# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_191109a_0m
_database_code_depnum_ccdc_archive 'CCDC 2017887'
loop_
_audit_author_name
_audit_author_address
h
;CCNU
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-29
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 B P'
_chemical_formula_sum            'C17 H24 B P'
_chemical_formula_weight         270.14
_chemical_absolute_configuration ?
_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 0.0030 0.0020 '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 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1020 0.0940 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.6359(9)
_cell_length_b                   7.5137(10)
_cell_length_c                   34.018(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1696.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.19
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            12341
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         1.197
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3102
_reflns_number_total             3135
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       0.045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.248
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.0238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1430
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All B(H,H,H) groups, All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12) 
2.b Idealised Me refined as rotating group: 
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B, 
 H17C) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
B1 B 0.6859(8) 0.2869(9) 0.42769(17) 0.0532(13) Uani 1 1 d . . . . .
H1A H 0.717(9) 0.307(8) 0.4602(18) 0.080 Uiso 1 1 d R . . . .
H1B H 0.694(9) 0.150(9) 0.4209(17) 0.080 Uiso 1 1 d R . . . .
H1C H 0.782(9) 0.356(9) 0.4057(17) 0.080 Uiso 1 1 d R . . . .
C1 C 0.3538(6) 0.3728(6) 0.36686(11) 0.0367(8) Uani 1 1 d . . . . .
C2 C 0.1741(7) 0.3102(7) 0.35191(13) 0.0518(12) Uani 1 1 d . . . . .
H2 H 0.0765 0.2663 0.3690 0.062 Uiso 1 1 calc R . . . .
C3 C 0.1367(7) 0.3117(7) 0.31155(13) 0.0559(13) Uani 1 1 d . . . . .
H3 H 0.0149 0.2671 0.3023 0.067 Uiso 1 1 calc R . . . .
C4 C 0.2751(7) 0.3776(6) 0.28502(12) 0.0433(9) Uani 1 1 d . . . . .
C5 C 0.4559(8) 0.4412(8) 0.30042(14) 0.0603(14) Uani 1 1 d . . . . .
H5 H 0.5527 0.4872 0.2835 0.072 Uiso 1 1 calc R . . . .
C6 C 0.4945(8) 0.4374(8) 0.34030(14) 0.0579(14) Uani 1 1 d . . . . .
H6 H 0.6176 0.4790 0.3496 0.069 Uiso 1 1 calc R . . . .
C7 C 0.2336(7) 0.3798(6) 0.24161(12) 0.0472(10) Uani 1 1 d . . . . .
C8 C 0.0757(11) 0.2910(9) 0.22576(15) 0.0809(19) Uani 1 1 d . . . . .
H8 H -0.0084 0.2261 0.2423 0.097 Uiso 1 1 calc R . . . .
C9 C 0.0348(13) 0.2933(11) 0.18556(17) 0.095(3) Uani 1 1 d . . . . .
H9 H -0.0749 0.2304 0.1757 0.115 Uiso 1 1 calc R . . . .
C10 C 0.1543(10) 0.3871(8) 0.16072(14) 0.0687(15) Uani 1 1 d . . . . .
H10 H 0.1277 0.3888 0.1339 0.082 Uiso 1 1 calc R . . . .
C11 C 0.3112(12) 0.4770(10) 0.17546(17) 0.085(2) Uani 1 1 d . . . . .
H11 H 0.3930 0.5432 0.1588 0.102 Uiso 1 1 calc R . . . .
C12 C 0.3532(10) 0.4725(10) 0.21583(15) 0.0776(19) Uani 1 1 d . . . . .
H12 H 0.4647 0.5338 0.2254 0.093 Uiso 1 1 calc R . . . .
C13 C 0.2362(7) 0.2146(7) 0.44095(14) 0.0509(11) Uani 1 1 d . . . . .
H13A H 0.2430 0.1016 0.4278 0.076 Uiso 1 1 calc GR . . . .
H13B H 0.1025 0.2621 0.4386 0.076 Uiso 1 1 calc GR . . . .
H13C H 0.2686 0.1993 0.4682 0.076 Uiso 1 1 calc GR . . . .
C14 C 0.3582(7) 0.5906(6) 0.43899(12) 0.0443(10) Uani 1 1 d . . . . .
C15 C 0.1473(8) 0.6521(8) 0.42813(18) 0.0689(15) Uani 1 1 d . . . . .
H15A H 0.0499 0.5732 0.4396 0.103 Uiso 1 1 calc GR . . . .
H15B H 0.1326 0.6512 0.4001 0.103 Uiso 1 1 calc GR . . . .
H15C H 0.1260 0.7706 0.4378 0.103 Uiso 1 1 calc GR . . . .
C16 C 0.3786(12) 0.5802(8) 0.48386(15) 0.0816(19) Uani 1 1 d . . . . .
H16A H 0.3613 0.6967 0.4949 0.122 Uiso 1 1 calc GR . . . .
H16B H 0.5097 0.5356 0.4905 0.122 Uiso 1 1 calc GR . . . .
H16C H 0.2774 0.5018 0.4942 0.122 Uiso 1 1 calc GR . . . .
C17 C 0.5137(10) 0.7204(8) 0.4230(2) 0.0821(19) Uani 1 1 d . . . . .
H17A H 0.4914 0.7378 0.3954 0.123 Uiso 1 1 calc GR . . . .
H17B H 0.6465 0.6731 0.4271 0.123 Uiso 1 1 calc GR . . . .
H17C H 0.5014 0.8323 0.4364 0.123 Uiso 1 1 calc GR . . . .
P1 P 0.41329(15) 0.36581(14) 0.41885(3) 0.0367(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
B1 H1A 1.13(6) . ?
B1 H1B 1.06(7) . ?
B1 H1C 1.11(6) . ?
B1 P1 1.928(5) . ?
C1 C2 1.379(6) . ?
C1 C6 1.387(6) . ?
C1 P1 1.813(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 C5 1.394(7) . ?
C4 C7 1.502(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(8) . ?
C7 C12 1.372(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.356(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.339(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 P1 1.799(5) . ?
C14 C15 1.520(7) . ?
C14 C16 1.534(6) . ?
C14 C17 1.521(7) . ?
C14 P1 1.859(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
H1A B1 H1B 109(5) . . ?
H1A B1 H1C 119(5) . . ?
H1B B1 H1C 106(5) . . ?
P1 B1 H1A 106(3) . . ?
P1 B1 H1B 108(3) . . ?
P1 B1 H1C 107(3) . . ?
C2 C1 C6 117.4(4) . . ?
C2 C1 P1 122.6(3) . . ?
C6 C1 P1 119.9(3) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 116.8(4) . . ?
C3 C4 C7 121.7(4) . . ?
C5 C4 C7 121.5(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C4 121.8(4) . . ?
C8 C7 C12 116.3(4) . . ?
C12 C7 C4 121.9(5) . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.3(6) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(6) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(6) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 121.6(6) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
P1 C13 H13A 109.5 . . ?
P1 C13 H13B 109.5 . . ?
P1 C13 H13C 109.5 . . ?
C15 C14 C16 109.8(5) . . ?
C15 C14 C17 110.1(5) . . ?
C15 C14 P1 111.5(3) . . ?
C16 C14 P1 107.6(3) . . ?
C17 C14 C16 109.2(5) . . ?
C17 C14 P1 108.5(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 P1 B1 111.5(2) . . ?
C1 P1 C14 106.9(2) . . ?
C13 P1 B1 110.7(3) . . ?
C13 P1 C1 106.5(2) . . ?
C13 P1 C14 106.9(2) . . ?
C14 P1 B1 114.0(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
C1 C2 C3 C4 -0.9(8) . . . . ?
C2 C1 C6 C5 0.8(8) . . . . ?
C2 C1 P1 B1 136.3(4) . . . . ?
C2 C1 P1 C13 15.5(5) . . . . ?
C2 C1 P1 C14 -98.5(4) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C2 C3 C4 C7 -179.7(5) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C3 C4 C7 C8 -11.5(8) . . . . ?
C3 C4 C7 C12 168.3(6) . . . . ?
C4 C5 C6 C1 -1.1(9) . . . . ?
C4 C7 C8 C9 179.5(7) . . . . ?
C4 C7 C12 C11 -178.7(6) . . . . ?
C5 C4 C7 C8 168.2(6) . . . . ?
C5 C4 C7 C12 -12.0(8) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
C6 C1 P1 B1 -41.4(5) . . . . ?
C6 C1 P1 C13 -162.2(4) . . . . ?
C6 C1 P1 C14 83.7(4) . . . . ?
C7 C4 C5 C6 -179.4(5) . . . . ?
C7 C8 C9 C10 -0.2(13) . . . . ?
C8 C7 C12 C11 1.1(10) . . . . ?
C8 C9 C10 C11 -0.1(12) . . . . ?
C9 C10 C11 C12 0.9(12) . . . . ?
C10 C11 C12 C7 -1.5(12) . . . . ?
C12 C7 C8 C9 -0.3(11) . . . . ?
C15 C14 P1 B1 175.1(4) . . . . ?
C15 C14 P1 C1 51.6(4) . . . . ?
C15 C14 P1 C13 -62.2(4) . . . . ?
C16 C14 P1 B1 -64.4(5) . . . . ?
C16 C14 P1 C1 172.0(4) . . . . ?
C16 C14 P1 C13 58.3(4) . . . . ?
C17 C14 P1 B1 53.7(4) . . . . ?
C17 C14 P1 C1 -69.9(4) . . . . ?
C17 C14 P1 C13 176.4(4) . . . . ?
P1 C1 C2 C3 -177.6(4) . . . . ?
P1 C1 C6 C5 178.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_191104b_0m
_database_code_depnum_ccdc_archive 'CCDC 2017943'
loop_
_audit_author_name
_audit_author_address
q
;CCNU
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 B P'
_chemical_formula_sum            'C20 H28 B P'
_chemical_formula_weight         310.20
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.2902(16)
_cell_length_b                   12.3392(18)
_cell_length_c                   13.6341(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1899.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.81
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.866
_diffrn_reflns_theta_min         2.226
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                5696
_reflns_number_total             6144
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2397 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.007(14)
_refine_ls_extinction_coef       0.049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         6144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.078
_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)+(0.0570P)²+0.2237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All B(H,H,H) groups, All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13) 
2.b Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B, 
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.071 
;
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
B1 B 0.2875(3) 0.5289(2) 0.99347(16) 0.0542(6) Uani 1 1 d . . . . .
H1A H 0.342(3) 0.587(3) 1.033(2) 0.081 Uiso 1 1 d R . . . .
H1B H 0.320(3) 0.449(3) 1.018(2) 0.081 Uiso 1 1 d R . . . .
H1C H 0.195(3) 0.539(3) 1.015(3) 0.081 Uiso 1 1 d R . . . .
C1 C 0.25340(14) 0.68621(13) 0.81550(10) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.21793(14) 0.70589(13) 0.71830(10) 0.0309(3) Uani 1 1 d . . . . .
H2 H 0.2201 0.6506 0.6720 0.037 Uiso 1 1 calc R . . . .
C3 C 0.17974(13) 0.80859(12) 0.69233(10) 0.0284(3) Uani 1 1 d . . . . .
C4 C 0.17683(13) 0.89243(12) 0.76172(11) 0.0304(3) Uani 1 1 d . . . . .
C5 C 0.21043(16) 0.87309(14) 0.85817(12) 0.0383(3) Uani 1 1 d . . . . .
H5 H 0.2074 0.9284 0.9045 0.046 Uiso 1 1 calc R . . . .
C6 C 0.24855(16) 0.77007(14) 0.88452(11) 0.0375(3) Uani 1 1 d . . . . .
H6 H 0.2712 0.7566 0.9490 0.045 Uiso 1 1 calc R . . . .
C7 C 0.13659(13) 0.84832(12) 0.59265(10) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.11323(13) 0.96737(13) 0.61459(11) 0.0307(3) Uani 1 1 d . . . . .
C9 C 0.13596(14) 0.99181(13) 0.71340(11) 0.0315(3) Uani 1 1 d . . . . .
C10 C 0.11853(18) 1.09587(15) 0.74916(14) 0.0427(4) Uani 1 1 d . . . . .
H10 H 0.1333 1.1116 0.8148 0.051 Uiso 1 1 calc R . . . .
C11 C 0.0789(2) 1.17629(15) 0.68608(16) 0.0470(4) Uani 1 1 d . . . . .
H11 H 0.0676 1.2464 0.7092 0.056 Uiso 1 1 calc R . . . .
C12 C 0.05597(19) 1.15211(16) 0.58827(15) 0.0457(4) Uani 1 1 d . . . . .
H12 H 0.0293 1.2064 0.5465 0.055 Uiso 1 1 calc R . . . .
C13 C 0.07248(16) 1.04793(16) 0.55220(13) 0.0405(3) Uani 1 1 d . . . . .
H13 H 0.0564 1.0323 0.4868 0.049 Uiso 1 1 calc R . . . .
C14 C 0.23069(17) 0.83340(17) 0.51267(12) 0.0421(4) Uani 1 1 d . . . . .
H14A H 0.3022 0.8698 0.5318 0.063 Uiso 1 1 calc GR . . . .
H14B H 0.2023 0.8635 0.4522 0.063 Uiso 1 1 calc GR . . . .
H14C H 0.2465 0.7576 0.5040 0.063 Uiso 1 1 calc GR . . . .
C15 C 0.02193(16) 0.78953(15) 0.56219(13) 0.0392(3) Uani 1 1 d . . . . .
H15A H 0.0363 0.7129 0.5592 0.059 Uiso 1 1 calc GR . . . .
H15B H -0.0029 0.8150 0.4989 0.059 Uiso 1 1 calc GR . . . .
H15C H -0.0390 0.8041 0.6095 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.21732(19) 0.45921(16) 0.78429(16) 0.0502(4) Uani 1 1 d . . . . .
H16A H 0.2346 0.3867 0.8055 0.075 Uiso 1 1 calc GR . . . .
H16B H 0.2362 0.4664 0.7160 0.075 Uiso 1 1 calc GR . . . .
H16C H 0.1347 0.4741 0.7941 0.075 Uiso 1 1 calc GR . . . .
C17 C 0.46010(15) 0.53970(17) 0.81218(13) 0.0428(4) Uani 1 1 d . . . . .
C18 C 0.5386(2) 0.6107(3) 0.8767(2) 0.0793(9) Uani 1 1 d . . . . .
H18A H 0.5316 0.5878 0.9438 0.119 Uiso 1 1 calc GR . . . .
H18B H 0.5140 0.6849 0.8711 0.119 Uiso 1 1 calc GR . . . .
H18C H 0.6195 0.6040 0.8560 0.119 Uiso 1 1 calc GR . . . .
C19 C 0.4950(3) 0.4202(3) 0.8215(3) 0.0819(9) Uani 1 1 d . . . . .
H19A H 0.5771 0.4118 0.8049 0.123 Uiso 1 1 calc GR . . . .
H19B H 0.4475 0.3775 0.7777 0.123 Uiso 1 1 calc GR . . . .
H19C H 0.4822 0.3965 0.8877 0.123 Uiso 1 1 calc GR . . . .
C20 C 0.4757(2) 0.5749(3) 0.70546(16) 0.0634(7) Uani 1 1 d . . . . .
H20A H 0.4582 0.6508 0.6996 0.095 Uiso 1 1 calc GR . . . .
H20B H 0.4227 0.5343 0.6645 0.095 Uiso 1 1 calc GR . . . .
H20C H 0.5559 0.5619 0.6853 0.095 Uiso 1 1 calc GR . . . .
P1 P 0.30473(4) 0.55409(3) 0.85457(3) 0.03338(11) 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
B1 H1A 1.09(3) . ?
B1 H1B 1.11(3) . ?
B1 H1C 1.09(3) . ?
B1 P1 1.929(2) . ?
C1 C2 1.406(2) . ?
C1 C6 1.400(2) . ?
C1 P1 1.8103(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C3 C4 1.4023(19) . ?
C3 C7 1.5247(19) . ?
C4 C5 1.389(2) . ?
C4 C9 1.466(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.522(2) . ?
C7 C14 1.534(2) . ?
C7 C15 1.541(2) . ?
C8 C9 1.404(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.388(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 P1 1.806(2) . ?
C17 C18 1.525(3) . ?
C17 C19 1.531(3) . ?
C17 C20 1.529(3) . ?
C17 P1 1.8554(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
H1A B1 H1B 104(2) . . ?
H1A B1 H1C 109(2) . . ?
H1B B1 H1C 110(3) . . ?
P1 B1 H1A 109.2(17) . . ?
P1 B1 H1B 113.8(18) . . ?
P1 B1 H1C 110.0(19) . . ?
C2 C1 P1 121.62(12) . . ?
C6 C1 C2 119.67(15) . . ?
C6 C1 P1 118.71(11) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.20(14) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.67(13) . . ?
C2 C3 C7 128.44(13) . . ?
C4 C3 C7 110.90(12) . . ?
C3 C4 C9 108.73(13) . . ?
C5 C4 C3 120.36(14) . . ?
C5 C4 C9 130.91(14) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.12(14) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.98(14) . . ?
C5 C6 H6 119.5 . . ?
C3 C7 C14 111.95(13) . . ?
C3 C7 C15 110.94(13) . . ?
C8 C7 C3 100.98(11) . . ?
C8 C7 C14 112.06(13) . . ?
C8 C7 C15 111.21(13) . . ?
C14 C7 C15 109.50(13) . . ?
C9 C8 C7 111.35(13) . . ?
C13 C8 C7 128.95(14) . . ?
C13 C8 C9 119.69(15) . . ?
C8 C9 C4 108.00(13) . . ?
C10 C9 C4 131.34(15) . . ?
C10 C9 C8 120.66(15) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.33(17) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.06(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.88(17) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.38(16) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
P1 C16 H16A 109.5 . . ?
P1 C16 H16B 109.5 . . ?
P1 C16 H16C 109.5 . . ?
C18 C17 C19 110.8(2) . . ?
C18 C17 C20 108.6(2) . . ?
C18 C17 P1 108.32(15) . . ?
C19 C17 P1 108.03(16) . . ?
C20 C17 C19 108.9(2) . . ?
C20 C17 P1 112.22(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 P1 B1 113.69(10) . . ?
C1 P1 C17 107.29(8) . . ?
C16 P1 B1 111.19(12) . . ?
C16 P1 C1 104.63(9) . . ?
C16 P1 C17 106.81(10) . . ?
C17 P1 B1 112.67(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
