# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_20180331-wz-bhcn_0m
_database_code_depnum_ccdc_archive 'CCDC 1853381'
loop_
_audit_author_name
_audit_author_address
qq caep
_audit_update_record             
;
2018-07-04 deposited with the CCDC.	2019-04-12 downloaded from the CCDC.
;
_audit_creation_date             2018-05-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 P, C3 H4 B N4'
_chemical_formula_sum            'C27 H24 B N4 P'
_chemical_formula_weight         446.28
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.170(2)
_cell_length_b                   14.187(4)
_cell_length_c                   20.986(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.499(8)
_cell_angle_gamma                90
_cell_volume                     2430.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.78
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8830.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         1.733
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3129
_reflns_number_total             4922
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C2(H2), C14(H14), C15(H15), C8(H8), C12(H12), C24(H24),
 C9(H9), C16(H16), C6(H6), C17(H17), C21(H21), C4(H4), C11(H11), C3(H3),
 C22(H22), C5(H5), C10(H10), C23(H23), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P1 P 0.51506(8) 0.34272(5) 0.80482(3) 0.02509(19) Uani 1 1 d . . . . .
N2 N 0.7338(3) 0.28099(16) 0.53454(10) 0.0325(5) Uani 1 1 d . . . . .
N3 N 0.8419(3) 0.21935(18) 0.56116(11) 0.0426(6) Uani 1 1 d . . . . .
N4 N 0.7715(3) 0.13558(18) 0.56316(12) 0.0466(7) Uani 1 1 d . . . . .
C1 C 0.6346(3) 0.44487(17) 0.82579(12) 0.0260(6) Uani 1 1 d . . . . .
C13 C 0.6522(3) 0.24622(18) 0.79355(12) 0.0263(6) Uani 1 1 d . . . . .
C7 C 0.3793(3) 0.31642(18) 0.86700(12) 0.0263(6) Uani 1 1 d . . . . .
N1 N 0.8152(3) 0.48567(19) 0.63192(13) 0.0500(7) Uani 1 1 d . . . . .
C19 C 0.3946(3) 0.36565(17) 0.73315(12) 0.0270(6) Uani 1 1 d . . . . .
C18 C 0.7107(3) 0.22721(18) 0.73387(12) 0.0304(6) Uani 1 1 d . . . . .
H18 H 0.6696 0.2615 0.6977 0.036 Uiso 1 1 calc R . . . .
C20 C 0.2319(3) 0.33485(18) 0.72621(13) 0.0327(6) Uani 1 1 d . . . . .
H20 H 0.1811 0.3057 0.7610 0.039 Uiso 1 1 calc R . . . .
C2 C 0.5705(3) 0.53514(18) 0.81542(13) 0.0346(7) Uani 1 1 d . . . . .
H2 H 0.4670 0.5429 0.7936 0.042 Uiso 1 1 calc R . . . .
C25 C 0.7992(3) 0.4427(2) 0.58558(15) 0.0374(7) Uani 1 1 d . . . . .
C14 C 0.7146(3) 0.19483(18) 0.84652(12) 0.0304(6) Uani 1 1 d . . . . .
H14 H 0.6753 0.2070 0.8877 0.036 Uiso 1 1 calc R . . . .
C15 C 0.8328(3) 0.12673(18) 0.83891(13) 0.0342(7) Uani 1 1 d . . . . .
H15 H 0.8744 0.0923 0.8749 0.041 Uiso 1 1 calc R . . . .
C8 C 0.3252(3) 0.38964(19) 0.90496(12) 0.0327(6) Uani 1 1 d . . . . .
H8 H 0.3653 0.4518 0.8992 0.039 Uiso 1 1 calc R . . . .
C12 C 0.3178(3) 0.22575(19) 0.87514(13) 0.0326(6) Uani 1 1 d . . . . .
H12 H 0.3528 0.1755 0.8491 0.039 Uiso 1 1 calc R . . . .
C24 C 0.4675(3) 0.40892(19) 0.68213(12) 0.0350(7) Uani 1 1 d . . . . .
H24 H 0.5769 0.4314 0.6868 0.042 Uiso 1 1 calc R . . . .
C9 C 0.2128(3) 0.3720(2) 0.95114(13) 0.0366(7) Uani 1 1 d . . . . .
H9 H 0.1762 0.4219 0.9772 0.044 Uiso 1 1 calc R . . . .
C16 C 0.8906(3) 0.10840(19) 0.77954(13) 0.0366(7) Uani 1 1 d . . . . .
H16 H 0.9725 0.0617 0.7746 0.044 Uiso 1 1 calc R . . . .
C6 C 0.7874(3) 0.43507(19) 0.85713(14) 0.0375(7) Uani 1 1 d . . . . .
H6 H 0.8322 0.3741 0.8646 0.045 Uiso 1 1 calc R . . . .
C17 C 0.8290(3) 0.1583(2) 0.72672(13) 0.0369(7) Uani 1 1 d . . . . .
H17 H 0.8680 0.1452 0.6857 0.044 Uiso 1 1 calc R . . . .
C21 C 0.1457(4) 0.3469(2) 0.66877(14) 0.0399(7) Uani 1 1 d . . . . .
H21 H 0.0351 0.3264 0.6641 0.048 Uiso 1 1 calc R . . . .
C4 C 0.8091(3) 0.6026(2) 0.86804(13) 0.0375(7) Uani 1 1 d . . . . .
H4 H 0.8681 0.6566 0.8829 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2050(3) 0.2093(2) 0.92152(13) 0.0378(7) Uani 1 1 d . . . . .
H11 H 0.1628 0.1476 0.9272 0.045 Uiso 1 1 calc R . . . .
C3 C 0.6575(3) 0.6131(2) 0.83696(14) 0.0402(7) Uani 1 1 d . . . . .
H3 H 0.6129 0.6744 0.8304 0.048 Uiso 1 1 calc R . . . .
C22 C 0.2194(4) 0.3885(2) 0.61816(14) 0.0438(8) Uani 1 1 d . . . . .
H22 H 0.1594 0.3962 0.5787 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8744(4) 0.5147(2) 0.87743(14) 0.0421(7) Uani 1 1 d . . . . .
H5 H 0.9797 0.5079 0.8979 0.051 Uiso 1 1 calc R . . . .
C10 C 0.1543(3) 0.2816(2) 0.95913(13) 0.0409(7) Uani 1 1 d . . . . .
H10 H 0.0781 0.2695 0.9911 0.049 Uiso 1 1 calc R . . . .
C23 C 0.3796(4) 0.4191(2) 0.62422(13) 0.0417(8) Uani 1 1 d . . . . .
H23 H 0.4298 0.4471 0.5889 0.050 Uiso 1 1 calc R . . . .
C26 C 0.5939(4) 0.2350(2) 0.52007(13) 0.0426(8) Uani 1 1 d . . . . .
H26 H 0.4964 0.2610 0.5010 0.051 Uiso 1 1 calc R . . . .
C27 C 0.6185(4) 0.1445(2) 0.53781(14) 0.0461(8) Uani 1 1 d . . . . .
H27 H 0.5403 0.0952 0.5331 0.055 Uiso 1 1 calc R . . . .
B1 B 0.7797(5) 0.3855(3) 0.52062(16) 0.0409(8) Uani 1 1 d . . . . .
H1A H 0.905(3) 0.3914(19) 0.4968(12) 0.045(8) Uiso 1 1 d . . . . .
H1B H 0.675(4) 0.416(2) 0.4924(13) 0.055(9) Uiso 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
P1 C1 1.792(3) . ?
P1 C13 1.791(3) . ?
P1 C7 1.788(3) . ?
P1 C19 1.791(3) . ?
N2 N3 1.347(3) . ?
N2 C26 1.339(4) . ?
N2 B1 1.560(4) . ?
N3 N4 1.322(3) . ?
N4 C27 1.343(4) . ?
C1 C2 1.397(3) . ?
C1 C6 1.393(4) . ?
C13 C18 1.386(3) . ?
C13 C14 1.406(4) . ?
C7 C8 1.393(3) . ?
C7 C12 1.394(4) . ?
N1 C25 1.150(4) . ?
C19 C20 1.400(4) . ?
C19 C24 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.387(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C25 B1 1.588(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(4) . ?
C24 H24 0.9500 . ?
C24 C23 1.392(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(4) . ?
C17 H17 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.376(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(4) . ?
C4 C5 1.368(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.370(4) . ?
C3 H3 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.379(4) . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C23 H23 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.349(4) . ?
C27 H27 0.9500 . ?
B1 H1A 1.16(3) . ?
B1 H1B 1.11(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
C13 P1 C1 108.26(12) . . ?
C7 P1 C1 109.77(12) . . ?
C7 P1 C13 110.38(12) . . ?
C7 P1 C19 108.36(12) . . ?
C19 P1 C1 109.45(12) . . ?
C19 P1 C13 110.61(12) . . ?
N3 N2 B1 122.4(2) . . ?
C26 N2 N3 108.4(2) . . ?
C26 N2 B1 129.1(2) . . ?
N4 N3 N2 108.5(2) . . ?
N3 N4 C27 107.5(2) . . ?
C2 C1 P1 120.4(2) . . ?
C6 C1 P1 120.20(19) . . ?
C6 C1 C2 119.2(2) . . ?
C18 C13 P1 120.7(2) . . ?
C18 C13 C14 119.1(2) . . ?
C14 C13 P1 119.94(19) . . ?
C8 C7 P1 119.0(2) . . ?
C8 C7 C12 119.5(2) . . ?
C12 C7 P1 121.35(19) . . ?
C20 C19 P1 121.00(19) . . ?
C24 C19 P1 119.2(2) . . ?
C24 C19 C20 119.6(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
N1 C25 B1 178.4(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C19 C24 H24 120.1 . . ?
C19 C24 C23 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
N2 C26 H26 126.7 . . ?
N2 C26 C27 106.6(3) . . ?
C27 C26 H26 126.7 . . ?
N4 C27 C26 108.9(3) . . ?
N4 C27 H27 125.5 . . ?
C26 C27 H27 125.5 . . ?
N2 B1 C25 109.9(2) . . ?
N2 B1 H1A 111.9(14) . . ?
N2 B1 H1B 106.4(15) . . ?
C25 B1 H1A 105.9(13) . . ?
C25 B1 H1B 107.8(15) . . ?
H1A B1 H1B 114.8(19) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
