# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_raines61

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 B N2 O'
_chemical_formula_sum            'C20 H21 B N2 O'
_chemical_formula_weight         316.20

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a     '
_symmetry_space_group_name_Hall  '-P 2ac 2ab  '
_symmetry_int_tables_number      61

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

_cell_length_a                   7.628(7)
_cell_length_b                   19.796(18)
_cell_length_c                   21.50(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3247(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4124
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.32

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9906

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50\% \w and 0.5\% \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23644
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         31.04
_reflns_number_total             5120
_reflns_number_gt                3704
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 Ver. 2010.11-3 (Bruker-AXS, 2010)'
_computing_cell_refinement       'SAINT Ver. 7.68A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.68A'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0480P)^2^+1.0940P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         5120
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.12260(18) 1.05194(7) 0.86070(7) 0.0310(3) Uani 1 1 d . . .
H1AA H 0.0957 1.0915 0.8872 0.037 Uiso 0.50 1 calc PR A 1
H1AB H 0.0523 1.0551 0.8221 0.037 Uiso 0.50 1 calc PR A 1
H1BC H 0.1012 1.0803 0.8979 0.037 Uiso 0.50 1 calc PR A 2
H1BD H 0.0552 1.0707 0.8254 0.037 Uiso 0.50 1 calc PR A 2
C2 C 0.31430(15) 1.04980(6) 0.84562(5) 0.0200(2) Uani 1 1 d . . .
C3 C 0.41533(17) 1.10164(6) 0.82085(6) 0.0227(2) Uani 1 1 d . . .
H3 H 0.3652 1.1446 0.8123 0.027 Uiso 1 1 calc R B .
C4 C 0.59075(17) 1.08931(6) 0.80894(6) 0.0272(3) Uani 1 1 d . . .
H4 H 0.6621 1.1240 0.7918 0.033 Uiso 1 1 calc R . .
C5 C 0.66283(17) 1.02647(7) 0.82190(7) 0.0310(3) Uani 1 1 d . . .
H5 H 0.7830 1.0183 0.8131 0.037 Uiso 1 1 calc R B .
C6 C 0.56102(16) 0.97542(6) 0.84762(6) 0.0234(2) Uani 1 1 d . . .
H6 H 0.6123 0.9329 0.8571 0.028 Uiso 1 1 calc R . .
C7 C 0.38417(15) 0.98648(6) 0.85955(5) 0.0178(2) Uani 1 1 d . . .
C8 C 0.32247(16) 0.82455(6) 0.85821(6) 0.0217(2) Uani 1 1 d . . .
C9 C 0.3537(2) 0.77512(7) 0.81430(6) 0.0324(3) Uani 1 1 d . . .
H9 H 0.2817 0.7726 0.7783 0.039 Uiso 1 1 calc R . .
C10 C 0.4904(2) 0.72850(7) 0.82221(7) 0.0369(3) Uani 1 1 d . . .
H10 H 0.5102 0.6951 0.7913 0.044 Uiso 1 1 calc R B .
C11 C 0.5950(2) 0.73030(7) 0.87327(7) 0.0329(3) Uani 1 1 d . . .
H11 H 0.6892 0.6992 0.8772 0.039 Uiso 1 1 calc R . .
C12 C 0.56435(17) 0.77824(6) 0.92060(6) 0.0239(2) Uani 1 1 d . . .
C13 C 0.66789(19) 0.77917(7) 0.97530(7) 0.0325(3) Uani 1 1 d . . .
H13 H 0.7637 0.7488 0.9793 0.039 Uiso 1 1 calc R . .
C14 C 0.63133(19) 0.82305(8) 1.02214(7) 0.0347(3) Uani 1 1 d . . .
H14 H 0.7003 0.8223 1.0589 0.042 Uiso 1 1 calc R B .
C15 C 0.49357(18) 0.86922(7) 1.01692(6) 0.0282(3) Uani 1 1 d . . .
H15 H 0.4687 0.8990 1.0504 0.034 Uiso 1 1 calc R . .
C16 C 0.39357(16) 0.87200(6) 0.96365(5) 0.0200(2) Uani 1 1 d . . .
C17 C 0.42569(16) 0.82568(5) 0.91383(5) 0.0193(2) Uani 1 1 d . . .
C18 C 0.1277(5) 0.89443(19) 0.79198(18) 0.0304(7) Uani 0.50 1 d P B 1
H18A H 0.2323 0.9088 0.7691 0.046 Uiso 0.50 1 calc PR B 1
H18B H 0.0423 0.9314 0.7927 0.046 Uiso 0.50 1 calc PR B 1
H18C H 0.0757 0.8550 0.7714 0.046 Uiso 0.50 1 calc PR B 1
O1 O 0.0842(7) 0.9917(2) 0.89250(17) 0.0268(8) Uani 0.50 1 d P B 1
N1 N 0.1782(17) 0.8760(7) 0.8580(4) 0.0227(13) Uani 0.50 1 d P B 1
N2 N 0.2743(9) 0.9200(5) 0.9602(4) 0.0229(12) Uani 0.50 1 d P B 1
B1 B 0.231(3) 0.9456(10) 0.8937(5) 0.0217(14) Uani 0.50 1 d P B 1
C19 C 0.0165(3) 0.84624(14) 0.88797(15) 0.0320(6) Uani 0.50 1 d P B 1
H19A H -0.0229 0.8071 0.8639 0.048 Uiso 0.50 1 calc PR B 1
H19B H -0.0767 0.8803 0.8890 0.048 Uiso 0.50 1 calc PR B 1
H19C H 0.0443 0.8321 0.9305 0.048 Uiso 0.50 1 calc PR B 1
C20 C 0.2458(11) 0.9678(4) 1.0121(2) 0.0323(12) Uani 0.50 1 d P B 1
H20A H 0.2042 0.9431 1.0487 0.048 Uiso 0.50 1 calc PR B 1
H20B H 0.1581 1.0015 0.9999 0.048 Uiso 0.50 1 calc PR B 1
H20C H 0.3563 0.9906 1.0221 0.048 Uiso 0.50 1 calc PR B 1
O1A O 0.0710(7) 0.9813(2) 0.87275(16) 0.0224(7) Uani 0.50 1 d P B 2
N1A N 0.2335(9) 0.9163(5) 0.9533(5) 0.0192(10) Uani 0.50 1 d P B 2
N2A N 0.2006(17) 0.8717(6) 0.8450(4) 0.0216(13) Uani 0.50 1 d P B 2
B1A B 0.222(3) 0.9390(9) 0.8796(5) 0.0217(14) Uani 0.50 1 d P B 2
C19A C 0.0713(3) 0.87666(12) 0.97037(12) 0.0239(5) Uani 0.50 1 d P B 2
H19D H 0.0685 0.8344 0.9466 0.036 Uiso 0.50 1 calc PR B 2
H19E H -0.0332 0.9035 0.9607 0.036 Uiso 0.50 1 calc PR B 2
H19F H 0.0733 0.8664 1.0149 0.036 Uiso 0.50 1 calc PR B 2
C20A C 0.0991(6) 0.86758(18) 0.7896(2) 0.0363(9) Uani 0.50 1 d P B 2
H20D H 0.1772 0.8679 0.7535 0.055 Uiso 0.50 1 calc PR B 2
H20E H 0.0195 0.9063 0.7874 0.055 Uiso 0.50 1 calc PR B 2
H20F H 0.0308 0.8257 0.7899 0.055 Uiso 0.50 1 calc PR B 2
C18A C 0.2407(9) 0.9763(3) 0.9931(2) 0.0235(9) Uani 0.50 1 d P B 2
H18D H 0.2286 0.9627 1.0367 0.035 Uiso 0.50 1 calc PR B 2
H18E H 0.1450 1.0070 0.9820 0.035 Uiso 0.50 1 calc PR B 2
H18F H 0.3533 0.9992 0.9872 0.035 Uiso 0.50 1 calc PR B 2

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
C1 0.0222(6) 0.0249(6) 0.0459(8) 0.0139(6) 0.0069(6) 0.0049(5)
C2 0.0196(5) 0.0202(5) 0.0201(5) -0.0001(4) -0.0011(4) -0.0007(4)
C3 0.0254(6) 0.0199(5) 0.0229(6) 0.0015(4) -0.0033(5) -0.0030(4)
C4 0.0237(6) 0.0273(6) 0.0306(7) 0.0036(5) -0.0003(5) -0.0078(5)
C5 0.0176(6) 0.0333(7) 0.0421(8) 0.0049(6) 0.0034(5) -0.0017(5)
C6 0.0189(5) 0.0232(5) 0.0281(6) 0.0006(5) -0.0004(5) 0.0006(4)
C7 0.0173(5) 0.0196(5) 0.0167(5) -0.0016(4) -0.0012(4) -0.0008(4)
C8 0.0220(6) 0.0197(5) 0.0235(6) 0.0032(4) 0.0002(5) -0.0043(4)
C9 0.0374(8) 0.0362(7) 0.0236(6) -0.0039(5) -0.0008(5) -0.0128(6)
C10 0.0452(9) 0.0281(7) 0.0374(8) -0.0133(6) 0.0128(7) -0.0062(6)
C11 0.0360(8) 0.0215(6) 0.0410(8) -0.0023(5) 0.0122(6) 0.0034(5)
C12 0.0249(6) 0.0191(5) 0.0276(6) 0.0032(4) 0.0035(5) 0.0019(4)
C13 0.0255(6) 0.0367(7) 0.0354(7) 0.0125(6) -0.0011(6) 0.0068(5)
C14 0.0293(7) 0.0496(9) 0.0252(6) 0.0067(6) -0.0067(5) -0.0020(6)
C15 0.0327(7) 0.0304(6) 0.0216(6) -0.0037(5) 0.0017(5) -0.0069(5)
C16 0.0216(5) 0.0178(5) 0.0207(5) 0.0033(4) 0.0036(4) 0.0000(4)
C17 0.0210(5) 0.0158(5) 0.0211(5) 0.0022(4) 0.0016(4) -0.0007(4)
C18 0.0307(16) 0.0312(18) 0.0294(15) 0.0045(16) -0.0055(12) -0.0075(15)
O1 0.0203(15) 0.0238(17) 0.036(2) 0.0072(14) 0.0093(16) 0.0041(11)
N1 0.023(2) 0.026(3) 0.019(3) 0.006(2) -0.004(2) -0.0032(17)
N2 0.027(3) 0.0274(17) 0.015(2) 0.0035(14) 0.002(2) 0.005(2)
B1 0.0177(17) 0.020(3) 0.028(5) 0.005(3) 0.003(3) 0.0025(17)
C19 0.0203(12) 0.0331(14) 0.0425(16) 0.0082(12) 0.0024(11) -0.0063(10)
C20 0.041(2) 0.034(2) 0.022(2) -0.0081(19) 0.012(2) 0.0057(17)
O1A 0.0163(10) 0.0171(14) 0.034(2) 0.0064(13) -0.0004(15) -0.0001(9)
N1A 0.018(3) 0.0173(15) 0.022(2) 0.0000(13) -0.0011(17) 0.0081(18)
N2A 0.029(4) 0.0161(14) 0.019(3) -0.001(2) -0.008(2) -0.0045(19)
B1A 0.0177(17) 0.020(3) 0.028(5) 0.005(3) 0.003(3) 0.0025(17)
C19A 0.0211(11) 0.0201(10) 0.0306(13) 0.0044(9) 0.0061(10) 0.0010(9)
C20A 0.039(2) 0.0273(18) 0.0422(18) -0.0028(17) -0.0256(16) 0.0036(15)
C18A 0.0278(16) 0.0222(16) 0.020(2) -0.0045(18) 0.0055(19) 0.0014(12)

_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 O1 1.405(5) . yes
C1 O1A 1.475(5) . yes
C1 C2 1.498(2) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C2 C3 1.3895(18) . ?
C2 C7 1.3946(19) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3893(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 B1 1.60(2) . ?
C7 B1A 1.61(2) . ?
C8 N2A 1.348(14) . ?
C8 C9 1.380(2) . ?
C8 C17 1.4320(19) . ?
C8 N1 1.500(13) . ?
C9 C10 1.403(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.358(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.417(2) . ?
C12 C17 1.4219(19) . ?
C13 C14 1.359(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(2) . ?
C15 H15 0.9500 . ?
C16 N2 1.318(10) . ?
C16 C17 1.4312(19) . ?
C16 N1A 1.520(8) . ?
C18 N1 1.515(12) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1 B1 1.45(2) . yes
N1 C19 1.511(12) . ?
N1 B1 1.629(19) . ?
N2 C20 1.480(12) . ?
N2 B1 1.552(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1A B1A 1.43(2) . yes
N1A C18A 1.464(11) . ?
N1A C19A 1.511(9) . ?
N1A B1A 1.649(17) . ?
N2A C20A 1.423(13) . ?
N2A B1A 1.533(18) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?

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 C1 O1A 19.08(18) . . ?
O1 C1 C2 106.5(2) . . ?
O1A C1 C2 105.7(2) . . ?
O1 C1 H1AA 110.4 . . ?
O1A C1 H1AA 126.4 . . ?
C2 C1 H1AA 110.4 . . ?
O1 C1 H1AB 110.4 . . ?
O1A C1 H1AB 93.6 . . ?
C2 C1 H1AB 110.4 . . ?
H1AA C1 H1AB 108.6 . . ?
O1 C1 H1BC 93.1 . . ?
O1A C1 H1BC 110.6 . . ?
C2 C1 H1BC 110.6 . . ?
H1AA C1 H1BC 18.8 . . ?
H1AB C1 H1BC 123.4 . . ?
O1 C1 H1BD 125.7 . . ?
O1A C1 H1BD 110.6 . . ?
C2 C1 H1BD 110.6 . . ?
H1AA C1 H1BD 92.1 . . ?
H1AB C1 H1BD 18.4 . . ?
H1BC C1 H1BD 108.7 . . ?
C3 C2 C7 122.28(12) . . ?
C3 C2 C1 127.11(11) . . ?
C7 C2 C1 110.61(11) . . ?
C4 C3 C2 118.48(12) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.25(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.68(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.08(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 118.21(11) . . ?
C6 C7 B1 135.5(7) . . ?
C2 C7 B1 105.9(7) . . ?
C6 C7 B1A 134.5(7) . . ?
C2 C7 B1A 106.8(7) . . ?
B1 C7 B1A 12.1(7) . . ?
N2A C8 C9 117.8(4) . . ?
N2A C8 C17 122.9(4) . . ?
C9 C8 C17 119.17(13) . . ?
N2A C8 N1 12.2(6) . . ?
C9 C8 N1 127.3(5) . . ?
C17 C8 N1 113.3(4) . . ?
C8 C9 C10 120.76(13) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.18(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.22(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.99(13) . . ?
C11 C12 C17 119.58(13) . . ?
C13 C12 C17 119.42(12) . . ?
C14 C13 C12 120.60(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.86(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.64(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
N2 C16 C15 117.3(4) . . ?
N2 C16 C17 122.6(4) . . ?
C15 C16 C17 120.13(12) . . ?
N2 C16 N1A 11.7(6) . . ?
C15 C16 N1A 126.2(4) . . ?
C17 C16 N1A 113.4(3) . . ?
C12 C17 C16 118.28(11) . . ?
C12 C17 C8 118.96(11) . . ?
C16 C17 C8 122.74(12) . . ?
C1 O1 B1 112.5(9) . . yes
C8 N1 C19 109.5(9) . . ?
C8 N1 C18 110.7(5) . . ?
C19 N1 C18 106.6(9) . . ?
C8 N1 B1 113.0(11) . . ?
C19 N1 B1 109.4(8) . . ?
C18 N1 B1 107.5(10) . . ?
C16 N2 C20 121.3(6) . . ?
C16 N2 B1 115.7(10) . . ?
C20 N2 B1 117.1(9) . . ?
O1 B1 N2 112.7(10) . . ?
O1 B1 C7 103.8(12) . . ?
N2 B1 C7 115.7(11) . . ?
O1 B1 N1 109.4(11) . . ?
N2 B1 N1 102.1(13) . . ?
C7 B1 N1 113.2(9) . . ?
B1A O1A C1 110.9(8) . . yes
C18A N1A C19A 108.0(7) . . ?
C18A N1A C16 110.6(5) . . ?
C19A N1A C16 108.8(6) . . ?
C18A N1A B1A 110.1(8) . . ?
C19A N1A B1A 109.4(8) . . ?
C16 N1A B1A 109.9(9) . . ?
C8 N2A C20A 120.7(7) . . ?
C8 N2A B1A 115.2(11) . . ?
C20A N2A B1A 121.0(11) . . ?
O1A B1A N2A 111.8(11) . . ?
O1A B1A C7 104.4(12) . . ?
N2A B1A C7 117.4(11) . . ?
O1A B1A N1A 107.4(10) . . ?
N2A B1A N1A 103.6(13) . . ?
C7 B1A N1A 112.1(8) . . ?
N1A C19A H19D 109.5 . . ?
N1A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
N1A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
N2A C20A H20D 109.5 . . ?
N2A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
N2A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
N1A C18A H18D 109.5 . . ?
N1A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
N1A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?

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 C1 C2 C3 -171.94(17) . . . . ?
O1A C1 C2 C3 168.20(17) . . . . ?
O1 C1 C2 C7 8.4(2) . . . . ?
O1A C1 C2 C7 -11.41(19) . . . . ?
C7 C2 C3 C4 0.88(18) . . . . ?
C1 C2 C3 C4 -178.69(13) . . . . ?
C2 C3 C4 C5 -0.27(19) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C2 -0.66(18) . . . . ?
C5 C6 C7 B1 -172.6(5) . . . . ?
C5 C6 C7 B1A 170.3(5) . . . . ?
C3 C2 C7 C6 -0.42(17) . . . . ?
C1 C2 C7 C6 179.22(11) . . . . ?
C3 C2 C7 B1 173.7(4) . . . . ?
C1 C2 C7 B1 -6.6(4) . . . . ?
C3 C2 C7 B1A -173.7(4) . . . . ?
C1 C2 C7 B1A 6.0(4) . . . . ?
N2A C8 C9 C10 173.6(5) . . . . ?
C17 C8 C9 C10 -3.26(19) . . . . ?
N1 C8 C9 C10 -177.3(6) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C10 C11 C12 C13 177.55(13) . . . . ?
C10 C11 C12 C17 -1.4(2) . . . . ?
C11 C12 C13 C14 -176.33(13) . . . . ?
C17 C12 C13 C14 2.6(2) . . . . ?
C12 C13 C14 C15 -1.5(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 N2 -175.2(5) . . . . ?
C14 C15 C16 C17 2.38(19) . . . . ?
C14 C15 C16 N1A 175.9(5) . . . . ?
C11 C12 C17 C16 177.66(11) . . . . ?
C13 C12 C17 C16 -1.33(17) . . . . ?
C11 C12 C17 C8 -1.36(17) . . . . ?
C13 C12 C17 C8 179.65(12) . . . . ?
N2 C16 C17 C12 176.3(5) . . . . ?
C15 C16 C17 C12 -1.14(17) . . . . ?
N1A C16 C17 C12 -175.4(4) . . . . ?
N2 C16 C17 C8 -4.8(5) . . . . ?
C15 C16 C17 C8 177.84(11) . . . . ?
N1A C16 C17 C8 3.6(4) . . . . ?
N2A C8 C17 C12 -173.0(6) . . . . ?
C9 C8 C17 C12 3.66(17) . . . . ?
N1 C8 C17 C12 178.5(5) . . . . ?
N2A C8 C17 C16 8.0(6) . . . . ?
C9 C8 C17 C16 -175.31(11) . . . . ?
N1 C8 C17 C16 -0.5(5) . . . . ?
O1A C1 O1 B1 83.7(13) . . . . ?
C2 C1 O1 B1 -6.7(5) . . . . ?
N2A C8 N1 C19 128(5) . . . . ?
C9 C8 N1 C19 86.5(6) . . . . ?
C17 C8 N1 C19 -87.8(7) . . . . ?
N2A C8 N1 C18 11(4) . . . . ?
C9 C8 N1 C18 -30.7(11) . . . . ?
C17 C8 N1 C18 155.0(6) . . . . ?
N2A C8 N1 B1 -110(5) . . . . ?
C9 C8 N1 B1 -151.3(7) . . . . ?
C17 C8 N1 B1 34.3(10) . . . . ?
C15 C16 N2 C20 -1.6(9) . . . . ?
C17 C16 N2 C20 -179.1(5) . . . . ?
N1A C16 N2 C20 140(5) . . . . ?
C15 C16 N2 B1 150.6(8) . . . . ?
C17 C16 N2 B1 -26.9(11) . . . . ?
N1A C16 N2 B1 -68(4) . . . . ?
C1 O1 B1 N2 128.8(10) . . . . ?
C1 O1 B1 C7 2.7(7) . . . . ?
C1 O1 B1 N1 -118.3(10) . . . . ?
C16 N2 B1 O1 172.5(9) . . . . ?
C20 N2 B1 O1 -34.1(15) . . . . ?
C16 N2 B1 C7 -68.2(13) . . . . ?
C20 N2 B1 C7 85.2(13) . . . . ?
C16 N2 B1 N1 55.2(13) . . . . ?
C20 N2 B1 N1 -151.4(9) . . . . ?
C6 C7 B1 O1 175.2(2) . . . . ?
C2 C7 B1 O1 2.6(6) . . . . ?
B1A C7 B1 O1 -93(7) . . . . ?
C6 C7 B1 N2 51.1(13) . . . . ?
C2 C7 B1 N2 -121.5(11) . . . . ?
B1A C7 B1 N2 143(8) . . . . ?
C6 C7 B1 N1 -66.3(12) . . . . ?
C2 C7 B1 N1 121.1(11) . . . . ?
B1A C7 B1 N1 25(6) . . . . ?
C8 N1 B1 O1 -178.8(8) . . . . ?
C19 N1 B1 O1 -56.6(14) . . . . ?
C18 N1 B1 O1 58.8(12) . . . . ?
C8 N1 B1 N2 -59.1(12) . . . . ?
C19 N1 B1 N2 63.1(13) . . . . ?
C18 N1 B1 N2 178.5(9) . . . . ?
C8 N1 B1 C7 66.0(13) . . . . ?
C19 N1 B1 C7 -171.8(9) . . . . ?
C18 N1 B1 C7 -56.4(14) . . . . ?
O1 C1 O1A B1A -82.5(13) . . . . ?
C2 C1 O1A B1A 12.7(5) . . . . ?
N2 C16 N1A C18A -18(4) . . . . ?
C15 C16 N1A C18A 25.5(9) . . . . ?
C17 C16 N1A C18A -160.7(5) . . . . ?
N2 C16 N1A C19A -136(4) . . . . ?
C15 C16 N1A C19A -93.0(5) . . . . ?
C17 C16 N1A C19A 80.8(6) . . . . ?
N2 C16 N1A B1A 104(4) . . . . ?
C15 C16 N1A B1A 147.2(7) . . . . ?
C17 C16 N1A B1A -39.0(8) . . . . ?
C9 C8 N2A C20A 4.5(11) . . . . ?
C17 C8 N2A C20A -178.8(5) . . . . ?
N1 C8 N2A C20A -139(6) . . . . ?
C9 C8 N2A B1A -155.7(8) . . . . ?
C17 C8 N2A B1A 21.1(12) . . . . ?
N1 C8 N2A B1A 61(5) . . . . ?
C1 O1A B1A N2A -137.0(10) . . . . ?
C1 O1A B1A C7 -9.1(6) . . . . ?
C1 O1A B1A N1A 110.1(10) . . . . ?
C8 N2A B1A O1A -168.6(9) . . . . ?
C20A N2A B1A O1A 31.3(16) . . . . ?
C8 N2A B1A C7 70.8(13) . . . . ?
C20A N2A B1A C7 -89.3(14) . . . . ?
C8 N2A B1A N1A -53.3(13) . . . . ?
C20A N2A B1A N1A 146.6(9) . . . . ?
C6 C7 B1A O1A -169.8(3) . . . . ?
C2 C7 B1A O1A 1.8(6) . . . . ?
B1 C7 B1A O1A 90(7) . . . . ?
C6 C7 B1A N2A -45.5(14) . . . . ?
C2 C7 B1A N2A 126.2(12) . . . . ?
B1 C7 B1A N2A -146(8) . . . . ?
C6 C7 B1A N1A 74.2(10) . . . . ?
C2 C7 B1A N1A -114.1(10) . . . . ?
B1 C7 B1A N1A -26(6) . . . . ?
C18A N1A B1A O1A -57.1(12) . . . . ?
C19A N1A B1A O1A 61.4(12) . . . . ?
C16 N1A B1A O1A -179.2(8) . . . . ?
C18A N1A B1A N2A -175.5(9) . . . . ?
C19A N1A B1A N2A -57.0(13) . . . . ?
C16 N1A B1A N2A 62.5(12) . . . . ?
C18A N1A B1A C7 57.0(13) . . . . ?
C19A N1A B1A C7 175.5(8) . . . . ?
C16 N1A B1A C7 -65.1(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.046
_iucr_refine_instruction_details 
;
TITL RAINES61 IN PBCA
CELL 0.71073 7.6283 19.7959 21.5005 90 90 90
ZERR 8 0.0068 0.0176 0.02 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H B N O
UNIT 160 168 8 16 8
EADP B1A B1
L.S. 12
PLAN  5
SIZE 0.26 0.14 0.12
TEMP -173
LIST 4
BOND $H
CONF
HTAB
WPDB -2
fmap 2
acta 50
OMIT 3 8 1
OMIT 3 12 9
OMIT 0 0 14
OMIT 3 3 6
OMIT 0 6 3
OMIT 3 6 3
OMIT 1 1 6
OMIT 2 2 9
OMIT 3 1 3
OMIT 2 9 3
OMIT 0 0 22
OMIT 1 3 11
OMIT 2 4 9
OMIT 0 6 9
OMIT 1 8 5
OMIT 1 8 2
OMIT 2 1 5
OMIT 1 10 7
OMIT 3 3 8
OMIT 4 6 0
OMIT 1 7 7
OMIT 2 6 5
OMIT 3 1 1
OMIT 6 3 3
OMIT 1 9 6
OMIT 2 3 9
OMIT 1 10 3
OMIT 5 14 3
OMIT 0 0 10
OMIT 2 6 7
OMIT 4 14 5
OMIT 3 3 1
OMIT 1 11 7
OMIT 2 6 11
OMIT 3 3 15
OMIT 3 4 7
OMIT 2 10 4
OMIT 1 5 11
WGHT    0.048000    1.094000
FVAR       0.32618
C1    1    0.122602    1.051942    0.860699    11.00000    0.02222    0.02487 =
         0.04594    0.01390    0.00691    0.00494
PART 1
AFIX  23
H1AA  2    0.095728    1.091536    0.887162    10.50000   -1.20000
H1AB  2    0.052327    1.055120    0.822099    10.50000   -1.20000
AFIX  23
PART 0
PART 2
H1BC  2    0.101194    1.080301    0.897857    10.50000   -1.20000
H1BD  2    0.055161    1.070697    0.825351    10.50000   -1.20000
AFIX   0
PART 0
C2    1    0.314300    1.049799    0.845619    11.00000    0.01963    0.02022 =
         0.02010   -0.00014   -0.00112   -0.00072
C3    1    0.415334    1.101639    0.820846    11.00000    0.02535    0.01991 =
         0.02290    0.00146   -0.00328   -0.00304
AFIX  43
H3    2    0.365153    1.144563    0.812278    11.00000   -1.20000
AFIX   0
C4    1    0.590748    1.089311    0.808939    11.00000    0.02375    0.02730 =
         0.03059    0.00356   -0.00035   -0.00780
AFIX  43
H4    2    0.662096    1.123981    0.791835    11.00000   -1.20000
AFIX   0
C5    1    0.662835    1.026467    0.821896    11.00000    0.01761    0.03330 =
         0.04212    0.00490    0.00339   -0.00172
AFIX  43
H5    2    0.783009    1.018289    0.813083    11.00000   -1.20000
AFIX   0
C6    1    0.561020    0.975422    0.847617    11.00000    0.01894    0.02316 =
         0.02815    0.00057   -0.00039    0.00064
AFIX  43
H6    2    0.612282    0.932908    0.857068    11.00000   -1.20000
AFIX   0
C7    1    0.384170    0.986482    0.859545    11.00000    0.01732    0.01956 =
         0.01665   -0.00156   -0.00117   -0.00085
C8    1    0.322468    0.824549    0.858209    11.00000    0.02202    0.01970 =
         0.02352    0.00318    0.00024   -0.00430
C9    1    0.353662    0.775119    0.814300    11.00000    0.03738    0.03620 =
         0.02359   -0.00390   -0.00079   -0.01280
AFIX  43
H9    2    0.281702    0.772629    0.778311    11.00000   -1.20000
AFIX   0
C10   1    0.490443    0.728504    0.822210    11.00000    0.04522    0.02805 =
         0.03736   -0.01329    0.01277   -0.00618
AFIX  43
H10   2    0.510215    0.695092    0.791279    11.00000   -1.20000
AFIX   0
C11   1    0.595022    0.730298    0.873274    11.00000    0.03603    0.02151 =
         0.04104   -0.00232    0.01225    0.00344
AFIX  43
H11   2    0.689170    0.699168    0.877155    11.00000   -1.20000
AFIX   0
C12   1    0.564350    0.778245    0.920604    11.00000    0.02493    0.01915 =
         0.02764    0.00320    0.00354    0.00193
C13   1    0.667885    0.779175    0.975298    11.00000    0.02548    0.03673 =
         0.03541    0.01248   -0.00113    0.00677
AFIX  43
H13   2    0.763749    0.748846    0.979264    11.00000   -1.20000
AFIX   0
C14   1    0.631328    0.823051    1.022140    11.00000    0.02926    0.04957 =
         0.02520    0.00671   -0.00668   -0.00201
AFIX  43
H14   2    0.700329    0.822324    1.058916    11.00000   -1.20000
AFIX   0
C15   1    0.493570    0.869221    1.016917    11.00000    0.03267    0.03037 =
         0.02159   -0.00368    0.00165   -0.00686
AFIX  43
H15   2    0.468654    0.898982    1.050434    11.00000   -1.20000
AFIX   0
C16   1    0.393565    0.872002    0.963652    11.00000    0.02155    0.01779 =
         0.02069    0.00333    0.00355   -0.00001
C17   1    0.425689    0.825679    0.913832    11.00000    0.02100    0.01582 =
         0.02110    0.00217    0.00158   -0.00069
PART 1
C18   1    0.127662    0.894434    0.791984    10.50000    0.03068    0.03121 =
         0.02939    0.00454   -0.00551   -0.00753
AFIX 137
H18A  2    0.232313    0.908780    0.769082    10.50000   -1.50000
H18B  2    0.042280    0.931414    0.792747    10.50000   -1.50000
H18C  2    0.075730    0.855039    0.771430    10.50000   -1.50000
AFIX   0
O1    5    0.084185    0.991725    0.892496    10.50000    0.02031    0.02377 =
         0.03644    0.00716    0.00929    0.00405
N1    4    0.178162    0.875986    0.857991    10.50000    0.02260    0.02640 =
         0.01901    0.00588   -0.00362   -0.00318
N2    4    0.274309    0.920038    0.960186    10.50000    0.02673    0.02737 =
         0.01472    0.00352    0.00243    0.00550
B1    3    0.231309    0.945639    0.893703    10.50000    0.01771    0.01973 =
         0.02762    0.00482    0.00316    0.00250
C19   1    0.016549    0.846242    0.887969    10.50000    0.02031    0.03314 =
         0.04247    0.00824    0.00242   -0.00629
AFIX 137
H19A  2   -0.022878    0.807065    0.863870    10.50000   -1.50000
H19B  2   -0.076654    0.880295    0.888971    10.50000   -1.50000
H19C  2    0.044337    0.832069    0.930514    10.50000   -1.50000
AFIX   0
C20   1    0.245812    0.967847    1.012106    10.50000    0.04072    0.03439 =
         0.02167   -0.00806    0.01209    0.00573
AFIX 137
H20A  2    0.204159    0.943078    1.048700    10.50000   -1.50000
H20B  2    0.158066    1.001495    0.999916    10.50000   -1.50000
H20C  2    0.356335    0.990634    1.022092    10.50000   -1.50000
AFIX   0
PART 0
PART 2
O1A   5    0.071030    0.981315    0.872751    10.50000    0.01630    0.01713 =
         0.03391    0.00636   -0.00037   -0.00008
N1A   4    0.233527    0.916313    0.953264    10.50000    0.01826    0.01732 =
         0.02206    0.00005   -0.00107    0.00810
N2A   4    0.200611    0.871744    0.845030    10.50000    0.02943    0.01608 =
         0.01937   -0.00114   -0.00785   -0.00445
B1A   3    0.222334    0.938999    0.879554    10.50000    0.01771    0.01973 =
         0.02762    0.00482    0.00316    0.00250
C19A  1    0.071253    0.876660    0.970374    10.50000    0.02114    0.02008 =
         0.03057    0.00442    0.00614    0.00104
AFIX 137
H19D  2    0.068508    0.834448    0.946581    10.50000   -1.50000
H19E  2   -0.033248    0.903464    0.960685    10.50000   -1.50000
H19F  2    0.073269    0.866355    1.014950    10.50000   -1.50000
AFIX   0
C20A  1    0.099131    0.867579    0.789645    10.50000    0.03950    0.02732 =
         0.04220   -0.00277   -0.02559    0.00358
AFIX 137
H20D  2    0.177243    0.867858    0.753459    10.50000   -1.50000
H20E  2    0.019480    0.906344    0.787393    10.50000   -1.50000
H20F  2    0.030767    0.825667    0.789933    10.50000   -1.50000
AFIX   0
C18A  1    0.240703    0.976257    0.993095    10.50000    0.02783    0.02224 =
         0.02032   -0.00453    0.00546    0.00140
AFIX 137
H18D  2    0.228573    0.962651    1.036709    10.50000   -1.50000
H18E  2    0.145025    1.007018    0.982002    10.50000   -1.50000
H18F  2    0.353314    0.999216    0.987231    10.50000   -1.50000
HKLF 4
END  
;

# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
_database_code_depnum_ccdc_archive 'CCDC 949879'