# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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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_cc117a

_audit_update_record             
;
2014-04-03 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49.20 H55.80 Cl N4 Rh'
_chemical_formula_weight         841.54

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'
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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.5336(10)
_cell_length_b                   13.3530(10)
_cell_length_c                   15.0479(12)
_cell_angle_alpha                61.6840(10)
_cell_angle_beta                 87.1810(10)
_cell_angle_gamma                79.8940(10)
_cell_volume                     2181.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1553
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.52

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             882
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8668
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      180(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 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21252
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.00
_reflns_number_total             8484
_reflns_number_gt                7447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0613P)²+1.8000P] 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_number_reflns         8484
_refine_ls_number_parameters     508
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_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
Rh1 Rh 0.193700(16) 0.169642(18) 0.707415(16) 0.02650(9) Uani 1 1 d . . .
Cl1 Cl 0.26035(6) 0.16918(7) 0.85564(6) 0.04084(19) Uani 1 1 d . . .
N1 N 0.43262(18) 0.17516(19) 0.63884(17) 0.0270(5) Uani 1 1 d . . .
N2 N 0.33057(18) 0.31773(19) 0.53718(17) 0.0276(5) Uani 1 1 d . . .
N3 N 0.05084(18) 0.1040(2) 0.78401(18) 0.0318(5) Uani 1 1 d . . .
N4 N 0.0751(2) -0.0675(2) 0.6489(2) 0.0364(6) Uani 1 1 d . . .
C1 C 0.3268(2) 0.2244(2) 0.6265(2) 0.0253(5) Uani 1 1 d . . .
C2 C 0.4983(2) 0.2339(2) 0.5579(2) 0.0308(6) Uani 1 1 d . . .
H2A H 0.5734 0.2114 0.5518 0.037 Uiso 1 1 calc R . .
C3 C 0.4353(2) 0.3233(3) 0.4952(2) 0.0316(6) Uani 1 1 d . . .
H3A H 0.4542 0.3822 0.4326 0.038 Uiso 1 1 calc R . .
C4 C 0.4822(2) 0.0898(2) 0.7314(2) 0.0289(6) Uani 1 1 d . . .
C5 C 0.4804(2) -0.0235(3) 0.7571(2) 0.0336(6) Uani 1 1 d . . .
C6 C 0.5368(3) -0.1005(3) 0.8432(3) 0.0461(8) Uani 1 1 d . . .
H6A H 0.5394 -0.1807 0.8667 0.055 Uiso 1 1 calc R . .
C7 C 0.5912(3) -0.0650(3) 0.8983(3) 0.0514(9) Uani 1 1 d . . .
H7A H 0.6309 -0.1224 0.9582 0.062 Uiso 1 1 calc R . .
C8 C 0.5906(3) 0.0473(3) 0.8711(3) 0.0437(8) Uani 1 1 d . . .
H8A H 0.6281 0.0680 0.9116 0.052 Uiso 1 1 calc R . .
C9 C 0.5368(2) 0.1276(3) 0.7870(2) 0.0340(6) Uani 1 1 d . . .
C10 C 0.4199(2) -0.0642(3) 0.6992(3) 0.0394(7) Uani 1 1 d . . .
H10A H 0.3756 0.0065 0.6447 0.047 Uiso 1 1 calc R . .
C11 C 0.3384(3) -0.1392(4) 0.7685(4) 0.0671(12) Uani 1 1 d . . .
H11A H 0.2928 -0.0970 0.7989 0.101 Uiso 1 1 calc R . .
H11B H 0.3782 -0.2114 0.8219 0.101 Uiso 1 1 calc R . .
H11C H 0.2926 -0.1567 0.7284 0.101 Uiso 1 1 calc R . .
C12 C 0.4953(4) -0.1247(5) 0.6441(4) 0.0780(15) Uani 1 1 d . . .
H12A H 0.5392 -0.0702 0.5956 0.117 Uiso 1 1 calc R . .
H12B H 0.4501 -0.1482 0.6084 0.117 Uiso 1 1 calc R . .
H12C H 0.5432 -0.1928 0.6944 0.117 Uiso 1 1 calc R . .
C13 C 0.5402(3) 0.2513(3) 0.7589(2) 0.0374(7) Uani 1 1 d . . .
H13A H 0.4841 0.3003 0.7033 0.045 Uiso 1 1 calc R . .
C14 C 0.6520(3) 0.2837(3) 0.7142(3) 0.0483(8) Uani 1 1 d . . .
H14A H 0.6648 0.2694 0.6561 0.072 Uiso 1 1 calc R . .
H14B H 0.7099 0.2366 0.7659 0.072 Uiso 1 1 calc R . .
H14C H 0.6513 0.3656 0.6924 0.072 Uiso 1 1 calc R . .
C15 C 0.5093(3) 0.2824(3) 0.8486(3) 0.0515(9) Uani 1 1 d . . .
H15A H 0.4368 0.2656 0.8713 0.077 Uiso 1 1 calc R . .
H15B H 0.5098 0.3646 0.8243 0.077 Uiso 1 1 calc R . .
H15C H 0.5623 0.2361 0.9052 0.077 Uiso 1 1 calc R . .
C16 C 0.2433(2) 0.4095(2) 0.4945(2) 0.0304(6) Uani 1 1 d . . .
C17 C 0.2045(2) 0.4763(2) 0.5470(2) 0.0336(6) Uani 1 1 d . . .
C18 C 0.1239(3) 0.5669(3) 0.5016(3) 0.0414(8) Uani 1 1 d . . .
H18A H 0.0935 0.6120 0.5330 0.050 Uiso 1 1 calc R . .
C19 C 0.0874(3) 0.5913(3) 0.4078(3) 0.0465(8) Uani 1 1 d . . .
H19A H 0.0310 0.6556 0.3746 0.056 Uiso 1 1 calc R . .
C20 C 0.1287(3) 0.5266(3) 0.3566(3) 0.0431(8) Uani 1 1 d . . .
H20A H 0.0999 0.5500 0.2911 0.052 Uiso 1 1 calc R . .
C21 C 0.2075(2) 0.4328(3) 0.3993(2) 0.0356(7) Uani 1 1 d . . .
C22 C 0.2526(3) 0.4599(3) 0.6439(2) 0.0368(7) Uani 1 1 d . . .
H22A H 0.2835 0.3759 0.6842 0.044 Uiso 1 1 calc R . .
C23 C 0.1708(3) 0.4930(3) 0.7153(3) 0.0539(9) Uani 1 1 d . . .
H23A H 0.1056 0.4589 0.7231 0.081 Uiso 1 1 calc R . .
H23B H 0.1505 0.5772 0.6845 0.081 Uiso 1 1 calc R . .
H23C H 0.2064 0.4632 0.7817 0.081 Uiso 1 1 calc R . .
C24 C 0.3486(3) 0.5256(3) 0.6182(3) 0.0527(9) Uani 1 1 d . . .
H24A H 0.4009 0.4988 0.5802 0.079 Uiso 1 1 calc R . .
H24B H 0.3839 0.5114 0.6807 0.079 Uiso 1 1 calc R . .
H24C H 0.3221 0.6086 0.5772 0.079 Uiso 1 1 calc R . .
C25 C 0.2507(3) 0.3657(3) 0.3382(3) 0.0431(8) Uani 1 1 d . . .
H25A H 0.3018 0.2951 0.3852 0.052 Uiso 1 1 calc R . .
C26 C 0.3165(4) 0.4342(3) 0.2439(3) 0.0612(11) Uani 1 1 d . . .
H26A H 0.3371 0.3890 0.2082 0.092 Uiso 1 1 calc R . .
H26B H 0.3819 0.4485 0.2659 0.092 Uiso 1 1 calc R . .
H26C H 0.2715 0.5081 0.1986 0.092 Uiso 1 1 calc R . .
C27 C 0.1586(4) 0.3237(3) 0.3091(3) 0.0663(12) Uani 1 1 d . . .
H27A H 0.1197 0.2796 0.3696 0.099 Uiso 1 1 calc R . .
H27B H 0.1888 0.2743 0.2792 0.099 Uiso 1 1 calc R . .
H27C H 0.1083 0.3904 0.2601 0.099 Uiso 1 1 calc R . .
C28 C -0.0157(2) 0.1352(3) 0.8516(2) 0.0334(7) Uani 1 1 d . . .
C29 C -0.0063(3) 0.2348(3) 0.8595(2) 0.0386(7) Uani 1 1 d . . .
H29A H 0.0470 0.2797 0.8227 0.046 Uiso 1 1 calc R . .
C30 C -0.0761(3) 0.2690(3) 0.9225(3) 0.0456(8) Uani 1 1 d . . .
H30A H -0.0694 0.3381 0.9238 0.055 Uiso 1 1 calc R . .
C31 C -0.1553(3) 0.2036(3) 0.9832(3) 0.0476(8) Uani 1 1 d . . .
H31A H -0.1998 0.2273 1.0252 0.057 Uiso 1 1 calc R . .
C32 C -0.1646(3) 0.1066(3) 0.9787(2) 0.0420(8) Uani 1 1 d . . .
H32A H -0.2157 0.0606 1.0193 0.050 Uiso 1 1 calc R . .
C33 C -0.0961(2) 0.0700(3) 0.9112(2) 0.0365(7) Uani 1 1 d . . .
C34 C -0.1059(2) -0.0268(3) 0.8996(2) 0.0403(8) Uani 1 1 d . . .
H34A H -0.1551 -0.0754 0.9403 0.048 Uiso 1 1 calc RD . .
C35 C -0.0442(2) -0.0552(3) 0.8283(2) 0.0393(7) Uani 1 1 d . . .
C36 C 0.0319(2) 0.0171(3) 0.7676(2) 0.0329(6) Uani 1 1 d . . .
C37 C 0.0937(2) 0.0082(2) 0.6788(2) 0.0321(6) Uani 1 1 d . . .
C38 C 0.1243(2) -0.0662(3) 0.5609(2) 0.0367(7) Uani 1 1 d . . .
C39 C 0.1038(3) -0.1454(3) 0.5261(3) 0.0452(8) Uani 1 1 d . . .
H39A H 0.0594 -0.2010 0.5646 0.054 Uiso 1 1 calc R . .
C40 C 0.1480(3) -0.1429(3) 0.4357(3) 0.0475(8) Uani 1 1 d . . .
H40A H 0.1316 -0.1963 0.4157 0.057 Uiso 1 1 calc R . .
C41 C 0.2146(3) -0.0642(3) 0.3764(3) 0.0419(8) Uani 1 1 d . . .
H41A H 0.2434 -0.0631 0.3164 0.050 Uiso 1 1 calc R . .
C42 C 0.2374(2) 0.0130(3) 0.4076(3) 0.0382(7) Uani 1 1 d . . .
H42A H 0.2830 0.0669 0.3682 0.046 Uiso 1 1 calc R . .
C43 C 0.1926(2) 0.0134(2) 0.5011(2) 0.0330(6) Uani 1 1 d . . .
C44 C 0.2134(2) 0.0905(2) 0.5379(2) 0.0315(6) Uani 1 1 d . . .
H44A H 0.2601 0.1443 0.5014 0.038 Uiso 1 1 calc R . .
C45 C 0.1668(2) 0.0895(2) 0.6272(2) 0.0294(6) Uani 1 1 d . . .
C46 C -0.0538(5) -0.1676(5) 0.8244(5) 0.0512(15) Uani 0.60 1 d PD . .
H46A H -0.0884 -0.1422 0.7569 0.061 Uiso 1 1 calc R . .
C47A C -0.1290(7) -0.2478(7) 0.9059(7) 0.062(2) Uani 0.45 1 d PD . .
H47A H -0.2051 -0.2172 0.8828 0.092 Uiso 0.45 1 calc PR . .
H47B H -0.1180 -0.2494 0.9705 0.092 Uiso 0.45 1 calc PRD . .
H47C H -0.1100 -0.3264 0.9144 0.092 Uiso 0.45 1 calc PR . .
C47B C 0.0395(18) -0.265(2) 0.840(2) 0.062(2) Uani 0.15 1 d PD . .
H47D H 0.1059 -0.2490 0.8594 0.092 Uiso 0.15 1 calc PR . .
H47E H 0.0503 -0.2697 0.7774 0.092 Uiso 0.15 1 calc PR . .
H47F H 0.0227 -0.3379 0.8939 0.092 Uiso 0.15 1 calc PR . .
C48 C 0.4529(15) -0.4643(17) 0.9766(16) 0.285(8) Uiso 1 1 d D . .
C49 C 0.3474(14) -0.5024(15) 0.9640(13) 0.255(7) Uiso 1 1 d D . .
C50 C 0.2739(16) -0.589(2) 0.9949(17) 0.225(9) Uiso 0.67 1 d PD . .
C51 C 0.1573(19) -0.536(2) 0.9965(19) 0.132(8) Uiso 0.33 1 d PD . .


_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
Rh1 C45 2.027(3) . ?
Rh1 C1 2.045(3) . ?
Rh1 N3 2.166(2) . ?
Rh1 Cl1 2.4170(8) . ?
N1 C1 1.352(3) . ?
N1 C4 1.399(3) . ?
N1 C2 1.414(4) . ?
N2 C1 1.337(3) . ?
N2 C16 1.401(3) . ?
N2 C3 1.428(4) . ?
N3 C36 1.356(4) . ?
N3 C28 1.449(4) . ?
N4 C37 1.342(4) . ?
N4 C38 1.428(4) . ?
C2 C3 1.269(4) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(4) . ?
C4 C9 1.415(4) . ?
C5 C6 1.344(4) . ?
C5 C10 1.513(4) . ?
C6 C7 1.385(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.353(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.322(4) . ?
C8 H8A 0.9500 . ?
C9 C13 1.507(4) . ?
C10 C11 1.549(5) . ?
C10 C12 1.587(5) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.564(5) . ?
C13 C15 1.603(5) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.393(4) . ?
C16 C17 1.461(4) . ?
C17 C18 1.344(4) . ?
C17 C22 1.509(5) . ?
C18 C19 1.372(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.430(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.350(4) . ?
C20 H20A 0.9500 . ?
C21 C25 1.582(5) . ?
C22 C24 1.539(5) . ?
C22 C23 1.607(5) . ?
C22 H22A 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.533(5) . ?
C25 C26 1.564(5) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.415(5) . ?
C28 C33 1.434(4) . ?
C29 C30 1.436(5) . ?
C29 H29A 0.9500 . ?
C30 C31 1.429(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.355(5) . ?
C31 H31A 0.9500 . ?
C32 C33 1.498(5) . ?
C32 H32A 0.9500 . ?
C33 C34 1.410(5) . ?
C34 C35 1.447(5) . ?
C34 H34A 0.9500 . ?
C35 C36 1.442(4) . ?
C35 C46 1.555(7) . ?
C36 C37 1.555(4) . ?
C37 C45 1.449(4) . ?
C38 C43 1.417(4) . ?
C38 C39 1.446(5) . ?
C39 C40 1.431(5) . ?
C39 H39A 0.9500 . ?
C40 C41 1.394(5) . ?
C40 H40A 0.9500 . ?
C41 C42 1.394(5) . ?
C41 H41A 0.9500 . ?
C42 C43 1.491(5) . ?
C42 H42A 0.9500 . ?
C43 C44 1.444(4) . ?
C44 C45 1.434(4) . ?
C44 H44A 0.9500 . ?
C46 C47B 1.519(18) . ?
C46 C47A 1.591(9) . ?
C46 H46A 1.0000 . ?
C47A H47A 0.9800 . ?
C47A H47B 0.9800 . ?
C47A H47C 0.9800 . ?
C47B H47D 0.9800 . ?
C47B H47E 0.9800 . ?
C47B H47F 0.9800 . ?
C48 C48 1.36(3) 2_647 ?
C48 C49 1.549(15) . ?
C49 C50 1.490(16) . ?
C50 C51 1.514(17) . ?

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
C45 Rh1 C1 91.56(11) . . ?
C45 Rh1 N3 82.90(11) . . ?
C1 Rh1 N3 174.47(10) . . ?
C45 Rh1 Cl1 152.33(8) . . ?
C1 Rh1 Cl1 93.59(8) . . ?
N3 Rh1 Cl1 91.37(7) . . ?
C1 N1 C4 124.0(2) . . ?
C1 N1 C2 115.2(2) . . ?
C4 N1 C2 119.1(2) . . ?
C1 N2 C16 123.0(2) . . ?
C1 N2 C3 114.2(2) . . ?
C16 N2 C3 122.3(2) . . ?
C36 N3 C28 120.4(2) . . ?
C36 N3 Rh1 110.61(19) . . ?
C28 N3 Rh1 128.8(2) . . ?
C37 N4 C38 119.9(3) . . ?
N2 C1 N1 98.9(2) . . ?
N2 C1 Rh1 128.40(19) . . ?
N1 C1 Rh1 132.4(2) . . ?
C3 C2 N1 105.1(2) . . ?
C3 C2 H2A 127.4 . . ?
N1 C2 H2A 127.4 . . ?
C2 C3 N2 106.5(3) . . ?
C2 C3 H3A 126.8 . . ?
N2 C3 H3A 126.8 . . ?
C5 C4 N1 117.5(3) . . ?
C5 C4 C9 125.7(3) . . ?
N1 C4 C9 116.6(3) . . ?
C6 C5 C4 113.9(3) . . ?
C6 C5 C10 120.2(3) . . ?
C4 C5 C10 125.8(3) . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C8 C7 C6 123.3(3) . . ?
C8 C7 H7A 118.4 . . ?
C6 C7 H7A 118.4 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8A 120.7 . . ?
C7 C8 H8A 120.7 . . ?
C8 C9 C4 117.3(3) . . ?
C8 C9 C13 116.7(3) . . ?
C4 C9 C13 126.0(3) . . ?
C5 C10 C11 109.7(3) . . ?
C5 C10 C12 114.6(3) . . ?
C11 C10 C12 112.9(3) . . ?
C5 C10 H10A 106.3 . . ?
C11 C10 H10A 106.3 . . ?
C12 C10 H10A 106.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 110.5(3) . . ?
C9 C13 C15 113.8(3) . . ?
C14 C13 C15 112.2(3) . . ?
C9 C13 H13A 106.6 . . ?
C14 C13 H13A 106.6 . . ?
C15 C13 H13A 106.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 N2 114.2(3) . . ?
C21 C16 C17 126.3(3) . . ?
N2 C16 C17 119.3(3) . . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 C22 116.0(3) . . ?
C16 C17 C22 126.1(3) . . ?
C17 C18 C19 116.9(3) . . ?
C17 C18 H18A 121.6 . . ?
C19 C18 H18A 121.6 . . ?
C18 C19 C20 124.5(3) . . ?
C18 C19 H19A 117.8 . . ?
C20 C19 H19A 117.8 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C20 C21 C16 113.2(3) . . ?
C20 C21 C25 119.0(3) . . ?
C16 C21 C25 127.8(3) . . ?
C17 C22 C24 108.5(3) . . ?
C17 C22 C23 116.7(3) . . ?
C24 C22 C23 110.8(3) . . ?
C17 C22 H22A 106.8 . . ?
C24 C22 H22A 106.8 . . ?
C23 C22 H22A 106.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C26 111.0(3) . . ?
C27 C25 C21 111.2(3) . . ?
C26 C25 C21 114.3(3) . . ?
C27 C25 H25A 106.6 . . ?
C26 C25 H25A 106.6 . . ?
C21 C25 H25A 106.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C33 116.5(3) . . ?
C29 C28 N3 121.0(3) . . ?
C33 C28 N3 122.4(3) . . ?
C28 C29 C30 121.0(3) . . ?
C28 C29 H29A 119.5 . . ?
C30 C29 H29A 119.5 . . ?
C31 C30 C29 122.8(3) . . ?
C31 C30 H30A 118.6 . . ?
C29 C30 H30A 118.6 . . ?
C32 C31 C30 117.5(3) . . ?
C32 C31 H31A 121.3 . . ?
C30 C31 H31A 121.3 . . ?
C31 C32 C33 121.5(3) . . ?
C31 C32 H32A 119.3 . . ?
C33 C32 H32A 119.3 . . ?
C34 C33 C28 115.3(3) . . ?
C34 C33 C32 124.0(3) . . ?
C28 C33 C32 120.7(3) . . ?
C33 C34 C35 122.8(3) . . ?
C33 C34 H34A 118.6 . . ?
C35 C34 H34A 118.6 . . ?
C36 C35 C34 118.8(3) . . ?
C36 C35 C46 121.0(3) . . ?
C34 C35 C46 119.9(3) . . ?
N3 C36 C35 119.6(3) . . ?
N3 C36 C37 114.9(2) . . ?
C35 C36 C37 125.4(3) . . ?
N4 C37 C45 122.4(3) . . ?
N4 C37 C36 120.9(3) . . ?
C45 C37 C36 116.6(3) . . ?
C43 C38 N4 122.9(3) . . ?
C43 C38 C39 116.1(3) . . ?
N4 C38 C39 121.0(3) . . ?
C40 C39 C38 122.4(3) . . ?
C40 C39 H39A 118.8 . . ?
C38 C39 H39A 118.8 . . ?
C41 C40 C39 121.6(3) . . ?
C41 C40 H40A 119.2 . . ?
C39 C40 H40A 119.2 . . ?
C42 C41 C40 118.0(3) . . ?
C42 C41 H41A 121.0 . . ?
C40 C41 H41A 121.0 . . ?
C41 C42 C43 122.0(3) . . ?
C41 C42 H42A 119.0 . . ?
C43 C42 H42A 119.0 . . ?
C38 C43 C44 115.3(3) . . ?
C38 C43 C42 119.9(3) . . ?
C44 C43 C42 124.8(3) . . ?
C45 C44 C43 122.9(3) . . ?
C45 C44 H44A 118.5 . . ?
C43 C44 H44A 118.5 . . ?
C44 C45 C37 116.5(3) . . ?
C44 C45 Rh1 132.4(2) . . ?
C37 C45 Rh1 110.8(2) . . ?
C47B C46 C35 125.5(11) . . ?
C47B C46 C47A 95.8(11) . . ?
C35 C46 C47A 115.7(5) . . ?
C47B C46 H46A 106.1 . . ?
C35 C46 H46A 106.1 . . ?
C47A C46 H46A 106.1 . . ?
C46 C47A H47A 109.5 . . ?
C46 C47A H47B 109.5 . . ?
H47A C47A H47B 109.5 . . ?
C46 C47A H47C 109.5 . . ?
H47A C47A H47C 109.5 . . ?
H47B C47A H47C 109.5 . . ?
C46 C47B H47D 109.5 . . ?
C46 C47B H47E 109.5 . . ?
H47D C47B H47E 109.5 . . ?
C46 C47B H47F 109.5 . . ?
H47D C47B H47F 109.5 . . ?
H47E C47B H47F 109.5 . . ?
C48 C48 C49 126(2) 2_647 . ?
C50 C49 C48 152.0(19) . . ?
C49 C50 C51 111(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.816
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.086

_database_code_depnum_ccdc_archive 'CCDC 995397'
#######################################################################
#
#                 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_ccoz_200a

# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2013 template'





# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 B N O2'
_chemical_formula_sum            'C19 H24 B N O2'
_chemical_formula_weight         309.20

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'

# Crystal Data

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0448(9)
_cell_length_b                   13.1778(10)
_cell_length_c                   13.6491(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.075(2)
_cell_angle_gamma                90
_cell_volume                     1796.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3207
_cell_measurement_theta_min      5.126
_cell_measurement_theta_max      50.353

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   0.7119
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.188
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'

_exptl_special_details           ?

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12196
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3403
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
; APEX2 software package v2013.10-0 (Bruker AXS)
;
_computing_cell_refinement       
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)
;
_computing_data_reduction        
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS
;
_computing_structure_solution    
; SIR-2004 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
  G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori
  and R. Spagna, 2005)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2012)'
_computing_molecular_graphics    
; XP (SHELXTL-NT v6.14, Bruker AXS)
;

# REFINEMENT DATA

_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 >
σ(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. The non-hydrogen atoms were refined anisotropically. Hydrogen
atoms of the phenyl, CH₂- and CH₃-groups were included at geometrically
idealized positions (C-H bond distances 0.95/0.98 Å) and were not refined.
The isotropic thermal parameters of these hydrogen atoms were fixed at 1.2
(phenyl and CH₂-groups) and 1.5 times (CH₃-groups) that of the preceding
carbon or nitrogen atom, respectively. The carbon and oxygen atoms within the
BO₂(C(CH₃)₂)₂ fragment were disordered over two sites. The site
occupancy factors for the two sites were initially refined and then set to the
resulting values of 0.718 and 0.282, respectively.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0476P)²+0.2010P]
 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_number_reflns         3403
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.87911(11) 0.02290(8) 0.30948(7) 0.0424(3) Uani 1 1 d . . . . .
C1 C 1.00520(13) 0.01585(10) 0.35497(9) 0.0391(3) Uani 1 1 d . . . . .
C2 C 1.08853(15) -0.06289(10) 0.33284(11) 0.0482(4) Uani 1 1 d . . . . .
H2 H 1.1767 -0.0680 0.3653 0.058 Uiso 1 1 calc R U . . .
C3 C 1.04216(18) -0.13362(12) 0.26331(11) 0.0581(4) Uani 1 1 d . . . . .
H3 H 1.0984 -0.1879 0.2475 0.070 Uiso 1 1 calc R U . . .
C4 C 0.91403(18) -0.12559(12) 0.21672(11) 0.0603(4) Uani 1 1 d . . . . .
H4 H 0.8812 -0.1736 0.1681 0.072 Uiso 1 1 calc R U . . .
C5 C 0.83445(17) -0.04675(12) 0.24190(10) 0.0554(4) Uani 1 1 d . . . . .
H5 H 0.7456 -0.0414 0.2107 0.066 Uiso 1 1 calc R U . . .
C6 C 1.03314(13) 0.10065(10) 0.42419(9) 0.0375(3) Uani 1 1 d . . . . .
C7 C 0.92203(14) 0.16415(10) 0.42470(9) 0.0413(3) Uani 1 1 d . . . . .
C8 C 0.93709(15) 0.24918(11) 0.48626(9) 0.0486(4) Uani 1 1 d . . . . .
H8 H 0.8637 0.2944 0.4880 0.058 Uiso 1 1 calc R U . . .
C9 C 1.05574(16) 0.26978(11) 0.54495(9) 0.0493(4) Uani 1 1 d . . . . .
C10 C 1.16262(15) 0.20246(11) 0.54300(10) 0.0482(4) Uani 1 1 d . . . . .
H10 H 1.2439 0.2154 0.5833 0.058 Uiso 1 1 calc R U . . .
C11 C 1.15245(14) 0.11728(10) 0.48355(10) 0.0427(3) Uani 1 1 d . . . . .
H11 H 1.2252 0.0712 0.4832 0.051 Uiso 1 1 calc R U . . .
O1A O 0.7460(17) 0.1844(11) 0.2726(13) 0.0448(13) Uani 0.718 1 d . . P A 1
O2A O 0.6790(2) 0.07313(14) 0.38674(13) 0.0430(5) Uani 0.718 1 d . . P A 1
C12A C 0.6033(2) 0.18320(17) 0.25661(19) 0.0499(5) Uani 0.718 1 d . . P A 1
C13A C 0.5669(8) 0.1308(5) 0.3557(4) 0.0463(9) Uani 0.718 1 d . . P A 1
C14A C 0.5594(2) 0.12066(19) 0.16453(17) 0.0666(7) Uani 0.718 1 d . . P A 1
H14A H 0.5780 0.0487 0.1781 0.100 Uiso 0.718 1 calc R U P A 1
H14B H 0.6087 0.1431 0.1102 0.100 Uiso 0.718 1 calc R U P A 1
H14C H 0.4631 0.1300 0.1462 0.100 Uiso 0.718 1 calc R U P A 1
C15A C 0.5553(3) 0.2924(2) 0.2392(2) 0.0768(8) Uani 0.718 1 d . . P A 1
H15A H 0.4575 0.2948 0.2368 0.115 Uiso 0.718 1 calc R U P A 1
H15B H 0.5826 0.3169 0.1765 0.115 Uiso 0.718 1 calc R U P A 1
H15C H 0.5951 0.3356 0.2930 0.115 Uiso 0.718 1 calc R U P A 1
C16A C 0.4425(4) 0.0644(5) 0.3409(4) 0.0751(14) Uani 0.718 1 d . . P A 1
H16A H 0.4246 0.0352 0.4042 0.113 Uiso 0.718 1 calc R U P A 1
H16B H 0.4569 0.0097 0.2946 0.113 Uiso 0.718 1 calc R U P A 1
H16C H 0.3658 0.1056 0.3144 0.113 Uiso 0.718 1 calc R U P A 1
C17A C 0.5459(3) 0.2108(2) 0.4343(2) 0.0745(8) Uani 0.718 1 d . . P A 1
H17A H 0.5379 0.1771 0.4974 0.112 Uiso 0.718 1 calc R U P A 1
H17B H 0.4639 0.2491 0.4143 0.112 Uiso 0.718 1 calc R U P A 1
H17C H 0.6225 0.2572 0.4414 0.112 Uiso 0.718 1 calc R U P A 1
O1B O 0.733(5) 0.195(3) 0.277(3) 0.0448(13) Uani 0.282 1 d . . P A 2
O2B O 0.6949(5) 0.1050(3) 0.4239(3) 0.0360(10) Uani 0.282 1 d . . P A 2
C12B C 0.5986(5) 0.2216(4) 0.3072(4) 0.0448(13) Uani 0.282 1 d . . P A 2
C13B C 0.557(2) 0.1451(15) 0.3762(14) 0.0463(9) Uani 0.282 1 d . . P A 2
C14B C 0.6128(6) 0.3259(3) 0.3573(4) 0.0532(13) Uani 0.282 1 d . . P A 2
H14D H 0.5239 0.3519 0.3674 0.080 Uiso 0.282 1 calc R U P A 2
H14E H 0.6566 0.3730 0.3153 0.080 Uiso 0.282 1 calc R U P A 2
H14F H 0.6669 0.3194 0.4210 0.080 Uiso 0.282 1 calc R U P A 2
C15B C 0.5045(7) 0.2332(7) 0.2141(5) 0.0715(19) Uani 0.282 1 d . . P A 2
H15D H 0.4147 0.2498 0.2311 0.107 Uiso 0.282 1 calc R U P A 2
H15E H 0.5013 0.1695 0.1768 0.107 Uiso 0.282 1 calc R U P A 2
H15F H 0.5365 0.2878 0.1738 0.107 Uiso 0.282 1 calc R U P A 2
C16B C 0.4924(10) 0.0460(9) 0.3252(9) 0.064(3) Uani 0.282 1 d . . P A 2
H16D H 0.4985 -0.0099 0.3729 0.097 Uiso 0.282 1 calc R U P A 2
H16E H 0.5405 0.0276 0.2689 0.097 Uiso 0.282 1 calc R U P A 2
H16F H 0.3982 0.0590 0.3024 0.097 Uiso 0.282 1 calc R U P A 2
C17B C 0.4815(7) 0.1722(5) 0.4604(5) 0.0583(16) Uani 0.282 1 d . . P A 2
H17D H 0.4575 0.1101 0.4941 0.087 Uiso 0.282 1 calc R U P A 2
H17E H 0.3998 0.2089 0.4359 0.087 Uiso 0.282 1 calc R U P A 2
H17F H 0.5372 0.2153 0.5067 0.087 Uiso 0.282 1 calc R U P A 2
C18 C 1.0710(2) 0.36304(12) 0.60985(12) 0.0693(5) Uani 1 1 d . . . . .
H18A H 1.1097 0.3428 0.6767 0.083 Uiso 1 1 calc R U . . .
H18B H 0.9814 0.3924 0.6154 0.083 Uiso 1 1 calc R U . . .
C19 C 1.1596(2) 0.44337(13) 0.57057(15) 0.0809(6) Uani 1 1 d . . . . .
H19A H 1.1664 0.5018 0.6152 0.121 Uiso 1 1 calc R U . . .
H19B H 1.1207 0.4651 0.5050 0.121 Uiso 1 1 calc R U . . .
H19C H 1.2490 0.4151 0.5660 0.121 Uiso 1 1 calc R U . . .
B1 B 0.79527(16) 0.12217(12) 0.35247(11) 0.0441(4) Uani 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.
;

# MOLECULAR GEOMETRY

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
N1 C5 1.3442(18) . ?
N1 C1 1.3535(17) . ?
N1 B1 1.694(2) . ?
C1 C2 1.3864(19) . ?
C1 C6 1.4710(18) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C11 1.3911(18) . ?
C6 C7 1.3955(18) . ?
C7 C8 1.3991(19) . ?
C7 B1 1.623(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 C18 1.513(2) . ?
C10 C11 1.3824(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O1A B1 1.412(16) . ?
O1A C12A 1.427(17) . ?
O2A C13A 1.387(8) . ?
O2A B1 1.455(3) . ?
C12A C15A 1.528(3) . ?
C12A C14A 1.529(3) . ?
C12A C13A 1.595(7) . ?
C13A C16A 1.521(10) . ?
C13A C17A 1.535(5) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O1B C12B 1.49(4) . ?
O1B B1 1.49(4) . ?
O2B B1 1.493(5) . ?
O2B C13B 1.56(2) . ?
C12B C13B 1.47(2) . ?
C12B C15B 1.510(8) . ?
C12B C14B 1.535(8) . ?
C13B C17B 1.488(16) . ?
C13B C16B 1.59(2) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18 C19 1.517(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C5 N1 C1 119.74(13) . . ?
C5 N1 B1 128.54(12) . . ?
C1 N1 B1 111.69(11) . . ?
N1 C1 C2 120.58(13) . . ?
N1 C1 C6 110.37(11) . . ?
C2 C1 C6 129.04(13) . . ?
C3 C2 C1 119.29(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.85(15) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.78(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.76(15) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C11 C6 C7 122.87(12) . . ?
C11 C6 C1 126.00(12) . . ?
C7 C6 C1 111.12(12) . . ?
C6 C7 C8 116.59(13) . . ?
C6 C7 B1 111.66(12) . . ?
C8 C7 B1 131.75(12) . . ?
C9 C8 C7 122.27(13) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 118.63(13) . . ?
C8 C9 C18 121.55(14) . . ?
C10 C9 C18 119.82(14) . . ?
C11 C10 C9 121.22(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 118.38(13) . . ?
C10 C11 H11 120.8 . . ?
C6 C11 H11 120.8 . . ?
B1 O1A C12A 112.1(12) . . ?
C13A O2A B1 108.2(4) . . ?
O1A C12A C15A 107.9(6) . . ?
O1A C12A C14A 109.3(6) . . ?
C15A C12A C14A 108.7(2) . . ?
O1A C12A C13A 101.1(8) . . ?
C15A C12A C13A 116.3(3) . . ?
C14A C12A C13A 113.1(3) . . ?
O2A C13A C16A 110.8(5) . . ?
O2A C13A C17A 109.3(5) . . ?
C16A C13A C17A 108.4(4) . . ?
O2A C13A C12A 104.2(4) . . ?
C16A C13A C12A 113.3(5) . . ?
C17A C13A C12A 110.9(5) . . ?
C12A C14A H14A 109.5 . . ?
C12A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C12A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C12A C15A H15A 109.5 . . ?
C12A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C12A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13A C16A H16A 109.5 . . ?
C13A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C13A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C13A C17A H17A 109.5 . . ?
C13A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C13A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C12B O1B B1 107(3) . . ?
B1 O2B C13B 107.8(8) . . ?
C13B C12B O1B 109.8(19) . . ?
C13B C12B C15B 114.5(10) . . ?
O1B C12B C15B 107.1(18) . . ?
C13B C12B C14B 110.4(7) . . ?
O1B C12B C14B 107.0(18) . . ?
C15B C12B C14B 107.7(5) . . ?
C12B C13B C17B 122.2(13) . . ?
C12B C13B O2B 101.7(14) . . ?
C17B C13B O2B 105.2(12) . . ?
C12B C13B C16B 114.5(12) . . ?
C17B C13B C16B 108.4(15) . . ?
O2B C13B C16B 102.1(11) . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C13B C16B H16D 109.5 . . ?
C13B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C13B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C13B C17B H17D 109.5 . . ?
C13B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C13B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C9 C18 C19 112.74(14) . . ?
C9 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C9 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1A B1 O2A 106.2(8) . . ?
O2B B1 O1B 106.5(17) . . ?
O1A B1 C7 117.4(8) . . ?
O2A B1 C7 124.14(13) . . ?
O2B B1 C7 101.29(19) . . ?
O1B B1 C7 116.6(19) . . ?
O1A B1 N1 109.1(5) . . ?
O2A B1 N1 102.35(12) . . ?
O2B B1 N1 120.3(2) . . ?
O1B B1 N1 116.3(15) . . ?
C7 B1 N1 94.98(10) . . ?

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
C5 N1 C1 C2 -0.33(18) . . . . ?
B1 N1 C1 C2 177.50(11) . . . . ?
C5 N1 C1 C6 178.93(11) . . . . ?
B1 N1 C1 C6 -3.23(13) . . . . ?
N1 C1 C2 C3 0.58(19) . . . . ?
C6 C1 C2 C3 -178.54(12) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C1 N1 C5 C4 -0.4(2) . . . . ?
B1 N1 C5 C4 -177.84(12) . . . . ?
C3 C4 C5 N1 0.9(2) . . . . ?
N1 C1 C6 C11 179.80(12) . . . . ?
C2 C1 C6 C11 -1.0(2) . . . . ?
N1 C1 C6 C7 0.63(14) . . . . ?
C2 C1 C6 C7 179.82(13) . . . . ?
C11 C6 C7 C8 2.15(18) . . . . ?
C1 C6 C7 C8 -178.65(11) . . . . ?
C11 C6 C7 B1 -176.84(11) . . . . ?
C1 C6 C7 B1 2.36(14) . . . . ?
C6 C7 C8 C9 -0.55(19) . . . . ?
B1 C7 C8 C9 178.19(13) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C7 C8 C9 C18 178.99(13) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C18 C9 C10 C11 -179.16(13) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C7 C6 C11 C10 -2.34(19) . . . . ?
C1 C6 C11 C10 178.59(12) . . . . ?
B1 O1A C12A C15A 135.7(7) . . . . ?
B1 O1A C12A C14A -106.2(9) . . . . ?
B1 O1A C12A C13A 13.2(10) . . . . ?
B1 O2A C13A C16A 151.2(3) . . . . ?
B1 O2A C13A C17A -89.5(5) . . . . ?
B1 O2A C13A C12A 29.1(4) . . . . ?
O1A C12A C13A O2A -25.7(7) . . . . ?
C15A C12A C13A O2A -142.3(3) . . . . ?
C14A C12A C13A O2A 90.9(4) . . . . ?
O1A C12A C13A C16A -146.2(7) . . . . ?
C15A C12A C13A C16A 97.3(4) . . . . ?
C14A C12A C13A C16A -29.5(5) . . . . ?
O1A C12A C13A C17A 91.7(7) . . . . ?
C15A C12A C13A C17A -24.9(6) . . . . ?
C14A C12A C13A C17A -151.7(4) . . . . ?
B1 O1B C12B C13B -19(3) . . . . ?
B1 O1B C12B C15B -144(2) . . . . ?
B1 O1B C12B C14B 101(2) . . . . ?
O1B C12B C13B C17B 144(2) . . . . ?
C15B C12B C13B C17B -95.9(17) . . . . ?
C14B C12B C13B C17B 26(2) . . . . ?
O1B C12B C13B O2B 27(2) . . . . ?
C15B C12B C13B O2B 147.5(8) . . . . ?
C14B C12B C13B O2B -90.7(8) . . . . ?
O1B C12B C13B C16B -82(2) . . . . ?
C15B C12B C13B C16B 38.3(15) . . . . ?
C14B C12B C13B C16B 160.1(10) . . . . ?
B1 O2B C13B C12B -25.5(10) . . . . ?
B1 O2B C13B C17B -153.8(10) . . . . ?
B1 O2B C13B C16B 93.0(11) . . . . ?
C8 C9 C18 C19 -106.98(18) . . . . ?
C10 C9 C18 C19 72.78(18) . . . . ?
C12A O1A B1 O2A 3.4(10) . . . . ?
C12A O1A B1 O2B -23.3(11) . . . . ?
C12A O1A B1 O1B -55(20) . . . . ?
C12A O1A B1 C7 -140.5(7) . . . . ?
C12A O1A B1 N1 113.1(8) . . . . ?
C13A O2A B1 O1A -21.6(6) . . . . ?
C13A O2A B1 O2B 87.3(6) . . . . ?
C13A O2A B1 O1B -15.3(16) . . . . ?
C13A O2A B1 C7 119.2(3) . . . . ?
C13A O2A B1 N1 -136.0(2) . . . . ?
C13B O2B B1 O1A 10.8(11) . . . . ?
C13B O2B B1 O2A -69.4(9) . . . . ?
C13B O2B B1 O1B 14.7(19) . . . . ?
C13B O2B B1 C7 137.1(8) . . . . ?
C13B O2B B1 N1 -120.3(8) . . . . ?
C12B O1B B1 O1A 152(23) . . . . ?
C12B O1B B1 O2A 28(3) . . . . ?
C12B O1B B1 O2B 2(3) . . . . ?
C12B O1B B1 C7 -110(2) . . . . ?
C12B O1B B1 N1 139.1(17) . . . . ?
C6 C7 B1 O1A -118.2(6) . . . . ?
C8 C7 B1 O1A 63.0(7) . . . . ?
C6 C7 B1 O2A 104.92(17) . . . . ?
C8 C7 B1 O2A -73.9(2) . . . . ?
C6 C7 B1 O2B 118.6(2) . . . . ?
C8 C7 B1 O2B -60.2(3) . . . . ?
C6 C7 B1 O1B -126.4(17) . . . . ?
C8 C7 B1 O1B 54.9(17) . . . . ?
C6 C7 B1 N1 -3.65(12) . . . . ?
C8 C7 B1 N1 177.56(13) . . . . ?
C5 N1 B1 O1A -57.1(8) . . . . ?
C1 N1 B1 O1A 125.3(8) . . . . ?
C5 N1 B1 O2A 55.13(17) . . . . ?
C1 N1 B1 O2A -122.47(13) . . . . ?
C5 N1 B1 O2B 75.5(3) . . . . ?
C1 N1 B1 O2B -102.1(2) . . . . ?
C5 N1 B1 O1B -55(2) . . . . ?
C1 N1 B1 O1B 127(2) . . . . ?
C5 N1 B1 C7 -178.31(12) . . . . ?
C1 N1 B1 C7 4.10(12) . . . . ?

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.028

_shelxl_version_number           2012-9



_database_code_depnum_ccdc_archive 'CCDC 995398'
