# 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/. 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1014485'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine_mono_H_BPh2 '
_chemical_melting_point          258-260
_chemical_formula_moiety         'C24 H18 B Cl N2 O'
_chemical_formula_sum            'C24 H18 B Cl N2 O'
_chemical_formula_weight         396.66

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   9.467(3)
_cell_length_b                   20.563(7)
_cell_length_c                   10.445(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.812(10)
_cell_angle_gamma                90.00
_cell_volume                     2019.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19713
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.58
_reflns_number_total             4594
_reflns_number_gt                3740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0679P)²+0.3363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48918(16) -0.06396(7) 0.76450(15) 0.0428(3) Uani 1 1 d . . .
C2 C 0.44664(18) -0.01653(7) 0.67671(16) 0.0479(4) Uani 1 1 d . . .
H2 H 0.4948 0.0230 0.6805 0.057 Uiso 1 1 calc R . .
C3 C 0.33093(16) -0.02633(7) 0.58033(15) 0.0424(3) Uani 1 1 d . . .
C4 C 0.26553(18) 0.02399(8) 0.50400(17) 0.0498(4) Uani 1 1 d . . .
H4 H 0.2966 0.0668 0.5144 0.060 Uiso 1 1 calc R . .
C5 C 0.16367(18) -0.09654(8) 0.47375(17) 0.0491(4) Uani 1 1 d . . .
C6 C 0.59720(18) -0.05560(8) 0.87683(16) 0.0480(4) Uani 1 1 d . . .
C7 C 0.6380(2) -0.10896(10) 0.9533(2) 0.0703(6) Uani 1 1 d . . .
H7 H 0.5950 -0.1490 0.9344 0.084 Uiso 1 1 calc R . .
C8 C 0.7412(3) -0.10330(13) 1.0569(3) 0.0915(8) Uani 1 1 d . . .
H8 H 0.7677 -0.1396 1.1071 0.110 Uiso 1 1 calc R . .
C9 C 0.8057(3) -0.04431(14) 1.0871(2) 0.0862(7) Uani 1 1 d . . .
H9 H 0.8755 -0.0406 1.1573 0.103 Uiso 1 1 calc R . .
C10 C 0.7660(3) 0.00798(13) 1.0133(3) 0.0896(8) Uani 1 1 d . . .
H10 H 0.8095 0.0479 1.0333 0.108 Uiso 1 1 calc R . .
C11 C 0.6623(3) 0.00365(10) 0.9086(2) 0.0727(6) Uani 1 1 d . . .
H11 H 0.6363 0.0404 0.8595 0.087 Uiso 1 1 calc R . .
C12 C 0.15518(18) 0.00791(8) 0.41439(16) 0.0489(4) Uani 1 1 d . . .
C13 C 0.48556(16) -0.16775(7) 0.53796(15) 0.0437(3) Uani 1 1 d . . .
C14 C 0.62297(17) -0.18495(7) 0.59088(18) 0.0503(4) Uani 1 1 d . . .
H14 H 0.6461 -0.1834 0.6799 0.060 Uiso 1 1 calc R . .
C15 C 0.72620(19) -0.20437(9) 0.5145(2) 0.0598(5) Uani 1 1 d . . .
H15 H 0.8165 -0.2158 0.5527 0.072 Uiso 1 1 calc R . .
C16 C 0.6950(2) -0.20667(10) 0.3829(2) 0.0653(5) Uani 1 1 d . . .
H16 H 0.7641 -0.2194 0.3317 0.078 Uiso 1 1 calc R . .
C17 C 0.5613(2) -0.19006(11) 0.3272(2) 0.0651(5) Uani 1 1 d . . .
H17 H 0.5394 -0.1917 0.2381 0.078 Uiso 1 1 calc R . .
C18 C 0.45860(18) -0.17075(9) 0.40385(18) 0.0553(4) Uani 1 1 d . . .
H18 H 0.3687 -0.1594 0.3644 0.066 Uiso 1 1 calc R . .
C19 C 0.25584(16) -0.20508(7) 0.65907(15) 0.0441(3) Uani 1 1 d . . .
C20 C 0.2460(2) -0.26448(8) 0.59545(19) 0.0591(4) Uani 1 1 d . . .
H20 H 0.3047 -0.2731 0.5322 0.071 Uiso 1 1 calc R . .
C21 C 0.1478(3) -0.31160(9) 0.6261(2) 0.0743(6) Uani 1 1 d . . .
H21 H 0.1426 -0.3512 0.5828 0.089 Uiso 1 1 calc R . .
C22 C 0.0599(2) -0.30014(10) 0.7183(2) 0.0685(6) Uani 1 1 d . . .
H22 H -0.0052 -0.3316 0.7369 0.082 Uiso 1 1 calc R . .
C23 C 0.0677(2) -0.24227(10) 0.7833(2) 0.0650(5) Uani 1 1 d . . .
H23 H 0.0090 -0.2342 0.8469 0.078 Uiso 1 1 calc R . .
H23A H 0.1263 -0.1384 0.4659 0.078 Uiso 1 1 d R . .
C24 C 0.16465(18) -0.19562(9) 0.75303(18) 0.0529(4) Uani 1 1 d . . .
H24 H 0.1689 -0.1563 0.7974 0.063 Uiso 1 1 calc R . .
B1 B 0.36507(18) -0.14818(8) 0.62934(17) 0.0414(4) Uani 1 1 d . . .
N1 N 0.27681(13) -0.08781(6) 0.56062(12) 0.0410(3) Uani 1 1 d . . .
N2 N 0.09948(15) -0.05179(7) 0.39785(14) 0.0528(3) Uani 1 1 d . . .
O1 O 0.43064(12) -0.12253(5) 0.75604(10) 0.0462(3) Uani 1 1 d . . .
Cl1 Cl 0.07542(6) 0.06706(2) 0.31334(5) 0.06906(18) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3244(18) . ?
C1 C2 1.366(2) . ?
C1 C6 1.472(2) . ?
C2 C3 1.412(2) . ?
C3 N1 1.3705(19) . ?
C3 C4 1.404(2) . ?
C4 C12 1.358(2) . ?
C5 N2 1.315(2) . ?
C5 N1 1.331(2) . ?
C6 C7 1.385(3) . ?
C6 C11 1.388(2) . ?
C7 C8 1.374(3) . ?
C8 C9 1.378(4) . ?
C9 C10 1.350(4) . ?
C10 C11 1.383(3) . ?
C12 N2 1.339(2) . ?
C12 Cl1 1.7247(17) . ?
C13 C18 1.395(2) . ?
C13 C14 1.397(2) . ?
C13 B1 1.622(2) . ?
C14 C15 1.391(3) . ?
C15 C16 1.372(3) . ?
C16 C17 1.372(3) . ?
C17 C18 1.389(3) . ?
C19 C20 1.388(2) . ?
C19 C24 1.395(2) . ?
C19 B1 1.616(2) . ?
C20 C21 1.405(3) . ?
C21 C22 1.367(3) . ?
C22 C23 1.368(3) . ?
C23 C24 1.390(2) . ?
B1 O1 1.490(2) . ?
B1 N1 1.616(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
O1 C1 C2 121.11(14) . . ?
O1 C1 C6 113.89(13) . . ?
C2 C1 C6 124.97(14) . . ?
C1 C2 C3 121.25(14) . . ?
N1 C3 C4 117.55(14) . . ?
N1 C3 C2 118.92(13) . . ?
C4 C3 C2 123.52(14) . . ?
C12 C4 C3 117.58(15) . . ?
N2 C5 N1 126.40(15) . . ?
C7 C6 C11 118.18(18) . . ?
C7 C6 C1 119.14(15) . . ?
C11 C6 C1 122.67(16) . . ?
C8 C7 C6 120.7(2) . . ?
C7 C8 C9 120.6(2) . . ?
C10 C9 C8 119.0(2) . . ?
C9 C10 C11 121.6(2) . . ?
C10 C11 C6 119.9(2) . . ?
N2 C12 C4 124.82(15) . . ?
N2 C12 Cl1 115.49(13) . . ?
C4 C12 Cl1 119.68(13) . . ?
C18 C13 C14 115.90(15) . . ?
C18 C13 B1 122.95(14) . . ?
C14 C13 B1 121.11(15) . . ?
C15 C14 C13 122.01(17) . . ?
C16 C15 C14 120.12(17) . . ?
C17 C16 C15 119.62(17) . . ?
C16 C17 C18 120.03(19) . . ?
C17 C18 C13 122.30(17) . . ?
C20 C19 C24 116.57(15) . . ?
C20 C19 B1 123.59(16) . . ?
C24 C19 B1 119.84(14) . . ?
C19 C20 C21 120.4(2) . . ?
C22 C21 C20 121.08(19) . . ?
C21 C22 C23 119.88(18) . . ?
C22 C23 C24 119.1(2) . . ?
C23 C24 C19 122.96(18) . . ?
O1 B1 C19 107.11(13) . . ?
O1 B1 N1 105.16(11) . . ?
C19 B1 N1 109.42(12) . . ?
O1 B1 C13 111.25(13) . . ?
C19 B1 C13 116.37(13) . . ?
N1 B1 C13 106.97(12) . . ?
C5 N1 C3 118.88(13) . . ?
C5 N1 B1 122.07(12) . . ?
C3 N1 B1 118.52(12) . . ?
C5 N2 C12 114.63(15) . . ?
C1 O1 B1 120.54(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.4(2) . . . . ?
C6 C1 C2 C3 -172.58(15) . . . . ?
C1 C2 C3 N1 -11.5(2) . . . . ?
C1 C2 C3 C4 167.35(15) . . . . ?
N1 C3 C4 C12 -1.3(2) . . . . ?
C2 C3 C4 C12 179.88(16) . . . . ?
O1 C1 C6 C7 6.5(2) . . . . ?
C2 C1 C6 C7 -175.41(18) . . . . ?
O1 C1 C6 C11 -174.62(18) . . . . ?
C2 C1 C6 C11 3.5(3) . . . . ?
C11 C6 C7 C8 -0.7(3) . . . . ?
C1 C6 C7 C8 178.3(2) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C10 C11 C6 -0.5(4) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
C1 C6 C11 C10 -178.2(2) . . . . ?
C3 C4 C12 N2 3.6(3) . . . . ?
C3 C4 C12 Cl1 -177.34(12) . . . . ?
C18 C13 C14 C15 -0.5(2) . . . . ?
B1 C13 C14 C15 177.41(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
B1 C13 C18 C17 -177.40(17) . . . . ?
C24 C19 C20 C21 0.2(3) . . . . ?
B1 C19 C20 C21 -179.69(16) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C19 -0.3(3) . . . . ?
C20 C19 C24 C23 -0.1(2) . . . . ?
B1 C19 C24 C23 179.75(16) . . . . ?
C20 C19 B1 O1 -135.83(15) . . . . ?
C24 C19 B1 O1 44.31(18) . . . . ?
C20 C19 B1 N1 110.67(17) . . . . ?
C24 C19 B1 N1 -69.19(18) . . . . ?
C20 C19 B1 C13 -10.7(2) . . . . ?
C24 C19 B1 C13 169.47(14) . . . . ?
C18 C13 B1 O1 -156.59(14) . . . . ?
C14 C13 B1 O1 25.68(19) . . . . ?
C18 C13 B1 C19 80.37(19) . . . . ?
C14 C13 B1 C19 -97.35(17) . . . . ?
C18 C13 B1 N1 -42.26(19) . . . . ?
C14 C13 B1 N1 140.01(14) . . . . ?
N2 C5 N1 C3 3.4(3) . . . . ?
N2 C5 N1 B1 -168.11(16) . . . . ?
C4 C3 N1 C5 -1.9(2) . . . . ?
C2 C3 N1 C5 177.01(14) . . . . ?
C4 C3 N1 B1 169.93(13) . . . . ?
C2 C3 N1 B1 -11.2(2) . . . . ?
O1 B1 N1 C5 -153.34(14) . . . . ?
C19 B1 N1 C5 -38.58(19) . . . . ?
C13 B1 N1 C5 88.28(17) . . . . ?
O1 B1 N1 C3 35.11(17) . . . . ?
C19 B1 N1 C3 149.87(13) . . . . ?
C13 B1 N1 C3 -83.26(16) . . . . ?
N1 C5 N2 C12 -1.3(3) . . . . ?
C4 C12 N2 C5 -2.3(3) . . . . ?
Cl1 C12 N2 C5 178.55(13) . . . . ?
C2 C1 O1 B1 25.7(2) . . . . ?
C6 C1 O1 B1 -156.15(13) . . . . ?
C19 B1 O1 C1 -158.99(13) . . . . ?
N1 B1 O1 C1 -42.64(17) . . . . ?
C13 B1 O1 C1 72.81(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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/. 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1014486'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine_mono_CF3_BPh2 '
_chemical_melting_point          220-222
_chemical_formula_moiety         'C25 H17 B Cl F3 N2 O'
_chemical_formula_sum            'C25 H17 B Cl F3 N2 O'
_chemical_formula_weight         464.67

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   10.343(3)
_cell_length_b                   20.367(8)
_cell_length_c                   10.514(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.628(11)
_cell_angle_gamma                90.00
_cell_volume                     2212.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22535
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.92
_reflns_number_total             5121
_reflns_number_gt                3910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0739P)²+0.4255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5121
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54807(18) 1.06352(8) 1.23125(18) 0.0418(4) Uani 1 1 d . . .
C2 C 0.57928(19) 1.01542(9) 1.14790(18) 0.0450(4) Uani 1 1 d . . .
H2 H 0.5326 0.9764 1.1460 0.054 Uiso 1 1 calc R . .
C3 C 0.68224(18) 1.02379(9) 1.06345(17) 0.0422(4) Uani 1 1 d . . .
C4 C 0.7349(2) 0.97215(9) 0.99470(19) 0.0484(4) Uani 1 1 d . . .
H4 H 0.7035 0.9296 1.0018 0.058 Uiso 1 1 calc R . .
C5 C 0.8355(2) 1.09192(10) 0.9740(2) 0.0528(5) Uani 1 1 d . . .
H5 H 0.8717 1.1336 0.9694 0.063 Uiso 1 1 calc R . .
C6 C 0.45174(18) 1.05575(9) 1.33065(17) 0.0411(4) Uani 1 1 d . . .
C7 C 0.4167(2) 1.11037(9) 1.4021(2) 0.0528(5) Uani 1 1 d . . .
H7 H 0.4560 1.1507 1.3885 0.063 Uiso 1 1 calc R . .
C8 C 0.3244(2) 1.10523(10) 1.4928(2) 0.0555(5) Uani 1 1 d . . .
H8 H 0.3013 1.1421 1.5387 0.067 Uiso 1 1 calc R . .
C9 C 0.26614(19) 1.04526(10) 1.51532(19) 0.0473(4) Uani 1 1 d . . .
C10 C 0.3005(2) 0.99059(10) 1.4461(2) 0.0537(5) Uani 1 1 d . . .
H10 H 0.2616 0.9503 1.4609 0.064 Uiso 1 1 calc R . .
C11 C 0.3929(2) 0.99565(9) 1.3546(2) 0.0504(5) Uani 1 1 d . . .
H11 H 0.4157 0.9586 1.3089 0.060 Uiso 1 1 calc R . .
C12 C 0.8340(2) 0.98605(10) 0.91661(19) 0.0509(5) Uani 1 1 d . . .
C13 C 0.5482(2) 1.16896(9) 1.00918(19) 0.0478(4) Uani 1 1 d . . .
C14 C 0.4241(2) 1.18478(9) 1.0477(2) 0.0539(5) Uani 1 1 d . . .
H14 H 0.4066 1.1816 1.1335 0.065 Uiso 1 1 calc R . .
C15 C 0.3261(2) 1.20505(10) 0.9613(3) 0.0664(6) Uani 1 1 d . . .
H15 H 0.2446 1.2151 0.9896 0.080 Uiso 1 1 calc R . .
C16 C 0.3501(3) 1.21016(12) 0.8338(3) 0.0726(7) Uani 1 1 d . . .
H16 H 0.2847 1.2234 0.7758 0.087 Uiso 1 1 calc R . .
C17 C 0.4712(3) 1.19555(13) 0.7925(3) 0.0724(7) Uani 1 1 d . . .
H17 H 0.4878 1.1993 0.7066 0.087 Uiso 1 1 calc R . .
C18 C 0.5680(2) 1.17535(12) 0.8786(2) 0.0617(6) Uani 1 1 d . . .
H18 H 0.6492 1.1656 0.8490 0.074 Uiso 1 1 calc R . .
C19 C 0.76702(19) 1.20255(9) 1.1527(2) 0.0478(4) Uani 1 1 d . . .
C20 C 0.7758(2) 1.26307(11) 1.0923(3) 0.0686(6) Uani 1 1 d . . .
H20 H 0.7183 1.2730 1.0245 0.082 Uiso 1 1 calc R . .
C21 C 0.8689(3) 1.30894(12) 1.1313(3) 0.0846(9) Uani 1 1 d . . .
H21 H 0.8732 1.3489 1.0889 0.102 Uiso 1 1 calc R . .
C22 C 0.9542(3) 1.29599(13) 1.2312(3) 0.0779(8) Uani 1 1 d . . .
H22 H 1.0156 1.3271 1.2573 0.094 Uiso 1 1 calc R . .
C23 C 0.9485(3) 1.23659(14) 1.2928(3) 0.0783(7) Uani 1 1 d . . .
H23 H 1.0066 1.2271 1.3605 0.094 Uiso 1 1 calc R . .
C24 C 0.8558(2) 1.19088(11) 1.2535(2) 0.0641(6) Uani 1 1 d . . .
H24 H 0.8527 1.1509 1.2962 0.077 Uiso 1 1 calc R . .
C25 C 0.1640(2) 1.04079(11) 1.6113(2) 0.0574(5) Uani 1 1 d . . .
O1 O 0.60527(13) 1.12171(6) 1.23095(12) 0.0464(3) Uani 1 1 d . . .
N1 N 0.73488(15) 1.08482(7) 1.04990(15) 0.0429(3) Uani 1 1 d . . .
N2 N 0.88774(18) 1.04516(9) 0.90505(18) 0.0573(4) Uani 1 1 d . . .
F1 F 0.14639(16) 0.98022(7) 1.65420(16) 0.0816(5) Uani 1 1 d . . .
F2 F 0.04928(14) 1.06198(9) 1.56560(16) 0.0845(5) Uani 1 1 d . . .
F3 F 0.19185(16) 1.07801(8) 1.71521(14) 0.0785(4) Uani 1 1 d . . .
Cl1 Cl 0.89752(6) 0.92415(3) 0.82586(6) 0.0694(2) Uani 1 1 d . . .
B1 B 0.6615(2) 1.14736(10) 1.1117(2) 0.0446(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.325(2) . ?
C1 C2 1.363(3) . ?
C1 C6 1.485(3) . ?
C2 C3 1.428(3) . ?
C3 N1 1.367(2) . ?
C3 C4 1.400(3) . ?
C4 C12 1.372(3) . ?
C5 N2 1.327(3) . ?
C5 N1 1.348(3) . ?
C6 C11 1.395(3) . ?
C6 C7 1.399(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.386(3) . ?
C9 C25 1.497(3) . ?
C10 C11 1.391(3) . ?
C12 N2 1.334(3) . ?
C12 Cl1 1.729(2) . ?
C13 C14 1.401(3) . ?
C13 C18 1.404(3) . ?
C13 B1 1.616(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.379(4) . ?
C16 C17 1.376(4) . ?
C17 C18 1.382(3) . ?
C19 C24 1.391(3) . ?
C19 C20 1.391(3) . ?
C19 B1 1.612(3) . ?
C20 C21 1.390(3) . ?
C21 C22 1.365(4) . ?
C22 C23 1.375(4) . ?
C23 C24 1.386(3) . ?
C25 F1 1.329(3) . ?
C25 F2 1.331(3) . ?
C25 F3 1.350(3) . ?
O1 B1 1.500(3) . ?
N1 B1 1.633(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.51(17) . . ?
O1 C1 C6 114.27(16) . . ?
C2 C1 C6 124.21(16) . . ?
C1 C2 C3 121.29(17) . . ?
N1 C3 C4 117.58(18) . . ?
N1 C3 C2 119.04(16) . . ?
C4 C3 C2 123.36(17) . . ?
C12 C4 C3 118.21(18) . . ?
N2 C5 N1 126.26(19) . . ?
C11 C6 C7 118.35(18) . . ?
C11 C6 C1 122.18(16) . . ?
C7 C6 C1 119.46(16) . . ?
C8 C7 C6 120.91(18) . . ?
C7 C8 C9 120.21(18) . . ?
C10 C9 C8 119.60(19) . . ?
C10 C9 C25 120.76(18) . . ?
C8 C9 C25 119.62(18) . . ?
C9 C10 C11 120.33(18) . . ?
C10 C11 C6 120.60(18) . . ?
N2 C12 C4 124.51(18) . . ?
N2 C12 Cl1 115.96(16) . . ?
C4 C12 Cl1 119.53(16) . . ?
C14 C13 C18 116.0(2) . . ?
C14 C13 B1 121.03(19) . . ?
C18 C13 B1 122.90(19) . . ?
C15 C14 C13 121.9(2) . . ?
C16 C15 C14 120.0(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.0(3) . . ?
C17 C18 C13 122.3(2) . . ?
C24 C19 C20 116.4(2) . . ?
C24 C19 B1 119.99(18) . . ?
C20 C19 B1 123.6(2) . . ?
C21 C20 C19 121.3(2) . . ?
C22 C21 C20 120.8(2) . . ?
C21 C22 C23 119.5(2) . . ?
C22 C23 C24 119.6(3) . . ?
C23 C24 C19 122.4(2) . . ?
F1 C25 F2 106.9(2) . . ?
F1 C25 F3 105.94(19) . . ?
F2 C25 F3 105.30(18) . . ?
F1 C25 C9 113.39(17) . . ?
F2 C25 C9 112.42(19) . . ?
F3 C25 C9 112.34(19) . . ?
C1 O1 B1 120.24(15) . . ?
C5 N1 C3 118.76(16) . . ?
C5 N1 B1 122.51(15) . . ?
C3 N1 B1 118.24(15) . . ?
C5 N2 C12 114.60(19) . . ?
O1 B1 C19 107.63(16) . . ?
O1 B1 C13 110.81(16) . . ?
C19 B1 C13 116.74(16) . . ?
O1 B1 N1 105.42(14) . . ?
C19 B1 N1 109.20(16) . . ?
C13 B1 N1 106.47(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.1(3) . . . . ?
C6 C1 C2 C3 -173.42(17) . . . . ?
C1 C2 C3 N1 -11.8(3) . . . . ?
C1 C2 C3 C4 166.90(19) . . . . ?
N1 C3 C4 C12 -1.1(3) . . . . ?
C2 C3 C4 C12 -179.79(18) . . . . ?
O1 C1 C6 C11 -172.60(17) . . . . ?
C2 C1 C6 C11 6.0(3) . . . . ?
O1 C1 C6 C7 8.3(3) . . . . ?
C2 C1 C6 C7 -173.09(19) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C1 C6 C7 C8 178.03(19) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C25 -178.5(2) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C25 C9 C10 C11 178.2(2) . . . . ?
C9 C10 C11 C6 -0.4(3) . . . . ?
C7 C6 C11 C10 0.8(3) . . . . ?
C1 C6 C11 C10 -178.26(18) . . . . ?
C3 C4 C12 N2 2.8(3) . . . . ?
C3 C4 C12 Cl1 -177.67(14) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
B1 C13 C14 C15 178.38(18) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
B1 C13 C18 C17 -178.2(2) . . . . ?
C24 C19 C20 C21 0.2(4) . . . . ?
B1 C19 C20 C21 -179.9(2) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C19 0.2(4) . . . . ?
C20 C19 C24 C23 0.0(4) . . . . ?
B1 C19 C24 C23 -180.0(2) . . . . ?
C10 C9 C25 F1 22.5(3) . . . . ?
C8 C9 C25 F1 -159.4(2) . . . . ?
C10 C9 C25 F2 -98.8(2) . . . . ?
C8 C9 C25 F2 79.3(3) . . . . ?
C10 C9 C25 F3 142.6(2) . . . . ?
C8 C9 C25 F3 -39.3(3) . . . . ?
C2 C1 O1 B1 25.9(3) . . . . ?
C6 C1 O1 B1 -155.49(16) . . . . ?
N2 C5 N1 C3 2.7(3) . . . . ?
N2 C5 N1 B1 -169.2(2) . . . . ?
C4 C3 N1 C5 -1.4(3) . . . . ?
C2 C3 N1 C5 177.38(17) . . . . ?
C4 C3 N1 B1 170.88(17) . . . . ?
C2 C3 N1 B1 -10.4(2) . . . . ?
N1 C5 N2 C12 -1.2(3) . . . . ?
C4 C12 N2 C5 -1.6(3) . . . . ?
Cl1 C12 N2 C5 178.80(16) . . . . ?
C1 O1 B1 C19 -158.84(16) . . . . ?
C1 O1 B1 C13 72.4(2) . . . . ?
C1 O1 B1 N1 -42.4(2) . . . . ?
C24 C19 B1 O1 45.3(3) . . . . ?
C20 C19 B1 O1 -134.7(2) . . . . ?
C24 C19 B1 C13 170.5(2) . . . . ?
C20 C19 B1 C13 -9.4(3) . . . . ?
C24 C19 B1 N1 -68.7(2) . . . . ?
C20 C19 B1 N1 111.4(2) . . . . ?
C14 C13 B1 O1 22.5(2) . . . . ?
C18 C13 B1 O1 -159.84(18) . . . . ?
C14 C13 B1 C19 -101.2(2) . . . . ?
C18 C13 B1 C19 76.5(2) . . . . ?
C14 C13 B1 N1 136.60(17) . . . . ?
C18 C13 B1 N1 -45.7(2) . . . . ?
C5 N1 B1 O1 -153.71(17) . . . . ?
C3 N1 B1 O1 34.4(2) . . . . ?
C5 N1 B1 C19 -38.3(2) . . . . ?
C3 N1 B1 C19 149.76(16) . . . . ?
C5 N1 B1 C13 88.5(2) . . . . ?
C3 N1 B1 C13 -83.39(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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/. 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1014487'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine_mono_CN_BPh2 '
_chemical_melting_point          237-238
_chemical_formula_moiety         'C25 H17 B Cl N3 O'
_chemical_formula_sum            'C25 H17 B Cl N3 O'
_chemical_formula_weight         421.68

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   10.425(4)
_cell_length_b                   21.350(6)
_cell_length_c                   10.573(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.211(8)
_cell_angle_gamma                90.00
_cell_volume                     2092.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20973
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4786
_reflns_number_gt                3386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0786P)²+0.2222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4786
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7371(2) 0.91308(9) 0.5258(2) 0.0462(4) Uani 1 1 d . . .
C2 C 0.7826(2) 0.96239(9) 0.4764(2) 0.0512(5) Uani 1 1 d . . .
H2 H 0.7880 1.0018 0.5160 0.061 Uiso 1 1 calc R . .
C3 C 0.8223(2) 0.95510(8) 0.3653(2) 0.0447(4) Uani 1 1 d . . .
C4 C 0.8459(2) 1.00476(9) 0.2932(2) 0.0538(5) Uani 1 1 d . . .
H4 H 0.8376 1.0461 0.3161 0.065 Uiso 1 1 calc R . .
C5 C 0.8658(2) 0.88798(9) 0.2171(2) 0.0525(5) Uani 1 1 d . . .
H5 H 0.8697 0.8470 0.1892 0.063 Uiso 1 1 calc R . .
C6 C 0.6816(2) 0.91798(9) 0.6313(2) 0.0476(4) Uani 1 1 d . . .
C7 C 0.6671(2) 0.86377(9) 0.6958(2) 0.0541(5) Uani 1 1 d . . .
H7 H 0.6886 0.8252 0.6691 0.065 Uiso 1 1 calc R . .
C8 C 0.6216(2) 0.86629(10) 0.7983(2) 0.0588(5) Uani 1 1 d . . .
H8 H 0.6144 0.8297 0.8425 0.071 Uiso 1 1 calc R . .
C9 C 0.5862(2) 0.92350(10) 0.8360(2) 0.0524(5) Uani 1 1 d . . .
C10 C 0.5966(3) 0.97774(11) 0.7709(2) 0.0611(6) Uani 1 1 d . . .
H10 H 0.5710 1.0160 0.7951 0.073 Uiso 1 1 calc R . .
C11 C 0.6449(3) 0.97514(10) 0.6696(2) 0.0602(6) Uani 1 1 d . . .
H11 H 0.6531 1.0118 0.6265 0.072 Uiso 1 1 calc R . .
C12 C 0.8817(2) 0.99038(9) 0.1879(2) 0.0540(5) Uani 1 1 d . . .
N1 N 0.83544(17) 0.89555(7) 0.32535(16) 0.0441(4) Uani 1 1 d . . .
N2 N 0.8906(2) 0.93245(8) 0.14594(19) 0.0549(4) Uani 1 1 d . . .
N3 N 0.5044(3) 0.92397(11) 1.0312(2) 0.0775(6) Uani 1 1 d . . .
O1 O 0.73643(15) 0.85530(6) 0.48109(14) 0.0491(3) Uani 1 1 d . . .
B1 B 0.8358(2) 0.83642(9) 0.4217(2) 0.0439(5) Uani 1 1 d . . .
C13 C 0.9983(2) 0.82811(8) 0.5453(2) 0.0460(4) Uani 1 1 d . . .
C14 C 1.0280(2) 0.81620(9) 0.6855(2) 0.0520(5) Uani 1 1 d . . .
H14 H 0.9520 0.8151 0.7086 0.062 Uiso 1 1 calc R . .
C15 C 1.1664(3) 0.80596(11) 0.7914(2) 0.0600(5) Uani 1 1 d . . .
H15 H 1.1823 0.7987 0.8841 0.072 Uiso 1 1 calc R . .
C16 C 1.2800(3) 0.80644(12) 0.7607(2) 0.0658(6) Uani 1 1 d . . .
H16 H 1.3732 0.7993 0.8320 0.079 Uiso 1 1 calc R . .
C17 C 1.2558(3) 0.81750(13) 0.6236(3) 0.0685(6) Uani 1 1 d . . .
H17 H 1.3325 0.8179 0.6015 0.082 Uiso 1 1 calc R . .
C18 C 1.1175(2) 0.82802(11) 0.5190(2) 0.0588(5) Uani 1 1 d . . .
H18 H 1.1031 0.8354 0.4267 0.071 Uiso 1 1 calc R . .
C19 C 0.7669(2) 0.77696(9) 0.3202(2) 0.0495(5) Uani 1 1 d . . .
C20 C 0.8436(3) 0.72230(10) 0.3305(3) 0.0705(7) Uani 1 1 d . . .
H20 H 0.9399 0.7193 0.3978 0.085 Uiso 1 1 calc R . .
C21 C 0.7764(5) 0.67197(13) 0.2404(5) 0.1066(13) Uani 1 1 d . . .
H21 H 0.8288 0.6357 0.2477 0.128 Uiso 1 1 calc R . .
C22 C 0.6340(5) 0.67515(18) 0.1409(4) 0.1141(15) Uani 1 1 d . . .
H22 H 0.5899 0.6410 0.0826 0.137 Uiso 1 1 calc R . .
C23 C 0.5577(4) 0.72874(17) 0.1280(3) 0.0935(11) Uani 1 1 d . . .
H23 H 0.4619 0.7315 0.0595 0.112 Uiso 1 1 calc R . .
C24 C 0.6228(3) 0.77883(12) 0.2166(2) 0.0656(6) Uani 1 1 d . . .
H24 H 0.5692 0.8149 0.2071 0.079 Uiso 1 1 calc R . .
C25 C 0.5389(3) 0.92458(10) 0.9447(2) 0.0595(5) Uani 1 1 d . . .
Cl1 Cl 0.91968(10) 1.04868(3) 0.09909(8) 0.0909(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.320(2) . ?
C1 C2 1.354(3) . ?
C1 C6 1.477(3) . ?
C2 C3 1.422(3) . ?
C3 N1 1.366(2) . ?
C3 C4 1.392(3) . ?
C4 C12 1.362(3) . ?
C5 N2 1.309(3) . ?
C5 N1 1.329(2) . ?
C6 C7 1.386(3) . ?
C6 C11 1.394(3) . ?
C7 C8 1.369(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.377(3) . ?
C9 C25 1.442(3) . ?
C10 C11 1.377(3) . ?
C12 N2 1.331(3) . ?
C12 Cl1 1.711(2) . ?
N1 B1 1.621(3) . ?
N3 C25 1.127(3) . ?
O1 B1 1.492(2) . ?
B1 C19 1.604(3) . ?
B1 C13 1.608(3) . ?
C13 C18 1.392(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.364(3) . ?
C16 C17 1.373(3) . ?
C17 C18 1.376(3) . ?
C19 C20 1.390(3) . ?
C19 C24 1.398(3) . ?
C20 C21 1.394(4) . ?
C21 C22 1.373(6) . ?
C22 C23 1.364(5) . ?
C23 C24 1.378(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.30(17) . . ?
O1 C1 C6 113.38(17) . . ?
C2 C1 C6 124.31(17) . . ?
C1 C2 C3 121.29(17) . . ?
N1 C3 C4 118.18(17) . . ?
N1 C3 C2 117.73(16) . . ?
C4 C3 C2 124.08(17) . . ?
C12 C4 C3 117.34(18) . . ?
N2 C5 N1 126.47(18) . . ?
C7 C6 C11 118.80(18) . . ?
C7 C6 C1 118.75(16) . . ?
C11 C6 C1 122.45(19) . . ?
C8 C7 C6 120.80(18) . . ?
C7 C8 C9 119.8(2) . . ?
C10 C9 C8 120.35(19) . . ?
C10 C9 C25 121.23(18) . . ?
C8 C9 C25 118.4(2) . . ?
C9 C10 C11 119.69(19) . . ?
C10 C11 C6 120.5(2) . . ?
N2 C12 C4 124.66(19) . . ?
N2 C12 Cl1 115.11(16) . . ?
C4 C12 Cl1 120.23(16) . . ?
C5 N1 C3 118.43(16) . . ?
C5 N1 B1 120.86(15) . . ?
C3 N1 B1 120.18(15) . . ?
C5 N2 C12 114.84(18) . . ?
C1 O1 B1 120.79(15) . . ?
O1 B1 C19 108.08(16) . . ?
O1 B1 C13 111.36(15) . . ?
C19 B1 C13 116.07(16) . . ?
O1 B1 N1 104.56(14) . . ?
C19 B1 N1 108.93(15) . . ?
C13 B1 N1 107.21(15) . . ?
C18 C13 C14 115.39(19) . . ?
C18 C13 B1 122.89(17) . . ?
C14 C13 B1 121.59(17) . . ?
C15 C14 C13 122.2(2) . . ?
C16 C15 C14 120.4(2) . . ?
C15 C16 C17 119.5(2) . . ?
C16 C17 C18 119.7(2) . . ?
C17 C18 C13 122.9(2) . . ?
C20 C19 C24 117.3(2) . . ?
C20 C19 B1 123.1(2) . . ?
C24 C19 B1 119.58(19) . . ?
C19 C20 C21 120.2(3) . . ?
C22 C21 C20 121.0(3) . . ?
C23 C22 C21 119.6(3) . . ?
C22 C23 C24 120.0(3) . . ?
C23 C24 C19 121.9(3) . . ?
N3 C25 C9 178.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 4.7(3) . . . . ?
C6 C1 C2 C3 -174.09(19) . . . . ?
C1 C2 C3 N1 -10.3(3) . . . . ?
C1 C2 C3 C4 168.5(2) . . . . ?
N1 C3 C4 C12 -0.4(3) . . . . ?
C2 C3 C4 C12 -179.2(2) . . . . ?
O1 C1 C6 C7 14.6(3) . . . . ?
C2 C1 C6 C7 -166.5(2) . . . . ?
O1 C1 C6 C11 -166.26(19) . . . . ?
C2 C1 C6 C11 12.7(3) . . . . ?
C11 C6 C7 C8 -1.8(3) . . . . ?
C1 C6 C7 C8 177.4(2) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C7 C8 C9 C25 -179.8(2) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C25 C9 C10 C11 178.7(2) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
C1 C6 C11 C10 -178.5(2) . . . . ?
C3 C4 C12 N2 2.5(3) . . . . ?
C3 C4 C12 Cl1 -177.34(16) . . . . ?
N2 C5 N1 C3 2.9(3) . . . . ?
N2 C5 N1 B1 -168.7(2) . . . . ?
C4 C3 N1 C5 -2.0(3) . . . . ?
C2 C3 N1 C5 176.87(18) . . . . ?
C4 C3 N1 B1 169.68(18) . . . . ?
C2 C3 N1 B1 -11.4(3) . . . . ?
N1 C5 N2 C12 -1.0(3) . . . . ?
C4 C12 N2 C5 -1.8(3) . . . . ?
Cl1 C12 N2 C5 178.02(17) . . . . ?
C2 C1 O1 B1 24.8(3) . . . . ?
C6 C1 O1 B1 -156.24(17) . . . . ?
C1 O1 B1 C19 -156.29(16) . . . . ?
C1 O1 B1 C13 75.1(2) . . . . ?
C1 O1 B1 N1 -40.4(2) . . . . ?
C5 N1 B1 O1 -154.64(17) . . . . ?
C3 N1 B1 O1 33.9(2) . . . . ?
C5 N1 B1 C19 -39.3(2) . . . . ?
C3 N1 B1 C19 149.20(17) . . . . ?
C5 N1 B1 C13 87.0(2) . . . . ?
C3 N1 B1 C13 -84.46(19) . . . . ?
O1 B1 C13 C18 -161.59(18) . . . . ?
C19 B1 C13 C18 74.2(2) . . . . ?
N1 B1 C13 C18 -47.8(2) . . . . ?
O1 B1 C13 C14 22.8(2) . . . . ?
C19 B1 C13 C14 -101.4(2) . . . . ?
N1 B1 C13 C14 136.65(17) . . . . ?
C18 C13 C14 C15 0.9(3) . . . . ?
B1 C13 C14 C15 176.79(19) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
B1 C13 C18 C17 -176.3(2) . . . . ?
O1 B1 C19 C20 -129.8(2) . . . . ?
C13 B1 C19 C20 -3.9(3) . . . . ?
N1 B1 C19 C20 117.2(2) . . . . ?
O1 B1 C19 C24 49.6(2) . . . . ?
C13 B1 C19 C24 175.50(17) . . . . ?
N1 B1 C19 C24 -63.4(2) . . . . ?
C24 C19 C20 C21 -0.4(3) . . . . ?
B1 C19 C20 C21 179.0(2) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C20 C21 C22 C23 1.3(5) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C20 C19 C24 C23 0.3(3) . . . . ?
B1 C19 C24 C23 -179.07(19) . . . . ?
C10 C9 C25 N3 -150(8) . . . . ?
C8 C9 C25 N3 30(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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/. 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1014488'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine_mono_OMe_BPh2 '
_chemical_melting_point          258-260
_chemical_formula_moiety         'C25 H20 B Cl N2 O2'
_chemical_formula_sum            'C25 H20 B Cl N2 O2'
_chemical_formula_weight         426.69

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   10.102(2)
_cell_length_b                   20.037(4)
_cell_length_c                   10.665(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.7166(10)
_cell_angle_gamma                90.00
_cell_volume                     2156.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9607
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21280
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         27.66
_reflns_number_total             4931
_reflns_number_gt                3873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0866P)²+0.4731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4931
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04867(17) 1.07028(9) 0.72176(16) 0.0413(4) Uani 1 1 d . . .
C2 C 0.08112(19) 1.01925(9) 0.64431(19) 0.0474(4) Uani 1 1 d . . .
H2 H 0.0344 0.9793 0.6472 0.057 Uiso 1 1 calc R . .
C3 C 0.18440(17) 1.02564(9) 0.55952(17) 0.0416(4) Uani 1 1 d . . .
C4 C 0.23662(19) 0.97090(9) 0.49593(19) 0.0492(4) Uani 1 1 d . . .
H4 H 0.2044 0.9280 0.5076 0.059 Uiso 1 1 calc R . .
C5 C 0.33918(19) 1.09157(10) 0.46149(19) 0.0482(4) Uani 1 1 d . . .
H5 H 0.3763 1.1337 0.4521 0.058 Uiso 1 1 calc R . .
C6 C -0.04768(19) 1.06479(10) 0.82099(17) 0.0460(4) Uani 1 1 d . . .
C7 C -0.0885(2) 1.12189(12) 0.8835(2) 0.0571(5) Uani 1 1 d . . .
H7 H -0.0515 1.1629 0.8645 0.069 Uiso 1 1 calc R . .
C8 C -0.1828(3) 1.11865(13) 0.9732(2) 0.0669(6) Uani 1 1 d . . .
H8 H -0.2099 1.1575 1.0122 0.080 Uiso 1 1 calc R . .
C9 C -0.2368(2) 1.05830(13) 1.0051(2) 0.0628(6) Uani 1 1 d . . .
C10 C -0.1958(2) 1.00093(13) 0.9473(2) 0.0647(6) Uani 1 1 d . . .
H10 H -0.2304 0.9599 0.9697 0.078 Uiso 1 1 calc R . .
C11 C -0.1021(2) 1.00423(12) 0.8546(2) 0.0568(5) Uani 1 1 d . . .
H11 H -0.0761 0.9653 0.8152 0.068 Uiso 1 1 calc R . .
C12 C 0.33558(19) 0.98257(10) 0.41697(19) 0.0486(4) Uani 1 1 d . . .
C13 C 0.04662(18) 1.17064(8) 0.48986(18) 0.0430(4) Uani 1 1 d . . .
C14 C -0.08071(19) 1.18692(9) 0.5259(2) 0.0492(4) Uani 1 1 d . . .
H14 H -0.0980 1.1874 0.6108 0.059 Uiso 1 1 calc R . .
C15 C -0.1817(2) 1.20231(11) 0.4382(3) 0.0631(6) Uani 1 1 d . . .
H15 H -0.2657 1.2128 0.4644 0.076 Uiso 1 1 calc R . .
C16 C -0.1573(3) 1.20201(13) 0.3123(3) 0.0703(7) Uani 1 1 d . . .
H16 H -0.2254 1.2117 0.2534 0.084 Uiso 1 1 calc R . .
C17 C -0.0326(3) 1.18735(13) 0.2733(2) 0.0685(6) Uani 1 1 d . . .
H17 H -0.0158 1.1879 0.1883 0.082 Uiso 1 1 calc R . .
C18 C 0.0670(2) 1.17182(11) 0.3613(2) 0.0569(5) Uani 1 1 d . . .
H18 H 0.1507 1.1618 0.3340 0.068 Uiso 1 1 calc R . .
C19 C 0.26999(18) 1.20976(9) 0.62663(18) 0.0444(4) Uani 1 1 d . . .
C20 C 0.2805(3) 1.26823(11) 0.5587(3) 0.0662(6) Uani 1 1 d . . .
H20 H 0.2221 1.2760 0.4902 0.079 Uiso 1 1 calc R . .
C21 C 0.3770(3) 1.31579(12) 0.5911(3) 0.0830(8) Uani 1 1 d . . .
H21 H 0.3830 1.3544 0.5432 0.100 Uiso 1 1 calc R . .
C22 C 0.4625(3) 1.30642(13) 0.6919(3) 0.0765(7) Uani 1 1 d . . .
H22 H 0.5265 1.3384 0.7132 0.092 Uiso 1 1 calc R . .
C23 C 0.4533(3) 1.24922(14) 0.7621(3) 0.0724(7) Uani 1 1 d . . .
H23 H 0.5108 1.2424 0.8316 0.087 Uiso 1 1 calc R . .
C24 C 0.3581(2) 1.20174(11) 0.7289(2) 0.0571(5) Uani 1 1 d . . .
H24 H 0.3534 1.1632 0.7770 0.069 Uiso 1 1 calc R . .
C25 C -0.3809(3) 1.00151(17) 1.1416(3) 0.0818(8) Uani 1 1 d . . .
H25 H -0.4410 0.9823 1.0792 0.123 Uiso 1 1 calc R . .
H25A H -0.4272 1.0106 1.2163 0.123 Uiso 1 1 calc R . .
H25B H -0.3097 0.9709 1.1607 0.123 Uiso 1 1 calc R . .
N1 N 0.23809(14) 1.08699(7) 0.53882(14) 0.0396(3) Uani 1 1 d . . .
N2 N 0.39107(17) 1.04241(9) 0.39760(17) 0.0526(4) Uani 1 1 d . . .
O1 O 0.10528(13) 1.12964(6) 0.71283(12) 0.0444(3) Uani 1 1 d . . .
O2 O -0.3293(2) 1.06116(10) 1.09552(19) 0.0879(6) Uani 1 1 d . . .
Cl1 Cl 0.39867(6) 0.91644(3) 0.33441(6) 0.0671(2) Uani 1 1 d . . .
B1 B 0.16298(19) 1.15190(10) 0.59335(19) 0.0403(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.325(2) . ?
C1 C2 1.364(3) . ?
C1 C6 1.476(3) . ?
C2 C3 1.419(3) . ?
C3 N1 1.366(2) . ?
C3 C4 1.405(3) . ?
C4 C12 1.358(3) . ?
C5 N2 1.320(2) . ?
C5 N1 1.346(2) . ?
C6 C11 1.386(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.376(4) . ?
C9 O2 1.375(3) . ?
C9 C10 1.378(4) . ?
C10 C11 1.402(3) . ?
C12 N2 1.344(3) . ?
C12 Cl1 1.7293(19) . ?
C13 C18 1.397(3) . ?
C13 C14 1.398(3) . ?
C13 B1 1.618(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.376(4) . ?
C16 C17 1.377(4) . ?
C17 C18 1.378(3) . ?
C19 C20 1.384(3) . ?
C19 C24 1.385(3) . ?
C19 B1 1.613(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.360(4) . ?
C22 C23 1.374(4) . ?
C23 C24 1.386(3) . ?
C25 O2 1.402(3) . ?
N1 B1 1.627(2) . ?
O1 B1 1.494(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
O1 C1 C2 120.82(16) . . ?
O1 C1 C6 114.84(16) . . ?
C2 C1 C6 124.34(16) . . ?
C1 C2 C3 121.57(16) . . ?
N1 C3 C4 117.61(17) . . ?
N1 C3 C2 119.60(16) . . ?
C4 C3 C2 122.79(17) . . ?
C12 C4 C3 117.98(17) . . ?
N2 C5 N1 126.63(18) . . ?
C11 C6 C7 117.64(18) . . ?
C11 C6 C1 122.27(18) . . ?
C7 C6 C1 120.09(17) . . ?
C8 C7 C6 121.4(2) . . ?
C9 C8 C7 120.4(2) . . ?
O2 C9 C8 115.3(2) . . ?
O2 C9 C10 125.3(2) . . ?
C8 C9 C10 119.4(2) . . ?
C9 C10 C11 120.3(2) . . ?
C6 C11 C10 120.8(2) . . ?
N2 C12 C4 125.02(17) . . ?
N2 C12 Cl1 116.04(15) . . ?
C4 C12 Cl1 118.93(15) . . ?
C18 C13 C14 116.49(18) . . ?
C18 C13 B1 122.54(17) . . ?
C14 C13 B1 120.97(17) . . ?
C15 C14 C13 121.6(2) . . ?
C16 C15 C14 119.8(2) . . ?
C15 C16 C17 120.3(2) . . ?
C16 C17 C18 119.4(2) . . ?
C17 C18 C13 122.4(2) . . ?
C20 C19 C24 116.64(19) . . ?
C20 C19 B1 124.07(18) . . ?
C24 C19 B1 119.29(17) . . ?
C19 C20 C21 121.2(2) . . ?
C22 C21 C20 120.8(3) . . ?
C21 C22 C23 119.3(2) . . ?
C22 C23 C24 119.8(3) . . ?
C19 C24 C23 122.2(2) . . ?
C5 N1 C3 118.62(15) . . ?
C5 N1 B1 123.01(14) . . ?
C3 N1 B1 117.79(14) . . ?
C5 N2 C12 114.06(17) . . ?
C1 O1 B1 121.09(14) . . ?
C9 O2 C25 119.1(2) . . ?
O1 B1 C19 108.14(15) . . ?
O1 B1 C13 110.54(15) . . ?
C19 B1 C13 116.16(15) . . ?
O1 B1 N1 105.87(13) . . ?
C19 B1 N1 109.52(14) . . ?
C13 B1 N1 106.12(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.8(3) . . . . ?
C6 C1 C2 C3 -173.36(17) . . . . ?
C1 C2 C3 N1 -11.2(3) . . . . ?
C1 C2 C3 C4 167.81(18) . . . . ?
N1 C3 C4 C12 -0.9(3) . . . . ?
C2 C3 C4 C12 -179.89(18) . . . . ?
O1 C1 C6 C11 -170.94(17) . . . . ?
C2 C1 C6 C11 8.2(3) . . . . ?
O1 C1 C6 C7 9.9(3) . . . . ?
C2 C1 C6 C7 -170.89(19) . . . . ?
C11 C6 C7 C8 -1.9(3) . . . . ?
C1 C6 C7 C8 177.2(2) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
C7 C8 C9 O2 179.8(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
O2 C9 C10 C11 179.0(2) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
C1 C6 C11 C10 -178.47(19) . . . . ?
C9 C10 C11 C6 1.0(4) . . . . ?
C3 C4 C12 N2 2.3(3) . . . . ?
C3 C4 C12 Cl1 -178.32(14) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
B1 C13 C14 C15 -179.25(17) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
B1 C13 C18 C17 179.5(2) . . . . ?
C24 C19 C20 C21 1.2(4) . . . . ?
B1 C19 C20 C21 -178.8(2) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C20 C19 C24 C23 -0.5(3) . . . . ?
B1 C19 C24 C23 179.4(2) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
N2 C5 N1 C3 2.7(3) . . . . ?
N2 C5 N1 B1 -168.34(18) . . . . ?
C4 C3 N1 C5 -1.4(3) . . . . ?
C2 C3 N1 C5 177.64(17) . . . . ?
C4 C3 N1 B1 170.13(16) . . . . ?
C2 C3 N1 B1 -10.8(2) . . . . ?
N1 C5 N2 C12 -1.4(3) . . . . ?
C4 C12 N2 C5 -1.2(3) . . . . ?
Cl1 C12 N2 C5 179.40(14) . . . . ?
C2 C1 O1 B1 24.0(2) . . . . ?
C6 C1 O1 B1 -156.79(15) . . . . ?
C8 C9 O2 C25 -174.5(2) . . . . ?
C10 C9 O2 C25 5.1(4) . . . . ?
C1 O1 B1 C19 -158.17(15) . . . . ?
C1 O1 B1 C13 73.64(19) . . . . ?
C1 O1 B1 N1 -40.9(2) . . . . ?
C20 C19 B1 O1 -136.1(2) . . . . ?
C24 C19 B1 O1 44.0(2) . . . . ?
C20 C19 B1 C13 -11.2(3) . . . . ?
C24 C19 B1 C13 168.87(18) . . . . ?
C20 C19 B1 N1 109.0(2) . . . . ?
C24 C19 B1 N1 -71.0(2) . . . . ?
C18 C13 B1 O1 -158.65(17) . . . . ?
C14 C13 B1 O1 21.6(2) . . . . ?
C18 C13 B1 C19 77.7(2) . . . . ?
C14 C13 B1 C19 -102.04(19) . . . . ?
C18 C13 B1 N1 -44.3(2) . . . . ?
C14 C13 B1 N1 135.99(16) . . . . ?
C5 N1 B1 O1 -155.15(16) . . . . ?
C3 N1 B1 O1 33.7(2) . . . . ?
C5 N1 B1 C19 -38.8(2) . . . . ?
C3 N1 B1 C19 150.08(15) . . . . ?
C5 N1 B1 C13 87.34(19) . . . . ?
C3 N1 B1 C13 -83.81(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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/. 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1014489'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine_mono_NMe2_BPh2 '
_chemical_melting_point          241-243
_chemical_formula_moiety         'C26 H23 B Cl N3 O'
_chemical_formula_sum            'C26 H23 B Cl N3 O'
_chemical_formula_weight         439.73

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   8.885(8)
_cell_length_b                   12.288(11)
_cell_length_c                   20.917(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.033(12)
_cell_angle_gamma                90.00
_cell_volume                     2267(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21423
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5132
_reflns_number_gt                3860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0572P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5132
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9588(2) 1.17296(14) 1.08306(8) 0.0465(4) Uani 1 1 d . . .
C2 C 0.9054(2) 1.11136(15) 1.03070(8) 0.0490(4) Uani 1 1 d . . .
H2 H 0.9375 1.1271 0.9911 0.059 Uiso 1 1 calc R . .
C3 C 0.80347(19) 1.02509(14) 1.03494(8) 0.0453(4) Uani 1 1 d . . .
C4 C 0.7238(2) 0.97416(15) 0.98094(9) 0.0493(4) Uani 1 1 d . . .
H4 H 0.7371 0.9957 0.9394 0.059 Uiso 1 1 calc R . .
C5 C 0.6759(2) 0.90875(16) 1.09822(10) 0.0566(5) Uani 1 1 d . . .
H5 H 0.6575 0.8879 1.1393 0.068 Uiso 1 1 calc R . .
C6 C 1.0534(2) 1.26938(14) 1.07903(9) 0.0476(4) Uani 1 1 d . . .
C7 C 1.1356(2) 1.31411(15) 1.13381(9) 0.0553(5) Uani 1 1 d . . .
H7 H 1.1261 1.2835 1.1738 0.066 Uiso 1 1 calc R . .
C8 C 1.2299(2) 1.40183(16) 1.13066(10) 0.0585(5) Uani 1 1 d . . .
H8 H 1.2853 1.4276 1.1682 0.070 Uiso 1 1 calc R . .
C9 C 1.2445(2) 1.45327(15) 1.07205(10) 0.0543(5) Uani 1 1 d . . .
C10 C 1.1618(3) 1.40855(17) 1.01675(10) 0.0646(5) Uani 1 1 d . . .
H10 H 1.1693 1.4399 0.9768 0.078 Uiso 1 1 calc R . .
C11 C 1.0703(2) 1.31962(16) 1.02048(10) 0.0596(5) Uani 1 1 d . . .
H11 H 1.0178 1.2918 0.9828 0.071 Uiso 1 1 calc R . .
C12 C 0.6267(2) 0.89243(15) 0.99141(9) 0.0507(4) Uani 1 1 d . . .
C19 C 0.8021(2) 1.02790(16) 1.21937(9) 0.0522(4) Uani 1 1 d . . .
C24 C 0.7219(3) 1.11619(19) 1.23724(11) 0.0704(6) Uani 1 1 d . . .
H24 H 0.7217 1.1800 1.2134 0.085 Uiso 1 1 calc R . .
C23 C 0.6405(3) 1.1125(2) 1.29042(13) 0.0879(8) Uani 1 1 d . . .
H23 H 0.5896 1.1742 1.3021 0.105 Uiso 1 1 calc R . .
C22 C 0.6354(3) 1.0192(2) 1.32525(11) 0.0795(8) Uani 1 1 d . . .
H22 H 0.5791 1.0164 1.3599 0.095 Uiso 1 1 calc R . .
C21 C 0.7130(3) 0.9304(2) 1.30906(11) 0.0789(7) Uani 1 1 d . . .
H21 H 0.7107 0.8664 1.3327 0.095 Uiso 1 1 calc R . .
C20 C 0.7963(3) 0.93521(19) 1.25681(10) 0.0689(6) Uani 1 1 d . . .
H20 H 0.8500 0.8739 1.2467 0.083 Uiso 1 1 calc R . .
C13 C 1.0444(2) 0.96080(15) 1.16190(8) 0.0475(4) Uani 1 1 d . . .
C14 C 1.1811(2) 1.00625(17) 1.18935(9) 0.0595(5) Uani 1 1 d . . .
H14 H 1.1824 1.0785 1.2027 0.071 Uiso 1 1 calc R . .
C15 C 1.3155(2) 0.9472(2) 1.19741(11) 0.0701(6) Uani 1 1 d . . .
H15 H 1.4047 0.9803 1.2155 0.084 Uiso 1 1 calc R . .
C16 C 1.3168(2) 0.8411(2) 1.17891(11) 0.0705(6) Uani 1 1 d . . .
H16 H 1.4064 0.8012 1.1848 0.085 Uiso 1 1 calc R . .
C17 C 1.1844(2) 0.79346(19) 1.15144(11) 0.0674(6) Uani 1 1 d . . .
H17 H 1.1846 0.7211 1.1385 0.081 Uiso 1 1 calc R . .
C18 C 1.0510(2) 0.85259(16) 1.14299(9) 0.0542(4) Uani 1 1 d . . .
H18 H 0.9629 0.8189 1.1241 0.065 Uiso 1 1 calc R . .
C25 C 1.3416(3) 1.6003(2) 1.00840(14) 0.0840(7) Uani 1 1 d . . .
H25 H 1.2407 1.6149 0.9882 0.126 Uiso 1 1 calc R . .
H25A H 1.3939 1.5561 0.9804 0.126 Uiso 1 1 calc R . .
H25B H 1.3951 1.6677 1.0167 0.126 Uiso 1 1 calc R . .
C26 C 1.4415(3) 1.5747(2) 1.12292(14) 0.0851(7) Uani 1 1 d . . .
H26 H 1.5109 1.5159 1.1341 0.128 Uiso 1 1 calc R . .
H26A H 1.3881 1.5912 1.1589 0.128 Uiso 1 1 calc R . .
H26B H 1.4968 1.6377 1.1119 0.128 Uiso 1 1 calc R . .
N1 N 0.77949(16) 0.98753(11) 1.09468(7) 0.0463(3) Uani 1 1 d . . .
N2 N 0.59795(18) 0.85824(14) 1.04973(8) 0.0579(4) Uani 1 1 d . . .
N3 N 1.3343(2) 1.54332(15) 1.06847(10) 0.0716(5) Uani 1 1 d . . .
O1 O 0.92542(15) 1.14758(10) 1.14143(6) 0.0525(3) Uani 1 1 d . . .
Cl1 Cl 0.52757(6) 0.82666(5) 0.92661(3) 0.06879(18) Uani 1 1 d . . .
B1 B 0.8901(2) 1.03167(17) 1.15608(10) 0.0489(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.328(2) . ?
C1 C2 1.368(3) . ?
C1 C6 1.461(3) . ?
C2 C3 1.404(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.373(2) . ?
C3 C4 1.404(3) . ?
C4 C12 1.359(3) . ?
C4 H4 0.9300 . ?
C5 N2 1.312(3) . ?
C5 N1 1.344(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C11 1.396(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.372(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 N2 1.344(3) . ?
C12 Cl1 1.724(2) . ?
C19 C24 1.375(3) . ?
C19 C20 1.387(3) . ?
C19 B1 1.619(3) . ?
C24 C23 1.400(3) . ?
C24 H24 0.9300 . ?
C23 C22 1.363(4) . ?
C23 H23 0.9300 . ?
C22 C21 1.356(4) . ?
C22 H22 0.9300 . ?
C21 C20 1.394(3) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C13 C18 1.390(3) . ?
C13 C14 1.395(3) . ?
C13 B1 1.616(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C25 N3 1.447(3) . ?
C25 H25 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C26 N3 1.445(3) . ?
C26 H26 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
N1 B1 1.613(3) . ?
O1 B1 1.498(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 120.75(17) . . ?
O1 C1 C6 115.99(16) . . ?
C2 C1 C6 123.26(16) . . ?
C1 C2 C3 122.06(16) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
N1 C3 C2 118.97(16) . . ?
N1 C3 C4 117.59(17) . . ?
C2 C3 C4 123.44(16) . . ?
C12 C4 C3 117.84(17) . . ?
C12 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N2 C5 N1 126.74(18) . . ?
N2 C5 H5 116.6 . . ?
N1 C5 H5 116.6 . . ?
C7 C6 C11 116.41(18) . . ?
C7 C6 C1 121.29(17) . . ?
C11 C6 C1 122.26(18) . . ?
C8 C7 C6 122.14(18) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 121.31(19) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
N3 C9 C8 121.95(19) . . ?
N3 C9 C10 121.34(19) . . ?
C8 C9 C10 116.72(19) . . ?
C11 C10 C9 121.31(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 122.1(2) . . ?
C10 C11 H11 119.0 . . ?
C6 C11 H11 119.0 . . ?
N2 C12 C4 124.90(17) . . ?
N2 C12 Cl1 115.55(15) . . ?
C4 C12 Cl1 119.54(15) . . ?
C24 C19 C20 115.98(19) . . ?
C24 C19 B1 121.22(18) . . ?
C20 C19 B1 122.73(18) . . ?
C19 C24 C23 121.8(2) . . ?
C19 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C21 C22 C23 119.5(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C19 C20 C21 122.5(2) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C18 C13 C14 115.78(18) . . ?
C18 C13 B1 123.97(17) . . ?
C14 C13 B1 120.21(18) . . ?
C15 C14 C13 122.2(2) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 122.1(2) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N3 C25 H25 109.5 . . ?
N3 C25 H25A 109.5 . . ?
H25 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C26 H26 109.5 . . ?
N3 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C5 N1 C3 118.41(16) . . ?
C5 N1 B1 123.58(15) . . ?
C3 N1 B1 117.67(15) . . ?
C5 N2 C12 114.38(17) . . ?
C9 N3 C26 120.3(2) . . ?
C9 N3 C25 121.7(2) . . ?
C26 N3 C25 117.4(2) . . ?
C1 O1 B1 119.15(14) . . ?
O1 B1 N1 106.22(15) . . ?
O1 B1 C13 109.32(16) . . ?
N1 B1 C13 107.90(15) . . ?
O1 B1 C19 109.19(14) . . ?
N1 B1 C19 109.47(16) . . ?
C13 B1 C19 114.41(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.5(3) . . . . ?
C6 C1 C2 C3 -174.02(16) . . . . ?
C1 C2 C3 N1 -13.0(3) . . . . ?
C1 C2 C3 C4 167.14(17) . . . . ?
N1 C3 C4 C12 1.0(2) . . . . ?
C2 C3 C4 C12 -179.11(16) . . . . ?
O1 C1 C6 C7 16.4(2) . . . . ?
C2 C1 C6 C7 -164.07(18) . . . . ?
O1 C1 C6 C11 -165.66(17) . . . . ?
C2 C1 C6 C11 13.9(3) . . . . ?
C11 C6 C7 C8 -0.9(3) . . . . ?
C1 C6 C7 C8 177.19(17) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
C7 C8 C9 N3 177.70(18) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
N3 C9 C10 C11 -179.0(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C1 C6 C11 C10 -178.47(19) . . . . ?
C3 C4 C12 N2 1.8(3) . . . . ?
C3 C4 C12 Cl1 -179.46(13) . . . . ?
C20 C19 C24 C23 0.5(3) . . . . ?
B1 C19 C24 C23 177.5(2) . . . . ?
C19 C24 C23 C22 -1.8(4) . . . . ?
C24 C23 C22 C21 1.7(4) . . . . ?
C23 C22 C21 C20 -0.4(4) . . . . ?
C24 C19 C20 C21 0.8(3) . . . . ?
B1 C19 C20 C21 -176.1(2) . . . . ?
C22 C21 C20 C19 -0.9(4) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
B1 C13 C14 C15 177.67(17) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
B1 C13 C18 C17 -177.09(18) . . . . ?
N2 C5 N1 C3 3.7(3) . . . . ?
N2 C5 N1 B1 -169.49(18) . . . . ?
C2 C3 N1 C5 176.60(16) . . . . ?
C4 C3 N1 C5 -3.5(2) . . . . ?
C2 C3 N1 B1 -9.8(2) . . . . ?
C4 C3 N1 B1 170.11(15) . . . . ?
N1 C5 N2 C12 -1.0(3) . . . . ?
C4 C12 N2 C5 -1.9(3) . . . . ?
Cl1 C12 N2 C5 179.34(14) . . . . ?
C8 C9 N3 C26 13.1(3) . . . . ?
C10 C9 N3 C26 -167.3(2) . . . . ?
C8 C9 N3 C25 -176.0(2) . . . . ?
C10 C9 N3 C25 3.6(3) . . . . ?
C2 C1 O1 B1 26.4(2) . . . . ?
C6 C1 O1 B1 -154.03(16) . . . . ?
C1 O1 B1 N1 -43.7(2) . . . . ?
C1 O1 B1 C13 72.5(2) . . . . ?
C1 O1 B1 C19 -161.69(16) . . . . ?
C5 N1 B1 O1 -151.56(15) . . . . ?
C3 N1 B1 O1 35.2(2) . . . . ?
C5 N1 B1 C13 91.31(19) . . . . ?
C3 N1 B1 C13 -81.97(19) . . . . ?
C5 N1 B1 C19 -33.8(2) . . . . ?
C3 N1 B1 C19 152.94(15) . . . . ?
C18 C13 B1 O1 -146.02(17) . . . . ?
C14 C13 B1 O1 36.4(2) . . . . ?
C18 C13 B1 N1 -30.9(2) . . . . ?
C14 C13 B1 N1 151.52(15) . . . . ?
C18 C13 B1 C19 91.2(2) . . . . ?
C14 C13 B1 C19 -86.4(2) . . . . ?
C24 C19 B1 O1 24.2(3) . . . . ?
C20 C19 B1 O1 -159.01(19) . . . . ?
C24 C19 B1 N1 -91.7(2) . . . . ?
C20 C19 B1 N1 85.1(2) . . . . ?
C24 C19 B1 C13 147.10(19) . . . . ?
C20 C19 B1 C13 -36.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
