# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_20151208
_database_code_depnum_ccdc_archive 'CCDC 1446356'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 B N2 O2'
_chemical_formula_weight         402.24

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

_symmetry_cell_setting           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                   9.261(3)
_cell_length_b                   10.162(3)
_cell_length_c                   21.929(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.901(7)
_cell_angle_gamma                90.00
_cell_volume                     2052.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1656
_cell_measurement_theta_min      2.2110
_cell_measurement_theta_max      20.6693

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_T_max  0.7228
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11516
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.23
_reflns_number_total             3677
_reflns_number_gt                1965
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0940P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3677
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3832(4) 0.3698(3) 0.16430(14) 0.0459(8) Uani 1 1 d . . .
C2 C 0.4241(4) 0.5005(3) 0.17299(16) 0.0622(10) Uani 1 1 d . . .
H2 H 0.5128 0.5279 0.1611 0.075 Uiso 1 1 calc R . .
C3 C 0.3369(5) 0.5909(3) 0.19882(18) 0.0747(12) Uani 1 1 d . . .
H3 H 0.3675 0.6778 0.2038 0.090 Uiso 1 1 calc R . .
C4 C 0.2075(5) 0.5542(4) 0.21698(17) 0.0706(11) Uani 1 1 d . . .
H4 H 0.1491 0.6153 0.2343 0.085 Uiso 1 1 calc R . .
C5 C 0.1638(4) 0.4260(4) 0.20945(17) 0.0697(11) Uani 1 1 d . . .
H5 H 0.0750 0.3992 0.2216 0.084 Uiso 1 1 calc R . .
C6 C 0.2512(4) 0.3377(3) 0.18410(16) 0.0609(10) Uani 1 1 d . . .
H6 H 0.2199 0.2509 0.1799 0.073 Uiso 1 1 calc R . .
C7 C 0.7434(4) 0.3476(4) 0.12184(19) 0.0714(11) Uani 1 1 d . . .
H7 H 0.7679 0.3263 0.1628 0.086 Uiso 1 1 calc R . .
C8 C 0.8480(5) 0.4036(5) 0.0888(2) 0.0914(14) Uani 1 1 d . . .
H8 H 0.9404 0.4209 0.1078 0.110 Uiso 1 1 calc R . .
C9 C 0.8151(5) 0.4329(4) 0.0290(2) 0.0817(12) Uani 1 1 d . . .
H9 H 0.8848 0.4705 0.0067 0.098 Uiso 1 1 calc R . .
C10 C 0.6807(5) 0.4075(4) 0.0015(2) 0.0825(13) Uani 1 1 d . . .
H10 H 0.6581 0.4263 -0.0399 0.099 Uiso 1 1 calc R . .
C11 C 0.5782(4) 0.3542(3) 0.03457(17) 0.0625(10) Uani 1 1 d . . .
H11 H 0.4860 0.3386 0.0148 0.075 Uiso 1 1 calc R . .
C12 C 0.6045(4) 0.3225(3) 0.09570(15) 0.0467(8) Uani 1 1 d . . .
C13 C 0.6912(4) -0.0140(3) 0.20952(17) 0.0625(10) Uani 1 1 d . . .
H13 H 0.7353 0.0304 0.2435 0.075 Uiso 1 1 calc R . .
C14 C 0.7317(4) -0.1413(4) 0.1981(2) 0.0711(11) Uani 1 1 d . . .
H14 H 0.8045 -0.1814 0.2240 0.085 Uiso 1 1 calc R . .
C15 C 0.6656(4) -0.2096(3) 0.1488(2) 0.0708(12) Uani 1 1 d . . .
H15 H 0.6939 -0.2956 0.1417 0.085 Uiso 1 1 calc R . .
C16 C 0.5589(4) -0.1523(3) 0.11028(18) 0.0632(10) Uani 1 1 d . . .
H16 H 0.5130 -0.1992 0.0774 0.076 Uiso 1 1 calc R . .
C17 C 0.5193(4) -0.0217(3) 0.12082(15) 0.0485(8) Uani 1 1 d . . .
C18 C 0.5858(4) 0.0478(3) 0.17088(15) 0.0484(8) Uani 1 1 d . . .
C19 C 0.1298(4) 0.0837(3) -0.03679(15) 0.0523(9) Uani 1 1 d . . .
C20 C 0.0380(4) 0.1864(4) -0.05401(18) 0.0702(11) Uani 1 1 d . . .
H20 H 0.0445 0.2644 -0.0317 0.084 Uiso 1 1 calc R . .
C21 C -0.0627(5) 0.1742(4) -0.1037(2) 0.0851(13) Uani 1 1 d . . .
H21 H -0.1251 0.2437 -0.1150 0.102 Uiso 1 1 calc R . .
C22 C -0.0720(5) 0.0587(6) -0.1372(2) 0.0892(14) Uani 1 1 d . . .
H22 H -0.1389 0.0514 -0.1716 0.107 Uiso 1 1 calc R . .
C23 C 0.0169(5) -0.0444(5) -0.11967(19) 0.0810(13) Uani 1 1 d . . .
H23 H 0.0089 -0.1226 -0.1418 0.097 Uiso 1 1 calc R . .
C24 C 0.1184(4) -0.0334(4) -0.06947(16) 0.0638(10) Uani 1 1 d . . .
H24 H 0.1788 -0.1039 -0.0576 0.077 Uiso 1 1 calc R . .
C25 C 0.2374(4) 0.1007(3) 0.01467(15) 0.0480(8) Uani 1 1 d . . .
C26 C 0.4103(3) 0.0460(3) 0.08332(14) 0.0449(8) Uani 1 1 d . . .
B1 B 0.4825(4) 0.2652(3) 0.13439(17) 0.0474(10) Uani 1 1 d . . .
N1 N 0.2688(3) 0.2068(2) 0.04578(12) 0.0500(7) Uani 1 1 d . . .
N2 N 0.3803(3) 0.1706(2) 0.08970(12) 0.0459(7) Uani 1 1 d . . .
O1 O 0.3234(2) -0.00388(18) 0.03641(10) 0.0524(6) Uani 1 1 d . . .
O2 O 0.5445(2) 0.17122(19) 0.18356(10) 0.0549(7) 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 C6 1.378(5) . ?
C1 C2 1.388(4) . ?
C1 B1 1.591(5) . ?
C2 C3 1.382(5) . ?
C3 C4 1.354(6) . ?
C4 C5 1.370(5) . ?
C5 C6 1.365(5) . ?
C7 C12 1.377(5) . ?
C7 C8 1.391(6) . ?
C8 C9 1.349(6) . ?
C9 C10 1.351(6) . ?
C10 C11 1.365(5) . ?
C11 C12 1.376(5) . ?
C12 B1 1.591(5) . ?
C13 C14 1.376(5) . ?
C13 C18 1.377(4) . ?
C14 C15 1.374(5) . ?
C15 C16 1.363(5) . ?
C16 C17 1.403(4) . ?
C17 C18 1.394(4) . ?
C17 C26 1.413(4) . ?
C18 O2 1.349(4) . ?
C19 C20 1.374(5) . ?
C19 C24 1.388(4) . ?
C19 C25 1.437(4) . ?
C20 C21 1.365(5) . ?
C21 C22 1.383(6) . ?
C22 C23 1.362(6) . ?
C23 C24 1.377(5) . ?
C25 N1 1.293(4) . ?
C25 O1 1.384(4) . ?
C26 N2 1.307(4) . ?
C26 O1 1.339(3) . ?
B1 O2 1.509(4) . ?
B1 N2 1.610(4) . ?
N1 N2 1.387(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
C6 C1 C2 115.0(3) . . ?
C6 C1 B1 122.7(3) . . ?
C2 C1 B1 122.3(3) . . ?
C3 C2 C1 122.0(4) . . ?
C4 C3 C2 120.6(4) . . ?
C3 C4 C5 119.1(4) . . ?
C6 C5 C4 119.6(4) . . ?
C5 C6 C1 123.7(3) . . ?
C12 C7 C8 122.0(4) . . ?
C9 C8 C7 119.8(4) . . ?
C8 C9 C10 119.8(4) . . ?
C9 C10 C11 119.9(4) . . ?
C10 C11 C12 123.2(4) . . ?
C11 C12 C7 115.3(3) . . ?
C11 C12 B1 122.7(3) . . ?
C7 C12 B1 122.0(3) . . ?
C14 C13 C18 120.4(4) . . ?
C15 C14 C13 120.7(4) . . ?
C16 C15 C14 120.5(3) . . ?
C15 C16 C17 119.2(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 C26 116.3(3) . . ?
C16 C17 C26 123.2(3) . . ?
O2 C18 C13 119.7(3) . . ?
O2 C18 C17 121.4(3) . . ?
C13 C18 C17 118.8(3) . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 C25 119.0(3) . . ?
C24 C19 C25 121.2(3) . . ?
C21 C20 C19 120.2(4) . . ?
C20 C21 C22 120.0(4) . . ?
C23 C22 C21 120.0(4) . . ?
C22 C23 C24 120.4(4) . . ?
C23 C24 C19 119.5(4) . . ?
N1 C25 O1 111.6(3) . . ?
N1 C25 C19 128.0(3) . . ?
O1 C25 C19 120.4(3) . . ?
N2 C26 O1 109.4(3) . . ?
N2 C26 C17 123.8(3) . . ?
O1 C26 C17 126.9(3) . . ?
O2 B1 C1 108.8(3) . . ?
O2 B1 C12 112.0(3) . . ?
C1 B1 C12 116.6(3) . . ?
O2 B1 N2 102.3(2) . . ?
C1 B1 N2 108.7(3) . . ?
C12 B1 N2 107.4(3) . . ?
C25 N1 N2 104.9(2) . . ?
C26 N2 N1 109.5(2) . . ?
C26 N2 B1 121.7(3) . . ?
N1 N2 B1 127.8(2) . . ?
C26 O1 C25 104.7(2) . . ?
C18 O2 B1 122.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.066
