# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DP-II-163
_database_code_depnum_ccdc_archive 'CCDC 1403306'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
8-(Dimesitylboryl)-N,N-dimethylnaphthalen-1-amine
_chemical_formula_moiety         'C30 H34 B N'
_chemical_formula_sum            'C30 H34 B N'
_chemical_formula_weight         419.39
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8952(2)
_cell_length_b                   9.1463(2)
_cell_length_c                   15.7704(4)
_cell_angle_alpha                100.1220(10)
_cell_angle_beta                 97.4700(10)
_cell_angle_gamma                104.9290(10)
_cell_volume                     1199.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.81
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_T_max  0.7463

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_number            30766
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_full        31.88
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             8186
_reflns_number_gt                6571
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1005P)²+0.3075P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8186
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.176
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.122

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.43184(13) 0.69058(13) 0.28541(7) 0.0219(2) Uani 1 1 d . . .
C10 C 0.65127(12) 0.92997(12) 0.25130(7) 0.0248(2) Uani 1 1 d . . .
C1 C 0.59723(12) 0.81685(12) 0.30176(7) 0.02401(19) Uani 1 1 d . . .
C9 C 0.54730(13) 0.97016(13) 0.18878(7) 0.0270(2) Uani 1 1 d . . .
C5 C 0.81642(14) 1.01216(14) 0.26615(8) 0.0326(2) Uani 1 1 d . . .
C8 C 0.60592(17) 1.08211(16) 0.14365(9) 0.0397(3) Uani 1 1 d . . .
H8 H 0.5348 1.1077 0.1024 0.048 Uiso 1 1 calc R . .
C2 C 0.70739(14) 0.80077(14) 0.36762(8) 0.0326(2) Uani 1 1 d . . .
H2 H 0.672 0.7333 0.405 0.039 Uiso 1 1 calc R . .
C12 C 0.31997(16) 0.80720(15) 0.08388(7) 0.0343(2) Uani 1 1 d . . .
H12A H 0.3315 0.8782 0.0437 0.051 Uiso 1 1 calc R . .
H12B H 0.208 0.7504 0.0773 0.051 Uiso 1 1 calc R . .
H12C H 0.3809 0.7336 0.0702 0.051 Uiso 1 1 calc R . .
C4 C 0.92292(14) 0.98247(16) 0.33107(10) 0.0403(3) Uani 1 1 d . . .
H4 H 1.0328 1.0344 0.3396 0.048 Uiso 1 1 calc R . .
C6 C 0.87067(16) 1.12455(16) 0.21684(10) 0.0421(3) Uani 1 1 d . . .
H6 H 0.9805 1.1765 0.2256 0.051 Uiso 1 1 calc R . .
C11 C 0.29119(17) 1.01031(16) 0.19290(9) 0.0378(3) Uani 1 1 d . . .
H11A H 0.3391 1.0795 0.2503 0.057 Uiso 1 1 calc R . .
H11B H 0.1808 0.9563 0.1931 0.057 Uiso 1 1 calc R . .
H11C H 0.295 1.0713 0.1476 0.057 Uiso 1 1 calc R . .
C7 C 0.76792(19) 1.15875(17) 0.15738(10) 0.0455(3) Uani 1 1 d . . .
H7 H 0.8058 1.2346 0.1251 0.055 Uiso 1 1 calc R . .
C3 C 0.87044(15) 0.88083(17) 0.38138(10) 0.0414(3) Uani 1 1 d . . .
H3 H 0.9429 0.8635 0.4256 0.05 Uiso 1 1 calc R . .
N1 N 0.37917(11) 0.89619(11) 0.17448(6) 0.02545(18) Uani 1 1 d . . .
C13 C 0.36029(11) 0.56580(11) 0.19650(6) 0.02160(18) Uani 1 1 d . . .
C18 C 0.19419(12) 0.51479(12) 0.16690(7) 0.0248(2) Uani 1 1 d . . .
C14 C 0.45414(12) 0.49656(12) 0.14588(6) 0.02393(19) Uani 1 1 d . . .
C17 C 0.12812(13) 0.39990(14) 0.09057(7) 0.0303(2) Uani 1 1 d . . .
H17 H 0.0167 0.3694 0.071 0.036 Uiso 1 1 calc R . .
C15 C 0.38215(14) 0.37956(13) 0.07101(7) 0.0285(2) Uani 1 1 d . . .
H15 H 0.4471 0.3331 0.0386 0.034 Uiso 1 1 calc R . .
C16 C 0.21972(15) 0.32887(14) 0.04232(7) 0.0310(2) Uani 1 1 d . . .
C19 C 0.63177(14) 0.53688(16) 0.16988(8) 0.0342(2) Uani 1 1 d . . .
H19A H 0.6606 0.5052 0.2245 0.051 Uiso 1 1 calc R . .
H19B H 0.6777 0.6491 0.1779 0.051 Uiso 1 1 calc R . .
H19C H 0.6725 0.4827 0.1229 0.051 Uiso 1 1 calc R . .
C21 C 0.08221(13) 0.58361(16) 0.21370(8) 0.0341(2) Uani 1 1 d . . .
H21A H -0.0194 0.5596 0.174 0.051 Uiso 1 1 calc R . .
H21B H 0.1277 0.6963 0.2323 0.051 Uiso 1 1 calc R . .
H21C H 0.0657 0.5395 0.2652 0.051 Uiso 1 1 calc R . .
C20 C 0.14555(19) 0.20008(18) -0.03749(9) 0.0473(3) Uani 1 1 d . . .
H20A H 0.0659 0.118 -0.022 0.071 Uiso 1 1 calc R . .
H20B H 0.2275 0.1577 -0.059 0.071 Uiso 1 1 calc R . .
H20C H 0.095 0.2408 -0.0833 0.071 Uiso 1 1 calc R . .
C22 C 0.35859(12) 0.66450(12) 0.37006(6) 0.02391(19) Uani 1 1 d . . .
C27 C 0.33421(13) 0.51974(13) 0.39459(7) 0.0270(2) Uani 1 1 d . . .
C23 C 0.32214(13) 0.78444(13) 0.42587(7) 0.0265(2) Uani 1 1 d . . .
C24 C 0.26038(14) 0.75779(15) 0.50070(7) 0.0317(2) Uani 1 1 d . . .
H24 H 0.2349 0.8395 0.5366 0.038 Uiso 1 1 calc R . .
C26 C 0.27417(15) 0.49836(14) 0.47036(7) 0.0323(2) Uani 1 1 d . . .
H26 H 0.2594 0.4005 0.4858 0.039 Uiso 1 1 calc R . .
C25 C 0.23532(15) 0.61530(16) 0.52391(7) 0.0335(2) Uani 1 1 d . . .
C28 C 0.34121(16) 0.94157(14) 0.40467(8) 0.0343(2) Uani 1 1 d . . .
H28A H 0.258 0.9343 0.3555 0.052 Uiso 1 1 calc R . .
H28B H 0.4451 0.9779 0.3887 0.052 Uiso 1 1 calc R . .
H28C H 0.3329 1.0148 0.456 0.052 Uiso 1 1 calc R . .
C30 C 0.37343(18) 0.38329(14) 0.34267(8) 0.0369(3) Uani 1 1 d . . .
H30A H 0.3759 0.3063 0.3785 0.055 Uiso 1 1 calc R . .
H30B H 0.4772 0.4189 0.3263 0.055 Uiso 1 1 calc R . .
H30C H 0.2926 0.3364 0.2896 0.055 Uiso 1 1 calc R . .
C29 C 0.1694(2) 0.5886(2) 0.60516(9) 0.0476(3) Uani 1 1 d . . .
H29A H 0.152 0.4796 0.6083 0.071 Uiso 1 1 calc R . .
H29B H 0.0687 0.6141 0.6028 0.071 Uiso 1 1 calc R . .
H29C H 0.2446 0.6548 0.6571 0.071 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.5767(15) . ?
B1 C13 1.5826(14) . ?
B1 C22 1.5879(15) . ?
C10 C9 1.4242(16) . ?
C10 C5 1.4345(15) . ?
C10 C1 1.4377(15) . ?
C1 C2 1.3871(15) . ?
C9 C8 1.3800(16) . ?
C9 N1 1.4432(14) . ?
C5 C4 1.413(2) . ?
C5 C6 1.4202(18) . ?
C8 C7 1.400(2) . ?
C8 H8 0.95 . ?
C2 C3 1.4149(18) . ?
C2 H2 0.95 . ?
C12 N1 1.4684(14) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C4 C3 1.358(2) . ?
C4 H4 0.95 . ?
C6 C7 1.357(2) . ?
C6 H6 0.95 . ?
C11 N1 1.4696(15) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C7 H7 0.95 . ?
C3 H3 0.95 . ?
C13 C14 1.4153(14) . ?
C13 C18 1.4169(14) . ?
C18 C17 1.3971(15) . ?
C18 C21 1.5113(16) . ?
C14 C15 1.3985(14) . ?
C14 C19 1.5070(15) . ?
C17 C16 1.3875(17) . ?
C17 H17 0.95 . ?
C15 C16 1.3850(17) . ?
C15 H15 0.95 . ?
C16 C20 1.5065(16) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C22 C23 1.4146(14) . ?
C22 C27 1.4155(15) . ?
C27 C26 1.3948(15) . ?
C27 C30 1.5130(16) . ?
C23 C24 1.3981(15) . ?
C23 C28 1.5046(16) . ?
C24 C25 1.3861(18) . ?
C24 H24 0.95 . ?
C26 C25 1.3877(17) . ?
C26 H26 0.95 . ?
C25 C29 1.5090(17) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?

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
C1 B1 C13 123.25(9) . . ?
C1 B1 C22 116.05(8) . . ?
C13 B1 C22 118.91(8) . . ?
C9 C10 C5 117.44(10) . . ?
C9 C10 C1 123.09(9) . . ?
C5 C10 C1 119.42(10) . . ?
C2 C1 C10 117.58(10) . . ?
C2 C1 B1 113.38(9) . . ?
C10 C1 B1 128.55(9) . . ?
C8 C9 C10 120.42(11) . . ?
C8 C9 N1 119.94(11) . . ?
C10 C9 N1 119.62(9) . . ?
C4 C5 C6 120.74(11) . . ?
C4 C5 C10 119.49(11) . . ?
C6 C5 C10 119.76(12) . . ?
C9 C8 C7 121.45(13) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C1 C2 C3 122.60(12) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C4 C5 120.93(11) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C7 C6 C5 120.97(12) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C7 C8 119.91(12) . . ?
C6 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C4 C3 C2 119.75(12) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C9 N1 C12 111.00(9) . . ?
C9 N1 C11 111.40(9) . . ?
C12 N1 C11 108.84(10) . . ?
C14 C13 C18 117.50(9) . . ?
C14 C13 B1 123.07(9) . . ?
C18 C13 B1 119.37(9) . . ?
C17 C18 C13 120.28(10) . . ?
C17 C18 C21 117.32(10) . . ?
C13 C18 C21 122.38(9) . . ?
C15 C14 C13 120.06(10) . . ?
C15 C14 C19 116.34(9) . . ?
C13 C14 C19 123.54(9) . . ?
C16 C17 C18 122.22(10) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C16 C15 C14 122.48(10) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 117.42(10) . . ?
C15 C16 C20 121.17(12) . . ?
C17 C16 C20 121.40(11) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C22 C27 117.33(9) . . ?
C23 C22 B1 122.26(9) . . ?
C27 C22 B1 120.34(9) . . ?
C26 C27 C22 120.29(10) . . ?
C26 C27 C30 116.81(10) . . ?
C22 C27 C30 122.89(10) . . ?
C24 C23 C22 120.61(10) . . ?
C24 C23 C28 117.96(10) . . ?
C22 C23 C28 121.37(10) . . ?
C25 C24 C23 121.76(11) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C25 C26 C27 122.19(11) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C24 C25 C26 117.79(10) . . ?
C24 C25 C29 121.13(12) . . ?
C26 C25 C29 121.08(12) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1403307'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.1467(5)
_cell_length_b                   10.7629(5)
_cell_length_c                   16.8959(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2208.86(17)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C12 H12 B1 F2 N1 
# Dc =      1.32 Fooo =    912.00 Mu =      0.99 M =    219.04
# Found Formula = C12 H12 B1 F2 N1 
# Dc =      1.32 FOOO =    912.00 Mu =      0.99 M =    219.04

_chemical_formula_sum            'C12 H12 B1 F2 N1'
_chemical_formula_moiety         'C12 H12 B1 F2 N1'
_chemical_compound_source        ?
_chemical_formula_weight         219.04


_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2
_cell_measurement_theta_max      29
_cell_measurement_temperature    295

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.099

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            42628
_reflns_number_total             2999
_diffrn_reflns_av_R_equivalents  0.022
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2999 
# Theoretical number of reflections is about 6370 


_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         29.874
_diffrn_measured_fraction_theta_max 0.944

_diffrn_reflns_theta_full        25.094
_diffrn_measured_fraction_theta_full 0.993


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              0
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.27


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_number_parameters     145
_oxford_refine_ls_R_factor_ref   0.0466
_refine_ls_wR_factor_ref         0.0499
_refine_ls_goodness_of_fit_ref   1.0244
_refine_ls_shift/su_max          0.0004995
_refine_ls_shift/su_mean         0.0000477


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2993
_refine_ls_R_factor_all          0.0594
_refine_ls_wR_factor_all         0.0781

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2624
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_gt          0.0532

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.193 0.164 0.463E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.65790(8) 0.42511(10) 0.59909(7) 0.0378 1.0000 Uani . . . . . .
C2 C 0.71494(11) 0.52342(13) 0.56931(9) 0.0575 1.0000 Uani . . . . . .
C3 C 0.71366(14) 0.54106(17) 0.48629(10) 0.0725 1.0000 Uani . . . . . .
C4 C 0.65798(13) 0.46305(16) 0.43675(9) 0.0674 1.0000 Uani . . . . . .
C5 C 0.53688(14) 0.27370(15) 0.42298(8) 0.0667 1.0000 Uani . . . . . .
C6 C 0.48204(16) 0.18051(15) 0.46025(10) 0.0738 1.0000 Uani . . . . . .
C7 C 0.48417(13) 0.16660(13) 0.54328(10) 0.0612 1.0000 Uani . . . . . .
C8 C 0.54343(9) 0.24746(10) 0.58929(7) 0.0408 1.0000 Uani . . . . . .
C9 C 0.59963(9) 0.34364(10) 0.54989(6) 0.0367 1.0000 Uani . . . . . .
C10 C 0.59875(11) 0.36074(12) 0.46701(7) 0.0503 1.0000 Uani . . . . . .
C11 C 0.76037(11) 0.35963(14) 0.71520(9) 0.0577 1.0000 Uani . . . . . .
C12 C 0.59948(15) 0.49226(13) 0.72995(9) 0.0657 1.0000 Uani . . . . . .
N1 N 0.64846(7) 0.38921(8) 0.68290(5) 0.0375 1.0000 Uani . . . . . .
B1 B 0.56470(10) 0.25970(12) 0.68185(8) 0.0398 1.0000 Uani . . . . . .
F1 F 0.47466(6) 0.28688(9) 0.72790(5) 0.0667 1.0000 Uani . . . . . .
F2 F 0.62368(6) 0.16439(7) 0.71694(5) 0.0541 1.0000 Uani . . . . . .
H21 H 0.7545 0.5826 0.6035 0.0715 1.0000 Uiso R . . . . .
H31 H 0.7528 0.6127 0.4654 0.0868 1.0000 Uiso R . . . . .
H41 H 0.6581 0.4800 0.3806 0.0818 1.0000 Uiso R . . . . .
H51 H 0.5348 0.2805 0.3659 0.0799 1.0000 Uiso R . . . . .
H61 H 0.4431 0.1237 0.4288 0.0913 1.0000 Uiso R . . . . .
H71 H 0.4447 0.0993 0.5677 0.0752 1.0000 Uiso R . . . . .
H111 H 0.7926 0.2936 0.6804 0.0865 1.0000 Uiso R . . . . .
H112 H 0.8056 0.4345 0.7157 0.0869 1.0000 Uiso R . . . . .
H113 H 0.7512 0.3255 0.7683 0.0872 1.0000 Uiso R . . . . .
H121 H 0.5263 0.5113 0.7082 0.0976 1.0000 Uiso R . . . . .
H122 H 0.6467 0.5649 0.7263 0.0978 1.0000 Uiso R . . . . .
H123 H 0.5905 0.4637 0.7843 0.0994 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1934(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.3611(16) yes
C1 . C9 . 1.4004(15) yes
C1 . N1 . 1.4722(14) yes
C2 . C3 . 1.416(2) yes
C2 . H21 . 0.985 no
C3 . C4 . 1.365(2) yes
C3 . H31 . 0.972 no
C4 . C10 . 1.411(2) yes
C4 . H41 . 0.965 no
C5 . C6 . 1.359(2) yes
C5 . C10 . 1.413(2) yes
C5 . H51 . 0.967 no
C6 . C7 . 1.411(2) yes
C6 . H61 . 0.938 no
C7 . C8 . 1.3711(17) yes
C7 . H71 . 0.962 no
C8 . C9 . 1.4074(15) yes
C8 . B1 . 1.5905(17) yes
C9 . C10 . 1.4125(16) yes
C11 . N1 . 1.4990(15) yes
C11 . H111 . 1.002 no
C11 . H112 . 0.975 no
C11 . H113 . 0.977 no
C12 . N1 . 1.4887(15) yes
C12 . H121 . 0.983 no
C12 . H122 . 0.971 no
C12 . H123 . 0.975 no
N1 . B1 . 1.7259(16) yes
B1 . F1 . 1.3736(14) yes
B1 . F2 . 1.3846(14) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C9 . 121.64(11) yes
C2 . C1 . N1 . 126.81(11) yes
C9 . C1 . N1 . 111.55(9) yes
C1 . C2 . C3 . 117.71(13) yes
C1 . C2 . H21 . 122.3 no
C3 . C2 . H21 . 120.0 no
C2 . C3 . C4 . 122.05(13) yes
C2 . C3 . H31 . 117.5 no
C4 . C3 . H31 . 120.5 no
C3 . C4 . C10 . 120.69(13) yes
C3 . C4 . H41 . 119.0 no
C10 . C4 . H41 . 120.3 no
C6 . C5 . C10 . 120.42(13) yes
C6 . C5 . H51 . 120.3 no
C10 . C5 . H51 . 119.2 no
C5 . C6 . C7 . 122.01(13) yes
C5 . C6 . H61 . 117.8 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C8 . 120.40(14) yes
C6 . C7 . H71 . 119.8 no
C8 . C7 . H71 . 119.8 no
C7 . C8 . C9 . 116.96(12) yes
C7 . C8 . B1 . 134.05(12) yes
C9 . C8 . B1 . 108.99(9) yes
C8 . C9 . C1 . 115.14(10) yes
C8 . C9 . C10 . 124.13(11) yes
C1 . C9 . C10 . 120.72(11) yes
C5 . C10 . C9 . 116.08(12) yes
C5 . C10 . C4 . 126.72(13) yes
C9 . C10 . C4 . 117.19(12) yes
N1 . C11 . H111 . 106.9 no
N1 . C11 . H112 . 109.8 no
H111 . C11 . H112 . 111.8 no
N1 . C11 . H113 . 108.1 no
H111 . C11 . H113 . 108.5 no
H112 . C11 . H113 . 111.6 no
N1 . C12 . H121 . 108.5 no
N1 . C12 . H122 . 109.2 no
H121 . C12 . H122 . 109.9 no
N1 . C12 . H123 . 108.3 no
H121 . C12 . H123 . 108.5 no
H122 . C12 . H123 . 112.3 no
C11 . N1 . C12 . 109.04(11) yes
C11 . N1 . C1 . 109.59(9) yes
C12 . N1 . C1 . 110.44(9) yes
C11 . N1 . B1 . 111.52(9) yes
C12 . N1 . B1 . 111.82(10) yes
C1 . N1 . B1 . 104.36(8) yes
N1 . B1 . C8 . 99.95(8) yes
N1 . B1 . F1 . 106.95(9) yes
C8 . B1 . F1 . 116.44(10) yes
N1 . B1 . F2 . 106.79(9) yes
C8 . B1 . F2 . 116.34(10) yes
F1 . B1 . F2 . 109.10(10) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 25/04/14 at 17:12:04
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 123,X'S) H   ( 122,X'S) H   ( 121,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 25/04/14 at 17:12:04
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 2 0 x .
_chemical_name_systematic        
'8-(Difluoroboryl)-N,N-dimethylnaphthalen-1-amine '
_exptl_crystal_recrystallization_method 
'Vapour diffusion crystalization in CDCl3 - cyclohexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1403308'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.38334(18)
_cell_length_b                   11.57825(19)
_cell_length_c                   14.9187(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1793.54(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H26 B1 N1 O2 
# Dc =      1.20 Fooo =    696.00 Mu =      0.75 M =    323.24
# Found Formula = C20 H26 B1 N1 O2 
# Dc =      1.20 FOOO =    696.00 Mu =      0.75 M =    323.24

_chemical_formula_sum            'C20 H26 B1 N1 O2'
_chemical_formula_moiety         'C20 H26 B1 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         323.24


_cell_measurement_reflns_used    17066
_cell_measurement_theta_min      4
_cell_measurement_theta_max      31
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.075

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            46361
_reflns_number_total             3008
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 5249 
# Number of reflections with Friedels Law is 3008 
# Theoretical number of reflections is about 2791 


_diffrn_reflns_theta_min         2.968
_diffrn_reflns_theta_max         30.726
_diffrn_measured_fraction_theta_max 0.957

_diffrn_reflns_theta_full        27.039
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              0
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              21

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

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.26


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_number_parameters     217
_oxford_refine_ls_R_factor_ref   0.0310
_refine_ls_wR_factor_ref         0.0343
_refine_ls_goodness_of_fit_ref   1.1278
_refine_ls_shift/su_max          0.0005834
_refine_ls_shift/su_mean         0.0000524


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3000
_refine_ls_R_factor_all          0.0349
_refine_ls_wR_factor_all         0.0350

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2830
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_gt          0.0344

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration unk


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.60 -2.13 4.08 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.55735(13) 0.71878(11) 0.62411(9) 0.0241 1.0000 Uani . . . . . .
C2 C 0.49590(12) 0.65685(11) 0.70622(8) 0.0208 1.0000 Uani . . . . . .
C3 C 0.59634(12) 0.48582(10) 0.80004(8) 0.0209 1.0000 Uani . . . . . .
C4 C 0.70317(12) 0.41029(10) 0.80660(8) 0.0196 1.0000 Uani . . . . . .
C5 C 0.80586(11) 0.41382(9) 0.74798(7) 0.0145 1.0000 Uani . . . . . .
C6 C 0.90114(11) 0.50753(9) 0.60940(7) 0.0143 1.0000 Uani . . . . . .
C7 C 0.88535(12) 0.59508(10) 0.54682(8) 0.0197 1.0000 Uani . . . . . .
C8 C 0.77874(13) 0.67167(10) 0.54570(8) 0.0215 1.0000 Uani . . . . . .
C9 C 0.59375(11) 0.56608(9) 0.73291(8) 0.0167 1.0000 Uani . . . . . .
C10 C 0.80543(10) 0.49629(9) 0.67705(7) 0.0131 1.0000 Uani . . . . . .
C11 C 0.68382(12) 0.65731(10) 0.60837(7) 0.0173 1.0000 Uani . . . . . .
C12 C 0.69856(11) 0.57029(9) 0.67325(7) 0.0143 1.0000 Uani . . . . . .
C13 C 0.88521(14) 0.22088(10) 0.77977(9) 0.0244 1.0000 Uani . . . . . .
C14 C 1.01233(12) 0.38802(11) 0.81653(8) 0.0231 1.0000 Uani . . . . . .
C15 C 1.23155(11) 0.38248(10) 0.57672(9) 0.0197 1.0000 Uani . . . . . .
C16 C 1.14616(11) 0.28403(11) 0.53774(9) 0.0209 1.0000 Uani . . . . . .
C17 C 1.33881(12) 0.34020(12) 0.63737(10) 0.0288 1.0000 Uani . . . . . .
C18 C 1.28421(15) 0.46420(14) 0.50574(12) 0.0367 1.0000 Uani . . . . . .
C19 C 1.18176(14) 0.24832(16) 0.44297(11) 0.0392 1.0000 Uani . . . . . .
C20 C 1.13765(14) 0.17940(12) 0.59823(13) 0.0354 1.0000 Uani . . . . . .
O1 O 1.14041(8) 0.45006(7) 0.62916(6) 0.0193 1.0000 Uani . . . . . .
O2 O 1.01843(8) 0.33720(7) 0.53626(6) 0.0197 1.0000 Uani . . . . . .
B1 B 1.01987(12) 0.42601(11) 0.59709(8) 0.0154 1.0000 Uani . . . . . .
N1 N 0.91621(9) 0.33998(8) 0.75481(6) 0.0165 1.0000 Uani . . . . . .
H11 H 0.5710 0.8024 0.6373 0.0291 1.0000 Uiso R . . . . .
H12 H 0.5018 0.7121 0.5731 0.0307 1.0000 Uiso R . . . . .
H21 H 0.4781 0.7095 0.7563 0.0256 1.0000 Uiso R . . . . .
H22 H 0.4129 0.6184 0.6919 0.0269 1.0000 Uiso R . . . . .
H31 H 0.5290 0.4821 0.8417 0.0262 1.0000 Uiso R . . . . .
H41 H 0.7087 0.3560 0.8536 0.0240 1.0000 Uiso R . . . . .
H71 H 0.9500 0.6066 0.5016 0.0252 1.0000 Uiso R . . . . .
H81 H 0.7743 0.7326 0.5012 0.0271 1.0000 Uiso R . . . . .
H131 H 0.9635 0.1768 0.7735 0.0354 1.0000 Uiso R . . . . .
H132 H 0.8548 0.2148 0.8426 0.0367 1.0000 Uiso R . . . . .
H133 H 0.8184 0.1935 0.7373 0.0366 1.0000 Uiso R . . . . .
H141 H 1.0880 0.3410 0.8110 0.0334 1.0000 Uiso R . . . . .
H142 H 0.9816 0.3878 0.8801 0.0344 1.0000 Uiso R . . . . .
H143 H 1.0316 0.4664 0.7976 0.0334 1.0000 Uiso R . . . . .
H172 H 1.3896 0.4046 0.6560 0.0433 1.0000 Uiso R . . . . .
H171 H 1.3924 0.2846 0.6050 0.0420 1.0000 Uiso R . . . . .
H173 H 1.3014 0.3034 0.6914 0.0423 1.0000 Uiso R . . . . .
H182 H 1.3234 0.5307 0.5369 0.0542 1.0000 Uiso R . . . . .
H181 H 1.3480 0.4219 0.4703 0.0533 1.0000 Uiso R . . . . .
H183 H 1.2142 0.4883 0.4655 0.0553 1.0000 Uiso R . . . . .
H192 H 1.1290 0.1829 0.4264 0.0591 1.0000 Uiso R . . . . .
H191 H 1.2701 0.2244 0.4418 0.0573 1.0000 Uiso R . . . . .
H193 H 1.1675 0.3113 0.3983 0.0587 1.0000 Uiso R . . . . .
H202 H 1.0699 0.1290 0.5769 0.0527 1.0000 Uiso R . . . . .
H201 H 1.2183 0.1366 0.5979 0.0523 1.0000 Uiso R . . . . .
H203 H 1.1177 0.2031 0.6597 0.0510 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.5562(18) yes
C1 . C11 . 1.5120(16) yes
C1 . H11 . 0.998 no
C1 . H12 . 0.958 no
C2 . C9 . 1.5150(16) yes
C2 . H21 . 0.982 no
C2 . H22 . 0.993 no
C3 . C4 . 1.4159(17) yes
C3 . C9 . 1.3666(16) yes
C3 . H31 . 0.936 no
C4 . C5 . 1.3796(16) yes
C4 . H41 . 0.944 no
C5 . C10 . 1.4254(14) yes
C5 . N1 . 1.4332(14) yes
C6 . C7 . 1.3877(15) yes
C6 . C10 . 1.4223(15) yes
C6 . B1 . 1.5635(16) yes
C7 . C8 . 1.4185(16) yes
C7 . H71 . 0.961 no
C8 . C11 . 1.3686(17) yes
C8 . H81 . 0.970 no
C9 . C12 . 1.4067(15) yes
C10 . C12 . 1.4031(14) yes
C11 . C12 . 1.4055(15) yes
C13 . N1 . 1.4641(15) yes
C13 . H131 . 0.964 no
C13 . H132 . 0.991 no
C13 . H133 . 0.991 no
C14 . N1 . 1.4674(15) yes
C14 . H141 . 0.960 no
C14 . H142 . 1.001 no
C14 . H143 . 0.971 no
C15 . C16 . 1.5569(17) yes
C15 . C17 . 1.5162(17) yes
C15 . C18 . 1.5217(19) yes
C15 . O1 . 1.4560(14) yes
C16 . C19 . 1.5187(18) yes
C16 . C20 . 1.513(2) yes
C16 . O2 . 1.4623(13) yes
C17 . H172 . 0.955 no
C17 . H171 . 0.978 no
C17 . H173 . 0.992 no
C18 . H182 . 0.988 no
C18 . H181 . 0.979 no
C18 . H183 . 0.983 no
C19 . H192 . 0.967 no
C19 . H191 . 0.958 no
C19 . H193 . 0.999 no
C20 . H202 . 0.967 no
C20 . H201 . 0.973 no
C20 . H203 . 0.979 no
O1 . B1 . 1.3687(15) yes
O2 . B1 . 1.3716(15) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C11 . 105.15(9) yes
C2 . C1 . H11 . 110.5 no
C11 . C1 . H11 . 111.3 no
C2 . C1 . H12 . 110.0 no
C11 . C1 . H12 . 111.2 no
H11 . C1 . H12 . 108.7 no
C1 . C2 . C9 . 104.57(10) yes
C1 . C2 . H21 . 113.0 no
C9 . C2 . H21 . 110.9 no
C1 . C2 . H22 . 113.1 no
C9 . C2 . H22 . 109.1 no
H21 . C2 . H22 . 106.2 no
C4 . C3 . C9 . 119.08(11) yes
C4 . C3 . H31 . 120.7 no
C9 . C3 . H31 . 120.2 no
C3 . C4 . C5 . 122.92(10) yes
C3 . C4 . H41 . 120.7 no
C5 . C4 . H41 . 116.4 no
C4 . C5 . C10 . 119.21(10) yes
C4 . C5 . N1 . 123.72(10) yes
C10 . C5 . N1 . 117.06(9) yes
C7 . C6 . C10 . 117.49(10) yes
C7 . C6 . B1 . 117.07(10) yes
C10 . C6 . B1 . 125.38(9) yes
C6 . C7 . C8 . 123.83(11) yes
C6 . C7 . H71 . 119.4 no
C8 . C7 . H71 . 116.7 no
C7 . C8 . C11 . 118.55(10) yes
C7 . C8 . H81 . 120.0 no
C11 . C8 . H81 . 121.5 no
C2 . C9 . C3 . 132.65(11) yes
C2 . C9 . C12 . 109.18(10) yes
C3 . C9 . C12 . 118.17(10) yes
C5 . C10 . C6 . 125.87(10) yes
C5 . C10 . C12 . 116.20(10) yes
C6 . C10 . C12 . 117.91(9) yes
C1 . C11 . C8 . 132.40(10) yes
C1 . C11 . C12 . 108.97(10) yes
C8 . C11 . C12 . 118.63(10) yes
C9 . C12 . C11 . 112.10(10) yes
C9 . C12 . C10 . 124.42(10) yes
C11 . C12 . C10 . 123.48(10) yes
N1 . C13 . H131 . 106.8 no
N1 . C13 . H132 . 112.2 no
H131 . C13 . H132 . 108.9 no
N1 . C13 . H133 . 107.0 no
H131 . C13 . H133 . 111.0 no
H132 . C13 . H133 . 111.0 no
N1 . C14 . H141 . 106.7 no
N1 . C14 . H142 . 112.1 no
H141 . C14 . H142 . 109.9 no
N1 . C14 . H143 . 108.2 no
H141 . C14 . H143 . 109.7 no
H142 . C14 . H143 . 110.1 no
C16 . C15 . C17 . 113.88(10) yes
C16 . C15 . C18 . 113.57(12) yes
C17 . C15 . C18 . 110.62(11) yes
C16 . C15 . O1 . 102.95(9) yes
C17 . C15 . O1 . 109.29(10) yes
C18 . C15 . O1 . 105.87(10) yes
C15 . C16 . C19 . 114.11(12) yes
C15 . C16 . C20 . 113.36(11) yes
C19 . C16 . C20 . 110.58(12) yes
C15 . C16 . O2 . 102.35(9) yes
C19 . C16 . O2 . 108.75(10) yes
C20 . C16 . O2 . 107.04(10) yes
C15 . C17 . H172 . 109.1 no
C15 . C17 . H171 . 109.7 no
H172 . C17 . H171 . 110.1 no
C15 . C17 . H173 . 109.6 no
H172 . C17 . H173 . 108.4 no
H171 . C17 . H173 . 110.0 no
C15 . C18 . H182 . 107.8 no
C15 . C18 . H181 . 107.9 no
H182 . C18 . H181 . 111.5 no
C15 . C18 . H183 . 109.6 no
H182 . C18 . H183 . 111.8 no
H181 . C18 . H183 . 108.2 no
C16 . C19 . H192 . 108.2 no
C16 . C19 . H191 . 109.2 no
H192 . C19 . H191 . 108.1 no
C16 . C19 . H193 . 112.7 no
H192 . C19 . H193 . 108.5 no
H191 . C19 . H193 . 109.9 no
C16 . C20 . H202 . 109.2 no
C16 . C20 . H201 . 110.7 no
H202 . C20 . H201 . 108.5 no
C16 . C20 . H203 . 110.3 no
H202 . C20 . H203 . 108.9 no
H201 . C20 . H203 . 109.2 no
C15 . O1 . B1 . 107.29(9) yes
C16 . O2 . B1 . 107.20(9) yes
C6 . B1 . O2 . 121.45(10) yes
C6 . B1 . O1 . 123.86(10) yes
O2 . B1 . O1 . 113.19(10) yes
C14 . N1 . C13 . 110.30(10) yes
C14 . N1 . C5 . 111.24(9) yes
C13 . N1 . C5 . 113.84(10) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 09/01/15 at 15:40:22
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) H   ( 203,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 09/01/15 at 15:40:22
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        
'N,N-Dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroacenaphthylen-5-amine '
_exptl_crystal_recrystallization_method 
'vapour diffusion crystallization in heptane/cyclohexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1403309'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.2629(5)
_cell_length_b                   14.1537(5)
_cell_length_c                   23.1015(7)
_cell_angle_alpha                82.829(3)
_cell_angle_beta                 82.555(3)
_cell_angle_gamma                69.131(4)
_cell_volume                     3399.7(2)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            6

# Given Formula = C21 H27 B1 F3 N1 O5 S1 
# Dc =      1.39 Fooo =   1488.00 Mu =      2.00 M =   1419.96
# Found Formula = C21 H27.00 B1 F3 N1 O5 S1 
# Dc =      1.39 FOOO =   1488.00 Mu =      2.00 M =   1419.96

_chemical_formula_sum            'C21 H27 B1 F3 N1 O5 S1'
_chemical_formula_moiety         'C20 H27 B N O2, C F3 O3 S  '
_chemical_compound_source        ?
_chemical_formula_weight         473.32


_cell_measurement_reflns_used    8271
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_temperature    100

_exptl_crystal_description       planar
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.200

# Sheldrick geometric approximatio 0.98 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            64803
_reflns_number_total             16467
_diffrn_reflns_av_R_equivalents  0.068
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 16467 
# Theoretical number of reflections is about 36744 


_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         29.293
_diffrn_measured_fraction_theta_max 0.886

_diffrn_reflns_theta_full        25.192
_diffrn_measured_fraction_theta_full 0.972


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              -18
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              31

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

_refine_diff_density_min         -0.97
_refine_diff_density_max         2.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.5\s(I)
_refine_ls_number_reflns         8778
_refine_ls_number_restraints     0
_refine_ls_number_parameters     865
_oxford_refine_ls_R_factor_ref   0.0737
_refine_ls_wR_factor_ref         0.0831
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_shift/su_max          0.0006394
_refine_ls_shift/su_mean         0.0000235


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        16432
_refine_ls_R_factor_all          0.1415
_refine_ls_wR_factor_all         0.1220

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9732
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_gt          0.0868

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 21.5 9.43 16.5 8.42 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.6033(4) 0.5917(3) 0.86511(16) 0.0238 1.0000 Uani . . . . . .
C2 C 0.6159(4) 0.5410(3) 0.80806(16) 0.0225 1.0000 Uani . . . . . .
C3 C 0.6311(4) 0.3546(3) 0.79806(16) 0.0239 1.0000 Uani . . . . . .
C4 C 0.6493(4) 0.2591(3) 0.82885(16) 0.0235 1.0000 Uani . . . . . .
C5 C 0.6650(4) 0.2425(3) 0.88801(16) 0.0196 1.0000 Uani . . . . . .
C6 C 0.6814(3) 0.3184(3) 0.98345(15) 0.0196 1.0000 Uani . . . . . .
C7 C 0.6766(4) 0.4079(3) 1.00374(15) 0.0226 1.0000 Uani . . . . . .
C8 C 0.6536(4) 0.5020(3) 0.96973(16) 0.0232 1.0000 Uani . . . . . .
C9 C 0.6277(3) 0.4322(3) 0.82804(15) 0.0189 1.0000 Uani . . . . . .
C10 C 0.6634(3) 0.3198(3) 0.92215(16) 0.0183 1.0000 Uani . . . . . .
C11 C 0.6351(4) 0.5045(3) 0.91229(16) 0.0198 1.0000 Uani . . . . . .
C12 C 0.6419(3) 0.4151(3) 0.88898(15) 0.0171 1.0000 Uani . . . . . .
C13 C 0.5811(5) 0.1008(4) 0.9119(2) 0.0405 1.0000 Uani . . . . . .
C14 C 0.8127(5) 0.0653(4) 0.8901(2) 0.0431 1.0000 Uani . . . . . .
C15 C 0.7244(4) 0.0746(3) 1.08299(18) 0.0284 1.0000 Uani . . . . . .
C16 C 0.7318(5) 0.1496(3) 1.12546(18) 0.0333 1.0000 Uani . . . . . .
C17 C 0.5962(5) 0.0609(4) 1.0852(3) 0.0501 1.0000 Uani . . . . . .
C18 C 0.8271(5) -0.0263(3) 1.0860(2) 0.0386 1.0000 Uani . . . . . .
C19 C 0.6400(7) 0.1553(4) 1.1801(2) 0.0632 1.0000 Uani . . . . . .
C20 C 0.8635(6) 0.1324(4) 1.1397(2) 0.0483 1.0000 Uani . . . . . .
C21 C 0.2741(4) 0.4329(3) 0.88210(16) 0.0235 1.0000 Uani . . . . . .
C22 C 0.2725(4) 0.5303(3) 0.84292(16) 0.0240 1.0000 Uani . . . . . .
C23 C 0.3251(3) 0.5508(3) 0.72917(16) 0.0197 1.0000 Uani . . . . . .
C24 C 0.3615(4) 0.4982(3) 0.67805(16) 0.0206 1.0000 Uani . . . . . .
C25 C 0.3744(3) 0.3976(3) 0.67908(15) 0.0175 1.0000 Uani . . . . . .
C26 C 0.3568(3) 0.2353(3) 0.74136(15) 0.0172 1.0000 Uani . . . . . .
C27 C 0.3348(3) 0.1985(3) 0.79874(16) 0.0200 1.0000 Uani . . . . . .
C28 C 0.3062(4) 0.2549(3) 0.84808(15) 0.0211 1.0000 Uani . . . . . .
C29 C 0.3047(3) 0.4991(3) 0.78096(15) 0.0182 1.0000 Uani . . . . . .
C30 C 0.3501(3) 0.3396(3) 0.73175(14) 0.0149 1.0000 Uani . . . . . .
C31 C 0.2981(3) 0.3533(3) 0.83922(15) 0.0186 1.0000 Uani . . . . . .
C32 C 0.3169(3) 0.3959(3) 0.78172(15) 0.0170 1.0000 Uani . . . . . .
C33 C 0.5675(5) 0.3212(4) 0.6157(2) 0.0413 1.0000 Uani . . . . . .
C34 C 0.3674(5) 0.4073(3) 0.57036(17) 0.0389 1.0000 Uani . . . . . .
C35 C 0.4202(4) 0.0796(3) 0.60933(16) 0.0232 1.0000 Uani . . . . . .
C36 C 0.4046(4) 0.0029(3) 0.66233(16) 0.0220 1.0000 Uani . . . . . .
C41 C 0.0120(4) 0.2380(3) 0.77944(19) 0.0284 1.0000 Uani . . . . . .
C42 C -0.0176(4) 0.2849(3) 0.83918(18) 0.0248 1.0000 Uani . . . . . .
C43 C -0.0642(4) 0.4735(3) 0.85867(16) 0.0234 1.0000 Uani . . . . . .
C44 C -0.0765(4) 0.5709(3) 0.83103(16) 0.0224 1.0000 Uani . . . . . .
C45 C -0.0578(3) 0.5886(3) 0.77126(15) 0.0188 1.0000 Uani . . . . . .
C46 C 0.0128(4) 0.5106(3) 0.67046(16) 0.0213 1.0000 Uani . . . . . .
C47 C 0.0442(4) 0.4195(3) 0.64527(17) 0.0291 1.0000 Uani . . . . . .
C48 C 0.0446(4) 0.3273(3) 0.67534(18) 0.0303 1.0000 Uani . . . . . .
C49 C -0.0327(3) 0.3951(3) 0.82430(16) 0.0212 1.0000 Uani . . . . . .
C50 C -0.0193(3) 0.5090(3) 0.73314(15) 0.0186 1.0000 Uani . . . . . .
C51 C 0.0175(4) 0.3243(3) 0.73476(18) 0.0237 1.0000 Uani . . . . . .
C52 C -0.0121(3) 0.4136(3) 0.76295(16) 0.0199 1.0000 Uani . . . . . .
C53 C -0.2276(4) 0.7561(3) 0.75807(17) 0.0247 1.0000 Uani . . . . . .
C54 C -0.0104(4) 0.7477(3) 0.77182(16) 0.0228 1.0000 Uani . . . . . .
C55 C 0.0089(4) 0.7586(3) 0.58118(16) 0.0249 1.0000 Uani . . . . . .
C56 C 0.0646(4) 0.6772(3) 0.53563(17) 0.0305 1.0000 Uani . . . . . .
C61 C 0.8781(5) 0.1097(4) 0.6433(2) 0.0415 1.0000 Uani . . . . . .
C69 C 0.6715(5) 0.5991(4) 0.6171(2) 0.0418 1.0000 Uani . . . . . .
C77 C 0.0910(6) 0.2973(5) 1.0204(2) 0.0637 1.0000 Uani . . . . . .
F62 F 0.8641(4) 0.2052(3) 0.65130(17) 0.0759 1.0000 Uani . . . . . .
F63 F 0.8152(3) 0.1138(2) 0.59733(11) 0.0411 1.0000 Uani . . . . . .
F64 F 0.9984(3) 0.0603(4) 0.62854(18) 0.0836 1.0000 Uani . . . . . .
F70 F 0.7137(3) 0.6558(2) 0.64564(15) 0.0607 1.0000 Uani . . . . . .
F71 F 0.6630(4) 0.5209(2) 0.65476(15) 0.0627 1.0000 Uani . . . . . .
F72 F 0.7616(3) 0.5608(3) 0.57443(17) 0.0685 1.0000 Uani . . . . . .
F78 F 0.0836(4) 0.4011(3) 1.02723(17) 0.0842 1.0000 Uani . . . . . .
F79 F 0.0022(4) 0.2960(5) 1.05613(17) 0.1115 1.0000 Uani . . . . . .
F80 F 0.0765(3) 0.3053(2) 0.96560(11) 0.0468 1.0000 Uani . . . . . .
S65 S 0.81663(12) 0.04972(8) 0.70925(4) 0.0321 1.0000 Uani . . . . . .
S73 S 0.52017(11) 0.67183(8) 0.58865(4) 0.0306 1.0000 Uani . . . . . .
S81 S 0.24837(12) 0.21705(7) 1.03962(4) 0.0316 1.0000 Uani . . . . . .
O1 O 0.7408(3) 0.1288(2) 1.02508(12) 0.0266 1.0000 Uani . . . . . .
O2 O 0.6881(3) 0.2469(2) 1.09072(12) 0.0306 1.0000 Uani . . . . . .
O66 O 0.6870(4) 0.1177(3) 0.71896(15) 0.0498 1.0000 Uani . . . . . .
O67 O 0.8289(3) -0.0469(2) 0.69107(13) 0.0368 1.0000 Uani . . . . . .
O68 O 0.9005(4) 0.0458(3) 0.75174(16) 0.0603 1.0000 Uani . . . . . .
O74 O 0.4940(4) 0.5969(3) 0.56033(13) 0.0438 1.0000 Uani . . . . . .
O75 O 0.4372(4) 0.7056(3) 0.64013(16) 0.0476 1.0000 Uani . . . . . .
O76 O 0.5491(4) 0.7493(3) 0.54943(15) 0.0457 1.0000 Uani . . . . . .
O82 O 0.2481(5) 0.2208(4) 1.09977(17) 0.1036 1.0000 Uani . . . . . .
O83 O 0.2668(5) 0.1257(3) 1.0187(2) 0.0709 1.0000 Uani . . . . . .
O84 O 0.3377(5) 0.2610(4) 1.0025(2) 0.0798 1.0000 Uani . . . . . .
B1 B 0.7041(4) 0.2303(3) 1.03293(19) 0.0234 1.0000 Uani . . . . . .
B21 B 0.3806(4) 0.1552(3) 0.69632(18) 0.0198 1.0000 Uani . . . . . .
B41 B 0.0224(4) 0.5997(3) 0.62503(18) 0.0227 1.0000 Uani . . . . . .
N10 N 0.6894(3) 0.1366(2) 0.91437(14) 0.0227 1.0000 Uani . . . . . .
N21 N 0.4259(3) 0.3491(2) 0.62381(13) 0.0210 1.0000 Uani . . . . . .
N41 N -0.0878(3) 0.6965(2) 0.74864(13) 0.0193 1.0000 Uani . . . . . .
O210 O 0.3670(6) 0.1793(5) 0.6376(3) 0.0210 0.5000 Uani . . . . . .
O21 O 0.4223(6) 0.1631(5) 0.6387(3) 0.0210 0.5000 Uani . . . . . .
O22 O 0.3528(6) 0.0666(5) 0.7101(3) 0.0210 0.5000 Uani . . . . . .
O220 O 0.4126(6) 0.0552(5) 0.7142(3) 0.0210 0.5000 Uani . . . . . .
C37 C 0.5453(9) 0.0402(8) 0.5696(4) 0.0304 0.5000 Uani . . . . . .
C370 C 0.5567(9) 0.0658(8) 0.5875(4) 0.0304 0.5000 Uani . . . . . .
C390 C 0.5138(10) -0.0971(7) 0.6632(4) 0.0294 0.5000 Uani . . . . . .
C39 C 0.5305(10) -0.0758(7) 0.6786(4) 0.0294 0.5000 Uani . . . . . .
C38 C 0.3090(10) 0.1199(8) 0.5721(4) 0.0304 0.5000 Uani . . . . . .
C380 C 0.3398(10) 0.0916(8) 0.5591(4) 0.0304 0.5000 Uani . . . . . .
C400 C 0.2749(9) -0.0083(7) 0.6708(4) 0.0294 0.5000 Uani . . . . . .
C40 C 0.3089(9) -0.0489(7) 0.6543(4) 0.0294 0.5000 Uani . . . . . .
O42 O 0.0926(4) 0.5781(4) 0.57354(19) 0.0236 0.7000 Uani . . . . . .
O410 O 0.0063(11) 0.6974(11) 0.6343(6) 0.0236 0.3000 Uani . . . . . .
C60 C 0.1869(8) 0.6732(6) 0.5009(3) 0.0359 0.7000 Uani . . . . . .
C600 C 0.2102(19) 0.6651(14) 0.5207(7) 0.0359 0.3000 Uani . . . . . .
C580 C 0.0802(17) 0.8316(13) 0.5860(7) 0.0361 0.3000 Uani . . . . . .
C58 C 0.1152(7) 0.7840(5) 0.6042(3) 0.0361 0.7000 Uani . . . . . .
C59 C -0.0359(8) 0.6748(6) 0.4976(3) 0.0456 0.7000 Uani . . . . . .
C590 C -0.002(2) 0.7042(14) 0.4786(7) 0.0456 0.3000 Uani . . . . . .
C570 C -0.1385(16) 0.8296(13) 0.5730(7) 0.0278 0.3000 Uani . . . . . .
C57 C -0.0981(7) 0.8478(5) 0.5631(3) 0.0278 0.7000 Uani . . . . . .
O420 O 0.0482(11) 0.5921(9) 0.5643(5) 0.0236 0.3000 Uani . . . . . .
O41 O -0.0385(4) 0.7014(4) 0.6326(2) 0.0236 0.7000 Uani . . . . . .
H11 H 0.6623 0.6288 0.8626 0.0303 1.0000 Uiso R . . . . .
H12 H 0.5157 0.6371 0.8731 0.0301 1.0000 Uiso R . . . . .
H22 H 0.6924 0.5426 0.7838 0.0281 1.0000 Uiso R . . . . .
H21 H 0.5410 0.5749 0.7860 0.0281 1.0000 Uiso R . . . . .
H31 H 0.6213 0.3643 0.7577 0.0312 1.0000 Uiso R . . . . .
H41 H 0.6519 0.2045 0.8088 0.0291 1.0000 Uiso R . . . . .
H71 H 0.6891 0.4066 1.0436 0.0278 1.0000 Uiso R . . . . .
H81 H 0.6526 0.5598 0.9860 0.0283 1.0000 Uiso R . . . . .
H132 H 0.6012 0.0337 0.9327 0.0660 1.0000 Uiso R . . . . .
H131 H 0.5041 0.1478 0.9307 0.0660 1.0000 Uiso R . . . . .
H133 H 0.5726 0.0973 0.8707 0.0659 1.0000 Uiso R . . . . .
H142 H 0.8282 -0.0003 0.9114 0.0720 1.0000 Uiso R . . . . .
H141 H 0.8805 0.0905 0.8947 0.0721 1.0000 Uiso R . . . . .
H143 H 0.8082 0.0611 0.8490 0.0722 1.0000 Uiso R . . . . .
H173 H 0.5945 0.0248 1.0525 0.0811 1.0000 Uiso R . . . . .
H172 H 0.5826 0.0232 1.1215 0.0810 1.0000 Uiso R . . . . .
H171 H 0.5287 0.1266 1.0840 0.0809 1.0000 Uiso R . . . . .
H183 H 0.8155 -0.0675 1.0594 0.0581 1.0000 Uiso R . . . . .
H182 H 0.8241 -0.0576 1.1249 0.0579 1.0000 Uiso R . . . . .
H181 H 0.9080 -0.0175 1.0762 0.0579 1.0000 Uiso R . . . . .
H193 H 0.6448 0.2065 1.2027 0.0980 1.0000 Uiso R . . . . .
H192 H 0.6660 0.0902 1.2018 0.0980 1.0000 Uiso R . . . . .
H191 H 0.5549 0.1723 1.1680 0.0981 1.0000 Uiso R . . . . .
H203 H 0.8616 0.1898 1.1584 0.0770 1.0000 Uiso R . . . . .
H202 H 0.8913 0.0722 1.1665 0.0767 1.0000 Uiso R . . . . .
H201 H 0.9203 0.1247 1.1042 0.0770 1.0000 Uiso R . . . . .
H211 H 0.3429 0.4114 0.9076 0.0310 1.0000 Uiso R . . . . .
H212 H 0.1920 0.4431 0.9055 0.0311 1.0000 Uiso R . . . . .
H222 H 0.3358 0.5556 0.8530 0.0312 1.0000 Uiso R . . . . .
H221 H 0.1885 0.5828 0.8473 0.0311 1.0000 Uiso R . . . . .
H231 H 0.3164 0.6197 0.7272 0.0240 1.0000 Uiso R . . . . .
H241 H 0.3790 0.5322 0.6423 0.0260 1.0000 Uiso R . . . . .
H271 H 0.3396 0.1308 0.8055 0.0251 1.0000 Uiso R . . . . .
H281 H 0.2932 0.2255 0.8857 0.0262 1.0000 Uiso R . . . . .
H333 H 0.5997 0.2844 0.5818 0.0639 1.0000 Uiso R . . . . .
H332 H 0.6045 0.2803 0.6498 0.0641 1.0000 Uiso R . . . . .
H331 H 0.5872 0.3822 0.6107 0.0642 1.0000 Uiso R . . . . .
H343 H 0.3922 0.3638 0.5388 0.0599 1.0000 Uiso R . . . . .
H342 H 0.3980 0.4635 0.5602 0.0601 1.0000 Uiso R . . . . .
H341 H 0.2758 0.4319 0.5784 0.0600 1.0000 Uiso R . . . . .
H411 H 0.0941 0.1825 0.7778 0.0350 1.0000 Uiso R . . . . .
H412 H -0.0552 0.2137 0.7724 0.0351 1.0000 Uiso R . . . . .
H422 H 0.0536 0.2519 0.8633 0.0299 1.0000 Uiso R . . . . .
H421 H -0.0959 0.2779 0.8597 0.0302 1.0000 Uiso R . . . . .
H431 H -0.0767 0.4631 0.8997 0.0289 1.0000 Uiso R . . . . .
H441 H -0.0997 0.6259 0.8541 0.0270 1.0000 Uiso R . . . . .
H471 H 0.0653 0.4209 0.6045 0.0373 1.0000 Uiso R . . . . .
H481 H 0.0645 0.2693 0.6555 0.0371 1.0000 Uiso R . . . . .
H532 H -0.2426 0.8227 0.7386 0.0409 1.0000 Uiso R . . . . .
H531 H -0.2504 0.7598 0.7995 0.0409 1.0000 Uiso R . . . . .
H533 H -0.2751 0.7224 0.7418 0.0408 1.0000 Uiso R . . . . .
H542 H -0.0279 0.8147 0.7524 0.0380 1.0000 Uiso R . . . . .
H541 H -0.0345 0.7526 0.8132 0.0381 1.0000 Uiso R . . . . .
H543 H 0.0790 0.7089 0.7647 0.0378 1.0000 Uiso R . . . . .
H5701 H -0.1420 0.8706 0.5370 0.0420 0.3000 Uiso R . . . . .
H5702 H -0.1685 0.8717 0.6046 0.0420 0.3000 Uiso R . . . . .
H5703 H -0.1906 0.7895 0.5732 0.0420 0.3000 Uiso R . . . . .
H571 H -0.0700 0.8851 0.5305 0.0420 0.7000 Uiso R . . . . .
H572 H -0.1323 0.8900 0.5945 0.0420 0.7000 Uiso R . . . . .
H573 H -0.1620 0.8258 0.5523 0.0420 0.7000 Uiso R . . . . .
H5801 H 0.0850 0.8748 0.5515 0.0520 0.3000 Uiso R . . . . .
H5802 H 0.0497 0.8710 0.6187 0.0520 0.3000 Uiso R . . . . .
H5803 H 0.1626 0.7834 0.5918 0.0520 0.3000 Uiso R . . . . .
H581 H 0.1513 0.8211 0.5745 0.0520 0.7000 Uiso R . . . . .
H582 H 0.0789 0.8238 0.6365 0.0520 0.7000 Uiso R . . . . .
H583 H 0.1798 0.7231 0.6168 0.0520 0.7000 Uiso R . . . . .
H6001 H 0.2532 0.6503 0.5552 0.0600 0.3000 Uiso R . . . . .
H6002 H 0.2269 0.7201 0.4975 0.0600 0.3000 Uiso R . . . . .
H6003 H 0.2397 0.6070 0.4990 0.0600 0.3000 Uiso R . . . . .
H601 H 0.2447 0.6731 0.5275 0.0600 0.7000 Uiso R . . . . .
H603 H 0.2226 0.6143 0.4799 0.0600 0.7000 Uiso R . . . . .
H5901 H 0.0073 0.7629 0.4564 0.0785 0.3000 Uiso R . . . . .
H5902 H -0.0891 0.7167 0.4914 0.0785 0.3000 Uiso R . . . . .
H5903 H 0.0290 0.6487 0.4549 0.0785 0.3000 Uiso R . . . . .
H591 H -0.0586 0.7360 0.4727 0.0785 0.7000 Uiso R . . . . .
H592 H -0.1096 0.6700 0.5212 0.0785 0.7000 Uiso R . . . . .
H593 H -0.0010 0.6185 0.4745 0.0785 0.7000 Uiso R . . . . .
H4001 H 0.2666 -0.0406 0.6387 0.0382 0.5000 Uiso R . . . . .
H4002 H 0.2674 -0.0486 0.7063 0.0382 0.5000 Uiso R . . . . .
H4003 H 0.2096 0.0565 0.6722 0.0382 0.5000 Uiso R . . . . .
H401 H 0.3402 -0.0920 0.6232 0.0382 0.5000 Uiso R . . . . .
H402 H 0.2957 -0.0877 0.6896 0.0382 0.5000 Uiso R . . . . .
H403 H 0.2304 0.0024 0.6454 0.0382 0.5000 Uiso R . . . . .
H3901 H 0.5930 -0.0860 0.6585 0.0382 0.5000 Uiso R . . . . .
H3902 H 0.5071 -0.1356 0.6994 0.0382 0.5000 Uiso R . . . . .
H3903 H 0.5093 -0.1331 0.6320 0.0382 0.5000 Uiso R . . . . .
H391 H 0.5882 -0.0424 0.6828 0.0382 0.5000 Uiso R . . . . .
H392 H 0.5165 -0.1124 0.7146 0.0382 0.5000 Uiso R . . . . .
H393 H 0.5655 -0.1216 0.6489 0.0382 0.5000 Uiso R . . . . .
H3701 H 0.5933 0.0038 0.5694 0.0387 0.5000 Uiso R . . . . .
H3702 H 0.6039 0.0640 0.6191 0.0387 0.5000 Uiso R . . . . .
H3703 H 0.5588 0.1206 0.5595 0.0387 0.5000 Uiso R . . . . .
H371 H 0.6141 0.0141 0.5936 0.0387 0.5000 Uiso R . . . . .
H372 H 0.5553 0.0951 0.5437 0.0387 0.5000 Uiso R . . . . .
H373 H 0.5445 -0.0118 0.5474 0.0387 0.5000 Uiso R . . . . .
H381 H 0.3257 0.1657 0.5412 0.0387 0.5000 Uiso R . . . . .
H382 H 0.2344 0.1546 0.5959 0.0387 0.5000 Uiso R . . . . .
H383 H 0.2964 0.0658 0.5562 0.0387 0.5000 Uiso R . . . . .
H3801 H 0.3703 0.0303 0.5403 0.0387 0.5000 Uiso R . . . . .
H3802 H 0.2535 0.1047 0.5743 0.0387 0.5000 Uiso R . . . . .
H3803 H 0.3453 0.1461 0.5316 0.0387 0.5000 Uiso R . . . . .
H101 H 0.6966 0.1374 0.9509 0.0275 1.0000 Uiso R . . . . .
H213 H 0.4107 0.2931 0.6277 0.0256 1.0000 Uiso R . . . . .
H413 H -0.0686 0.6970 0.7114 0.0231 1.0000 Uiso R . . . . .
H602 H 0.1726 0.7319 0.4740 0.0600 0.7000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.545(5) yes
C1 . C11 . 1.513(5) yes
C1 . H11 . 0.975 no
C1 . H12 . 0.975 no
C2 . C9 . 1.516(5) yes
C2 . H22 . 0.972 no
C2 . H21 . 0.982 no
C3 . C4 . 1.406(6) yes
C3 . C9 . 1.356(5) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.381(5) yes
C4 . H41 . 0.940 no
C5 . C10 . 1.421(5) yes
C5 . N10 . 1.488(5) yes
C6 . C7 . 1.387(5) yes
C6 . C10 . 1.453(5) yes
C6 . B1 . 1.555(6) yes
C7 . C8 . 1.415(5) yes
C7 . H71 . 0.946 no
C8 . C11 . 1.364(5) yes
C8 . H81 . 0.938 no
C9 . C12 . 1.418(5) yes
C10 . C12 . 1.422(5) yes
C11 . C12 . 1.410(5) yes
C13 . N10 . 1.489(5) yes
C13 . H132 . 0.973 no
C13 . H131 . 0.974 no
C13 . H133 . 0.978 no
C14 . N10 . 1.484(6) yes
C14 . H142 . 0.963 no
C14 . H141 . 0.972 no
C14 . H143 . 0.969 no
C15 . C16 . 1.563(6) yes
C15 . C17 . 1.518(6) yes
C15 . C18 . 1.484(6) yes
C15 . O1 . 1.481(5) yes
C16 . C19 . 1.516(7) yes
C16 . C20 . 1.489(7) yes
C16 . O2 . 1.459(5) yes
C17 . H173 . 0.970 no
C17 . H172 . 0.961 no
C17 . H171 . 0.969 no
C18 . H183 . 0.949 no
C18 . H182 . 0.953 no
C18 . H181 . 0.958 no
C19 . H193 . 0.964 no
C19 . H192 . 0.957 no
C19 . H191 . 0.971 no
C20 . H203 . 0.960 no
C20 . H202 . 0.968 no
C20 . H201 . 0.965 no
C21 . C22 . 1.548(5) yes
C21 . C31 . 1.521(5) yes
C21 . H211 . 0.972 no
C21 . H212 . 0.981 no
C22 . C29 . 1.511(5) yes
C22 . H222 . 0.968 no
C22 . H221 . 0.975 no
C23 . C24 . 1.412(5) yes
C23 . C29 . 1.360(5) yes
C23 . H231 . 0.941 no
C24 . C25 . 1.376(5) yes
C24 . H241 . 0.937 no
C25 . C30 . 1.433(5) yes
C25 . N21 . 1.477(4) yes
C26 . C27 . 1.387(5) yes
C26 . C30 . 1.442(5) yes
C26 . B21 . 1.564(5) yes
C27 . C28 . 1.410(5) yes
C27 . H271 . 0.935 no
C28 . C31 . 1.354(5) yes
C28 . H281 . 0.934 no
C29 . C32 . 1.415(5) yes
C30 . C32 . 1.419(5) yes
C31 . C32 . 1.411(5) yes
C33 . N21 . 1.492(6) yes
C33 . H333 . 0.956 no
C33 . H332 . 0.963 no
C33 . H331 . 0.956 no
C34 . N21 . 1.486(5) yes
C34 . H343 . 0.962 no
C34 . H342 . 0.966 no
C34 . H341 . 0.965 no
C35 . C36 . 1.567(5) yes
C35 . O210 . 1.518(8) yes
C35 . O21 . 1.443(8) yes
C35 . C37 . 1.540(10) yes
C35 . C370 . 1.505(11) yes
C35 . C38 . 1.511(11) yes
C35 . C380 . 1.520(11) yes
C36 . O22 . 1.441(7) yes
C36 . O220 . 1.512(7) yes
C36 . C390 . 1.508(10) yes
C36 . C39 . 1.517(10) yes
C36 . C400 . 1.510(10) yes
C36 . C40 . 1.543(10) yes
C41 . C42 . 1.552(6) yes
C41 . C51 . 1.511(5) yes
C41 . H411 . 0.976 no
C41 . H412 . 0.974 no
C42 . C49 . 1.508(5) yes
C42 . H422 . 0.978 no
C42 . H421 . 0.976 no
C43 . C44 . 1.413(5) yes
C43 . C49 . 1.361(6) yes
C43 . H431 . 0.940 no
C44 . C45 . 1.374(5) yes
C44 . H441 . 0.938 no
C45 . C50 . 1.425(5) yes
C45 . N41 . 1.483(4) yes
C46 . C47 . 1.391(6) yes
C46 . C50 . 1.446(5) yes
C46 . B41 . 1.562(6) yes
C47 . C48 . 1.399(6) yes
C47 . H471 . 0.940 no
C48 . C51 . 1.366(6) yes
C48 . H481 . 0.933 no
C49 . C52 . 1.413(5) yes
C50 . C52 . 1.418(5) yes
C51 . C52 . 1.408(5) yes
C53 . N41 . 1.500(5) yes
C53 . H532 . 0.959 no
C53 . H531 . 0.962 no
C53 . H533 . 0.965 no
C54 . N41 . 1.496(5) yes
C54 . H542 . 0.960 no
C54 . H541 . 0.963 no
C54 . H543 . 0.964 no
C55 . C56 . 1.564(6) yes
C55 . O410 . 1.415(14) yes
C55 . C580 . 1.539(17) yes
C55 . C58 . 1.538(8) yes
C55 . C570 . 1.626(17) yes
C55 . C57 . 1.461(8) yes
C55 . O41 . 1.502(6) yes
C56 . O42 . 1.511(6) yes
C56 . C60 . 1.489(9) yes
C56 . C600 . 1.58(2) yes
C56 . C59 . 1.531(9) yes
C56 . C590 . 1.537(18) yes
C56 . O420 . 1.361(13) yes
C61 . F62 . 1.338(6) yes
C61 . F63 . 1.335(5) yes
C61 . F64 . 1.306(6) yes
C61 . S65 . 1.829(5) yes
C69 . F70 . 1.339(5) yes
C69 . F71 . 1.343(6) yes
C69 . F72 . 1.333(6) yes
C69 . S73 . 1.807(5) yes
C77 . F78 . 1.470(8) yes
C77 . F79 . 1.216(7) yes
C77 . F80 . 1.283(5) yes
C77 . S81 . 1.809(5) yes
S65 . O66 . 1.440(4) yes
S65 . O67 . 1.435(3) yes
S65 . O68 . 1.431(4) yes
S73 . O74 . 1.444(3) yes
S73 . O75 . 1.432(3) yes
S73 . O76 . 1.435(3) yes
S81 . O82 . 1.397(4) yes
S81 . O83 . 1.374(4) yes
S81 . O84 . 1.491(5) yes
O1 . B1 . 1.375(5) yes
O2 . B1 . 1.362(5) yes
B21 . O210 . 1.371(8) yes
B21 . O21 . 1.358(8) yes
B21 . O22 . 1.389(8) yes
B21 . O220 . 1.354(8) yes
B41 . O42 . 1.345(6) yes
B41 . O410 . 1.370(15) yes
B41 . O420 . 1.405(12) yes
B41 . O41 . 1.378(7) yes
N10 . H101 . 0.860 no
N21 . H213 . 0.860 no
N41 . H413 . 0.860 no
C37 . H371 . 0.950 no
C37 . H372 . 0.950 no
C37 . H373 . 0.950 no
C370 . H3701 . 0.950 no
C370 . H3702 . 0.950 no
C370 . H3703 . 0.950 no
C390 . H3901 . 0.950 no
C390 . H3902 . 0.950 no
C390 . H3903 . 0.950 no
C39 . H391 . 0.950 no
C39 . H392 . 0.950 no
C39 . H393 . 0.950 no
C38 . H381 . 0.950 no
C38 . H382 . 0.950 no
C38 . H383 . 0.950 no
C380 . H3801 . 0.950 no
C380 . H3802 . 0.950 no
C380 . H3803 . 0.950 no
C400 . H4001 . 0.950 no
C400 . H4002 . 0.950 no
C400 . H4003 . 0.950 no
C40 . H401 . 0.950 no
C40 . H402 . 0.950 no
C40 . H403 . 0.950 no
C60 . H601 . 0.950 no
C60 . H603 . 0.950 no
C60 . H602 . 0.950 no
C600 . H6001 . 0.950 no
C600 . H6002 . 0.950 no
C600 . H6003 . 0.950 no
C580 . H5801 . 0.950 no
C580 . H5802 . 0.950 no
C580 . H5803 . 0.950 no
C58 . H581 . 0.950 no
C58 . H582 . 0.950 no
C58 . H583 . 0.950 no
C59 . H591 . 0.950 no
C59 . H592 . 0.950 no
C59 . H593 . 0.950 no
C590 . H5901 . 0.950 no
C590 . H5902 . 0.950 no
C590 . H5903 . 0.950 no
C570 . H5701 . 0.950 no
C570 . H5702 . 0.950 no
C570 . H5703 . 0.950 no
C57 . H571 . 0.950 no
C57 . H572 . 0.950 no
C57 . H573 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C11 . 104.6(3) yes
C2 . C1 . H11 . 111.2 no
C11 . C1 . H11 . 111.0 no
C2 . C1 . H12 . 109.7 no
C11 . C1 . H12 . 109.8 no
H11 . C1 . H12 . 110.4 no
C1 . C2 . C9 . 104.9(3) yes
C1 . C2 . H22 . 110.1 no
C9 . C2 . H22 . 109.8 no
C1 . C2 . H21 . 111.3 no
C9 . C2 . H21 . 111.0 no
H22 . C2 . H21 . 109.6 no
C4 . C3 . C9 . 118.4(3) yes
C4 . C3 . H31 . 120.6 no
C9 . C3 . H31 . 121.0 no
C3 . C4 . C5 . 121.8(3) yes
C3 . C4 . H41 . 119.5 no
C5 . C4 . H41 . 118.6 no
C4 . C5 . C10 . 122.9(3) yes
C4 . C5 . N10 . 116.1(3) yes
C10 . C5 . N10 . 120.9(3) yes
C7 . C6 . C10 . 117.9(3) yes
C7 . C6 . B1 . 111.9(3) yes
C10 . C6 . B1 . 130.2(3) yes
C6 . C7 . C8 . 125.3(3) yes
C6 . C7 . H71 . 117.7 no
C8 . C7 . H71 . 117.0 no
C7 . C8 . C11 . 117.3(3) yes
C7 . C8 . H81 . 121.1 no
C11 . C8 . H81 . 121.6 no
C2 . C9 . C3 . 131.6(3) yes
C2 . C9 . C12 . 108.8(3) yes
C3 . C9 . C12 . 119.5(3) yes
C6 . C10 . C5 . 131.9(3) yes
C6 . C10 . C12 . 115.4(3) yes
C5 . C10 . C12 . 112.7(3) yes
C1 . C11 . C8 . 130.9(3) yes
C1 . C11 . C12 . 109.3(3) yes
C8 . C11 . C12 . 119.8(3) yes
C10 . C12 . C9 . 124.6(3) yes
C10 . C12 . C11 . 124.2(3) yes
C9 . C12 . C11 . 111.1(3) yes
N10 . C13 . H132 . 108.0 no
N10 . C13 . H131 . 108.8 no
H132 . C13 . H131 . 110.1 no
N10 . C13 . H133 . 107.9 no
H132 . C13 . H133 . 110.2 no
H131 . C13 . H133 . 111.7 no
N10 . C14 . H142 . 108.7 no
N10 . C14 . H141 . 108.9 no
H142 . C14 . H141 . 109.7 no
N10 . C14 . H143 . 109.0 no
H142 . C14 . H143 . 110.5 no
H141 . C14 . H143 . 110.0 no
C16 . C15 . C17 . 115.7(4) yes
C16 . C15 . C18 . 114.8(3) yes
C17 . C15 . C18 . 109.5(4) yes
C16 . C15 . O1 . 101.6(3) yes
C17 . C15 . O1 . 105.6(3) yes
C18 . C15 . O1 . 108.8(4) yes
C15 . C16 . C19 . 112.5(4) yes
C15 . C16 . C20 . 114.1(4) yes
C19 . C16 . C20 . 111.9(5) yes
C15 . C16 . O2 . 102.2(3) yes
C19 . C16 . O2 . 107.9(4) yes
C20 . C16 . O2 . 107.5(4) yes
C15 . C17 . H173 . 110.2 no
C15 . C17 . H172 . 108.8 no
H173 . C17 . H172 . 109.9 no
C15 . C17 . H171 . 109.7 no
H173 . C17 . H171 . 109.9 no
H172 . C17 . H171 . 108.3 no
C15 . C18 . H183 . 109.7 no
C15 . C18 . H182 . 109.1 no
H183 . C18 . H182 . 109.9 no
C15 . C18 . H181 . 109.0 no
H183 . C18 . H181 . 109.9 no
H182 . C18 . H181 . 109.3 no
C16 . C19 . H193 . 108.1 no
C16 . C19 . H192 . 107.8 no
H193 . C19 . H192 . 110.6 no
C16 . C19 . H191 . 108.0 no
H193 . C19 . H191 . 111.5 no
H192 . C19 . H191 . 110.7 no
C16 . C20 . H203 . 108.2 no
C16 . C20 . H202 . 109.3 no
H203 . C20 . H202 . 109.0 no
C16 . C20 . H201 . 109.6 no
H203 . C20 . H201 . 110.4 no
H202 . C20 . H201 . 110.3 no
C22 . C21 . C31 . 104.6(3) yes
C22 . C21 . H211 . 111.0 no
C31 . C21 . H211 . 109.6 no
C22 . C21 . H212 . 111.0 no
C31 . C21 . H212 . 110.4 no
H211 . C21 . H212 . 110.1 no
C21 . C22 . C29 . 105.5(3) yes
C21 . C22 . H222 . 110.9 no
C29 . C22 . H222 . 109.8 no
C21 . C22 . H221 . 110.4 no
C29 . C22 . H221 . 111.0 no
H222 . C22 . H221 . 109.2 no
C24 . C23 . C29 . 118.4(3) yes
C24 . C23 . H231 . 120.4 no
C29 . C23 . H231 . 121.3 no
C23 . C24 . C25 . 122.1(3) yes
C23 . C24 . H241 . 119.2 no
C25 . C24 . H241 . 118.7 no
C24 . C25 . C30 . 122.4(3) yes
C24 . C25 . N21 . 116.4(3) yes
C30 . C25 . N21 . 120.9(3) yes
C27 . C26 . C30 . 117.0(3) yes
C27 . C26 . B21 . 113.0(3) yes
C30 . C26 . B21 . 130.0(3) yes
C26 . C27 . C28 . 125.3(3) yes
C26 . C27 . H271 . 117.7 no
C28 . C27 . H271 . 117.0 no
C27 . C28 . C31 . 117.9(3) yes
C27 . C28 . H281 . 121.3 no
C31 . C28 . H281 . 120.8 no
C22 . C29 . C23 . 131.7(3) yes
C22 . C29 . C32 . 108.9(3) yes
C23 . C29 . C32 . 119.3(3) yes
C26 . C30 . C25 . 130.5(3) yes
C26 . C30 . C32 . 116.7(3) yes
C25 . C30 . C32 . 112.8(3) yes
C21 . C31 . C28 . 131.3(3) yes
C21 . C31 . C32 . 109.2(3) yes
C28 . C31 . C32 . 119.5(3) yes
C30 . C32 . C29 . 125.0(3) yes
C30 . C32 . C31 . 123.4(3) yes
C29 . C32 . C31 . 111.6(3) yes
N21 . C33 . H333 . 108.9 no
N21 . C33 . H332 . 109.8 no
H333 . C33 . H332 . 110.1 no
N21 . C33 . H331 . 108.4 no
H333 . C33 . H331 . 110.1 no
H332 . C33 . H331 . 109.5 no
N21 . C34 . H343 . 109.3 no
N21 . C34 . H342 . 108.2 no
H343 . C34 . H342 . 109.9 no
N21 . C34 . H341 . 109.1 no
H343 . C34 . H341 . 110.1 no
H342 . C34 . H341 . 110.2 no
C36 . C35 . O210 . 101.3(4) yes
C36 . C35 . O21 . 101.8(4) yes
C36 . C35 . C37 . 114.3(4) yes
O210 . C35 . C37 . 127.4(5) yes
O21 . C35 . C37 . 109.0(5) yes
C36 . C35 . C370 . 114.2(4) yes
O210 . C35 . C370 . 106.5(5) yes
O21 . C35 . C370 . 86.0(5) yes
C36 . C35 . C38 . 114.4(5) yes
O21 . C35 . C38 . 107.4(5) yes
C37 . C35 . C38 . 109.4(5) yes
C370 . C35 . C38 . 125.1(6) yes
C36 . C35 . C380 . 115.9(5) yes
O210 . C35 . C380 . 106.2(5) yes
O21 . C35 . C380 . 124.0(5) yes
C370 . C35 . C380 . 111.5(6) yes
C35 . C36 . O22 . 103.2(4) yes
C35 . C36 . O220 . 102.3(4) yes
C35 . C36 . C390 . 113.2(5) yes
O22 . C36 . C390 . 126.7(5) yes
O220 . C36 . C390 . 106.6(5) yes
C35 . C36 . C39 . 113.2(5) yes
O22 . C36 . C39 . 107.8(5) yes
C35 . C36 . C400 . 113.9(4) yes
O22 . C36 . C400 . 83.0(5) yes
O220 . C36 . C400 . 106.1(5) yes
C390 . C36 . C400 . 113.5(6) yes
C39 . C36 . C400 . 127.4(6) yes
C35 . C36 . C40 . 113.6(4) yes
O22 . C36 . C40 . 108.1(5) yes
O220 . C36 . C40 . 128.9(5) yes
C39 . C36 . C40 . 110.5(5) yes
C42 . C41 . C51 . 104.4(3) yes
C42 . C41 . H411 . 110.9 no
C51 . C41 . H411 . 110.1 no
C42 . C41 . H412 . 110.9 no
C51 . C41 . H412 . 110.5 no
H411 . C41 . H412 . 109.8 no
C41 . C42 . C49 . 105.3(3) yes
C41 . C42 . H422 . 110.1 no
C49 . C42 . H422 . 109.9 no
C41 . C42 . H421 . 110.5 no
C49 . C42 . H421 . 110.9 no
H422 . C42 . H421 . 110.0 no
C44 . C43 . C49 . 118.1(3) yes
C44 . C43 . H431 . 120.8 no
C49 . C43 . H431 . 121.0 no
C43 . C44 . C45 . 122.3(4) yes
C43 . C44 . H441 . 119.1 no
C45 . C44 . H441 . 118.6 no
C44 . C45 . C50 . 122.3(3) yes
C44 . C45 . N41 . 115.7(3) yes
C50 . C45 . N41 . 122.0(3) yes
C47 . C46 . C50 . 117.1(3) yes
C47 . C46 . B41 . 112.9(3) yes
C50 . C46 . B41 . 129.9(3) yes
C46 . C47 . C48 . 125.4(4) yes
C46 . C47 . H471 . 116.8 no
C48 . C47 . H471 . 117.8 no
C47 . C48 . C51 . 118.0(4) yes
C47 . C48 . H481 . 121.0 no
C51 . C48 . H481 . 121.0 no
C42 . C49 . C43 . 131.4(3) yes
C42 . C49 . C52 . 109.2(3) yes
C43 . C49 . C52 . 119.3(3) yes
C46 . C50 . C45 . 130.7(3) yes
C46 . C50 . C52 . 116.3(3) yes
C45 . C50 . C52 . 113.0(3) yes
C41 . C51 . C48 . 131.0(4) yes
C41 . C51 . C52 . 109.8(3) yes
C48 . C51 . C52 . 119.2(4) yes
C50 . C52 . C49 . 124.9(3) yes
C50 . C52 . C51 . 123.9(3) yes
C49 . C52 . C51 . 111.2(3) yes
N41 . C53 . H532 . 108.2 no
N41 . C53 . H531 . 108.2 no
H532 . C53 . H531 . 110.5 no
N41 . C53 . H533 . 109.2 no
H532 . C53 . H533 . 110.1 no
H531 . C53 . H533 . 110.6 no
N41 . C54 . H542 . 109.4 no
N41 . C54 . H541 . 108.5 no
H542 . C54 . H541 . 109.3 no
N41 . C54 . H543 . 109.5 no
H542 . C54 . H543 . 109.5 no
H541 . C54 . H543 . 110.6 no
C56 . C55 . O410 . 101.8(7) yes
C56 . C55 . C580 . 118.7(7) yes
O410 . C55 . C580 . 110.6(8) yes
C56 . C55 . C58 . 111.4(4) yes
C56 . C55 . C570 . 112.9(6) yes
O410 . C55 . C570 . 106.1(8) yes
C580 . C55 . C570 . 106.1(9) yes
C58 . C55 . C570 . 129.7(7) yes
C56 . C55 . C57 . 115.1(4) yes
O410 . C55 . C57 . 124.3(6) yes
C58 . C55 . C57 . 113.9(5) yes
C56 . C55 . O41 . 102.5(3) yes
C580 . C55 . O41 . 124.4(7) yes
C58 . C55 . O41 . 104.1(4) yes
C57 . C55 . O41 . 108.5(4) yes
C55 . C56 . O42 . 103.1(3) yes
C55 . C56 . C60 . 117.3(4) yes
O42 . C56 . C60 . 106.1(4) yes
C55 . C56 . C600 . 106.4(7) yes
C55 . C56 . C59 . 112.7(4) yes
O42 . C56 . C59 . 103.2(4) yes
C60 . C56 . C59 . 112.6(5) yes
C600 . C56 . C59 . 131.7(7) yes
C55 . C56 . C590 . 114.7(7) yes
O42 . C56 . C590 . 126.3(8) yes
C60 . C56 . C590 . 89.4(8) yes
C600 . C56 . C590 . 109.2(10) yes
C55 . C56 . O420 . 104.3(6) yes
C60 . C56 . O420 . 121.3(7) yes
C600 . C56 . O420 . 112.7(9) yes
C590 . C56 . O420 . 109.6(10) yes
F62 . C61 . F63 . 107.0(4) yes
F62 . C61 . F64 . 108.8(4) yes
F63 . C61 . F64 . 106.7(5) yes
F62 . C61 . S65 . 110.3(4) yes
F63 . C61 . S65 . 111.6(3) yes
F64 . C61 . S65 . 112.2(3) yes
F70 . C69 . F71 . 107.2(4) yes
F70 . C69 . F72 . 107.0(4) yes
F71 . C69 . F72 . 107.3(4) yes
F70 . C69 . S73 . 111.8(3) yes
F71 . C69 . S73 . 111.6(4) yes
F72 . C69 . S73 . 111.7(4) yes
F78 . C77 . F79 . 96.8(5) yes
F78 . C77 . F80 . 100.0(4) yes
F79 . C77 . F80 . 119.2(6) yes
F78 . C77 . S81 . 105.1(5) yes
F79 . C77 . S81 . 116.4(4) yes
F80 . C77 . S81 . 114.4(3) yes
C61 . S65 . O66 . 103.0(2) yes
C61 . S65 . O67 . 102.5(2) yes
O66 . S65 . O67 . 114.6(2) yes
C61 . S65 . O68 . 103.3(2) yes
O66 . S65 . O68 . 115.9(2) yes
O67 . S65 . O68 . 115.0(2) yes
C69 . S73 . O74 . 102.1(2) yes
C69 . S73 . O75 . 103.4(2) yes
O74 . S73 . O75 . 114.8(2) yes
C69 . S73 . O76 . 103.1(2) yes
O74 . S73 . O76 . 114.7(2) yes
O75 . S73 . O76 . 115.9(2) yes
C77 . S81 . O82 . 106.4(2) yes
C77 . S81 . O83 . 104.4(3) yes
O82 . S81 . O83 . 118.8(3) yes
C77 . S81 . O84 . 105.0(3) yes
O82 . S81 . O84 . 114.4(4) yes
O83 . S81 . O84 . 106.5(3) yes
C15 . O1 . B1 . 107.7(3) yes
C16 . O2 . B1 . 109.0(3) yes
C6 . B1 . O1 . 125.9(4) yes
C6 . B1 . O2 . 122.3(4) yes
O1 . B1 . O2 . 111.8(3) yes
C26 . B21 . O210 . 124.0(4) yes
C26 . B21 . O21 . 126.7(4) yes
C26 . B21 . O22 . 123.1(4) yes
O210 . B21 . O22 . 105.4(5) yes
O21 . B21 . O22 . 110.0(5) yes
C26 . B21 . O220 . 120.8(4) yes
O210 . B21 . O220 . 115.2(5) yes
O21 . B21 . O220 . 107.6(5) yes
C46 . B41 . O42 . 119.1(4) yes
C46 . B41 . O410 . 129.2(6) yes
O42 . B41 . O410 . 108.2(7) yes
C46 . B41 . O420 . 124.0(6) yes
O410 . B41 . O420 . 106.8(8) yes
C46 . B41 . O41 . 125.2(4) yes
O42 . B41 . O41 . 115.8(4) yes
O420 . B41 . O41 . 106.4(6) yes
C13 . N10 . C5 . 113.0(3) yes
C13 . N10 . C14 . 112.4(4) yes
C5 . N10 . C14 . 112.1(3) yes
C13 . N10 . H101 . 106.3 no
C5 . N10 . H101 . 106.2 no
C14 . N10 . H101 . 106.3 no
C33 . N21 . C34 . 110.7(4) yes
C33 . N21 . C25 . 110.3(3) yes
C34 . N21 . C25 . 115.7(3) yes
C33 . N21 . H213 . 106.6 no
C34 . N21 . H213 . 106.5 no
C25 . N21 . H213 . 106.5 no
C53 . N41 . C54 . 110.8(3) yes
C53 . N41 . C45 . 111.9(3) yes
C54 . N41 . C45 . 113.7(3) yes
C53 . N41 . H413 . 106.6 no
C54 . N41 . H413 . 106.7 no
C45 . N41 . H413 . 106.6 no
C35 . O210 . B21 . 106.2(5) yes
C35 . O21 . B21 . 111.3(5) yes
C36 . O22 . B21 . 108.7(5) yes
C36 . O220 . B21 . 106.6(5) yes
C35 . C37 . H371 . 108.4 no
C35 . C37 . H372 . 108.8 no
H371 . C37 . H372 . 109.5 no
C35 . C37 . H373 . 111.1 no
H371 . C37 . H373 . 109.5 no
H372 . C37 . H373 . 109.5 no
C35 . C370 . H3701 . 108.9 no
C35 . C370 . H3702 . 110.3 no
H3701 . C370 . H3702 . 109.5 no
C35 . C370 . H3703 . 109.2 no
H3701 . C370 . H3703 . 109.5 no
H3702 . C370 . H3703 . 109.5 no
C36 . C390 . H3901 . 110.3 no
C36 . C390 . H3902 . 109.5 no
H3901 . C390 . H3902 . 109.5 no
C36 . C390 . H3903 . 108.6 no
H3901 . C390 . H3903 . 109.5 no
H3902 . C390 . H3903 . 109.5 no
C36 . C39 . H391 . 109.0 no
C36 . C39 . H392 . 109.1 no
H391 . C39 . H392 . 109.5 no
C36 . C39 . H393 . 110.2 no
H391 . C39 . H393 . 109.5 no
H392 . C39 . H393 . 109.5 no
C35 . C38 . H381 . 109.2 no
C35 . C38 . H382 . 108.8 no
H381 . C38 . H382 . 109.5 no
C35 . C38 . H383 . 110.5 no
H381 . C38 . H383 . 109.5 no
H382 . C38 . H383 . 109.5 no
C35 . C380 . H3801 . 108.7 no
C35 . C380 . H3802 . 109.1 no
H3801 . C380 . H3802 . 109.5 no
C35 . C380 . H3803 . 110.6 no
H3801 . C380 . H3803 . 109.5 no
H3802 . C380 . H3803 . 109.5 no
C36 . C400 . H4001 . 108.2 no
C36 . C400 . H4002 . 109.9 no
H4001 . C400 . H4002 . 109.5 no
C36 . C400 . H4003 . 110.3 no
H4001 . C400 . H4003 . 109.5 no
H4002 . C400 . H4003 . 109.5 no
C36 . C40 . H401 . 110.5 no
C36 . C40 . H402 . 109.4 no
H401 . C40 . H402 . 109.5 no
C36 . C40 . H403 . 108.4 no
H401 . C40 . H403 . 109.5 no
H402 . C40 . H403 . 109.5 no
C56 . O42 . B41 . 106.5(4) yes
C55 . O410 . B41 . 112.1(10) yes
C56 . C60 . H601 . 107.5 no
C56 . C60 . H603 . 112.1 no
H601 . C60 . H603 . 109.5 no
C56 . C60 . H602 . 109.3 no
H601 . C60 . H602 . 109.2 no
H603 . C60 . H602 . 109.2 no
C56 . C600 . H6001 . 111.2 no
C56 . C600 . H6002 . 116.0 no
H6001 . C600 . H6002 . 109.5 no
C56 . C600 . H6003 . 100.9 no
H6001 . C600 . H6003 . 109.5 no
H6002 . C600 . H6003 . 109.5 no
C55 . C580 . H5801 . 114.5 no
C55 . C580 . H5802 . 114.0 no
H5801 . C580 . H5802 . 109.5 no
C55 . C580 . H5803 . 99.4 no
H5801 . C580 . H5803 . 109.5 no
H5802 . C580 . H5803 . 109.5 no
C55 . C58 . H581 . 110.5 no
C55 . C58 . H582 . 108.2 no
H581 . C58 . H582 . 109.5 no
C55 . C58 . H583 . 109.7 no
H581 . C58 . H583 . 109.5 no
H582 . C58 . H583 . 109.5 no
C56 . C59 . H591 . 107.6 no
C56 . C59 . H592 . 111.0 no
H591 . C59 . H592 . 109.5 no
C56 . C59 . H593 . 109.7 no
H591 . C59 . H593 . 109.5 no
H592 . C59 . H593 . 109.5 no
C56 . C590 . H5901 . 113.5 no
C56 . C590 . H5902 . 104.1 no
H5901 . C590 . H5902 . 109.5 no
C56 . C590 . H5903 . 110.7 no
H5901 . C590 . H5903 . 109.5 no
H5902 . C590 . H5903 . 109.5 no
C55 . C570 . H5701 . 109.2 no
C55 . C570 . H5702 . 108.0 no
H5701 . C570 . H5702 . 109.5 no
C55 . C570 . H5703 . 111.1 no
H5701 . C570 . H5703 . 109.5 no
H5702 . C570 . H5703 . 109.5 no
C55 . C57 . H571 . 109.7 no
C55 . C57 . H572 . 110.1 no
H571 . C57 . H572 . 109.5 no
C55 . C57 . H573 . 108.6 no
H571 . C57 . H573 . 109.5 no
H572 . C57 . H573 . 109.5 no
C56 . O420 . B41 . 111.8(9) yes
C55 . O41 . B41 . 106.6(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C1 . H12 . O2 2_667 169.0 0.975 2.413 3.377(8) yes
C4 . H41 . O66 . 152.0 0.940 2.459 3.318(8) yes
C13 . H132 . O83 2_657 157.0 0.973 2.442 3.361(8) yes
C13 . H131 . O84 . 165.0 0.974 2.558 3.508(8) yes
C14 . H143 . O68 . 152.0 0.969 2.351 3.237(8) yes
C18 . H183 . O83 2_657 162.0 0.949 2.478 3.395(8) yes
C24 . H241 . O74 . 161.0 0.937 2.425 3.326(8) yes
C33 . H332 . O66 . 157.0 0.963 2.580 3.486(8) yes
C34 . H343 . O74 2_666 124.0 0.962 2.575 3.211(8) yes
C34 . H342 . O74 . 165.0 0.966 2.489 3.432(8) yes
C34 . H341 . O42 . 143.0 0.965 2.348 3.176(8) yes
C44 . H441 . O82 2_567 156.0 0.938 2.484 3.361(8) yes
C53 . H532 . O67 1_465 152.0 0.959 2.364 3.242(8) yes
C53 . H531 . O82 2_567 163.0 0.962 2.380 3.311(8) yes
C54 . H542 . O67 1_465 147.0 0.960 2.469 3.313(8) yes
C570 . H5702 . O67 1_465 161.0 0.950 2.420 3.332(8) yes
C57 . H5702 . O67 1_465 136.0 1.164 2.420 3.351(8) yes
C570 . H572 . O67 1_465 141.0 1.067 2.435 3.332(8) yes
C57 . H572 . O67 1_465 162.0 0.950 2.435 3.351(8) yes
C600 . H6001 . O74 . 126.0 0.950 2.557 3.213(8) yes
C390 . H3903 . O76 1_545 168.0 0.950 2.579 3.513(8) yes
N10 . H101 . O1 . 170.0 0.860 1.824 2.675(8) yes
N21 . H213 . O210 . 176.0 0.860 1.826 2.685(8) yes
N21 . H213 . O21 . 165.0 0.860 1.786 2.626(8) yes
N41 . H413 . O410 . 168.0 0.860 1.869 2.716(8) yes
N41 . H413 . O41 . 176.0 0.860 1.805 2.664(8) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/10/14 at 17:17:31
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE O(41,U'S) O(410,U'S) O(42,U'S) O(420,U'S) 
RIDE C(57,U'S) C(570,U'S) C(58,U'S) C(580,U'S) 
RIDE C(59,U'S) C(590,U'S) C(60,U'S) C(600,U'S) 
REM 
RIDE O(21,U'S) O(210,U'S) O(22,U'S) O(220,U'S) 
RIDE C(37,U'S) C(370,U'S) C(38,U'S) C(380,U'S) 
RIDE C(39,U'S) C(390,U'S) C(40,U'S) C(400,U'S) 
REM 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   2,X'S) H   (  22,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  17,X'S) H   ( 173,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 193,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 203,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 222,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  33,X'S) H   ( 333,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 343,X'S) H   ( 342,X'S) H   ( 341,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  53,X'S) H   ( 532,X'S) H   ( 531,X'S) H   ( 533,X'S) 
RIDE C   (  54,X'S) H   ( 542,X'S) H   ( 541,X'S) H   ( 543,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) H   ( 373,X'S) 
RIDE C   ( 370,X'S) H   (3701,X'S) H   (3702,X'S) H   (3703,X'S) 
RIDE C   ( 390,X'S) H   (3901,X'S) H   (3902,X'S) H   (3903,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) H   ( 393,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) H   ( 383,X'S) 
RIDE C   ( 380,X'S) H   (3801,X'S) H   (3802,X'S) H   (3803,X'S) 
RIDE C   ( 400,X'S) H   (4001,X'S) H   (4002,X'S) H   (4003,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) H   ( 403,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) H   ( 602,X'S) H   ( 603,X'S) 
RIDE C   ( 600,X'S) H   (6001,X'S) H   (6002,X'S) H   (6003,X'S) 
RIDE C   ( 580,X'S) H   (5801,X'S) H   (5802,X'S) H   (5803,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) H   ( 583,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) H   ( 593,X'S) 
RIDE C   ( 590,X'S) H   (5901,X'S) H   (5902,X'S) H   (5903,X'S) 
RIDE C   ( 570,X'S) H   (5701,X'S) H   (5702,X'S) H   (5703,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) H   ( 573,X'S) 
RIDE N(10,X'S) H(101,X'S) 
RIDE N(21,X'S) H(213,X'S) 
RIDE N(41,X'S) H(413,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 06/10/14 at 17:17:31
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        
'N,N-Dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroacenaphthylen-5-ammonium trifluoromethanesulfonate '
_exptl_crystal_recrystallization_method 
'Vapour diffusion crystalization in CHCl3-cyclohexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1403310'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
6-(Dimethylammonium)-1,2-dihydroacenaphthylen-5-yl)trifluoroborate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 B F3 N, C3 H6 O'
_chemical_formula_sum            'C17 H21 B F3 N O'
_chemical_formula_weight         323.16

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'
F F 0.0171 0.0103 '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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.7848(9)
_cell_length_b                   8.3548(10)
_cell_length_c                   13.5437(14)
_cell_angle_alpha                101.869(2)
_cell_angle_beta                 103.288(3)
_cell_angle_gamma                99.358(3)
_cell_volume                     818.35(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4959
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      30.01

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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            15726
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.597
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        26.370
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3327
_reflns_number_gt                2739
_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 (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.2593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3327
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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_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 0.08108(16) 0.33461(14) 0.15179(8) 0.0250(3) Uani 1 1 d . . . . .
H1 H 0.041(2) 0.417(2) 0.1310(12) 0.030 Uiso 1 1 d . U . . .
B1 B -0.0122(2) 0.68216(19) 0.17772(12) 0.0267(3) Uani 1 1 d . . . . .
F1 F -0.16973(11) 0.55195(10) 0.13135(7) 0.0363(2) Uani 1 1 d . . . . .
F2 F -0.05859(12) 0.83463(10) 0.17112(7) 0.0376(2) Uani 1 1 d . . . . .
F3 F 0.10489(12) 0.65170(11) 0.11193(6) 0.0367(2) Uani 1 1 d . . . . .
C1 C 0.2832(2) 0.67379(18) 0.62359(10) 0.0312(3) Uani 1 1 d . . . . .
H1A H 0.1930 0.6838 0.6642 0.037 Uiso 1 1 calc R U . . .
H1B H 0.3969 0.7569 0.6630 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3171(2) 0.49398(18) 0.60305(10) 0.0302(3) Uani 1 1 d . . . . .
H2A H 0.4463 0.4956 0.6327 0.036 Uiso 1 1 calc R U . . .
H2B H 0.2429 0.4227 0.6347 0.036 Uiso 1 1 calc R U . . .
C3 C 0.26250(19) 0.27942(17) 0.42176(10) 0.0274(3) Uani 1 1 d . . . . .
H3 H 0.3031 0.1937 0.4509 0.033 Uiso 1 1 calc R U . . .
C4 C 0.20085(18) 0.25473(16) 0.31229(10) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.2007 0.1508 0.2677 0.031 Uiso 1 1 calc R U . . .
C5 C 0.14096(17) 0.37657(15) 0.26817(9) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.07827(17) 0.67722(15) 0.29661(10) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.09192(18) 0.81801(16) 0.37549(11) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.0540 0.9115 0.3549 0.033 Uiso 1 1 calc R U . . .
C8 C 0.15770(19) 0.83324(17) 0.48402(11) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.1636 0.9338 0.5338 0.036 Uiso 1 1 calc R U . . .
C9 C 0.26243(17) 0.42962(16) 0.48487(10) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.13785(16) 0.53692(15) 0.32959(10) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.21267(18) 0.70082(17) 0.51599(10) 0.0256(3) Uani 1 1 d . . . . .
C12 C 0.20257(17) 0.55471(16) 0.43890(10) 0.0219(3) Uani 1 1 d . . . . .
C13 C -0.0752(2) 0.18745(19) 0.10558(12) 0.0430(4) Uani 1 1 d . . . . .
H13A H -0.0379 0.0867 0.1209 0.065 Uiso 1 1 calc R U . . .
H13B H -0.1153 0.1717 0.0295 0.065 Uiso 1 1 calc R U . . .
H13C H -0.1748 0.2074 0.1360 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2335(2) 0.3132(2) 0.10401(12) 0.0451(4) Uani 1 1 d . . . . .
H14A H 0.3333 0.4119 0.1354 0.068 Uiso 1 1 calc R U . . .
H14B H 0.1918 0.3006 0.0283 0.068 Uiso 1 1 calc R U . . .
H14C H 0.2753 0.2130 0.1170 0.068 Uiso 1 1 calc R U . . .
O1 O 0.4255(2) 1.01014(16) 0.15245(11) 0.0706(4) Uani 1 1 d . . . . .
C15 C 0.4771(2) 0.88253(19) 0.15694(12) 0.0367(3) Uani 1 1 d . . . . .
C16 C 0.5279(2) 0.8353(2) 0.25870(13) 0.0473(4) Uani 1 1 d . . . . .
H16A H 0.4986 0.9144 0.3133 0.071 Uiso 1 1 calc R U . . .
H16B H 0.6580 0.8390 0.2785 0.071 Uiso 1 1 calc R U . . .
H16C H 0.4605 0.7217 0.2511 0.071 Uiso 1 1 calc R U . . .
C17 C 0.4916(2) 0.7652(2) 0.06161(13) 0.0427(4) Uani 1 1 d . . . . .
H17A H 0.3840 0.6732 0.0351 0.064 Uiso 1 1 calc R U . . .
H17B H 0.5997 0.7197 0.0795 0.064 Uiso 1 1 calc R U . . .
H17C H 0.5005 0.8257 0.0075 0.064 Uiso 1 1 calc R U . . .


_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
N1 C5 1.4854(16) . ?
N1 C13 1.4934(19) . ?
N1 C14 1.4943(19) . ?
B1 F2 1.3939(16) . ?
B1 F1 1.4189(17) . ?
B1 F3 1.4299(18) . ?
B1 C6 1.614(2) . ?
C1 C11 1.5113(19) . ?
C1 C2 1.548(2) . ?
C2 C9 1.5134(18) . ?
C3 C9 1.3655(19) . ?
C3 C4 1.4092(18) . ?
C4 C5 1.3738(18) . ?
C5 C10 1.4314(17) . ?
C6 C7 1.3880(18) . ?
C6 C10 1.4442(17) . ?
C7 C8 1.412(2) . ?
C8 C11 1.364(2) . ?
C9 C12 1.4106(18) . ?
C10 C12 1.4176(17) . ?
C11 C12 1.4118(18) . ?
O1 C15 1.2071(19) . ?
C15 C17 1.491(2) . ?
C15 C16 1.495(2) . ?

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 C13 113.11(11) . . ?
C5 N1 C14 112.23(11) . . ?
C13 N1 C14 111.38(13) . . ?
F2 B1 F1 108.54(11) . . ?
F2 B1 F3 107.64(11) . . ?
F1 B1 F3 104.93(11) . . ?
F2 B1 C6 112.85(11) . . ?
F1 B1 C6 110.53(11) . . ?
F3 B1 C6 111.98(11) . . ?
C11 C1 C2 105.03(11) . . ?
C9 C2 C1 104.95(11) . . ?
C9 C3 C4 118.39(12) . . ?
C5 C4 C3 121.93(12) . . ?
C4 C5 C10 122.61(11) . . ?
C4 C5 N1 116.39(11) . . ?
C10 C5 N1 120.99(11) . . ?
C7 C6 C10 116.55(12) . . ?
C7 C6 B1 117.08(11) . . ?
C10 C6 B1 126.28(11) . . ?
C6 C7 C8 125.16(12) . . ?
C11 C8 C7 118.72(12) . . ?
C3 C9 C12 119.32(12) . . ?
C3 C9 C2 131.32(12) . . ?
C12 C9 C2 109.35(11) . . ?
C12 C10 C5 112.85(11) . . ?
C12 C10 C6 117.31(11) . . ?
C5 C10 C6 129.84(11) . . ?
C8 C11 C12 118.44(12) . . ?
C8 C11 C1 132.18(12) . . ?
C12 C11 C1 109.36(12) . . ?
C9 C12 C11 111.29(11) . . ?
C9 C12 C10 124.90(11) . . ?
C11 C12 C10 123.81(12) . . ?
O1 C15 C17 121.56(15) . . ?
O1 C15 C16 121.09(16) . . ?
C17 C15 C16 117.35(14) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DP-II-162
_database_code_depnum_ccdc_archive 'CCDC 1403311'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
6-(Dimesitylboryl)-N,N-dimethyl-1,2-dihydroacenaphthylen-5-amine
_chemical_formula_moiety         'C32 H36 B1 N1'
_chemical_formula_sum            'C32 H36 B N'
_chemical_formula_weight         445.43
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2908(6)
_cell_length_b                   9.5397(6)
_cell_length_c                   15.6546(10)
_cell_angle_alpha                97.351(2)
_cell_angle_beta                 101.400(2)
_cell_angle_gamma                105.609(2)
_cell_volume                     1285.62(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.21
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7296
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_number            34934
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             6369
_reflns_number_gt                4967
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0595P)²+0.4979P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6369
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.138
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 1.0998(2) 1.03097(17) 0.33519(12) 0.0435(4) Uani 1 1 d . . .
H1A H 1.1763 1.0653 0.3932 0.052 Uiso 1 1 calc R . .
H1B H 1.046 1.1063 0.3256 0.052 Uiso 1 1 calc R . .
C2 C 1.17918(19) 1.00446(17) 0.25926(11) 0.0376(3) Uani 1 1 d . . .
H2A H 1.1531 1.0602 0.2124 0.045 Uiso 1 1 calc R . .
H2B H 1.2925 1.0354 0.282 0.045 Uiso 1 1 calc R . .
C3 C 1.15243(18) 0.74835(17) 0.16179(10) 0.0360(3) Uani 1 1 d . . .
H3 H 1.2291 0.7875 0.1317 0.043 Uiso 1 1 calc R . .
C4 C 1.07271(18) 0.59521(17) 0.14353(10) 0.0344(3) Uani 1 1 d . . .
H4 H 1.0988 0.5321 0.1011 0.041 Uiso 1 1 calc R . .
C5 C 0.95875(15) 0.53231(15) 0.18415(9) 0.0260(3) Uani 1 1 d . . .
C6 C 0.80707(15) 0.57766(15) 0.29998(8) 0.0255(3) Uani 1 1 d . . .
C7 C 0.79994(16) 0.68524(16) 0.36688(9) 0.0314(3) Uani 1 1 d . . .
H7 H 0.7331 0.6542 0.4042 0.038 Uiso 1 1 calc R . .
C8 C 0.88511(17) 0.83732(17) 0.38329(10) 0.0349(3) Uani 1 1 d . . .
H8 H 0.8724 0.9062 0.4285 0.042 Uiso 1 1 calc R . .
C9 C 1.11663(16) 0.83901(16) 0.22382(9) 0.0297(3) Uani 1 1 d . . .
C10 C 0.91761(14) 0.62402(14) 0.24877(8) 0.0238(3) Uani 1 1 d . . .
C11 C 0.98595(16) 0.88237(16) 0.33238(10) 0.0307(3) Uani 1 1 d . . .
C12 C 1.00241(15) 0.77569(15) 0.26670(9) 0.0261(3) Uani 1 1 d . . .
C13 C 0.79250(18) 0.32147(18) 0.07367(9) 0.0368(3) Uani 1 1 d . . .
H13A H 0.7198 0.3784 0.0617 0.055 Uiso 1 1 calc R . .
H13B H 0.7354 0.2161 0.0652 0.055 Uiso 1 1 calc R . .
H13C H 0.8604 0.3349 0.0328 0.055 Uiso 1 1 calc R . .
C14 C 0.99739(18) 0.29256(18) 0.18297(11) 0.0385(4) Uani 1 1 d . . .
H14A H 1.0581 0.3002 0.1383 0.058 Uiso 1 1 calc R . .
H14B H 0.9432 0.188 0.1803 0.058 Uiso 1 1 calc R . .
H14C H 1.0661 0.3351 0.2421 0.058 Uiso 1 1 calc R . .
C15 C 0.65020(15) 0.36150(15) 0.37043(8) 0.0256(3) Uani 1 1 d . . .
C16 C 0.50900(15) 0.34543(14) 0.39493(8) 0.0249(3) Uani 1 1 d . . .
C17 C 0.48568(16) 0.28630(15) 0.46995(9) 0.0287(3) Uani 1 1 d . . .
H17 H 0.3905 0.2772 0.4858 0.034 Uiso 1 1 calc R . .
C18 C 0.59683(18) 0.24030(16) 0.52225(9) 0.0333(3) Uani 1 1 d . . .
C19 C 0.73710(18) 0.26061(17) 0.49946(10) 0.0351(3) Uani 1 1 d . . .
H19 H 0.8157 0.2322 0.5351 0.042 Uiso 1 1 calc R . .
C20 C 0.76610(16) 0.32128(17) 0.42600(9) 0.0313(3) Uani 1 1 d . . .
C21 C 0.38222(16) 0.39556(17) 0.34437(10) 0.0307(3) Uani 1 1 d . . .
H21A H 0.3349 0.3286 0.2867 0.046 Uiso 1 1 calc R . .
H21B H 0.4253 0.4966 0.3352 0.046 Uiso 1 1 calc R . .
H21C H 0.304 0.394 0.3784 0.046 Uiso 1 1 calc R . .
C22 C 0.5660(2) 0.1713(2) 0.60093(11) 0.0469(4) Uani 1 1 d . . .
H22A H 0.5668 0.0681 0.5901 0.07 Uiso 1 1 calc R . .
H22B H 0.4651 0.1743 0.6095 0.07 Uiso 1 1 calc R . .
H22C H 0.6461 0.2268 0.6543 0.07 Uiso 1 1 calc R . .
C23 C 0.92102(19) 0.3382(2) 0.40545(11) 0.0447(4) Uani 1 1 d . . .
H23A H 0.984 0.3003 0.4491 0.067 Uiso 1 1 calc R . .
H23B H 0.9728 0.4433 0.408 0.067 Uiso 1 1 calc R . .
H23C H 0.9069 0.2821 0.3459 0.067 Uiso 1 1 calc R . .
C24 C 0.55526(15) 0.35159(15) 0.19272(8) 0.0249(3) Uani 1 1 d . . .
C25 C 0.50819(16) 0.19566(15) 0.16373(9) 0.0280(3) Uani 1 1 d . . .
C26 C 0.39315(17) 0.12878(17) 0.08610(10) 0.0344(3) Uani 1 1 d . . .
H26 H 0.3641 0.0243 0.0673 0.041 Uiso 1 1 calc R . .
C27 C 0.31992(17) 0.21033(18) 0.03561(10) 0.0374(3) Uani 1 1 d . . .
C28 C 0.36707(17) 0.36255(18) 0.06330(10) 0.0342(3) Uani 1 1 d . . .
H28 H 0.3187 0.4201 0.0291 0.041 Uiso 1 1 calc R . .
C29 C 0.48340(16) 0.43498(16) 0.13978(9) 0.0281(3) Uani 1 1 d . . .
C30 C 0.58356(18) 0.09669(16) 0.21198(11) 0.0359(3) Uani 1 1 d . . .
H30A H 0.5553 0.0927 0.2689 0.054 Uiso 1 1 calc R . .
H30B H 0.6957 0.1366 0.2226 0.054 Uiso 1 1 calc R . .
H30C H 0.5485 -0.0034 0.1758 0.054 Uiso 1 1 calc R . .
C31 C 0.1928(2) 0.1353(2) -0.04724(12) 0.0575(5) Uani 1 1 d . . .
H31A H 0.2375 0.1027 -0.095 0.086 Uiso 1 1 calc R . .
H31B H 0.1384 0.2055 -0.0656 0.086 Uiso 1 1 calc R . .
H31C H 0.1203 0.0493 -0.0348 0.086 Uiso 1 1 calc R . .
C32 C 0.52237(19) 0.60181(17) 0.16287(11) 0.0379(3) Uani 1 1 d . . .
H32A H 0.4604 0.6363 0.1167 0.057 Uiso 1 1 calc R . .
H32B H 0.632 0.6473 0.1667 0.057 Uiso 1 1 calc R . .
H32C H 0.5 0.6299 0.2201 0.057 Uiso 1 1 calc R . .
B1 B 0.67741(17) 0.42589(17) 0.28443(10) 0.0246(3) Uani 1 1 d . . .
N1 N 0.88515(13) 0.37374(13) 0.16535(7) 0.0267(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C11 1.513(2) . ?
C1 C2 1.546(2) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C9 1.514(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C9 1.367(2) . ?
C3 C4 1.411(2) . ?
C3 H3 0.95 . ?
C4 C5 1.3811(19) . ?
C4 H4 0.95 . ?
C5 C10 1.4287(18) . ?
C5 N1 1.4465(17) . ?
C6 C7 1.3940(19) . ?
C6 C10 1.4370(18) . ?
C6 B1 1.569(2) . ?
C7 C8 1.415(2) . ?
C7 H7 0.95 . ?
C8 C11 1.365(2) . ?
C8 H8 0.95 . ?
C9 C12 1.4078(19) . ?
C10 C12 1.4100(19) . ?
C11 C12 1.4122(19) . ?
C13 N1 1.4653(18) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N1 1.4624(18) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.4132(18) . ?
C15 C20 1.4145(19) . ?
C15 B1 1.586(2) . ?
C16 C17 1.3960(19) . ?
C16 C21 1.5080(19) . ?
C17 C18 1.390(2) . ?
C17 H17 0.95 . ?
C18 C19 1.389(2) . ?
C18 C22 1.509(2) . ?
C19 C20 1.392(2) . ?
C19 H19 0.95 . ?
C20 C23 1.508(2) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 C29 1.4145(19) . ?
C24 C25 1.4173(19) . ?
C24 B1 1.5856(19) . ?
C25 C26 1.3956(19) . ?
C25 C30 1.510(2) . ?
C26 C27 1.387(2) . ?
C26 H26 0.95 . ?
C27 C28 1.382(2) . ?
C27 C31 1.513(2) . ?
C28 C29 1.398(2) . ?
C28 H28 0.95 . ?
C29 C32 1.512(2) . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?

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
C11 C1 C2 105.34(12) . . ?
C11 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
C11 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C9 C2 C1 104.60(12) . . ?
C9 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C9 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C9 C3 C4 118.37(13) . . ?
C9 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 123.41(13) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C4 C5 C10 119.67(13) . . ?
C4 C5 N1 120.97(12) . . ?
C10 C5 N1 119.30(11) . . ?
C7 C6 C10 116.91(12) . . ?
C7 C6 B1 113.78(12) . . ?
C10 C6 B1 128.88(11) . . ?
C6 C7 C8 124.74(13) . . ?
C6 C7 H7 117.6 . . ?
C8 C7 H7 117.6 . . ?
C11 C8 C7 118.22(13) . . ?
C11 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C3 C9 C12 118.68(13) . . ?
C3 C9 C2 131.97(13) . . ?
C12 C9 C2 109.34(13) . . ?
C12 C10 C5 115.18(12) . . ?
C12 C10 C6 117.35(12) . . ?
C5 C10 C6 127.37(12) . . ?
C8 C11 C12 118.89(13) . . ?
C8 C11 C1 132.15(14) . . ?
C12 C11 C1 108.82(13) . . ?
C9 C12 C10 124.65(12) . . ?
C9 C12 C11 111.59(13) . . ?
C10 C12 C11 123.74(12) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 117.77(12) . . ?
C16 C15 B1 120.55(12) . . ?
C20 C15 B1 121.67(12) . . ?
C17 C16 C15 119.94(12) . . ?
C17 C16 C21 117.88(12) . . ?
C15 C16 C21 122.13(12) . . ?
C18 C17 C16 122.31(13) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 117.47(13) . . ?
C19 C18 C22 121.42(14) . . ?
C17 C18 C22 121.11(14) . . ?
C18 C19 C20 122.07(13) . . ?
C18 C19 H19 119 . . ?
C20 C19 H19 119 . . ?
C19 C20 C15 120.33(13) . . ?
C19 C20 C23 118.67(13) . . ?
C15 C20 C23 120.96(13) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 117.70(12) . . ?
C29 C24 B1 122.19(12) . . ?
C25 C24 B1 120.01(12) . . ?
C26 C25 C24 120.23(13) . . ?
C26 C25 C30 117.48(13) . . ?
C24 C25 C30 122.23(12) . . ?
C27 C26 C25 121.96(14) . . ?
C27 C26 H26 119 . . ?
C25 C26 H26 119 . . ?
C28 C27 C26 117.80(13) . . ?
C28 C27 C31 121.03(15) . . ?
C26 C27 C31 121.17(15) . . ?
C27 C28 C29 122.39(14) . . ?
C27 C28 H28 118.8 . . ?
C29 C28 H28 118.8 . . ?
C28 C29 C24 119.88(13) . . ?
C28 C29 C32 116.86(13) . . ?
C24 C29 C32 123.23(12) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C6 B1 C24 123.87(12) . . ?
C6 B1 C15 116.41(11) . . ?
C24 B1 C15 118.67(11) . . ?
C5 N1 C14 111.68(11) . . ?
C5 N1 C13 111.67(11) . . ?
C14 N1 C13 109.88(12) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DP-II-162-B(OH)2
_database_code_depnum_ccdc_archive 'CCDC 1403312'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'6-(Dihydroxyboryl)-N,N-dimethyl-1,2-dihydroacenaphthylen-5-amine '
_chemical_formula_moiety         'C14 H16 B N O2'
_chemical_formula_sum            'C14 H16 B N O2'
_chemical_formula_weight         241.09
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5658(12)
_cell_length_b                   10.1745(10)
_cell_length_c                   12.0844(12)
_cell_angle_alpha                90
_cell_angle_beta                 117.252(3)
_cell_angle_gamma                90
_cell_volume                     1264.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6952
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.52
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.7461

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_number            30829
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         30.69
_diffrn_reflns_theta_full        30.69
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3915
_reflns_number_gt                2927
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#


_computing_data_collection       APEX2
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0696P)²+0.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3915
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.051
_refine_ls_wR_factor_ref         0.154
_refine_ls_wR_factor_gt          0.139
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.23270(14) 0.39127(18) -0.01084(16) 0.0479(4) Uani 1 1 d . . .
H1A H -0.2749 0.4659 -0.0678 0.057 Uiso 1 1 calc R . .
H1B H -0.287 0.3657 0.0295 0.057 Uiso 1 1 calc R . .
C2 C -0.21472(13) 0.27432(17) -0.08231(14) 0.0449(4) Uani 1 1 d . . .
H2A H -0.2635 0.1965 -0.0772 0.054 Uiso 1 1 calc R . .
H2B H -0.245 0.2969 -0.171 0.054 Uiso 1 1 calc R . .
C3 C 0.00164(15) 0.15763(16) -0.04232(14) 0.0442(3) Uani 1 1 d . . .
H3 H -0.0383 0.0973 -0.1093 0.053 Uiso 1 1 calc R . .
C4 C 0.13698(15) 0.15580(15) 0.03486(13) 0.0412(3) Uani 1 1 d . . .
H4 H 0.1874 0.0917 0.0192 0.049 Uiso 1 1 calc R . .
C5 C 0.19984(12) 0.24239(13) 0.13193(12) 0.0324(3) Uani 1 1 d . . .
C6 C 0.17505(12) 0.44707(13) 0.25051(11) 0.0299(3) Uani 1 1 d . . .
C7 C 0.08284(13) 0.53429(14) 0.25056(13) 0.0371(3) Uani 1 1 d . . .
H7 H 0.1129 0.604 0.3093 0.044 Uiso 1 1 calc R . .
C8 C -0.05211(14) 0.52775(16) 0.17024(14) 0.0417(3) Uani 1 1 d . . .
H8 H -0.11 0.5911 0.175 0.05 Uiso 1 1 calc R . .
C9 C -0.06987(13) 0.24802(14) -0.01818(12) 0.0368(3) Uani 1 1 d . . .
C10 C 0.12937(11) 0.34288(12) 0.15864(11) 0.0282(2) Uani 1 1 d . . .
C11 C -0.09679(12) 0.42831(15) 0.08597(13) 0.0363(3) Uani 1 1 d . . .
C12 C -0.00700(12) 0.33870(13) 0.07949(11) 0.0312(3) Uani 1 1 d . . .
C13 C 0.37463(19) 0.1041(2) 0.2769(2) 0.0772(7) Uani 1 1 d . . .
H13A H 0.3285 0.0977 0.3274 0.116 Uiso 1 1 calc R . .
H13B H 0.4686 0.1017 0.3313 0.116 Uiso 1 1 calc R . .
H13C H 0.3498 0.0302 0.2185 0.116 Uiso 1 1 calc R . .
C14 C 0.41255(17) 0.2427(2) 0.13511(18) 0.0617(5) Uani 1 1 d . . .
H14A H 0.3944 0.1675 0.0788 0.093 Uiso 1 1 calc R . .
H14B H 0.5059 0.2463 0.1919 0.093 Uiso 1 1 calc R . .
H14C H 0.3857 0.324 0.0864 0.093 Uiso 1 1 calc R . .
B1 B 0.31846(14) 0.47748(16) 0.35373(13) 0.0330(3) Uani 1 1 d . . .
N1 N 0.34021(11) 0.22800(12) 0.20716(11) 0.0368(3) Uani 1 1 d . . .
O1 O 0.42477(10) 0.40838(12) 0.36991(10) 0.0484(3) Uani 1 1 d D . .
O2 O 0.33388(11) 0.57889(12) 0.43242(10) 0.0484(3) Uani 1 1 d D . .
H2 H 0.4103(12) 0.585(2) 0.4912(16) 0.077(7) Uiso 1 1 d D . .
H1 H 0.401(3) 0.344(2) 0.318(2) 0.103(9) Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C11 1.5157(19) . ?
C1 C2 1.539(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C9 1.5132(19) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C9 1.355(2) . ?
C3 C4 1.408(2) . ?
C3 H3 0.95 . ?
C4 C5 1.3783(18) . ?
C4 H4 0.95 . ?
C5 C10 1.4334(18) . ?
C5 N1 1.4602(16) . ?
C6 C7 1.3877(18) . ?
C6 C10 1.4485(17) . ?
C6 B1 1.5838(18) . ?
C7 C8 1.4125(19) . ?
C7 H7 0.95 . ?
C8 C11 1.359(2) . ?
C8 H8 0.95 . ?
C9 C12 1.4097(19) . ?
C10 C12 1.4222(16) . ?
C11 C12 1.4108(19) . ?
C13 N1 1.466(2) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N1 1.465(2) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
B1 O1 1.3506(19) . ?
B1 O2 1.3584(18) . ?
O1 H1 0.859(10) . ?
O2 H2 0.846(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
C11 C1 C2 105.45(12) . . ?
C11 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
C11 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C9 C2 C1 104.58(12) . . ?
C9 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C9 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C9 C3 C4 117.99(13) . . ?
C9 C3 H3 121 . . ?
C4 C3 H3 121 . . ?
C5 C4 C3 123.26(14) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C10 120.99(12) . . ?
C4 C5 N1 117.94(12) . . ?
C10 C5 N1 121.07(11) . . ?
C7 C6 C10 117.24(11) . . ?
C7 C6 B1 113.74(11) . . ?
C10 C6 B1 129.02(11) . . ?
C6 C7 C8 125.25(13) . . ?
C6 C7 H7 117.4 . . ?
C8 C7 H7 117.4 . . ?
C11 C8 C7 118.14(13) . . ?
C11 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C3 C9 C12 119.53(12) . . ?
C3 C9 C2 130.66(13) . . ?
C12 C9 C2 109.80(13) . . ?
C12 C10 C5 113.39(11) . . ?
C12 C10 C6 116.12(11) . . ?
C5 C10 C6 130.48(11) . . ?
C8 C11 C12 119.07(12) . . ?
C8 C11 C1 131.90(14) . . ?
C12 C11 C1 109.03(13) . . ?
C9 C12 C11 111.03(12) . . ?
C9 C12 C10 124.80(12) . . ?
C11 C12 C10 124.14(12) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 B1 O2 118.37(12) . . ?
O1 B1 C6 124.61(12) . . ?
O2 B1 C6 117.01(12) . . ?
C5 N1 C14 113.23(12) . . ?
C5 N1 C13 112.08(12) . . ?
C14 N1 C13 110.52(16) . . ?
B1 O1 H1 109.1(19) . . ?
B1 O2 H2 113.2(16) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'vapour-diffusion crystallization from CDCl3-cyclohexane '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DP-II-162-BMesOH
_database_code_depnum_ccdc_archive 'CCDC 1403313'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
N,N-Dimethyl-6-(hydroxymesitylboryl)-1,2-dihydroacenaphthylen-5-amine
_chemical_formula_moiety         'C23 H26 B N O, C18 H23 B O'
_chemical_formula_sum            'C41 H49 B2 N O2'
_chemical_formula_weight         609.43
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4501(8)
_cell_length_b                   29.6982(17)
_cell_length_c                   11.6740(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.774(6)
_cell_angle_gamma                90
_cell_volume                     3589.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    13020
_cell_measurement_theta_min      3.145
_cell_measurement_theta_max      29.421
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.89751
_exptl_absorpt_correction_T_max  1.0

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measurement_method       ω-φ
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_number            60154
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             8202
_reflns_number_gt                6281
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0393P)²+2.2305P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8202
_refine_ls_number_parameters     432
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C22 C 1.0186(2) 0.24302(8) -0.0591(2) 0.0583(6) Uani 1 1 d . . .
H22A H 1.0945 0.2298 -0.0873 0.087 Uiso 1 1 calc R . .
H22B H 1.0457 0.2683 -0.0074 0.087 Uiso 1 1 calc R . .
H22C H 0.9582 0.2538 -0.1249 0.087 Uiso 1 1 calc R . .
C1 C 1.0036(2) 0.04943(7) 0.65696(16) 0.0427(5) Uani 1 1 d . . .
H1A H 0.997 0.0731 0.7156 0.051 Uiso 1 1 calc R . .
H1B H 1.095 0.0399 0.6616 0.051 Uiso 1 1 calc R . .
C2 C 0.9161(2) 0.00892(7) 0.67617(16) 0.0436(5) Uani 1 1 d . . .
H2A H 0.9677 -0.019 0.6894 0.052 Uiso 1 1 calc R . .
H2B H 0.8698 0.0142 0.7435 0.052 Uiso 1 1 calc R . .
C3 C 0.7253(2) -0.02407(6) 0.53180(16) 0.0414(4) Uani 1 1 d . . .
H3 H 0.7056 -0.0476 0.5819 0.05 Uiso 1 1 calc R . .
C4 C 0.65482(19) -0.01932(6) 0.42112(16) 0.0389(4) Uani 1 1 d . . .
H4 H 0.5876 -0.0402 0.3972 0.047 Uiso 1 1 calc R . .
C5 C 0.67938(17) 0.01448(5) 0.34548(14) 0.0296(4) Uani 1 1 d . . .
C6 C 0.82151(16) 0.08416(5) 0.31053(14) 0.0277(3) Uani 1 1 d . . .
C7 C 0.92759(17) 0.10848(6) 0.36196(15) 0.0340(4) Uani 1 1 d . . .
H7 H 0.9573 0.1325 0.3187 0.041 Uiso 1 1 calc R . .
C8 C 0.99484(18) 0.10042(6) 0.47336(16) 0.0382(4) Uani 1 1 d . . .
H8 H 1.0671 0.1184 0.503 0.046 Uiso 1 1 calc R . .
C9 C 0.82193(19) 0.00554(6) 0.56587(15) 0.0352(4) Uani 1 1 d . . .
C10 C 0.77964(16) 0.04679(5) 0.37693(13) 0.0264(3) Uani 1 1 d . . .
C11 C 0.95376(17) 0.06645(6) 0.53696(14) 0.0327(4) Uani 1 1 d . . .
C12 C 0.84843(16) 0.03990(5) 0.48885(14) 0.0286(3) Uani 1 1 d . . .
C13 C 0.6719(2) -0.01262(8) 0.15069(18) 0.0514(5) Uani 1 1 d . . .
H13A H 0.7618 -0.0029 0.1531 0.077 Uiso 1 1 calc R . .
H13B H 0.627 -0.0094 0.0718 0.077 Uiso 1 1 calc R . .
H13C H 0.6698 -0.0442 0.1744 0.077 Uiso 1 1 calc R . .
C14 C 0.47026(19) 0.00296(7) 0.22332(19) 0.0471(5) Uani 1 1 d . . .
H14A H 0.4629 -0.0297 0.233 0.071 Uiso 1 1 calc R . .
H14B H 0.4246 0.0118 0.1478 0.071 Uiso 1 1 calc R . .
H14C H 0.432 0.0184 0.2846 0.071 Uiso 1 1 calc R . .
C15 C 0.82849(16) 0.14172(6) 0.12559(14) 0.0311(4) Uani 1 1 d . . .
C16 C 0.81035(17) 0.18773(6) 0.14597(16) 0.0347(4) Uani 1 1 d . . .
C17 C 0.87338(18) 0.21976(6) 0.08654(17) 0.0396(4) Uani 1 1 d . . .
H17 H 0.8613 0.2508 0.1018 0.048 Uiso 1 1 calc R . .
C18 C 0.95311(18) 0.20771(7) 0.00596(17) 0.0409(4) Uani 1 1 d . . .
C19 C 0.96877(18) 0.16219(7) -0.01492(17) 0.0420(5) Uani 1 1 d . . .
H19 H 1.022 0.1533 -0.0707 0.05 Uiso 1 1 calc R . .
C20 C 0.90854(18) 0.12917(6) 0.04371(16) 0.0371(4) Uani 1 1 d . . .
C21 C 0.7223(2) 0.20296(7) 0.23055(18) 0.0454(5) Uani 1 1 d . . .
H21A H 0.6332 0.2042 0.1916 0.068 Uiso 1 1 calc R . .
H21B H 0.7488 0.2329 0.26 0.068 Uiso 1 1 calc R . .
H21C H 0.7276 0.1816 0.2951 0.068 Uiso 1 1 calc R . .
C23 C 0.9291(2) 0.07998(7) 0.0185(2) 0.0552(6) Uani 1 1 d . . .
H23A H 0.9911 0.0772 -0.0371 0.083 Uiso 1 1 calc R . .
H23B H 0.8468 0.0664 -0.0141 0.083 Uiso 1 1 calc R . .
H23C H 0.9629 0.0644 0.0902 0.083 Uiso 1 1 calc R . .
C24 C 0.48161(16) 0.13573(5) -0.27547(14) 0.0276(3) Uani 1 1 d . . .
C25 C 0.36297(17) 0.14829(6) -0.33882(14) 0.0304(4) Uani 1 1 d . . .
C26 C 0.34731(18) 0.14759(6) -0.45949(15) 0.0355(4) Uani 1 1 d . . .
H26 H 0.2666 0.1564 -0.5009 0.043 Uiso 1 1 calc R . .
C27 C 0.4459(2) 0.13448(6) -0.52070(15) 0.0390(4) Uani 1 1 d . . .
C28 C 0.56194(19) 0.12201(6) -0.45858(16) 0.0378(4) Uani 1 1 d . . .
H28 H 0.6304 0.1128 -0.4992 0.045 Uiso 1 1 calc R . .
C29 C 0.58226(17) 0.12242(5) -0.33815(15) 0.0314(4) Uani 1 1 d . . .
C30 C 0.24804(18) 0.16153(7) -0.28010(16) 0.0400(4) Uani 1 1 d . . .
H30A H 0.1814 0.175 -0.337 0.06 Uiso 1 1 calc R . .
H30B H 0.2752 0.1834 -0.2189 0.06 Uiso 1 1 calc R . .
H30C H 0.213 0.1347 -0.2464 0.06 Uiso 1 1 calc R . .
C31 C 0.4257(3) 0.13421(8) -0.65163(16) 0.0550(6) Uani 1 1 d . . .
H31A H 0.4448 0.1641 -0.6803 0.082 Uiso 1 1 calc R . .
H31B H 0.3358 0.1263 -0.6796 0.082 Uiso 1 1 calc R . .
H31C H 0.4834 0.112 -0.6797 0.082 Uiso 1 1 calc R . .
C32 C 0.71382(18) 0.10927(6) -0.27807(17) 0.0394(4) Uani 1 1 d . . .
H32A H 0.7089 0.0795 -0.2426 0.059 Uiso 1 1 calc R . .
H32B H 0.7429 0.1315 -0.2181 0.059 Uiso 1 1 calc R . .
H32C H 0.7752 0.1083 -0.3345 0.059 Uiso 1 1 calc R . .
C33 C 0.47282(15) 0.17906(6) -0.06486(13) 0.0268(3) Uani 1 1 d . . .
C34 C 0.52515(16) 0.22177(6) -0.08203(14) 0.0296(4) Uani 1 1 d . . .
C35 C 0.48936(18) 0.25872(6) -0.02049(15) 0.0346(4) Uani 1 1 d . . .
H35 H 0.5263 0.2873 -0.0325 0.042 Uiso 1 1 calc R . .
C36 C 0.40123(18) 0.25511(6) 0.05802(16) 0.0367(4) Uani 1 1 d . . .
C37 C 0.35067(17) 0.21291(6) 0.07541(15) 0.0348(4) Uani 1 1 d . . .
H37 H 0.2906 0.2098 0.1292 0.042 Uiso 1 1 calc R . .
C38 C 0.38505(16) 0.17503(6) 0.01660(14) 0.0296(4) Uani 1 1 d . . .
C39 C 0.62150(19) 0.22852(6) -0.16602(16) 0.0389(4) Uani 1 1 d . . .
H39A H 0.6522 0.2597 -0.1616 0.058 Uiso 1 1 calc R . .
H39B H 0.58 0.2221 -0.2447 0.058 Uiso 1 1 calc R . .
H39C H 0.6948 0.2081 -0.1463 0.058 Uiso 1 1 calc R . .
C40 C 0.3608(2) 0.29610(7) 0.1204(2) 0.0525(5) Uani 1 1 d . . .
H40A H 0.301 0.2871 0.174 0.079 Uiso 1 1 calc R . .
H40B H 0.3179 0.3176 0.064 0.079 Uiso 1 1 calc R . .
H40C H 0.4372 0.3103 0.1636 0.079 Uiso 1 1 calc R . .
C41 C 0.32432(18) 0.13029(6) 0.03967(16) 0.0375(4) Uani 1 1 d . . .
H41A H 0.3883 0.1112 0.0859 0.056 Uiso 1 1 calc R . .
H41B H 0.2945 0.1153 -0.0339 0.056 Uiso 1 1 calc R . .
H41C H 0.2508 0.1353 0.0821 0.056 Uiso 1 1 calc R . .
B1 B 0.75714(19) 0.10447(6) 0.19048(16) 0.0295(4) Uani 1 1 d . . .
B2 B 0.50642(18) 0.13692(6) -0.13821(16) 0.0273(4) Uani 1 1 d . . .
N1 N 0.60737(14) 0.01539(5) 0.23019(12) 0.0328(3) Uani 1 1 d . . .
O1 O 0.63900(13) 0.09167(4) 0.14062(11) 0.0387(3) Uani 1 1 d D . .
H1 H 0.619(3) 0.0677(6) 0.174(2) 0.086 Uiso 1 1 d D . .
O2 O 0.55902(13) 0.09940(4) -0.08675(10) 0.0356(3) Uani 1 1 d D . .
H2 H 0.584(2) 0.1010(8) -0.0144(9) 0.051 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C22 C18 1.512(3) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C1 C11 1.514(2) . ?
C1 C2 1.546(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C9 1.514(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C9 1.358(3) . ?
C3 C4 1.405(3) . ?
C3 H3 0.95 . ?
C4 C5 1.384(2) . ?
C4 H4 0.95 . ?
C5 C10 1.431(2) . ?
C5 N1 1.451(2) . ?
C6 C7 1.390(2) . ?
C6 C10 1.455(2) . ?
C6 B1 1.589(2) . ?
C7 C8 1.412(2) . ?
C7 H7 0.95 . ?
C8 C11 1.356(3) . ?
C8 H8 0.95 . ?
C9 C12 1.412(2) . ?
C10 C12 1.418(2) . ?
C11 C12 1.408(2) . ?
C13 N1 1.476(2) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N1 1.471(2) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C20 1.403(2) . ?
C15 C16 1.404(2) . ?
C15 B1 1.583(3) . ?
C16 C17 1.394(2) . ?
C16 C21 1.508(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.95 . ?
C18 C19 1.387(3) . ?
C19 C20 1.394(3) . ?
C19 H19 0.95 . ?
C20 C23 1.512(3) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 C25 1.405(2) . ?
C24 C29 1.416(2) . ?
C24 B2 1.589(2) . ?
C25 C26 1.396(2) . ?
C25 C30 1.513(2) . ?
C26 C27 1.386(3) . ?
C26 H26 0.95 . ?
C27 C28 1.377(3) . ?
C27 C31 1.514(3) . ?
C28 C29 1.393(2) . ?
C28 H28 0.95 . ?
C29 C32 1.508(3) . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 C34 1.406(2) . ?
C33 C38 1.413(2) . ?
C33 B2 1.582(2) . ?
C34 C35 1.390(2) . ?
C34 C39 1.511(2) . ?
C35 C36 1.389(2) . ?
C35 H35 0.95 . ?
C36 C37 1.386(3) . ?
C36 C40 1.508(3) . ?
C37 C38 1.390(2) . ?
C37 H37 0.95 . ?
C38 C41 1.512(2) . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?
B1 O1 1.346(2) . ?
B2 O2 1.348(2) . ?
O1 H1 0.855(10) . ?
O2 H2 0.851(9) . ?

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
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C1 C2 104.94(15) . . ?
C11 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
C11 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.8 . . ?
C9 C2 C1 104.92(15) . . ?
C9 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C9 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C9 C3 C4 118.74(17) . . ?
C9 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 122.71(17) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C10 121.00(16) . . ?
C4 C5 N1 119.19(15) . . ?
C10 C5 N1 119.70(14) . . ?
C7 C6 C10 116.50(15) . . ?
C7 C6 B1 113.68(15) . . ?
C10 C6 B1 129.61(15) . . ?
C6 C7 C8 125.33(17) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C11 C8 C7 118.37(17) . . ?
C11 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C3 C9 C12 118.93(17) . . ?
C3 C9 C2 131.62(17) . . ?
C12 C9 C2 109.43(17) . . ?
C12 C10 C5 113.69(14) . . ?
C12 C10 C6 116.71(15) . . ?
C5 C10 C6 129.59(15) . . ?
C8 C11 C12 119.11(16) . . ?
C8 C11 C1 131.31(17) . . ?
C12 C11 C1 109.56(16) . . ?
C11 C12 C9 111.15(15) . . ?
C11 C12 C10 123.94(16) . . ?
C9 C12 C10 124.90(16) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.71(16) . . ?
C20 C15 B1 120.21(15) . . ?
C16 C15 B1 121.05(15) . . ?
C17 C16 C15 119.73(17) . . ?
C17 C16 C21 119.51(17) . . ?
C15 C16 C21 120.75(16) . . ?
C18 C17 C16 121.98(18) . . ?
C18 C17 H17 119 . . ?
C16 C17 H17 119 . . ?
C17 C18 C19 117.86(17) . . ?
C17 C18 C22 121.12(19) . . ?
C19 C18 C22 121.01(19) . . ?
C18 C19 C20 121.83(18) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 119.88(17) . . ?
C19 C20 C23 119.90(17) . . ?
C15 C20 C23 120.22(16) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 117.78(15) . . ?
C25 C24 B2 122.48(14) . . ?
C29 C24 B2 119.73(15) . . ?
C26 C25 C24 120.12(16) . . ?
C26 C25 C30 117.97(16) . . ?
C24 C25 C30 121.89(15) . . ?
C27 C26 C25 122.02(17) . . ?
C27 C26 H26 119 . . ?
C25 C26 H26 119 . . ?
C28 C27 C26 117.84(16) . . ?
C28 C27 C31 121.49(18) . . ?
C26 C27 C31 120.67(19) . . ?
C27 C28 C29 122.15(17) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C24 120.09(17) . . ?
C28 C29 C32 118.16(16) . . ?
C24 C29 C32 121.74(15) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 118.21(15) . . ?
C34 C33 B2 121.14(14) . . ?
C38 C33 B2 120.60(15) . . ?
C35 C34 C33 120.09(15) . . ?
C35 C34 C39 118.69(16) . . ?
C33 C34 C39 121.22(15) . . ?
C36 C35 C34 121.94(17) . . ?
C36 C35 H35 119 . . ?
C34 C35 H35 119 . . ?
C37 C36 C35 117.81(16) . . ?
C37 C36 C40 121.48(17) . . ?
C35 C36 C40 120.70(18) . . ?
C36 C37 C38 122.04(16) . . ?
C36 C37 H37 119 . . ?
C38 C37 H37 119 . . ?
C37 C38 C33 119.90(16) . . ?
C37 C38 C41 118.71(15) . . ?
C33 C38 C41 121.38(15) . . ?
C34 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C34 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C40 H40A 109.5 . . ?
C36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O1 B1 C15 117.00(15) . . ?
O1 B1 C6 121.88(16) . . ?
C15 B1 C6 121.10(15) . . ?
O2 B2 C33 121.32(15) . . ?
O2 B2 C24 115.62(15) . . ?
C33 B2 C24 123.06(14) . . ?
C5 N1 C14 115.15(15) . . ?
C5 N1 C13 110.44(14) . . ?
C14 N1 C13 110.42(15) . . ?
B1 O1 H1 107.9(19) . . ?
B2 O2 H2 116.5(15) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane'
_chemical_properties_physical    Moisture-sensitive
