49 C48 119.2(4) . . ?
F33 C50 C49 120.9(4) . . ?
F33 C50 C51 120.6(4) . . ?
C49 C50 C51 118.5(4) . . ?
F34 C51 C50 119.0(4) . . ?
F34 C51 C52 120.4(4) . . ?
C50 C51 C52 120.6(4) . . ?
F35 C52 C51 114.3(4) . . ?
F35 C52 C47 122.6(4) . . ?
C51 C52 C47 123.1(4) . . ?
C54 C53 C58 113.9(4) . . ?
C54 C53 B4 126.9(4) . . ?
C58 C53 B4 118.3(4) . . ?
F36 C54 C53 121.3(4) . . ?
F36 C54 C55 115.0(4) . . ?
C53 C54 C55 123.7(4) . . ?
F37 C55 C56 119.1(4) . . ?
F37 C55 C54 121.1(4) . . ?
C56 C55 C54 119.8(4) . . ?
F38 C56 C57 121.2(4) . . ?
F38 C56 C55 120.0(4) . . ?
C57 C56 C55 118.8(4) . . ?
F39 C57 C56 120.2(4) . . ?
F39 C57 C58 120.0(4) . . ?
C56 C57 C58 119.9(4) . . ?
F40 C58 C57 116.5(4) . . ?
F40 C58 C53 119.5(4) . . ?
C57 C58 C53 124.0(4) . . ?
Cl2 C59 Cl1 109.8(5) . . ?
Cl2 C59 H59A 109.7 . . ?
Cl1 C59 H59A 109.7 . . ?
Cl2 C59 H59B 109.7 . . ?
Cl1 C59 H59B 109.7 . . ?
H59A C59 H59B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 B1 N1 C5 74.5(6) . . . . ?
N1 B1 O1 C3 -115.9(6) . . . . ?
N1 B1 O1 C1 105.4(6) . . . . ?
C3 O1 C1 C2 148.3(6) . . . . ?
B1 O1 C1 C2 -70.6(7) . . . . ?
C1 O1 C3 C4 65.6(7) . . . . ?
B1 O1 C3 C4 -75.6(7) . . . . ?
O2 B2 N2 C10 -66.7(6) . . . . ?
N2 B2 O2 C6 113.6(5) . . . . ?
N2 B2 O2 C8 -103.7(6) . . . . ?
B2 O2 C6 C7 85.1(7) . . . . ?
C8 O2 C6 C7 -59.8(6) . . . . ?
B2 O2 C8 C9 64.2(7) . . . . ?
C6 O2 C8 C9 -151.3(6) . . . . ?
C23 B3 C11 C16 171.8(4) . . . . ?
C29 B3 C11 C16 -65.1(5) . . . . ?
C17 B3 C11 C16 56.3(5) . . . . ?
C23 B3 C11 C12 -17.8(6) . . . . ?
C29 B3 C11 C12 105.3(5) . . . . ?
C17 B3 C11 C12 -133.3(4) . . . . ?
C16 C11 C12 F1 178.0(3) . . . . ?
B3 C11 C12 F1 6.9(6) . . . . ?
C16 C11 C12 C13 -1.3(6) . . . . ?
B3 C11 C12 C13 -172.4(4) . . . . ?
F1 C12 C13 F2 0.5(6) . . . . ?
C11 C12 C13 F2 179.8(4) . . . . ?
F1 C12 C13 C14 -178.7(4) . . . . ?
C11 C12 C13 C14 0.7(7) . . . . ?
F2 C13 C14 F3 -0.1(6) . . . . ?
C12 C13 C14 F3 179.1(4) . . . . ?
F2 C13 C14 C15 -178.7(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
F3 C14 C15 F4 -0.1(6) . . . . ?
C13 C14 C15 F4 178.5(4) . . . . ?
F3 C14 C15 C16 -179.4(4) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
F4 C15 C16 F5 -0.5(6) . . . . ?
C14 C15 C16 F5 178.7(4) . . . . ?
F4 C15 C16 C11 -179.3(4) . . . . ?
C14 C15 C16 C11 0.0(6) . . . . ?
C12 C11 C16 F5 -177.7(3) . . . . ?
B3 C11 C16 F5 -6.0(5) . . . . ?
C12 C11 C16 C15 1.0(6) . . . . ?
B3 C11 C16 C15 172.7(4) . . . . ?
C23 B3 C17 C22 66.5(5) . . . . ?
C29 B3 C17 C22 -57.0(5) . . . . ?
C11 B3 C17 C22 -171.6(4) . . . . ?
C23 B3 C17 C18 -105.2(5) . . . . ?
C29 B3 C17 C18 131.2(5) . . . . ?
C11 B3 C17 C18 16.7(6) . . . . ?
C22 C17 C18 F6 -177.9(4) . . . . ?
B3 C17 C18 F6 -5.8(7) . . . . ?
C22 C17 C18 C19 1.2(6) . . . . ?
B3 C17 C18 C19 173.4(4) . . . . ?
F6 C18 C19 F7 0.2(6) . . . . ?
C17 C18 C19 F7 -179.1(4) . . . . ?
F6 C18 C19 C20 179.6(4) . . . . ?
C17 C18 C19 C20 0.4(7) . . . . ?
F7 C19 C20 F8 0.6(7) . . . . ?
C18 C19 C20 F8 -178.8(4) . . . . ?
F7 C19 C20 C21 178.1(4) . . . . ?
C18 C19 C20 C21 -1.3(7) . . . . ?
F8 C20 C21 F9 -0.8(7) . . . . ?
C19 C20 C21 F9 -178.3(4) . . . . ?
F8 C20 C21 C22 178.0(4) . . . . ?
C19 C20 C21 C22 0.5(7) . . . . ?
C18 C17 C22 F10 177.3(4) . . . . ?
B3 C17 C22 F10 4.4(6) . . . . ?
C18 C17 C22 C21 -2.2(7) . . . . ?
B3 C17 C22 C21 -175.0(4) . . . . ?
F9 C21 C22 F10 0.7(6) . . . . ?
C20 C21 C22 F10 -178.1(4) . . . . ?
F9 C21 C22 C17 -179.9(4) . . . . ?
C20 C21 C22 C17 1.4(7) . . . . ?
C29 B3 C23 C24 16.1(6) . . . . ?
C11 B3 C23 C24 131.3(4) . . . . ?
C17 B3 C23 C24 -106.2(5) . . . . ?
C29 B3 C23 C28 -172.0(4) . . . . ?
C11 B3 C23 C28 -56.8(5) . . . . ?
C17 B3 C23 C28 65.7(5) . . . . ?
C28 C23 C24 F11 -177.6(4) . . . . ?
B3 C23 C24 F11 -5.3(6) . . . . ?
C28 C23 C24 C25 1.1(6) . . . . ?
B3 C23 C24 C25 173.4(4) . . . . ?
F11 C24 C25 F12 -0.7(6) . . . . ?
C23 C24 C25 F12 -179.5(4) . . . . ?
F11 C24 C25 C26 177.9(4) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
F12 C25 C26 F13 0.4(7) . . . . ?
C24 C25 C26 F13 -178.2(4) . . . . ?
F12 C25 C26 C27 179.6(4) . . . . ?
C24 C25 C26 C27 0.9(7) . . . . ?
F13 C26 C27 F14 -0.1(6) . . . . ?
C25 C26 C27 F14 -179.3(4) . . . . ?
F13 C26 C27 C28 177.9(4) . . . . ?
C25 C26 C27 C28 -1.3(6) . . . . ?
F14 C27 C28 F15 -0.3(6) . . . . ?
C26 C27 C28 F15 -178.2(4) . . . . ?
F14 C27 C28 C23 179.7(4) . . . . ?
C26 C27 C28 C23 1.7(7) . . . . ?
C24 C23 C28 F15 178.4(4) . . . . ?
B3 C23 C28 F15 5.4(6) . . . . ?
C24 C23 C28 C27 -1.5(6) . . . . ?
B3 C23 C28 C27 -174.6(4) . . . . ?
C23 B3 C29 C30 58.1(5) . . . . ?
C11 B3 C29 C30 -63.9(5) . . . . ?
C17 B3 C29 C30 174.1(4) . . . . ?
C23 B3 C29 C34 -129.7(5) . . . . ?
C11 B3 C29 C34 108.3(5) . . . . ?
C17 B3 C29 C34 -13.7(6) . . . . ?
C34 C29 C30 F16 -178.6(4) . . . . ?
B3 C29 C30 F16 -5.3(6) . . . . ?
C34 C29 C30 C31 2.1(6) . . . . ?
B3 C29 C30 C31 175.4(4) . . . . ?
F16 C30 C31 F17 0.3(6) . . . . ?
C29 C30 C31 F17 179.6(4) . . . . ?
F16 C30 C31 C32 -179.6(4) . . . . ?
C29 C30 C31 C32 -0.2(7) . . . . ?
F17 C31 C32 F18 -1.0(7) . . . . ?
C30 C31 C32 F18 178.9(4) . . . . ?
F17 C31 C32 C33 179.9(5) . . . . ?
C30 C31 C32 C33 -0.2(7) . . . . ?
F18 C32 C33 F19 1.5(8) . . . . ?
C31 C32 C33 F19 -179.3(5) . . . . ?
F18 C32 C33 C34 179.6(5) . . . . ?
C31 C32 C33 C34 -1.3(8) . . . . ?
F19 C33 C34 F20 1.1(7) . . . . ?
C32 C33 C34 F20 -176.9(5) . . . . ?
F19 C33 C34 C29 -178.5(5) . . . . ?
C32 C33 C34 C29 3.5(8) . . . . ?
C30 C29 C34 F20 176.7(4) . . . . ?
B3 C29 C34 F20 4.1(7) . . . . ?
C30 C29 C34 C33 -3.7(7) . . . . ?
B3 C29 C34 C33 -176.3(5) . . . . ?
C47 B4 C35 C40 132.3(4) . . . . ?
C53 B4 C35 C40 -104.3(5) . . . . ?
C41 B4 C35 C40 17.1(6) . . . . ?
C47 B4 C35 C36 -58.5(5) . . . . ?
C53 B4 C35 C36 64.9(5) . . . . ?
C41 B4 C35 C36 -173.7(4) . . . . ?
C40 C35 C36 F21 177.9(4) . . . . ?
B4 C35 C36 F21 7.2(6) . . . . ?
C40 C35 C36 C37 -4.1(6) . . . . ?
B4 C35 C36 C37 -174.8(4) . . . . ?
F21 C36 C37 F22 -1.0(6) . . . . ?
C35 C36 C37 F22 -179.0(4) . . . . ?
F21 C36 C37 C38 -178.8(4) . . . . ?
C35 C36 C37 C38 3.2(7) . . . . ?
F22 C37 C38 F23 2.6(7) . . . . ?
C36 C37 C38 F23 -179.6(4) . . . . ?
F22 C37 C38 C39 -178.8(4) . . . . ?
C36 C37 C38 C39 -1.0(7) . . . . ?
F23 C38 C39 F24 -1.6(7) . . . . ?
C37 C38 C39 F24 179.9(4) . . . . ?
F23 C38 C39 C40 178.7(4) . . . . ?
C37 C38 C39 C40 0.1(7) . . . . ?
F24 C39 C40 F25 -1.7(6) . . . . ?
C38 C39 C40 F25 178.0(4) . . . . ?
F24 C39 C40 C35 178.9(4) . . . . ?
C38 C39 C40 C35 -1.4(7) . . . . ?
C36 C35 C40 F25 -176.1(4) . . . . ?
B4 C35 C40 F25 -6.5(7) . . . . ?
C36 C35 C40 C39 3.2(7) . . . . ?
B4 C35 C40 C39 172.9(4) . . . . ?
C47 B4 C41 C46 107.1(5) . . . . ?
C35 B4 C41 C46 -130.1(4) . . . . ?
C53 B4 C41 C46 -15.8(6) . . . . ?
C47 B4 C41 C42 -65.4(4) . . . . ?
C35 B4 C41 C42 57.4(5) . . . . ?
C53 B4 C41 C42 171.7(4) . . . . ?
C46 C41 C42 F26 -178.8(4) . . . . ?
B4 C41 C42 F26 -5.3(6) . . . . ?
C46 C41 C42 C43 0.7(6) . . . . ?
B4 C41 C42 C43 174.2(4) . . . . ?
F26 C42 C43 F27 0.1(6) . . . . ?
C41 C42 C43 F27 -179.3(4) . . . . ?
F26 C42 C43 C44 179.6(4) . . . . ?
C41 C42 C43 C44 0.2(7) . . . . ?
F27 C43 C44 F28 -0.2(6) . . . . ?
C42 C43 C44 F28 -179.7(4) . . . . ?
F27 C43 C44 C45 178.4(4) . . . . ?
C42 C43 C44 C45 -1.1(6) . . . . ?
F28 C44 C45 F29 0.7(6) . . . . ?
C43 C44 C45 F29 -177.9(4) . . . . ?
F28 C44 C45 C46 179.8(4) . . . . ?
C43 C44 C45 C46 1.2(6) . . . . ?
C42 C41 C46 F30 177.5(4) . . . . ?
B4 C41 C46 F30 4.7(6) . . . . ?
C42 C41 C46 C45 -0.6(6) . . . . ?
B4 C41 C46 C45 -173.4(4) . . . . ?
F29 C45 C46 F30 0.6(6) . . . . ?
C44 C45 C46 F30 -178.5(4) . . . . ?
F29 C45 C46 C41 178.8(4) . . . . ?
C44 C45 C46 C41 -0.3(7) . . . . ?
C35 B4 C47 C52 -13.2(6) . . . . ?
C53 B4 C47 C52 -129.2(4) . . . . ?
C41 B4 C47 C52 108.6(4) . . . . ?
C35 B4 C47 C48 175.7(3) . . . . ?
C53 B4 C47 C48 59.7(5) . . . . ?
C41 B4 C47 C48 -62.5(4) . . . . ?
C52 C47 C48 F31 179.9(4) . . . . ?
B4 C47 C48 F31 -7.7(5) . . . . ?
C52 C47 C48 C49 -2.1(6) . . . . ?
B4 C47 C48 C49 170.2(4) . . . . ?
F31 C48 C49 F32 -0.8(6) . . . . ?
C47 C48 C49 F32 -178.7(4) . . . . ?
F31 C48 C49 C50 -179.1(4) . . . . ?
C47 C48 C49 C50 2.9(7) . . . . ?
F32 C49 C50 F33 0.3(6) . . . . ?
C48 C49 C50 F33 178.6(4) . . . . ?
F32 C49 C50 C51 179.7(4) . . . . ?
C48 C49 C50 C51 -1.9(6) . . . . ?
F33 C50 C51 F34 0.2(7) . . . . ?
C49 C50 C51 F34 -179.3(4) . . . . ?
F33 C50 C51 C52 180.0(4) . . . . ?
C49 C50 C51 C52 0.5(7) . . . . ?
F34 C51 C52 F35 1.4(6) . . . . ?
C50 C51 C52 F35 -178.4(4) . . . . ?
F34 C51 C52 C47 180.0(4) . . . . ?
C50 C51 C52 C47 0.2(7) . . . . ?
C48 C47 C52 F35 179.0(4) . . . . ?
B4 C47 C52 F35 7.5(6) . . . . ?
C48 C47 C52 C51 0.5(6) . . . . ?
B4 C47 C52 C51 -171.0(4) . . . . ?
C47 B4 C53 C54 16.9(6) . . . . ?
C35 B4 C53 C54 -106.5(4) . . . . ?
C41 B4 C53 C54 132.2(4) . . . . ?
C47 B4 C53 C58 -174.7(3) . . . . ?
C35 B4 C53 C58 61.9(4) . . . . ?
C41 B4 C53 C58 -59.3(5) . . . . ?
C58 C53 C54 F36 -179.8(3) . . . . ?
B4 C53 C54 F36 -10.9(6) . . . . ?
C58 C53 C54 C55 0.4(6) . . . . ?
B4 C53 C54 C55 169.2(4) . . . . ?
F36 C54 C55 F37 0.8(6) . . . . ?
C53 C54 C55 F37 -179.3(4) . . . . ?
F36 C54 C55 C56 179.1(4) . . . . ?
C53 C54 C55 C56 -1.0(7) . . . . ?
F37 C55 C56 F38 -1.0(6) . . . . ?
C54 C55 C56 F38 -179.2(4) . . . . ?
F37 C55 C56 C57 178.8(4) . . . . ?
C54 C55 C56 C57 0.5(6) . . . . ?
F38 C56 C57 F39 1.4(6) . . . . ?
C55 C56 C57 F39 -178.3(4) . . . . ?
F38 C56 C57 C58 -179.6(4) . . . . ?
C55 C56 C57 C58 0.7(6) . . . . ?
F39 C57 C58 F40 0.0(6) . . . . ?
C56 C57 C58 F40 -179.0(4) . . . . ?
F39 C57 C58 C53 177.5(4) . . . . ?
C56 C57 C58 C53 -1.4(6) . . . . ?
C54 C53 C58 F40 178.4(3) . . . . ?
B4 C53 C58 F40 8.5(5) . . . . ?
C54 C53 C58 C57 0.9(6) . . . . ?
B4 C53 C58 C57 -169.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.229
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 983367'
#######################################################################
#
#                 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_OM25
_audit_creation_date             2013-08-01
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.03.22 svn.r2654, GUI svn.r4446)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C H7 B Cl N'
_chemical_formula_sum            'C H7 B Cl N'
_chemical_formula_weight         79.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   12.7715(12)
_cell_length_b                   6.5471(6)
_cell_length_c                   5.2055(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     435.26(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5616
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.69
_cell_measurement_theta_min      3.19
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
Very weakly diffracting, react vigorously with air
;
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.69
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker Apex II kappa with CCD area detector'
_diffrn_measurement_method       'phi and omega scans, 2deg width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                939
_reflns_number_total             1044
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker Apex2 (Bruker, 2011)'
_computing_data_collection       'Bruker Apex2 (Bruker, 2011)'
_computing_data_reduction        'Bruker SAINT V7.68A'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     34
_refine_ls_number_reflns         1044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0978P)²+0.7538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0540
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H1(0.5) H2(0.5) H3(0.5)
 Fixed U12: C1(0) B1(0) N1(0) Cl1(0)
 Fixed U23: C1(0) B1(0) N1(0) Cl1(0)
 Fixed Uiso: H1(0.036) H2(0.036) H3(0.036)
 Fixed X: H1(0.4583) H2(0.4861) H3(0.4812)
 Fixed Y: C1(0.25) H1(0.2265) H2(0.1413) H3(0.3823) B1(0.25) N1(0.25) Cl1(0.25)
 Fixed Z: H1(-0.4417) H2(-0.1618) H3(-0.2116)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45037(7) 0.2500 -0.25684(16) 0.02383(15) Uani 1 2 d S . .
H1A H 0.4583 0.2265 -0.4417 0.036 Uiso 0.50 1 calc PR . .
H1B H 0.4861 0.1413 -0.1618 0.036 Uiso 0.50 1 calc PR . .
H1C H 0.4812 0.3823 -0.2116 0.036 Uiso 0.50 1 calc PR . .
B1 B 0.32046(7) 0.2500 0.11162(18) 0.02078(15) Uani 1 2 d S . .
N1 N 0.33738(5) 0.2500 -0.18924(12) 0.01712(12) Uani 1 2 d S . .
Cl1 Cl 0.173947(15) 0.2500 0.17305(4) 0.02376(7) Uani 1 2 d S . .
H2 H 0.3062(7) 0.1398(15) -0.2570(18) 0.028(2) Uiso 1 1 d . . .
H3 H 0.3544(8) 0.1083(16) 0.1913(16) 0.032(2) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 N1 1.4853(10) . ?
B1 N1 1.5810(11) . ?
B1 Cl1 1.8984(9) . ?
B1 H3 1.104(10) . ?
N1 H2 0.897(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
N1 B1 Cl1 107.55(5) . . ?
N1 B1 H3 108.6(4) . . ?
Cl1 B1 H3 108.9(5) . . ?
C1 N1 B1 111.56(6) . . ?
C1 N1 H2 109.8(6) . . ?
B1 N1 H2 109.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 B1 N1 C1 180.0 . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 983368'
