# 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_rac_BAmCl
_database_code_depnum_ccdc_archive 'CCDC 2033433'
loop_
_audit_author_name
_audit_author_address
'Shunsuke Ohtani'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-09-23 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 B Cl F N2 O2'
_chemical_formula_weight         346.58

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'
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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4212(8)
_cell_length_b                   14.1413(16)
_cell_length_c                   13.5406(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.611(7)
_cell_angle_gamma                90
_cell_volume                     1579.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    78(2)
_cell_measurement_reflns_used    11944
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      55.21

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      78(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'rigaku raxis rapid'
_diffrn_measurement_method       graphite
_diffrn_detector_area_resol_mean 'oscillation method'
_diffrn_reflns_number            14569
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3555
_reflns_number_gt                3118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0805P)²+0.2699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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_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
Cl01 Cl 0.70257(6) 0.03499(3) 0.51992(4) 0.03804(18) Uani 1 1 d . . . . .
F002 F 0.55092(13) 0.46266(7) 0.70026(8) 0.0342(3) Uani 1 1 d . . . . .
O003 O 0.45752(15) 0.30542(8) 0.69054(9) 0.0290(3) Uani 1 1 d . . . . .
O004 O 0.27437(15) 0.43917(8) 0.69200(9) 0.0280(3) Uani 1 1 d . . . . .
N005 N 0.39301(17) 0.40065(9) 0.54501(10) 0.0255(3) Uani 1 1 d . . . . .
N006 N -0.05578(19) 0.71277(10) 0.68150(11) 0.0286(3) Uani 1 1 d . . . . .
C007 C 0.4648(2) 0.31652(12) 0.52066(13) 0.0264(4) Uani 1 1 d . . . . .
C008 C 0.5002(2) 0.26310(12) 0.60978(13) 0.0281(4) Uani 1 1 d . . . . .
C009 C 0.2035(2) 0.51456(11) 0.63964(13) 0.0254(4) Uani 1 1 d . . . . .
C00A C 0.0312(2) 0.65267(11) 0.63435(13) 0.0264(4) Uani 1 1 d . . . . .
C00B C 0.6069(2) 0.14396(12) 0.52040(14) 0.0298(4) Uani 1 1 d . . . . .
C00C C 0.4992(2) 0.28366(12) 0.43135(13) 0.0276(4) Uani 1 1 d . . . . .
H1 H 0.4743 0.3204 0.3715 0.033 Uiso 1 1 calc R U . . .
C00D C 0.2181(2) 0.52979(11) 0.53750(13) 0.0255(4) Uani 1 1 d . . . . .
C00E C 0.1107(2) 0.57335(12) 0.68529(12) 0.0269(4) Uani 1 1 d . . . . .
H2 H 0.0997 0.5605 0.7525 0.032 Uiso 1 1 calc R U . . .
C00F C 0.5714(2) 0.19541(13) 0.43144(13) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.5962 0.1705 0.3712 0.036 Uiso 1 1 calc R U . . .
C00G C 0.3037(2) 0.46380(11) 0.48961(13) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.2964 0.4655 0.4187 0.032 Uiso 1 1 calc R U . . .
C00H C 0.1339(2) 0.60717(11) 0.48649(13) 0.0278(4) Uani 1 1 d . . . . .
H4 H 0.1392 0.6177 0.4179 0.033 Uiso 1 1 calc R U . . .
C00I C -0.0525(2) 0.70365(12) 0.79003(13) 0.0299(4) Uani 1 1 d . . . . .
H7 H -0.0761 0.7660 0.8169 0.036 Uiso 1 1 calc R U . . .
H8 H 0.0579 0.6847 0.8247 0.036 Uiso 1 1 calc R U . . .
C00J C 0.0451(2) 0.66745(12) 0.53211(13) 0.0279(4) Uani 1 1 d . . . . .
H17 H -0.0080 0.7198 0.4956 0.033 Uiso 1 1 calc R U . . .
C00K C -0.1147(2) 0.80359(12) 0.63603(14) 0.0296(4) Uani 1 1 d . . . . .
H9 H -0.2006 0.8280 0.6695 0.036 Uiso 1 1 calc R U . . .
H10 H -0.1629 0.7939 0.5638 0.036 Uiso 1 1 calc R U . . .
C00L C 0.5723(2) 0.17545(13) 0.61115(14) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.5971 0.1385 0.6709 0.037 Uiso 1 1 calc R U . . .
C00M C -0.1737(2) 0.63180(13) 0.81377(14) 0.0337(4) Uani 1 1 d . . . . .
H11 H -0.2841 0.6540 0.7867 0.051 Uiso 1 1 calc R U . . .
H12 H -0.1587 0.6241 0.8870 0.051 Uiso 1 1 calc R U . . .
H13 H -0.1563 0.5709 0.7830 0.051 Uiso 1 1 calc R U . . .
C00N C 0.0206(2) 0.87593(12) 0.64574(15) 0.0347(4) Uani 1 1 d . . . . .
H14 H 0.0663 0.8871 0.7172 0.052 Uiso 1 1 calc R U . . .
H15 H -0.0226 0.9353 0.6139 0.052 Uiso 1 1 calc R U . . .
H16 H 0.1056 0.8521 0.6124 0.052 Uiso 1 1 calc R U . . .
B00O B 0.4189(2) 0.40390(14) 0.66309(15) 0.0282(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
Cl01 C00B 1.7394(18) . ?
F002 B00O 1.398(2) . ?
O003 C008 1.357(2) . ?
O003 B00O 1.461(2) . ?
O004 C009 1.351(2) . ?
O004 B00O 1.441(2) . ?
N005 C00G 1.303(2) . ?
N005 C007 1.403(2) . ?
N005 B00O 1.570(2) . ?
N006 C00A 1.362(2) . ?
N006 C00K 1.467(2) . ?
N006 C00I 1.470(2) . ?
C007 C00C 1.380(2) . ?
C007 C008 1.404(2) . ?
C008 C00L 1.379(2) . ?
C009 C00E 1.370(2) . ?
C009 C00D 1.429(2) . ?
C00A C00E 1.413(2) . ?
C00A C00J 1.428(2) . ?
C00B C00F 1.387(3) . ?
C00B C00L 1.392(2) . ?
C00C C00F 1.388(2) . ?
C00C H1 0.9500 . ?
C00D C00H 1.407(2) . ?
C00D C00G 1.414(2) . ?
C00E H2 0.9500 . ?
C00F H3 0.9500 . ?
C00G H6 0.9500 . ?
C00H C00J 1.361(2) . ?
C00H H4 0.9500 . ?
C00I C00M 1.519(2) . ?
C00I H7 0.9900 . ?
C00I H8 0.9900 . ?
C00J H17 0.9500 . ?
C00K C00N 1.517(2) . ?
C00K H9 0.9900 . ?
C00K H10 0.9900 . ?
C00L H5 0.9500 . ?
C00M H11 0.9800 . ?
C00M H12 0.9800 . ?
C00M H13 0.9800 . ?
C00N H14 0.9800 . ?
C00N H15 0.9800 . ?
C00N H16 0.9800 . ?

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
C008 O003 B00O 107.26(13) . . ?
C009 O004 B00O 116.02(13) . . ?
C00G N005 C007 132.19(15) . . ?
C00G N005 B00O 120.79(14) . . ?
C007 N005 B00O 106.61(13) . . ?
C00A N006 C00K 121.20(14) . . ?
C00A N006 C00I 120.68(14) . . ?
C00K N006 C00I 115.67(13) . . ?
C00C C007 C008 121.77(16) . . ?
C00C C007 N005 131.90(16) . . ?
C008 C007 N005 106.33(14) . . ?
O003 C008 C00L 124.96(15) . . ?
O003 C008 C007 114.25(15) . . ?
C00L C008 C007 120.79(16) . . ?
O004 C009 C00E 118.28(15) . . ?
O004 C009 C00D 120.79(15) . . ?
C00E C009 C00D 120.85(15) . . ?
N006 C00A C00E 120.89(16) . . ?
N006 C00A C00J 121.34(15) . . ?
C00E C00A C00J 117.76(15) . . ?
C00F C00B C00L 123.49(16) . . ?
C00F C00B Cl01 118.72(13) . . ?
C00L C00B Cl01 117.79(14) . . ?
C007 C00C C00F 118.12(16) . . ?
C007 C00C H1 120.9 . . ?
C00F C00C H1 120.9 . . ?
C00H C00D C00G 122.76(16) . . ?
C00H C00D C009 117.34(15) . . ?
C00G C00D C009 119.70(15) . . ?
C009 C00E C00A 121.25(16) . . ?
C009 C00E H2 119.4 . . ?
C00A C00E H2 119.4 . . ?
C00B C00F C00C 119.35(16) . . ?
C00B C00F H3 120.3 . . ?
C00C C00F H3 120.3 . . ?
N005 C00G C00D 118.46(15) . . ?
N005 C00G H6 120.8 . . ?
C00D C00G H6 120.8 . . ?
C00J C00H C00D 122.18(16) . . ?
C00J C00H H4 118.9 . . ?
C00D C00H H4 118.9 . . ?
N006 C00I C00M 113.07(15) . . ?
N006 C00I H7 109.0 . . ?
C00M C00I H7 109.0 . . ?
N006 C00I H8 109.0 . . ?
C00M C00I H8 109.0 . . ?
H7 C00I H8 107.8 . . ?
C00H C00J C00A 120.54(16) . . ?
C00H C00J H17 119.7 . . ?
C00A C00J H17 119.7 . . ?
N006 C00K C00N 111.67(15) . . ?
N006 C00K H9 109.3 . . ?
C00N C00K H9 109.3 . . ?
N006 C00K H10 109.3 . . ?
C00N C00K H10 109.3 . . ?
H9 C00K H10 107.9 . . ?
C008 C00L C00B 116.47(16) . . ?
C008 C00L H5 121.8 . . ?
C00B C00L H5 121.8 . . ?
C00I C00M H11 109.5 . . ?
C00I C00M H12 109.5 . . ?
H11 C00M H12 109.5 . . ?
C00I C00M H13 109.5 . . ?
H11 C00M H13 109.5 . . ?
H12 C00M H13 109.5 . . ?
C00K C00N H14 109.5 . . ?
C00K C00N H15 109.5 . . ?
H14 C00N H15 109.5 . . ?
C00K C00N H16 109.5 . . ?
H14 C00N H16 109.5 . . ?
H15 C00N H16 109.5 . . ?
F002 B00O O004 110.52(14) . . ?
F002 B00O O003 110.79(15) . . ?
O004 B00O O003 114.69(14) . . ?
F002 B00O N005 108.76(14) . . ?
O004 B00O N005 109.56(15) . . ?
O003 B00O N005 102.09(13) . . ?

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
C00G N005 C007 C00C 18.3(3) . . . . ?
B00O N005 C007 C00C -169.27(18) . . . . ?
C00G N005 C007 C008 -161.09(17) . . . . ?
B00O N005 C007 C008 11.31(17) . . . . ?
B00O O003 C008 C00L 167.84(17) . . . . ?
B00O O003 C008 C007 -12.1(2) . . . . ?
C00C C007 C008 O003 -179.55(15) . . . . ?
N005 C007 C008 O003 -0.1(2) . . . . ?
C00C C007 C008 C00L 0.5(3) . . . . ?
N005 C007 C008 C00L 179.99(15) . . . . ?
B00O O004 C009 C00E -154.50(16) . . . . ?
B00O O004 C009 C00D 28.7(2) . . . . ?
C00K N006 C00A C00E 169.18(15) . . . . ?
C00I N006 C00A C00E 7.7(2) . . . . ?
C00K N006 C00A C00J -10.8(2) . . . . ?
C00I N006 C00A C00J -172.31(15) . . . . ?
C008 C007 C00C C00F -0.3(3) . . . . ?
N005 C007 C00C C00F -179.62(16) . . . . ?
O004 C009 C00D C00H 176.81(14) . . . . ?
C00E C009 C00D C00H 0.1(2) . . . . ?
O004 C009 C00D C00G 1.8(2) . . . . ?
C00E C009 C00D C00G -174.90(15) . . . . ?
O004 C009 C00E C00A -179.04(14) . . . . ?
C00D C009 C00E C00A -2.2(3) . . . . ?
N006 C00A C00E C009 -177.50(15) . . . . ?
C00J C00A C00E C009 2.5(2) . . . . ?
C00L C00B C00F C00C 0.8(3) . . . . ?
Cl01 C00B C00F C00C -178.20(13) . . . . ?
C007 C00C C00F C00B -0.4(3) . . . . ?
C007 N005 C00G C00D 165.47(16) . . . . ?
B00O N005 C00G C00D -6.0(2) . . . . ?
C00H C00D C00G N005 172.41(15) . . . . ?
C009 C00D C00G N005 -12.9(2) . . . . ?
C00G C00D C00H C00J 176.60(16) . . . . ?
C009 C00D C00H C00J 1.8(2) . . . . ?
C00A N006 C00I C00M -84.9(2) . . . . ?
C00K N006 C00I C00M 112.68(16) . . . . ?
C00D C00H C00J C00A -1.5(3) . . . . ?
N006 C00A C00J C00H 179.34(16) . . . . ?
C00E C00A C00J C00H -0.7(2) . . . . ?
C00A N006 C00K C00N -75.8(2) . . . . ?
C00I N006 C00K C00N 86.57(19) . . . . ?
O003 C008 C00L C00B 179.98(15) . . . . ?
C007 C008 C00L C00B -0.1(3) . . . . ?
C00F C00B C00L C008 -0.6(3) . . . . ?
Cl01 C00B C00L C008 178.43(13) . . . . ?
C009 O004 B00O F002 76.34(18) . . . . ?
C009 O004 B00O O003 -157.56(14) . . . . ?
C009 O004 B00O N005 -43.48(18) . . . . ?
C008 O003 B00O F002 -98.16(16) . . . . ?
C008 O003 B00O O004 135.88(15) . . . . ?
C008 O003 B00O N005 17.50(17) . . . . ?
C00G N005 B00O F002 -87.19(18) . . . . ?
C007 N005 B00O F002 99.37(15) . . . . ?
C00G N005 B00O O004 33.7(2) . . . . ?
C007 N005 B00O O004 -139.73(14) . . . . ?
C00G N005 B00O O003 155.68(14) . . . . ?
C007 N005 B00O O003 -17.77(16) . . . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_R_BAmCl
_database_code_depnum_ccdc_archive 'CCDC 2033434'
loop_
_audit_author_name
_audit_author_address
'Shunsuke Ohtani'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-09-23 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 B Cl F N2 O2'
_chemical_formula_weight         346.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   12.8397(12)
_cell_length_b                   12.8397(12)
_cell_length_c                   8.5551(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1221.4(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4485
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.257
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            9865
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3657
_reflns_number_gt                3271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.975

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.24704(8) 1.22728(8) 0.45894(10) 0.0505(2) Uani 1 1 d . . . . .
F002 F 0.55575(14) 0.95756(15) 0.76580(19) 0.0402(4) Uani 1 1 d . . . . .
O003 O 0.61004(15) 0.93845(15) 0.5130(2) 0.0310(4) Uani 1 1 d . . . . .
O004 O 0.54332(15) 1.08105(16) 0.5719(3) 0.0364(5) Uani 1 1 d . . . . .
N005 N 0.39905(17) 0.87443(18) 0.5692(2) 0.0257(4) Uani 1 1 d . . . . .
N6 N 0.7185(2) 0.6479(2) 0.3782(3) 0.0410(6) Uani 1 1 d . . . . .
C007 C 0.3412(2) 0.9418(2) 0.5496(3) 0.0270(5) Uani 1 1 d . . . . .
C008 C 0.4241(2) 0.6093(2) 0.4844(3) 0.0295(5) Uani 1 1 d . . . . .
H1 H 0.3449 0.5478 0.4965 0.035 Uiso 1 1 calc R U . . .
C009 C 0.4310(2) 1.0630(2) 0.5497(3) 0.0298(5) Uani 1 1 d . . . . .
C00A C 0.3644(2) 0.7621(2) 0.5349(3) 0.0259(5) Uani 1 1 d . . . . .
H2 H 0.2831 0.7054 0.5256 0.031 Uiso 1 1 calc R U . . .
C00B C 0.6320(2) 0.6738(2) 0.4189(3) 0.0319(6) Uani 1 1 d . . . . .
C00C C 0.5759(2) 0.8217(2) 0.4926(3) 0.0274(5) Uani 1 1 d . . . . .
C00D C 0.6607(2) 0.7935(2) 0.4449(3) 0.0316(6) Uani 1 1 d . . . . .
H3 H 0.7393 0.8551 0.4293 0.038 Uiso 1 1 calc R U . . .
C00E C 0.4032(2) 1.1524(3) 0.5232(3) 0.0340(6) Uani 1 1 d . . . . .
H4 H 0.4621 1.2333 0.5236 0.041 Uiso 1 1 calc R U . . .
C00F C 0.1932(2) 0.9967(3) 0.4966(3) 0.0367(6) Uani 1 1 d . . . . .
H5 H 0.1138 0.9767 0.4794 0.044 Uiso 1 1 calc R U . . .
C00G C 0.4529(2) 0.7292(2) 0.5126(3) 0.0261(5) Uani 1 1 d . . . . .
C00H C 0.2838(3) 1.1161(3) 0.4962(3) 0.0356(6) Uani 1 1 d . . . . .
C00I C 0.2218(2) 0.9065(3) 0.5227(3) 0.0318(5) Uani 1 1 d . . . . .
H6 H 0.1628 0.8256 0.5220 0.038 Uiso 1 1 calc R U . . .
C00J C 0.5093(3) 0.5813(2) 0.4399(3) 0.0329(6) Uani 1 1 d . . . . .
H7 H 0.4875 0.5014 0.4230 0.039 Uiso 1 1 calc R U . . .
C00K C 0.6903(3) 0.5261(3) 0.3330(3) 0.0402(6) Uani 1 1 d . . . . .
H8 H 0.7477 0.5315 0.2551 0.048 Uiso 1 1 calc R U . . .
H9 H 0.6108 0.4841 0.2864 0.048 Uiso 1 1 calc R U . . .
C00L C 0.8500(3) 0.7415(3) 0.3844(3) 0.0420(7) Uani 1 1 d . . . . .
H10 H 0.8635 0.7979 0.4680 0.050 Uiso 1 1 calc R U . . .
H11 H 0.8967 0.7029 0.4072 0.050 Uiso 1 1 calc R U . . .
B00M B 0.5339(3) 0.9656(3) 0.6074(4) 0.0303(6) Uani 1 1 d . . . . .
C00N C 0.8914(3) 0.8080(3) 0.2331(4) 0.0513(8) Uani 1 1 d . . . . .
H12 H 0.8823 0.7529 0.1512 0.077 Uiso 1 1 calc R U . . .
H13 H 0.9745 0.8690 0.2416 0.077 Uiso 1 1 calc R U . . .
H14 H 0.8440 0.8448 0.2093 0.077 Uiso 1 1 calc R U . . .
C00O C 0.6941(3) 0.4555(3) 0.4709(4) 0.0439(7) Uani 1 1 d . . . . .
H15 H 0.7720 0.4979 0.5190 0.066 Uiso 1 1 calc R U . . .
H16 H 0.6789 0.3780 0.4365 0.066 Uiso 1 1 calc R U . . .
H17 H 0.6338 0.4456 0.5453 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00H 1.742(3) . ?
F002 B00M 1.398(4) . ?
O003 C00C 1.347(3) . ?
O003 B00M 1.439(3) . ?
O004 C009 1.354(3) . ?
O004 B00M 1.458(3) . ?
N005 C00A 1.312(3) . ?
N005 C007 1.403(3) . ?
N005 B00M 1.564(3) . ?
N6 C00B 1.355(3) . ?
N6 C00K 1.470(3) . ?
N6 C00L 1.507(4) . ?
C007 C00I 1.384(3) . ?
C007 C009 1.398(4) . ?
C008 C00J 1.366(4) . ?
C008 C00G 1.412(3) . ?
C008 H1 0.9300 . ?
C009 C00E 1.382(4) . ?
C00A C00G 1.410(3) . ?
C00A H2 0.9300 . ?
C00B C00D 1.408(4) . ?
C00B C00J 1.432(4) . ?
C00C C00D 1.370(3) . ?
C00C C00G 1.434(3) . ?
C00D H3 0.9300 . ?
C00E C00H 1.381(4) . ?
C00E H4 0.9300 . ?
C00F C00H 1.386(4) . ?
C00F C00I 1.397(4) . ?
C00F H5 0.9300 . ?
C00I H6 0.9300 . ?
C00J H7 0.9300 . ?
C00K C00O 1.503(4) . ?
C00K H8 0.9700 . ?
C00K H9 0.9700 . ?
C00L C00N 1.495(5) . ?
C00L H10 0.9700 . ?
C00L H11 0.9700 . ?
C00N H12 0.9600 . ?
C00N H13 0.9600 . ?
C00N H14 0.9600 . ?
C00O H15 0.9600 . ?
C00O H16 0.9600 . ?
C00O H17 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
C00C O003 B00M 117.38(19) . . ?
C009 O004 B00M 108.3(2) . . ?
C00A N005 C007 131.1(2) . . ?
C00A N005 B00M 120.6(2) . . ?
C007 N005 B00M 107.00(19) . . ?
C00B N6 C00K 122.2(3) . . ?
C00B N6 C00L 121.6(2) . . ?
C00K N6 C00L 116.1(2) . . ?
C00I C007 C009 121.8(2) . . ?
C00I C007 N005 131.2(2) . . ?
C009 C007 N005 106.8(2) . . ?
C00J C008 C00G 121.8(2) . . ?
C00J C008 H1 119.1 . . ?
C00G C008 H1 119.1 . . ?
O004 C009 C00E 125.2(3) . . ?
O004 C009 C007 113.9(2) . . ?
C00E C009 C007 120.8(3) . . ?
N005 C00A C00G 118.6(2) . . ?
N005 C00A H2 120.7 . . ?
C00G C00A H2 120.7 . . ?
N6 C00B C00D 120.6(2) . . ?
N6 C00B C00J 121.7(2) . . ?
C00D C00B C00J 117.7(2) . . ?
O003 C00C C00D 118.2(2) . . ?
O003 C00C C00G 121.2(2) . . ?
C00D C00C C00G 120.5(2) . . ?
C00C C00D C00B 121.8(2) . . ?
C00C C00D H3 119.1 . . ?
C00B C00D H3 119.1 . . ?
C009 C00E C00H 116.9(3) . . ?
C009 C00E H4 121.6 . . ?
C00H C00E H4 121.6 . . ?
C00H C00F C00I 119.7(2) . . ?
C00H C00F H5 120.2 . . ?
C00I C00F H5 120.2 . . ?
C00A C00G C008 122.6(2) . . ?
C00A C00G C00C 119.1(2) . . ?
C008 C00G C00C 117.5(2) . . ?
C00E C00H C00F 123.3(3) . . ?
C00E C00H Cl01 117.6(2) . . ?
C00F C00H Cl01 119.1(2) . . ?
C007 C00I C00F 117.5(3) . . ?
C007 C00I H6 121.2 . . ?
C00F C00I H6 121.2 . . ?
C008 C00J C00B 120.7(2) . . ?
C008 C00J H7 119.7 . . ?
C00B C00J H7 119.7 . . ?
N6 C00K C00O 111.7(2) . . ?
N6 C00K H8 109.3 . . ?
C00O C00K H8 109.3 . . ?
N6 C00K H9 109.3 . . ?
C00O C00K H9 109.3 . . ?
H8 C00K H9 107.9 . . ?
C00N C00L N6 111.2(2) . . ?
C00N C00L H10 109.4 . . ?
N6 C00L H10 109.4 . . ?
C00N C00L H11 109.4 . . ?
N6 C00L H11 109.4 . . ?
H10 C00L H11 108.0 . . ?
F002 B00M O003 109.9(2) . . ?
F002 B00M O004 111.0(2) . . ?
O003 B00M O004 114.1(2) . . ?
F002 B00M N005 109.6(2) . . ?
O003 B00M N005 109.5(2) . . ?
O004 B00M N005 102.4(2) . . ?
C00L C00N H12 109.5 . . ?
C00L C00N H13 109.5 . . ?
H12 C00N H13 109.5 . . ?
C00L C00N H14 109.5 . . ?
H12 C00N H14 109.5 . . ?
H13 C00N H14 109.5 . . ?
C00K C00O H15 109.5 . . ?
C00K C00O H16 109.5 . . ?
H15 C00O H16 109.5 . . ?
C00K C00O H17 109.5 . . ?
H15 C00O H17 109.5 . . ?
H16 C00O H17 109.5 . . ?

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
C00A N005 C007 C00I 17.0(4) . . . . ?
B00M N005 C007 C00I -176.2(3) . . . . ?
C00A N005 C007 C009 -158.4(2) . . . . ?
B00M N005 C007 C009 8.4(3) . . . . ?
B00M O004 C009 C00E 175.8(3) . . . . ?
B00M O004 C009 C007 -6.5(3) . . . . ?
C00I C007 C009 O004 -177.5(2) . . . . ?
N005 C007 C009 O004 -1.6(3) . . . . ?
C00I C007 C009 C00E 0.2(4) . . . . ?
N005 C007 C009 C00E 176.1(2) . . . . ?
C007 N005 C00A C00G 156.8(2) . . . . ?
B00M N005 C00A C00G -8.5(3) . . . . ?
C00K N6 C00B C00D -173.0(3) . . . . ?
C00L N6 C00B C00D 10.1(4) . . . . ?
C00K N6 C00B C00J 8.2(4) . . . . ?
C00L N6 C00B C00J -168.7(3) . . . . ?
B00M O003 C00C C00D -161.0(3) . . . . ?
B00M O003 C00C C00G 22.0(3) . . . . ?
O003 C00C C00D C00B -179.2(2) . . . . ?
C00G C00C C00D C00B -2.2(4) . . . . ?
N6 C00B C00D C00C -177.2(3) . . . . ?
C00J C00B C00D C00C 1.7(4) . . . . ?
O004 C009 C00E C00H 177.2(3) . . . . ?
C007 C009 C00E C00H -0.3(4) . . . . ?
N005 C00A C00G C008 176.2(2) . . . . ?
N005 C00A C00G C00C -14.0(3) . . . . ?
C00J C008 C00G C00A 170.0(2) . . . . ?
C00J C008 C00G C00C 0.1(4) . . . . ?
O003 C00C C00G C00A 7.9(3) . . . . ?
C00D C00C C00G C00A -169.0(2) . . . . ?
O003 C00C C00G C008 178.2(2) . . . . ?
C00D C00C C00G C008 1.2(4) . . . . ?
C009 C00E C00H C00F 0.7(4) . . . . ?
C009 C00E C00H Cl01 -178.8(2) . . . . ?
C00I C00F C00H C00E -1.1(4) . . . . ?
C00I C00F C00H Cl01 178.5(2) . . . . ?
C009 C007 C00I C00F -0.5(4) . . . . ?
N005 C007 C00I C00F -175.3(2) . . . . ?
C00H C00F C00I C007 0.9(4) . . . . ?
C00G C008 C00J C00B -0.5(4) . . . . ?
N6 C00B C00J C008 178.5(3) . . . . ?
C00D C00B C00J C008 -0.4(4) . . . . ?
C00B N6 C00K C00O -91.9(3) . . . . ?
C00L N6 C00K C00O 85.1(3) . . . . ?
C00B N6 C00L C00N -89.6(3) . . . . ?
C00K N6 C00L C00N 93.4(3) . . . . ?
C00C O003 B00M F002 79.9(3) . . . . ?
C00C O003 B00M O004 -154.7(2) . . . . ?
C00C O003 B00M N005 -40.5(3) . . . . ?
C009 O004 B00M F002 -106.1(2) . . . . ?
C009 O004 B00M O003 129.0(2) . . . . ?
C009 O004 B00M N005 10.8(3) . . . . ?
C00A N005 B00M F002 -85.4(3) . . . . ?
C007 N005 B00M F002 106.1(2) . . . . ?
C00A N005 B00M O003 35.2(3) . . . . ?
C007 N005 B00M O003 -133.3(2) . . . . ?
C00A N005 B00M O004 156.6(2) . . . . ?
C007 N005 B00M O004 -11.8(3) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041

