# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_amji413
_database_code_depnum_ccdc_archive 'CCDC 1864774'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 B N2 O2'
_chemical_formula_sum            'C14 H21 B N2 O2'
_chemical_formula_weight         260.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H19BN2O2
_chemical_oxdiff_usercomment     JER386
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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   22.1499(9)
_cell_length_b                   7.8915(2)
_cell_length_c                   17.5288(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.175(4)
_cell_angle_gamma                90
_cell_volume                     2857.09(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      28.7170
_cell_measurement_theta_min      3.4600
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.974
_diffrn_reflns_theta_min         2.763
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  24.00   1.00    4.50    --  -18.77 -99.00 -60.00   41
  2  ω    -11.00  24.00   1.00    4.50    --  -18.77 -99.00-180.00   35
  3  ω    -19.00   7.00   1.00    4.50    --  -18.77  57.00-150.00   26
  4  ω     53.00  89.00   1.00    4.50    --   20.02  57.00  60.00   36
  5  ω      0.00  89.00   1.00    4.50    --   20.02  57.00 -30.00   89
  6  ω     -5.00  93.00   1.00    4.50    --   20.02  37.00-120.00   98
  7  ω     36.00  77.00   1.00    4.50    --   20.02 178.00  90.00   41
  8  ω     18.00  55.00   1.00    4.50    --   20.02  77.00  30.00   37
  9  ω    -49.00  35.00   1.00    4.50    --   20.02 -57.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0251542000
_diffrn_orient_matrix_UB_12      0.0587549000
_diffrn_orient_matrix_UB_13      -0.0037985000
_diffrn_orient_matrix_UB_21      0.0233710000
_diffrn_orient_matrix_UB_22      0.0623788000
_diffrn_orient_matrix_UB_23      0.0202377000
_diffrn_orient_matrix_UB_31      0.0007961000
_diffrn_orient_matrix_UB_32      0.0271477000
_diffrn_orient_matrix_UB_33      -0.0381872000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2814
_reflns_number_total             3381
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.223
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.071
_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)+(0.0490P)²+1.8190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C5(H5A,H5B,H5C)
;
_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
O1 O 0.58517(5) 0.40020(12) 0.46740(6) 0.0308(3) Uani 1 1 d . . . . .
O2 O 0.59512(6) 0.55866(14) 0.36726(6) 0.0376(3) Uani 1 1 d . . . . .
N2 N 0.69914(6) 0.60352(15) 0.63641(7) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.62401(6) 0.69377(14) 0.67770(7) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.71611(7) 0.54965(17) 0.71678(8) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.57774(6) 0.54699(17) 0.42475(8) 0.0243(3) Uani 1 1 d . . . . .
C6 C 0.64338(7) 0.69263(17) 0.61300(8) 0.0241(3) Uani 1 1 d . . . . .
C7 C 0.66802(7) 0.60779(17) 0.74308(8) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.54952(7) 0.68363(17) 0.45986(8) 0.0260(3) Uani 1 1 d . . . . .
H3 H 0.522657 0.632212 0.487442 0.031 Uiso 1 1 calc R . . . .
C4 C 0.50778(7) 0.80368(19) 0.39342(9) 0.0330(3) Uani 1 1 d . . . . .
H4A H 0.492665 0.894612 0.419220 0.040 Uiso 1 1 calc R . . . .
H4B H 0.534556 0.853937 0.366214 0.040 Uiso 1 1 calc R . . . .
C12 C 0.67014(8) 0.5783(2) 0.82227(9) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.637851 0.616588 0.840238 0.044 Uiso 1 1 calc R . . . .
C9 C 0.76926(8) 0.45966(19) 0.76748(10) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.801495 0.420784 0.749542 0.043 Uiso 1 1 calc R . . . .
C1 C 0.61340(8) 0.26221(19) 0.43834(10) 0.0374(4) Uani 1 1 d . . . . .
H1A H 0.589487 0.244573 0.381142 0.056 Uiso 1 1 calc GR . . . .
H1B H 0.611997 0.161105 0.468117 0.056 Uiso 1 1 calc GR . . . .
H1C H 0.657573 0.288779 0.446368 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.56497(8) 0.7712(2) 0.67993(10) 0.0354(4) Uani 1 1 d . . . . .
H13A H 0.542163 0.825112 0.628437 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.575853 0.854059 0.722889 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.537993 0.685438 0.689939 0.053 Uiso 1 1 calc GR . . . .
C14 C 0.73599(8) 0.5632(2) 0.58517(10) 0.0382(4) Uani 1 1 d . . . . .
H14A H 0.780527 0.593541 0.613127 0.057 Uiso 1 1 calc GR . . . .
H14B H 0.718876 0.625346 0.534824 0.057 Uiso 1 1 calc GR . . . .
H14C H 0.732950 0.443879 0.573638 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.72309(9) 0.4886(2) 0.87255(10) 0.0452(5) Uani 1 1 d . . . . .
H11 H 0.726506 0.465829 0.926006 0.054 Uiso 1 1 calc R . . . .
C10 C 0.77146(9) 0.4313(2) 0.84593(10) 0.0449(5) Uani 1 1 d . . . . .
H10 H 0.806343 0.372067 0.882184 0.054 Uiso 1 1 calc R . . . .
C5 C 0.44947(9) 0.7207(2) 0.32928(12) 0.0504(5) Uani 1 1 d . . . . .
H5A H 0.425209 0.804606 0.290735 0.076 Uiso 1 1 calc GR . . . .
H5B H 0.422491 0.670578 0.355428 0.076 Uiso 1 1 calc GR . . . .
H5C H 0.463910 0.634474 0.301174 0.076 Uiso 1 1 calc GR . . . .
B1 B 0.60895(9) 0.7917(2) 0.52778(9) 0.0285(4) Uani 1 1 d . . . . .
H1D H 0.6461(7) 0.8263(19) 0.5010(9) 0.026(4) Uiso 1 1 d . . . . .
H1E H 0.5869(8) 0.914(2) 0.5427(10) 0.036(4) 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
O1 C2 1.3561(16) . ?
O1 C1 1.4374(18) . ?
O2 C2 1.2052(17) . ?
N2 C8 1.3872(17) . ?
N2 C6 1.3498(18) . ?
N2 C14 1.4505(18) . ?
N1 C6 1.3498(17) . ?
N1 C7 1.3845(18) . ?
N1 C13 1.4567(19) . ?
C8 C7 1.383(2) . ?
C8 C9 1.387(2) . ?
C2 C3 1.487(2) . ?
C6 B1 1.613(2) . ?
C7 C12 1.3915(19) . ?
C3 H3 0.9800 . ?
C3 C4 1.5266(19) . ?
C3 B1 1.657(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.521(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.390(3) . ?
C10 H10 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
B1 H1D 1.119(15) . ?
B1 H1E 1.157(17) . ?

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
C2 O1 C1 115.70(11) . . ?
C8 N2 C14 123.71(13) . . ?
C6 N2 C8 110.54(11) . . ?
C6 N2 C14 125.72(12) . . ?
C6 N1 C7 110.47(12) . . ?
C6 N1 C13 125.89(12) . . ?
C7 N1 C13 123.63(12) . . ?
N2 C8 C9 131.56(14) . . ?
C7 C8 N2 106.15(12) . . ?
C7 C8 C9 122.27(14) . . ?
O1 C2 C3 112.15(11) . . ?
O2 C2 O1 120.95(13) . . ?
O2 C2 C3 126.85(13) . . ?
N2 C6 B1 127.50(12) . . ?
N1 C6 N2 106.36(11) . . ?
N1 C6 B1 125.98(13) . . ?
N1 C7 C12 131.90(14) . . ?
C8 C7 N1 106.47(12) . . ?
C8 C7 C12 121.63(14) . . ?
C2 C3 H3 109.0 . . ?
C2 C3 C4 111.33(12) . . ?
C2 C3 B1 109.10(12) . . ?
C4 C3 H3 109.0 . . ?
C4 C3 B1 109.50(11) . . ?
B1 C3 H3 109.0 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.54(13) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C7 C12 H12 122.0 . . ?
C11 C12 C7 115.94(16) . . ?
C11 C12 H12 122.0 . . ?
C8 C9 H9 122.0 . . ?
C10 C9 C8 116.02(16) . . ?
C10 C9 H9 122.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11 118.9 . . ?
C12 C11 C10 122.18(15) . . ?
C10 C11 H11 118.9 . . ?
C9 C10 C11 121.96(15) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 B1 C3 113.78(12) . . ?
C6 B1 H1D 109.5(8) . . ?
C6 B1 H1E 107.1(8) . . ?
C3 B1 H1D 109.8(8) . . ?
C3 B1 H1E 107.6(8) . . ?
H1D B1 H1E 109.0(12) . . ?

_olex2_date_sample_data_collection 2018-05-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.547
_oxdiff_exptl_absorpt_empirical_full_min 0.484
####################################################################### 
# 
# 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_xmji86
_database_code_depnum_ccdc_archive 'CCDC 1864777'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H19 B N2 O2'
_chemical_formula_sum            'C10 H19 B N2 O2'
_chemical_formula_weight         210.08
_chemical_absolute_configuration syn
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6119(2)
_cell_length_b                   12.8257(2)
_cell_length_c                   7.7086(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.978(3)
_cell_angle_gamma                90
_cell_volume                     606.20(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5966
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.2800
_cell_measurement_theta_min      6.1920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.1
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.623
_diffrn_reflns_theta_min         6.191
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     67.90 254.90   1.00   10.00    --   97.68  73.87 -25.79  187
  2  ω     83.90 268.90   1.00   10.00    --  112.68  73.87  64.21  185
  3  ω    -68.18 116.82   1.00   10.00    --  -39.39  73.87  19.21  185
  4  φ    -25.79 334.43   1.00   10.00  58.16  87.95  73.87    --   360
  5  ω    -68.18 116.82   1.00   10.00    --  -39.39  73.87 -25.79  185
  6  ω     83.90 268.90   1.00   10.00    --  112.68  73.87 124.21  185
  7  ω     83.90 268.90   1.00   10.00    --  112.68  73.87-145.79  185
  8  ω     83.90 268.90   1.00   10.00    --  112.68  73.87  34.21  185
  9  φ    -25.79 334.43   1.00   10.00  28.16  57.95  73.87    --   360
 10  ω     83.90 268.90   1.00   10.00    --  112.68  73.87 154.21  185
 11  φ    -25.79 334.43   1.00   10.00  73.16 102.95  73.87    --   360
 12  ω    -68.18 116.82   1.00   10.00    --  -39.39  73.87  64.21  185
 13  ω     83.90 268.90   1.00   10.00    --  112.68  73.87  94.21  185
 14  φ    -57.29 133.83   1.00   10.00 -11.66  18.13  73.87    --   191
 15  φ    -25.79 334.43   1.00   10.00 -72.95 -43.16  73.87    --   360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Prospector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0168801000
_diffrn_orient_matrix_UB_12      -0.0208445000
_diffrn_orient_matrix_UB_13      -0.2017467000
_diffrn_orient_matrix_UB_21      0.2187942000
_diffrn_orient_matrix_UB_22      -0.0589464000
_diffrn_orient_matrix_UB_23      0.0755778000
_diffrn_orient_matrix_UB_31      -0.1222963000
_diffrn_orient_matrix_UB_32      -0.1025967000
_diffrn_orient_matrix_UB_33      -0.0024195000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                2279
_reflns_number_total             2404
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.45
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.197
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.072
_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)+(0.0513P)²+0.1182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H008)
2.b Secondary CH2 refined with riding coordinates:
 C4(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H007), C8(H009)
2.d Idealised Me refined as rotating group:
 C5(H00A,H00B,H00C), C9(H00D,H00E,H00F), C10(H00G,H00H,H00I), C1(H00J,H00K,H00L)
;
_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
O001 O 0.4253(3) 0.72922(14) 0.9288(3) 0.0442(5) Uani 1 1 d . . . . .
O002 O 0.7330(3) 0.63989(14) 0.9910(3) 0.0388(5) Uani 1 1 d . . . . .
N003 N 0.3796(3) 0.34427(15) 0.5521(3) 0.0282(4) Uani 1 1 d . . . . .
N004 N 0.0593(3) 0.40834(15) 0.4335(3) 0.0282(4) Uani 1 1 d . . . . .
C005 C 0.2676(3) 0.43374(17) 0.5373(3) 0.0232(4) Uani 1 1 d . . . . .
C006 C 0.5136(4) 0.64783(19) 0.9253(3) 0.0293(5) Uani 1 1 d . . . . .
C007 C 0.2434(5) 0.2647(2) 0.4570(4) 0.0388(6) Uani 1 1 d . . . . .
H007 H 0.283316 0.196077 0.446978 0.047 Uiso 1 1 calc R . . . .
C008 C 0.4065(4) 0.54668(17) 0.8491(3) 0.0284(5) Uani 1 1 d . . . . .
H008 H 0.508212 0.490309 0.910502 0.034 Uiso 1 1 calc R . . . .
C009 C 0.0423(5) 0.3052(2) 0.3815(4) 0.0378(6) Uani 1 1 d . . . . .
H009 H -0.084119 0.270237 0.308235 0.045 Uiso 1 1 calc R . . . .
C00A C 0.2423(5) 0.5182(2) 1.0976(4) 0.0435(7) Uani 1 1 d . . . . .
H00A H 0.106163 0.509103 1.113500 0.065 Uiso 1 1 calc GR . . . .
H00B H 0.315038 0.578972 1.164976 0.065 Uiso 1 1 calc GR . . . .
H00C H 0.332522 0.458026 1.144691 0.065 Uiso 1 1 calc GR . . . .
C00B C 0.6116(4) 0.3300(2) 0.6626(4) 0.0391(6) Uani 1 1 d . . . . .
H00D H 0.683650 0.396456 0.683258 0.059 Uiso 1 1 calc GR . . . .
H00E H 0.674316 0.285196 0.596387 0.059 Uiso 1 1 calc GR . . . .
H00F H 0.629262 0.299048 0.780778 0.059 Uiso 1 1 calc GR . . . .
C00C C -0.1253(4) 0.4798(2) 0.3758(4) 0.0421(6) Uani 1 1 d . . . . .
H00G H -0.153657 0.501777 0.483571 0.063 Uiso 1 1 calc GR . . . .
H00H H -0.251719 0.445170 0.289599 0.063 Uiso 1 1 calc GR . . . .
H00I H -0.092214 0.539542 0.316154 0.063 Uiso 1 1 calc GR . . . .
C00D C 0.8522(5) 0.7344(2) 1.0625(4) 0.0479(7) Uani 1 1 d . . . . .
H00J H 0.805132 0.787649 0.968279 0.072 Uiso 1 1 calc GR . . . .
H00K H 1.005276 0.721881 1.096098 0.072 Uiso 1 1 calc GR . . . .
H00L H 0.825617 0.756788 1.170957 0.072 Uiso 1 1 calc GR . . . .
C00E C 0.1996(4) 0.5318(2) 0.8903(3) 0.0333(5) Uani 1 1 d . . . . .
H00M H 0.105576 0.591762 0.843358 0.040 Uiso 1 1 calc R . . . .
H00N H 0.122460 0.470898 0.822979 0.040 Uiso 1 1 calc R . . . .
B00F B 0.3652(4) 0.54535(19) 0.6241(4) 0.0283(5) Uani 1 1 d . . . . .
H00O H 0.245(4) 0.609(2) 0.554(4) 0.027(7) Uiso 1 1 d . . . . .
H00P H 0.525(5) 0.556(2) 0.607(4) 0.039(8) 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
O001 C006 1.201(3) . ?
O002 C006 1.350(3) . ?
O002 C00D 1.439(3) . ?
N003 C005 1.347(3) . ?
N003 C007 1.377(3) . ?
N003 C00B 1.461(3) . ?
N004 C005 1.349(3) . ?
N004 C009 1.375(3) . ?
N004 C00C 1.456(3) . ?
C005 B00F 1.609(3) . ?
C006 C008 1.489(3) . ?
C007 C009 1.341(4) . ?
C008 C00E 1.528(3) . ?
C008 B00F 1.652(3) . ?
C00A C00E 1.525(4) . ?

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
C006 O002 C00D 116.0(2) . . ?
C005 N003 C007 110.92(19) . . ?
C005 N003 C00B 125.5(2) . . ?
C007 N003 C00B 123.5(2) . . ?
C005 N004 C009 111.1(2) . . ?
C005 N004 C00C 125.6(2) . . ?
C009 N004 C00C 123.3(2) . . ?
N003 C005 N004 104.56(19) . . ?
N003 C005 B00F 126.9(2) . . ?
N004 C005 B00F 128.54(19) . . ?
O001 C006 O002 121.4(2) . . ?
O001 C006 C008 127.1(2) . . ?
O002 C006 C008 111.6(2) . . ?
C009 C007 N003 106.8(2) . . ?
C006 C008 C00E 111.0(2) . . ?
C006 C008 B00F 106.88(18) . . ?
C00E C008 B00F 114.04(19) . . ?
C007 C009 N004 106.7(2) . . ?
C00A C00E C008 113.8(2) . . ?
C005 B00F C008 109.19(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.764
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# 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_lmji9
_database_code_depnum_ccdc_archive 'CCDC 1864776'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H41 B N2 O2'
_chemical_formula_sum            'C30 H41 B N2 O2'
_chemical_formula_weight         472.46
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20B1N2O2
_chemical_oxdiff_usercomment     JER410
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.10720(10)
_cell_length_b                   15.5083(2)
_cell_length_c                   9.60940(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.8720(10)
_cell_angle_gamma                90
_cell_volume                     1350.08(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    149.9(2)
_cell_measurement_theta_max      70.7510
_cell_measurement_theta_min      4.5990
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method 
'Crystallised by slow cooling of a hot hexane solution'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13740
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.945
_diffrn_reflns_theta_min         4.626
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 144.00   0.50    0.50    --   55.00  53.00 139.00  118
  2  ω     44.00  70.00   0.50    0.50    --   55.00  53.00 139.00   52
  3  ω     71.00 198.00   0.50    1.00    --  110.00  53.00 139.00  254
  4  ω    -55.00 -25.00   0.50    0.50    --    0.00  40.00 -60.00   60
  5  ω    -89.00 -60.00   0.50    0.50    --    0.00  40.00 -60.00   58
  6  ω     52.00  86.00   0.50    0.50    --    0.00  53.00 139.00   68
  7  ω    -20.00  48.00   0.50    0.50    --    0.00  40.00 -60.00  136
  8  ω    -60.00 -13.00   0.50    0.50    --    0.00  53.00 139.00   94
  9  ω     52.00  80.00   0.50    0.50    --   55.00  40.00-120.00   56
 10  ω    112.00 144.00   0.50    0.50    --   55.00  50.00 -60.00   64
 11  ω     37.00  93.00   0.50    0.50    --   55.00  20.00 -90.00  112
 12  ω     15.00 144.00   0.50    0.50    --   55.00  50.00  60.00  258
 13  ω    -17.00 140.00   0.50    0.50    --   55.00  40.00  90.00  314
 14  ω    -32.00  45.00   0.50    0.50    --   55.00  40.00-120.00  154
 15  ω    -21.00   5.00   0.50    0.50    --   55.00  50.00 -60.00   52
 16  ω    -32.00 142.00   0.50    0.50    --   55.00  30.00-150.00  348
 17  ω     21.00  49.00   0.50    1.00    --  110.00  20.00 -90.00   56
 18  ω    125.00 154.00   0.50    1.00    --  110.00  20.00-150.00   58
 19  ω     70.00  96.00   0.50    1.00    --  110.00  40.00-150.00   52
 20  ω     21.00  47.00   0.50    1.00    --  110.00  40.00-150.00   52
 21  ω     21.00  48.00   0.50    1.00    --  110.00  20.00 -60.00   54
 22  ω     21.00  47.00   0.50    1.00    --  110.00  40.00-120.00   52
 23  ω     21.00 105.00   0.50    1.00    --  110.00  20.00  90.00  168
 24  ω     21.00  47.00   0.50    1.00    --  110.00  30.00 -60.00   52
 25  ω     89.00 164.00   0.50    1.00    --  110.00  40.00  60.00  150
 26  ω     22.00  47.00   0.50    1.00    --  110.00  20.00  60.00   50
 27  ω     24.00 102.00   0.50    1.00    --  110.00  10.00  60.00  156
 28  ω    146.00 172.00   0.50    1.00    --  110.00  20.00 -60.00   52
 29  ω     21.00 120.00   0.50    1.00    --  110.00  20.00-150.00  198
 30  ω     21.00  86.00   0.50    1.00    --  110.00  10.00 -60.00  130
 31  ω     21.00  47.00   0.50    1.00    --  110.00  30.00  60.00   52
 32  ω     22.00  47.00   0.50    1.00    --  110.00  40.00  60.00   50
 33  ω     23.00  48.00   0.50    1.00    --  110.00  20.00-120.00   50
 34  ω    123.00 148.00   0.50    1.00    --  110.00  40.00-180.00   50
 35  ω     22.00  48.00   0.50    1.00    --  110.00  30.00 -90.00   52
 36  ω     22.00  52.00   0.50    1.00    --  110.00  40.00-180.00   60
 37  ω    159.00 185.00   0.50    1.00    --  110.00  40.00 -90.00   52
 38  ω     21.00  47.00   0.50    1.00    --  110.00  30.00-120.00   52
 39  ω     69.00  94.00   0.50    1.00    --  110.00  30.00 -90.00   50
 40  ω     35.00  85.00   0.50    1.00    --  110.00   0.00-180.00  100
 41  ω     21.00  92.00   0.50    1.00    --  110.00  10.00-120.00  142
 42  ω     21.00 173.00   0.50    1.00    --  110.00  40.00  30.00  304
 43  ω     22.00 175.00   0.50    1.00    --  110.00  40.00 120.00  306
 44  ω     23.00  49.00   0.50    1.00    --  110.00  40.00  90.00   52
 45  ω     22.00  48.00   0.50    1.00    --  110.00  30.00-150.00   52
 46  ω     21.00  47.00   0.50    1.00    --  110.00  40.00 -90.00   52
 47  ω     21.00  47.00   0.50    1.00    --  110.00  30.00  90.00   52
 48  ω    154.00 186.00   0.50    1.00    --  110.00  30.00  90.00   64
 49  ω    124.00 151.00   0.50    1.00    --  110.00  40.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0374912000
_diffrn_orient_matrix_UB_12      -0.0523359000
_diffrn_orient_matrix_UB_13      0.1279729000
_diffrn_orient_matrix_UB_21      0.1317116000
_diffrn_orient_matrix_UB_22      -0.0602125000
_diffrn_orient_matrix_UB_23      -0.0162917000
_diffrn_orient_matrix_UB_31      0.1008064000
_diffrn_orient_matrix_UB_32      0.0592002000
_diffrn_orient_matrix_UB_33      0.0965816000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4852
_reflns_number_total             5068
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_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         0.129
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5068
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.018
_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)+(0.0425P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0712
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00D), C00E(H00E), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00I(H00I,H00J), C00Q(H00R,H00S), C00R(H00T,H00U)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00G(H00G), C00H(H00H), C00J(H00K), C00K(H00L), C00L(H00M),
 C00M(H00N), C00N(H00O), C00O(H00P), C00P(H00Q), C00U(H00Z), C00V(H00)
2.d Idealised Me refined as rotating group:
 C00S(H00V,H00W,H00X), C00T(H00Y,H,HA), C00W(H0AA,HB,HC), C00X(H1AA,HD,HE),
 C00Y(H2AA,HF,HG)
;
_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
O001 O 0.58233(13) 0.50625(8) 0.40734(12) 0.0228(3) Uani 1 1 d . . . . .
O002 O 0.72716(14) 0.38880(9) 0.43668(14) 0.0293(3) Uani 1 1 d . . . . .
N003 N 0.26319(17) 0.31314(10) 0.31028(17) 0.0284(3) Uani 1 1 d . . . . .
N004 N 0.15173(16) 0.38452(11) 0.45746(17) 0.0283(3) Uani 1 1 d . . . . .
C005 C 0.62625(18) 0.43154(11) 0.47223(17) 0.0206(3) Uani 1 1 d . . . . .
C006 C 0.76504(18) 0.44104(12) 0.77216(17) 0.0247(4) Uani 1 1 d . . . . .
C007 C 0.38627(18) 0.60439(12) -0.01093(18) 0.0239(3) Uani 1 1 d . . . . .
C008 C 0.64236(19) 0.38028(12) 0.71701(18) 0.0251(3) Uani 1 1 d . . . . .
H00A H 0.583270 0.367776 0.793005 0.030 Uiso 1 1 calc R . . . .
H00B H 0.687264 0.326500 0.691957 0.030 Uiso 1 1 calc R . . . .
C009 C 0.67460(18) 0.53908(12) 0.30347(17) 0.0223(3) Uani 1 1 d . . . . .
H009 H 0.717120 0.490377 0.256458 0.027 Uiso 1 1 calc R . . . .
C00A C 0.28151(19) 0.34562(11) 0.4402(2) 0.0253(4) Uani 1 1 d . . . . .
C00B C 0.7694(2) 0.52735(12) 0.73545(18) 0.0261(4) Uani 1 1 d . . . . .
H00C H 0.692677 0.550409 0.675639 0.031 Uiso 1 1 calc R . . . .
C00C C 0.53742(18) 0.41021(11) 0.59060(17) 0.0218(3) Uani 1 1 d . . . . .
H00D H 0.483789 0.461659 0.616219 0.026 Uiso 1 1 calc R . . . .
C00D C 0.44411(19) 0.54924(12) 0.11658(17) 0.0246(4) Uani 1 1 d . . . . .
C00E C 0.9071(2) 0.62723(13) 0.2829(2) 0.0286(4) Uani 1 1 d . . . . .
H00E H 0.956256 0.578444 0.242419 0.034 Uiso 1 1 calc R . . . .
C00F C 0.58371(19) 0.59452(11) 0.19434(17) 0.0226(3) Uani 1 1 d . . . . .
H00F H 0.549940 0.645542 0.242124 0.027 Uiso 1 1 calc R . . . .
C00G C 0.3305(2) 0.68708(13) 0.0084(2) 0.0289(4) Uani 1 1 d . . . . .
H00G H 0.330914 0.708897 0.098590 0.035 Uiso 1 1 calc R . . . .
C00H C 0.1232(2) 0.33023(13) 0.2476(2) 0.0340(4) Uani 1 1 d . . . . .
H00H H 0.084599 0.313674 0.158301 0.041 Uiso 1 1 calc R . . . .
C00I C 0.8216(2) 0.67713(13) 0.1644(2) 0.0306(4) Uani 1 1 d . . . . .
H00I H 0.888271 0.693060 0.096141 0.037 Uiso 1 1 calc R . . . .
H00J H 0.783425 0.729804 0.201498 0.037 Uiso 1 1 calc R . . . .
C00J C 0.3854(2) 0.57491(13) -0.14832(18) 0.0274(4) Uani 1 1 d . . . . .
H00K H 0.422976 0.520511 -0.164766 0.033 Uiso 1 1 calc R . . . .
C00K C 0.9995(2) 0.54809(15) 0.8787(2) 0.0339(4) Uani 1 1 d . . . . .
H00L H 1.076892 0.583534 0.913917 0.041 Uiso 1 1 calc R . . . .
C00L C 0.2747(2) 0.73721(13) -0.1045(2) 0.0332(4) Uani 1 1 d . . . . .
H00M H 0.238731 0.792138 -0.088972 0.040 Uiso 1 1 calc R . . . .
C00M C 0.8814(2) 0.40939(14) 0.8647(2) 0.0335(4) Uani 1 1 d . . . . .
H00N H 0.881705 0.351647 0.890882 0.040 Uiso 1 1 calc R . . . .
C00N C 0.3292(2) 0.62550(14) -0.26117(19) 0.0308(4) Uani 1 1 d . . . . .
H00O H 0.330396 0.604586 -0.351752 0.037 Uiso 1 1 calc R . . . .
C00O C 0.0537(2) 0.37513(13) 0.3398(2) 0.0342(4) Uani 1 1 d . . . . .
H00P H -0.042454 0.396009 0.326827 0.041 Uiso 1 1 calc R . . . .
C00P C 0.8863(2) 0.58025(13) 0.78617(19) 0.0302(4) Uani 1 1 d . . . . .
H00Q H 0.888269 0.637522 0.757750 0.036 Uiso 1 1 calc R . . . .
C00Q C 0.6937(2) 0.62496(14) 0.09204(19) 0.0294(4) Uani 1 1 d . . . . .
H00R H 0.732863 0.574973 0.047656 0.035 Uiso 1 1 calc R . . . .
H00S H 0.641508 0.659974 0.019367 0.035 Uiso 1 1 calc R . . . .
C00R C 0.79880(19) 0.59162(12) 0.38091(18) 0.0266(4) Uani 1 1 d . . . . .
H00T H 0.852337 0.555527 0.451293 0.032 Uiso 1 1 calc R . . . .
H00U H 0.756476 0.639283 0.428579 0.032 Uiso 1 1 calc R . . . .
C00S C 0.3186(2) 0.54418(14) 0.2128(2) 0.0320(4) Uani 1 1 d . . . . .
H00V H 0.304625 0.599819 0.253217 0.048 Uiso 1 1 calc GR . . . .
H00W H 0.344102 0.503039 0.285927 0.048 Uiso 1 1 calc GR . . . .
H00X H 0.228936 0.526543 0.159057 0.048 Uiso 1 1 calc GR . . . .
C00T C 0.4820(2) 0.45778(13) 0.0727(2) 0.0328(4) Uani 1 1 d . . . . .
H00Y H 0.398541 0.433120 0.017637 0.049 Uiso 1 1 calc GR . . . .
H H 0.506453 0.423130 0.154608 0.049 Uiso 1 1 calc GR . . . .
HA H 0.564720 0.459659 0.018408 0.049 Uiso 1 1 calc GR . . . .
C00U C 0.9957(2) 0.46215(16) 0.9179(2) 0.0383(5) Uani 1 1 d . . . . .
H00Z H 1.070711 0.439887 0.980595 0.046 Uiso 1 1 calc R . . . .
C00V C 0.2719(2) 0.70622(13) -0.2402(2) 0.0322(4) Uani 1 1 d . . . . .
H00 H 0.232114 0.739263 -0.315641 0.039 Uiso 1 1 calc R . . . .
C00W C 0.3740(3) 0.26393(15) 0.2445(3) 0.0468(6) Uani 1 1 d . . . . .
H0AA H 0.470831 0.281764 0.282585 0.070 Uiso 1 1 calc GR . . . .
HB H 0.362504 0.274063 0.145471 0.070 Uiso 1 1 calc GR . . . .
HC H 0.361605 0.203589 0.262336 0.070 Uiso 1 1 calc GR . . . .
C00X C 1.0247(2) 0.68284(16) 0.3643(2) 0.0395(5) Uani 1 1 d . . . . .
H1AA H 1.091777 0.704302 0.301642 0.059 Uiso 1 1 calc GR . . . .
HD H 1.077956 0.648771 0.435996 0.059 Uiso 1 1 calc GR . . . .
HE H 0.978204 0.730431 0.406267 0.059 Uiso 1 1 calc GR . . . .
C00Y C 0.1180(3) 0.42996(17) 0.5837(2) 0.0465(6) Uani 1 1 d . . . . .
H2AA H 0.183510 0.410595 0.662077 0.070 Uiso 1 1 calc GR . . . .
HF H 0.017814 0.418244 0.600627 0.070 Uiso 1 1 calc GR . . . .
HG H 0.130395 0.490849 0.571301 0.070 Uiso 1 1 calc GR . . . .
B00Z B 0.4194(2) 0.32971(15) 0.5567(3) 0.0324(5) Uani 1 1 d . . . . .
H3AA H 0.482(3) 0.2711(19) 0.528(3) 0.049(7) Uiso 1 1 d . . . . .
HH H 0.369(3) 0.313(2) 0.658(3) 0.055(8) 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
O001 C005 1.357(2) . ?
O001 C009 1.4606(19) . ?
O002 C005 1.210(2) . ?
N003 C00A 1.341(3) . ?
N003 C00H 1.379(3) . ?
N003 C00W 1.460(2) . ?
N004 C00A 1.352(2) . ?
N004 C00O 1.375(3) . ?
N004 C00Y 1.463(3) . ?
C005 C00C 1.499(2) . ?
C006 C008 1.515(2) . ?
C006 C00B 1.386(3) . ?
C006 C00M 1.401(3) . ?
C007 C00D 1.542(2) . ?
C007 C00G 1.399(3) . ?
C007 C00J 1.396(2) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C008 C00C 1.538(2) . ?
C009 H009 0.9800 . ?
C009 C00F 1.532(2) . ?
C009 C00R 1.525(2) . ?
C00A B00Z 1.614(3) . ?
C00B H00C 0.9300 . ?
C00B C00P 1.392(3) . ?
C00C H00D 0.9800 . ?
C00C B00Z 1.658(3) . ?
C00D C00F 1.573(2) . ?
C00D C00S 1.544(2) . ?
C00D C00T 1.529(3) . ?
C00E H00E 0.9800 . ?
C00E C00I 1.523(3) . ?
C00E C00R 1.534(2) . ?
C00E C00X 1.526(3) . ?
C00F H00F 0.9800 . ?
C00F C00Q 1.548(2) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.388(3) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.336(3) . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00I C00Q 1.526(3) . ?
C00J H00K 0.9300 . ?
C00J C00N 1.393(3) . ?
C00K H00L 0.9300 . ?
C00K C00P 1.384(3) . ?
C00K C00U 1.386(3) . ?
C00L H00M 0.9300 . ?
C00L C00V 1.388(3) . ?
C00M H00N 0.9300 . ?
C00M C00U 1.380(3) . ?
C00N H00O 0.9300 . ?
C00N C00V 1.379(3) . ?
C00O H00P 0.9300 . ?
C00P H00Q 0.9300 . ?
C00Q H00R 0.9700 . ?
C00Q H00S 0.9700 . ?
C00R H00T 0.9700 . ?
C00R H00U 0.9700 . ?
C00S H00V 0.9600 . ?
C00S H00W 0.9600 . ?
C00S H00X 0.9600 . ?
C00T H00Y 0.9600 . ?
C00T H 0.9600 . ?
C00T HA 0.9600 . ?
C00U H00Z 0.9300 . ?
C00V H00 0.9300 . ?
C00W H0AA 0.9600 . ?
C00W HB 0.9600 . ?
C00W HC 0.9600 . ?
C00X H1AA 0.9600 . ?
C00X HD 0.9600 . ?
C00X HE 0.9600 . ?
C00Y H2AA 0.9600 . ?
C00Y HF 0.9600 . ?
C00Y HG 0.9600 . ?
B00Z H3AA 1.12(3) . ?
B00Z HH 1.14(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
C005 O001 C009 116.66(13) . . ?
C00A N003 C00H 110.84(16) . . ?
C00A N003 C00W 125.01(18) . . ?
C00H N003 C00W 124.12(18) . . ?
C00A N004 C00O 110.74(16) . . ?
C00A N004 C00Y 125.25(17) . . ?
C00O N004 C00Y 124.01(17) . . ?
O001 C005 C00C 112.37(14) . . ?
O002 C005 O001 122.33(15) . . ?
O002 C005 C00C 125.30(16) . . ?
C00B C006 C008 123.45(15) . . ?
C00B C006 C00M 117.40(17) . . ?
C00M C006 C008 119.15(17) . . ?
C00G C007 C00D 120.14(16) . . ?
C00J C007 C00D 122.55(16) . . ?
C00J C007 C00G 117.30(17) . . ?
C006 C008 H00A 107.9 . . ?
C006 C008 H00B 107.9 . . ?
C006 C008 C00C 117.69(14) . . ?
H00A C008 H00B 107.2 . . ?
C00C C008 H00A 107.9 . . ?
C00C C008 H00B 107.9 . . ?
O001 C009 H009 109.2 . . ?
O001 C009 C00F 110.80(13) . . ?
O001 C009 C00R 107.62(13) . . ?
C00F C009 H009 109.2 . . ?
C00R C009 H009 109.2 . . ?
C00R C009 C00F 110.87(15) . . ?
N003 C00A N004 104.75(16) . . ?
N003 C00A B00Z 127.06(18) . . ?
N004 C00A B00Z 127.67(18) . . ?
C006 C00B H00C 119.3 . . ?
C006 C00B C00P 121.42(17) . . ?
C00P C00B H00C 119.3 . . ?
C005 C00C C008 109.02(13) . . ?
C005 C00C H00D 109.4 . . ?
C005 C00C B00Z 114.00(14) . . ?
C008 C00C H00D 109.4 . . ?
C008 C00C B00Z 105.41(14) . . ?
B00Z C00C H00D 109.4 . . ?
C007 C00D C00F 108.88(14) . . ?
C007 C00D C00S 106.87(14) . . ?
C00S C00D C00F 110.50(14) . . ?
C00T C00D C007 111.34(15) . . ?
C00T C00D C00F 110.55(15) . . ?
C00T C00D C00S 108.64(16) . . ?
C00I C00E H00E 108.3 . . ?
C00I C00E C00R 109.30(15) . . ?
C00I C00E C00X 111.95(17) . . ?
C00R C00E H00E 108.3 . . ?
C00X C00E H00E 108.3 . . ?
C00X C00E C00R 110.52(16) . . ?
C009 C00F C00D 115.38(14) . . ?
C009 C00F H00F 107.8 . . ?
C009 C00F C00Q 105.45(13) . . ?
C00D C00F H00F 107.8 . . ?
C00Q C00F C00D 112.26(13) . . ?
C00Q C00F H00F 107.8 . . ?
C007 C00G H00G 119.4 . . ?
C00L C00G C007 121.25(18) . . ?
C00L C00G H00G 119.4 . . ?
N003 C00H H00H 126.6 . . ?
C00O C00H N003 106.90(17) . . ?
C00O C00H H00H 126.6 . . ?
C00E C00I H00I 109.1 . . ?
C00E C00I H00J 109.1 . . ?
C00E C00I C00Q 112.27(16) . . ?
H00I C00I H00J 107.9 . . ?
C00Q C00I H00I 109.1 . . ?
C00Q C00I H00J 109.1 . . ?
C007 C00J H00K 119.4 . . ?
C00N C00J C007 121.19(18) . . ?
C00N C00J H00K 119.4 . . ?
C00P C00K H00L 120.5 . . ?
C00P C00K C00U 118.91(19) . . ?
C00U C00K H00L 120.5 . . ?
C00G C00L H00M 119.7 . . ?
C00G C00L C00V 120.70(19) . . ?
C00V C00L H00M 119.7 . . ?
C006 C00M H00N 119.3 . . ?
C00U C00M C006 121.3(2) . . ?
C00U C00M H00N 119.3 . . ?
C00J C00N H00O 119.6 . . ?
C00V C00N C00J 120.82(18) . . ?
C00V C00N H00O 119.6 . . ?
N004 C00O H00P 126.6 . . ?
C00H C00O N004 106.76(17) . . ?
C00H C00O H00P 126.6 . . ?
C00B C00P H00Q 119.8 . . ?
C00K C00P C00B 120.35(19) . . ?
C00K C00P H00Q 119.8 . . ?
C00F C00Q H00R 109.1 . . ?
C00F C00Q H00S 109.1 . . ?
C00I C00Q C00F 112.70(14) . . ?
C00I C00Q H00R 109.1 . . ?
C00I C00Q H00S 109.1 . . ?
H00R C00Q H00S 107.8 . . ?
C009 C00R C00E 112.59(14) . . ?
C009 C00R H00T 109.1 . . ?
C009 C00R H00U 109.1 . . ?
C00E C00R H00T 109.1 . . ?
C00E C00R H00U 109.1 . . ?
H00T C00R H00U 107.8 . . ?
C00D C00S H00V 109.5 . . ?
C00D C00S H00W 109.5 . . ?
C00D C00S H00X 109.5 . . ?
H00V C00S H00W 109.5 . . ?
H00V C00S H00X 109.5 . . ?
H00W C00S H00X 109.5 . . ?
C00D C00T H00Y 109.5 . . ?
C00D C00T H 109.5 . . ?
C00D C00T HA 109.5 . . ?
H00Y C00T H 109.5 . . ?
H00Y C00T HA 109.5 . . ?
H C00T HA 109.5 . . ?
C00K C00U H00Z 119.7 . . ?
C00M C00U C00K 120.54(19) . . ?
C00M C00U H00Z 119.7 . . ?
C00L C00V H00 120.6 . . ?
C00N C00V C00L 118.72(18) . . ?
C00N C00V H00 120.6 . . ?
N003 C00W H0AA 109.5 . . ?
N003 C00W HB 109.5 . . ?
N003 C00W HC 109.5 . . ?
H0AA C00W HB 109.5 . . ?
H0AA C00W HC 109.5 . . ?
HB C00W HC 109.5 . . ?
C00E C00X H1AA 109.5 . . ?
C00E C00X HD 109.5 . . ?
C00E C00X HE 109.5 . . ?
H1AA C00X HD 109.5 . . ?
H1AA C00X HE 109.5 . . ?
HD C00X HE 109.5 . . ?
N004 C00Y H2AA 109.5 . . ?
N004 C00Y HF 109.5 . . ?
N004 C00Y HG 109.5 . . ?
H2AA C00Y HF 109.5 . . ?
H2AA C00Y HG 109.5 . . ?
HF C00Y HG 109.5 . . ?
C00A B00Z C00C 117.65(15) . . ?
C00A B00Z H3AA 109.4(14) . . ?
C00A B00Z HH 105.7(14) . . ?
C00C B00Z H3AA 109.0(15) . . ?
C00C B00Z HH 108.1(15) . . ?
H3AA B00Z HH 106(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.302
_oxdiff_exptl_absorpt_empirical_full_min 0.626
####################################################################### 
# 
# 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_lmji4
_database_code_depnum_ccdc_archive 'CCDC 1864775'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H17 B F2 N2 O2'
_chemical_formula_sum            'C10 H17 B F2 N2 O2'
_chemical_formula_weight         246.06
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20B1N2O2F2
_chemical_oxdiff_usercomment     JER330
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6658(8)
_cell_length_b                   13.0852(10)
_cell_length_c                   7.7113(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.529(13)
_cell_angle_gamma                90
_cell_volume                     621.28(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4058
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.4820
_cell_measurement_theta_min      3.3490
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4616
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.919
_diffrn_reflns_theta_min         10.123
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -43.00   0.50    0.50    --    0.00  29.00 120.00   68
  2  ω    -37.00  20.00   0.50    0.50    --    0.00  29.00 120.00  114
  3  ω     27.00  65.00   0.50    0.50    --   55.00  14.00  30.00   76
  4  ω    -12.00 143.00   0.50    0.50    --   55.00  43.00 -30.00  310
  5  ω    -34.00 139.00   0.50    0.50    --   55.00  60.00 -60.00  346
  6  ω    -18.00   7.00   0.50    0.50    --   55.00  14.00  30.00   50
  7  ω    -33.00  47.00   0.50    0.50    --   55.00  43.00  60.00  160
  8  ω     53.00 115.00   0.50    0.50    --   55.00  43.00  60.00  124
  9  ω    -18.00  15.00   0.50    0.50    --   55.00  60.00 -90.00   66
 10  ω     12.00  86.00   0.50    0.50    --   55.00  60.00-150.00  148
 11  ω     89.00 119.00   0.50    0.50    --   55.00  14.00  30.00   60
 12  ω     64.00  90.00   0.50    0.50    --  110.00  60.00 -60.00   52
 13  ω    117.00 197.00   0.50    0.50    --  110.00   0.00-120.00  160
 14  ω     47.00 113.00   0.50    0.50    --  110.00  38.00 -60.00  132
 15  ω     79.00 110.00   0.50    0.50    --  110.00   0.00-120.00   62
 16  ω     69.00 198.00   0.50    0.50    --  110.00  29.00  60.00  258
 17  ω     77.00 172.00   0.50    0.50    --  110.00  60.00  90.00  190
 18  ω     90.00 115.00   0.50    0.50    --  110.00  10.00 -60.00   50
 19  ω     24.00  49.00   0.50    0.50    --  110.00  60.00   0.00   50
 20  ω     87.00 181.00   0.50    0.50    --  110.00  60.00  30.00  188
 21  ω     26.00  70.00   0.50    0.50    --  110.00  60.00  90.00   88
 22  ω    143.00 168.00   0.50    0.50    --  110.00  60.00   0.00   50
 23  ω     26.00  83.00   0.50    0.50    --  110.00  60.00-150.00  114
 24  ω    108.00 199.00   0.50    0.50    --  110.00  60.00-150.00  182
 25  ω     31.00  80.00   0.50    0.50    --  110.00  60.00  30.00   98
 26  ω    140.00 198.00   0.50    0.50    --  110.00  60.00-120.00  116
 27  ω     23.00 130.00   0.50    0.50    --  110.00  60.00-120.00  214
 28  ω    128.00 165.00   0.50    0.50    --  110.00  38.00 -60.00   74
 29  ω    146.00 181.00   0.50    0.50    --  110.00  60.00 -60.00   70
 30  ω     23.00  71.00   0.50    0.50    --  110.00  60.00  60.00   96
 31  ω    117.00 184.00   0.50    0.50    --  110.00  10.00 -60.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1594870000
_diffrn_orient_matrix_UB_12      0.0591781000
_diffrn_orient_matrix_UB_13      0.1705265000
_diffrn_orient_matrix_UB_21      -0.0080939000
_diffrn_orient_matrix_UB_22      0.0914464000
_diffrn_orient_matrix_UB_23      -0.1272018000
_diffrn_orient_matrix_UB_31      -0.1925630000
_diffrn_orient_matrix_UB_32      0.0446689000
_diffrn_orient_matrix_UB_33      0.0390241000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2263
_reflns_number_total             2294
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_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         0.415
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.079
_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)+(0.0950P)²+0.5479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1715
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 0.4382(5) 0.4423(2) 0.4011(5) 0.0458(8) Uani 1 1 d . . . . .
F2 F 0.7779(6) 0.3783(2) 0.4762(4) 0.0461(8) Uani 1 1 d . . . . .
O2 O 0.5750(6) 0.2717(3) 0.0745(6) 0.0521(11) Uani 1 1 d . . . . .
O1 O 0.2692(6) 0.3611(3) 0.0027(5) 0.0443(9) Uani 1 1 d . . . . .
N1 N 0.6205(6) 0.6547(3) 0.4452(5) 0.0289(8) Uani 1 1 d . . . . .
N2 N 0.9400(6) 0.5913(3) 0.5664(5) 0.0277(8) Uani 1 1 d . . . . .
C2 C 0.4859(8) 0.3523(4) 0.0751(6) 0.0334(10) Uani 1 1 d . . . . .
C10 C 0.3878(8) 0.6697(4) 0.3326(8) 0.0400(12) Uani 1 1 d . . . . .
H10A H 0.369099 0.695246 0.207847 0.060 Uiso 1 1 calc GR . . . .
H10B H 0.327993 0.719363 0.395024 0.060 Uiso 1 1 calc GR . . . .
H10C H 0.311322 0.604428 0.319828 0.060 Uiso 1 1 calc GR . . . .
C9 C 1.1270(8) 0.5226(5) 0.6248(8) 0.0424(12) Uani 1 1 d . . . . .
H9A H 1.128659 0.481059 0.731152 0.064 Uiso 1 1 calc GR . . . .
H9B H 1.260968 0.562827 0.662471 0.064 Uiso 1 1 calc GR . . . .
H9C H 1.116920 0.477702 0.520023 0.064 Uiso 1 1 calc GR . . . .
C3 C 0.5921(8) 0.4518(4) 0.1512(6) 0.0319(10) Uani 1 1 d . . . . .
H3 H 0.488214 0.507797 0.086831 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7325(7) 0.5668(3) 0.4619(6) 0.0258(9) Uani 1 1 d . . . . .
C7 C 0.9562(9) 0.6937(4) 0.6142(7) 0.0391(11) Uani 1 1 d . . . . .
H7 H 1.084985 0.729217 0.688105 0.047 Uiso 1 1 calc R . . . .
C8 C 0.7567(9) 0.7332(4) 0.5369(8) 0.0404(12) Uani 1 1 d . . . . .
H8 H 0.716737 0.802334 0.543940 0.048 Uiso 1 1 calc R . . . .
C1 C 0.1492(10) 0.2688(5) -0.0687(9) 0.0534(15) Uani 1 1 d . . . . .
H1A H -0.005681 0.281358 -0.100030 0.080 Uiso 1 1 calc GR . . . .
H1B H 0.200083 0.215111 0.026772 0.080 Uiso 1 1 calc GR . . . .
H1C H 0.171439 0.247121 -0.181701 0.080 Uiso 1 1 calc GR . . . .
C5 C 0.7549(10) 0.4826(5) -0.0943(7) 0.0491(14) Uani 1 1 d . . . . .
H5A H 0.681124 0.422276 -0.165618 0.074 Uiso 1 1 calc GR . . . .
H5B H 0.892804 0.492749 -0.109715 0.074 Uiso 1 1 calc GR . . . .
H5C H 0.662592 0.542892 -0.140776 0.074 Uiso 1 1 calc GR . . . .
C4 C 0.7986(8) 0.4670(4) 0.1121(7) 0.0376(11) Uani 1 1 d . . . . .
H4A H 0.878140 0.527109 0.183570 0.045 Uiso 1 1 calc R . . . .
H4B H 0.893336 0.406454 0.158099 0.045 Uiso 1 1 calc R . . . .
B1 B 0.6326(9) 0.4543(4) 0.3752(7) 0.0288(10) 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
F1 B1 1.393(6) . ?
F2 B1 1.399(6) . ?
O2 C2 1.211(6) . ?
O1 C2 1.340(6) . ?
O1 C1 1.436(7) . ?
N1 C10 1.472(6) . ?
N1 C6 1.351(6) . ?
N1 C8 1.374(7) . ?
N2 C9 1.461(6) . ?
N2 C6 1.346(6) . ?
N2 C7 1.383(7) . ?
C2 C3 1.491(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 1.0000 . ?
C3 C4 1.531(7) . ?
C3 B1 1.643(6) . ?
C6 B1 1.648(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.336(8) . ?
C8 H8 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C4 1.518(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C2 O1 C1 116.1(4) . . ?
C6 N1 C10 126.1(4) . . ?
C6 N1 C8 110.8(4) . . ?
C8 N1 C10 122.9(4) . . ?
C6 N2 C9 126.7(4) . . ?
C6 N2 C7 110.3(4) . . ?
C7 N2 C9 122.9(4) . . ?
O2 C2 O1 121.7(4) . . ?
O2 C2 C3 127.0(5) . . ?
O1 C2 C3 111.3(4) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C3 H3 108.1 . . ?
C2 C3 C4 111.3(4) . . ?
C2 C3 B1 107.1(4) . . ?
C4 C3 H3 108.1 . . ?
C4 C3 B1 114.0(4) . . ?
B1 C3 H3 108.1 . . ?
N1 C6 B1 126.8(4) . . ?
N2 C6 N1 105.0(4) . . ?
N2 C6 B1 128.2(4) . . ?
N2 C7 H7 126.5 . . ?
C8 C7 N2 107.1(4) . . ?
C8 C7 H7 126.5 . . ?
N1 C8 H8 126.6 . . ?
C7 C8 N1 106.8(4) . . ?
C7 C8 H8 126.6 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 C3 113.5(4) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
F1 B1 F2 108.9(4) . . ?
F1 B1 C3 111.2(4) . . ?
F1 B1 C6 107.2(3) . . ?
F2 B1 C3 111.8(4) . . ?
F2 B1 C6 108.9(4) . . ?
C3 B1 C6 108.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_lmji8
_database_code_depnum_ccdc_archive 'CCDC 1864778'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H15 B N2 O2'
_chemical_formula_sum            'C9 H15 B N2 O2'
_chemical_formula_weight         194.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H12N2B1O2
_chemical_oxdiff_usercomment     JER385
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6843(3)
_cell_length_b                   10.1231(2)
_cell_length_c                   12.0573(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.885(3)
_cell_angle_gamma                90
_cell_volume                     1040.91(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3480
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.3550
_cell_measurement_theta_min      5.7360
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8522
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.968
_diffrn_reflns_theta_min         5.750
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  81.00   0.50    0.50    --    0.00  40.00 120.00  130
  2  ω    -65.00   5.00   0.50    0.50    --    0.00  40.00 120.00  140
  3  ω    105.00 133.00   0.50    0.50    --   55.00  30.00-180.00   56
  4  ω     79.00 106.00   0.50    0.50    --   55.00  50.00  90.00   54
  5  ω    -26.00   1.00   0.50    0.50    --   55.00  20.00  30.00   54
  6  ω    -32.00 140.00   0.50    0.50    --   55.00  50.00-180.00  344
  7  ω      7.00  66.00   0.50    0.50    --   55.00  50.00 150.00  118
  8  ω     61.00 144.00   0.50    0.50    --   55.00  50.00  60.00  166
  9  ω    -34.00   4.00   0.50    0.50    --   55.00  50.00  30.00   76
 10  ω    -34.00  48.00   0.50    0.50    --   55.00  50.00  60.00  164
 11  ω      8.00 135.00   0.50    0.50    --   55.00  50.00  30.00  254
 12  ω    -31.00  77.00   0.50    0.50    --   55.00  50.00  90.00  216
 13  ω     87.00 127.00   0.50    0.50    --   55.00  50.00 150.00   80
 14  ω     73.00 105.00   0.50    0.80    --  110.00  40.00 -90.00   64
 15  ω     63.00  90.00   0.50    0.80    --  110.00  40.00-180.00   54
 16  ω     21.00  60.00   0.50    0.80    --  110.00  40.00-180.00   78
 17  ω    111.00 198.00   0.50    0.80    --  110.00  40.00 120.00  174
 18  ω     26.00  58.00   0.50    0.80    --  110.00  40.00 120.00   64
 19  ω    146.00 173.00   0.50    0.80    --  110.00  40.00-150.00   54
 20  ω    145.00 172.00   0.50    0.80    --  110.00  40.00 150.00   54
 21  ω     23.00  91.00   0.50    0.80    --  110.00  40.00-150.00  136
 22  ω    115.00 199.00   0.50    0.80    --  110.00  40.00 -30.00  168
 23  ω     94.00 197.00   0.50    0.80    --  110.00  40.00  30.00  206
 24  ω     68.00 108.00   0.50    0.80    --  110.00  40.00 120.00   80
 25  ω     87.00 123.00   0.50    0.80    --  110.00  40.00 150.00   72
 26  ω    100.00 127.00   0.50    0.80    --  110.00  40.00  60.00   54
 27  ω     22.00  83.00   0.50    0.80    --  110.00  40.00  30.00  122
 28  ω    115.00 176.00   0.50    0.80    --  110.00  40.00  90.00  122
 29  ω     94.00 125.00   0.50    0.80    --  110.00  40.00-180.00   62
 30  ω    141.00 166.00   0.50    0.80    --  110.00  40.00-180.00   50
 31  ω    123.00 150.00   0.50    0.80    --  110.00  40.00 -60.00   54
 32  ω    168.00 195.00   0.50    0.80    --  110.00  40.00-180.00   54
 33  ω    141.00 195.00   0.50    0.80    --  110.00  40.00 -90.00  108
 34  ω     21.00 165.00   0.50    0.80    --  110.00  40.00-120.00  288
 35  ω     87.00 197.00   0.50    0.80    --  110.00   0.00   0.00  220
 36  ω    132.00 157.00   0.50    0.80    --  110.00  40.00  60.00   50
 37  ω     23.00  83.00   0.50    0.80    --  110.00   0.00   0.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0370435000
_diffrn_orient_matrix_UB_12      -0.1488520000
_diffrn_orient_matrix_UB_13      0.0107662000
_diffrn_orient_matrix_UB_21      -0.0418519000
_diffrn_orient_matrix_UB_22      -0.0142815000
_diffrn_orient_matrix_UB_23      -0.1294340000
_diffrn_orient_matrix_UB_31      0.1717178000
_diffrn_orient_matrix_UB_32      0.0285231000
_diffrn_orient_matrix_UB_33      -0.0079678000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1768
_reflns_number_total             1892
_reflns_odcompleteness_completeness 94.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_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         0.472
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.116
_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)+(0.1002P)²+0.2816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H7(0.042) H6(0.043) H2(0.037) H9A(0.064) H9B(0.064) H9C(0.064)
 H8A(0.06) H8B(0.06) H8C(0.06)
 Fixed X: H7(0.337889) H6(0.142941) H2(0.075746) H9A(0.125106) H9B(0.090187)
 H9C(-0.015287) H8A(0.42234) H8B(0.531778) H8C(0.54942)
 Fixed Y: H7(0.653905) H6(0.682176) H2(0.176915) H9A(0.389675) H9B(0.541537)
 H9C(0.449616) H8A(0.352936) H8B(0.475835) H8C(0.352494)
 Fixed Z: H7(0.639654) H6(0.465276) H2(0.434416) H9A(0.286668) H9B(0.275717)
 H9C(0.334744) H8A(0.721678) H8B(0.720242) H8C(0.645017)
;
_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
O1 O 0.11824(15) 0.24414(12) 0.65556(11) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.24701(16) 0.05436(12) 0.65907(10) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.36280(17) 0.46352(14) 0.58295(12) 0.0300(4) Uani 1 1 d . . . . .
N2 N 0.19315(18) 0.48758(14) 0.43131(12) 0.0322(4) Uani 1 1 d . . . . .
C1 C 0.17286(19) 0.15944(16) 0.60299(14) 0.0297(4) Uani 1 1 d . . . . .
C5 C 0.2930(2) 0.39872(16) 0.48896(14) 0.0300(4) Uani 1 1 d . . . . .
C7 C 0.3073(2) 0.59079(17) 0.58379(15) 0.0348(4) Uani 1 1 d . . . . .
H7 H 0.337889 0.653905 0.639654 0.042 Uiso 1 1 calc R . . . .
C6 C 0.2006(2) 0.60632(17) 0.48836(15) 0.0362(4) Uani 1 1 d . . . . .
H6 H 0.142941 0.682176 0.465276 0.043 Uiso 1 1 calc R . . . .
C2 C 0.1770(2) 0.15193(16) 0.48032(14) 0.0309(4) Uani 1 1 d . . . . .
H2 H 0.075746 0.176915 0.434416 0.037 Uiso 1 1 calc R . . . .
C3 C 0.2133(2) 0.00612(17) 0.46375(16) 0.0352(4) Uani 1 1 d . . . . .
C9 C 0.0894(3) 0.4652(2) 0.32284(15) 0.0429(5) Uani 1 1 d . . . . .
H9A H 0.125106 0.389675 0.286668 0.064 Uiso 1 1 calc GR . . . .
H9B H 0.090187 0.541537 0.275717 0.064 Uiso 1 1 calc GR . . . .
H9C H -0.015287 0.449616 0.334744 0.064 Uiso 1 1 calc GR . . . .
C8 C 0.4763(2) 0.40629(19) 0.67540(16) 0.0400(5) Uani 1 1 d . . . . .
H8A H 0.422340 0.352936 0.721678 0.060 Uiso 1 1 calc GR . . . .
H8B H 0.531778 0.475835 0.720242 0.060 Uiso 1 1 calc GR . . . .
H8C H 0.549420 0.352494 0.645017 0.060 Uiso 1 1 calc GR . . . .
C4 C 0.3041(3) -0.0320(2) 0.57930(18) 0.0443(5) Uani 1 1 d . . . . .
B1 B 0.3199(3) 0.24883(19) 0.45319(17) 0.0346(5) Uani 1 1 d . . . . .
H1A H 0.434(3) 0.213(2) 0.5054(18) 0.038(5) Uiso 1 1 d . . . . .
H1B H 0.317(3) 0.248(3) 0.360(2) 0.055(7) Uiso 1 1 d . . . . .
H4A H 0.285(3) -0.123(3) 0.603(2) 0.050(6) Uiso 1 1 d . . . . .
H3A H 0.278(3) -0.013(2) 0.409(2) 0.042(6) Uiso 1 1 d . . . . .
H3B H 0.113(3) -0.043(3) 0.442(2) 0.051(7) Uiso 1 1 d . . . . .
H4B H 0.422(3) -0.014(2) 0.588(2) 0.045(6) 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
O1 C1 1.215(2) . ?
O2 C1 1.356(2) . ?
O2 C4 1.454(2) . ?
N1 C5 1.350(2) . ?
N1 C7 1.376(2) . ?
N1 C8 1.461(2) . ?
N2 C5 1.348(2) . ?
N2 C6 1.380(2) . ?
N2 C9 1.459(2) . ?
C1 C2 1.488(2) . ?
C5 B1 1.607(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.344(3) . ?
C6 H6 0.9300 . ?
C2 H2 0.9800 . ?
C2 C3 1.530(2) . ?
C2 B1 1.662(3) . ?
C3 C4 1.515(3) . ?
C3 H3A 0.96(2) . ?
C3 H3B 0.99(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4A 0.98(3) . ?
C4 H4B 1.03(3) . ?
B1 H1A 1.13(2) . ?
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
C1 O2 C4 109.31(14) . . ?
C5 N1 C7 111.02(14) . . ?
C5 N1 C8 125.39(15) . . ?
C7 N1 C8 123.52(15) . . ?
C5 N2 C6 111.06(15) . . ?
C5 N2 C9 125.93(16) . . ?
C6 N2 C9 123.01(16) . . ?
O1 C1 O2 119.27(16) . . ?
O1 C1 C2 129.78(15) . . ?
O2 C1 C2 110.92(14) . . ?
N1 C5 B1 128.26(16) . . ?
N2 C5 N1 104.59(14) . . ?
N2 C5 B1 127.15(16) . . ?
N1 C7 H7 126.6 . . ?
C6 C7 N1 106.81(15) . . ?
C6 C7 H7 126.6 . . ?
N2 C6 H6 126.7 . . ?
C7 C6 N2 106.53(15) . . ?
C7 C6 H6 126.7 . . ?
C1 C2 H2 111.1 . . ?
C1 C2 C3 102.91(13) . . ?
C1 C2 B1 108.95(13) . . ?
C3 C2 H2 111.1 . . ?
C3 C2 B1 111.34(15) . . ?
B1 C2 H2 111.1 . . ?
C2 C3 H3A 116.5(14) . . ?
C2 C3 H3B 109.1(15) . . ?
C4 C3 C2 102.09(14) . . ?
C4 C3 H3A 108.0(14) . . ?
C4 C3 H3B 113.4(14) . . ?
H3A C3 H3B 108(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C4 C3 105.79(15) . . ?
O2 C4 H4A 106.0(15) . . ?
O2 C4 H4B 106.6(14) . . ?
C3 C4 H4A 114.6(15) . . ?
C3 C4 H4B 112.4(13) . . ?
H4A C4 H4B 110.8(19) . . ?
C5 B1 C2 110.66(15) . . ?
C5 B1 H1A 108.2(11) . . ?
C5 B1 H1B 107.4(13) . . ?
C2 B1 H1A 108.1(11) . . ?
C2 B1 H1B 108.3(14) . . ?
H1A B1 H1B 114.2(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.047
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_rmji6_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1864779'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H37 B N2 O2'
_chemical_formula_sum            'C24 H37 B N2 O2'
_chemical_formula_weight         396.36
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H37BN2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.9618(3)
_cell_length_b                   13.0959(3)
_cell_length_c                   15.6088(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2445.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18016
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.7530
_cell_measurement_theta_min      4.3890
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.752
_diffrn_reflns_theta_min         4.407
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  34.00   1.00    1.00    --    5.00  53.00  69.00   25
  2  ω    -78.00  40.00   1.00    1.00    --  -45.10  53.00  69.00  118
  3  ω   -106.00 -79.00   1.00    1.00    --  -45.10 -53.00 -75.00   27
  4  ω   -151.00-126.00   1.00    2.00    -- -110.00 -53.00 -75.00   25
  5  ω    -50.00 -21.00   1.00    2.00    -- -110.00  53.00  69.00   29
  6  ω   -112.00 -56.00   1.00    2.00    -- -110.00  53.00  69.00   56
  7  ω    -47.00 -22.00   1.00    1.00    --    5.00 -53.00 -75.00   25
  8  ω    -79.00  34.00   1.00    1.00    --  -45.10  67.00-116.01  113
  9  ω    -77.00 -51.00   1.00    1.00    --  -45.10  46.00 -11.51   26
 10  ω    -49.00  35.00   1.00    1.00    --  -45.10  46.00 -11.51   84
 11  ω   -134.00 -34.00   1.00    1.00    --  -45.10 -64.00-132.05  100
 12  ω    -66.00 -40.00   1.00    2.00    -- -110.00 -19.00  60.00   26
 13  ω   -132.00-106.00   1.00    2.00    -- -110.00 -19.00  60.00   26
 14  ω   -103.00 -32.00   1.00    2.00    -- -110.00  38.00 -60.00   71
 15  ω   -133.00 -50.00   1.00    2.00    -- -110.00  57.00 -60.00   83
 16  ω   -110.00 -70.00   1.00    2.00    -- -110.00 -39.00 167.41   40
 17  ω    -99.00 -72.00   1.00    2.00    -- -110.00 -43.00 157.29   27
 18  ω   -151.00-125.00   1.00    2.00    -- -110.00 -38.00-150.00   26
 19  ω   -143.00 -24.00   1.00    2.00    -- -110.00  76.00  60.00  119
 20  ω   -113.00 -72.00   1.00    2.00    -- -110.00 -76.00-180.00   41
 21  ω    -94.00 -69.00   1.00    2.00    -- -110.00 -38.00-180.00   25
 22  ω   -154.00 -22.00   1.00    2.00    -- -110.00   0.00-120.00  132
 23  ω   -198.00-160.00   1.00    2.00    -- -110.00   0.00-120.00   38
 24  ω   -101.00 -73.00   1.00    2.00    -- -110.00 -76.00-120.00   28
 25  ω   -130.00 -80.00   1.00    2.00    -- -110.00 -57.00   0.00   50
 26  ω   -169.00 -71.00   1.00    2.00    -- -110.00 -76.00 150.00   98
 27  ω   -143.00 -75.00   1.00    2.00    -- -110.00 -43.00 143.50   68
 28  ω   -193.00-167.00   1.00    2.00    -- -110.00 -19.00 -30.00   26
 29  ω   -141.00-115.00   1.00    2.00    -- -110.00 -19.00 -30.00   26
 30  ω   -107.00 -29.00   1.00    2.00    -- -110.00 -19.00 -30.00   78
 31  ω   -118.00 -93.00   1.00    2.00    -- -110.00  57.00-180.00   25
 32  ω    -98.00 -71.00   1.00    2.00    -- -110.00 -38.00-150.00   27
 33  ω   -175.00 -71.00   1.00    2.00    -- -110.00 -42.00 164.68  104
 34  ω   -194.00-169.00   1.00    2.00    -- -110.00 -19.00 120.00   25
 35  ω    -88.00 -28.00   1.00    2.00    -- -110.00 -19.00 120.00   60
 36  ω   -188.00 -87.00   1.00    2.00    -- -110.00 -57.00  30.00  101
 37  ω    -95.00 -70.00   1.00    2.00    -- -110.00 -39.00 141.69   25
 38  ω   -172.00-146.00   1.00    2.00    -- -110.00 -76.00-120.00   26
 39  ω   -158.00-131.00   1.00    2.00    -- -110.00 -38.00-180.00   27
 40  ω   -119.00 -94.00   1.00    2.00    -- -110.00 -76.00  30.00   25
 41  ω   -118.00 -93.00   1.00    2.00    -- -110.00  38.00-150.00   25
 42  ω    -99.00 -74.00   1.00    2.00    -- -110.00  38.00 120.00   25
 43  ω   -139.00-112.00   1.00    2.00    -- -110.00  38.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0821619000
_diffrn_orient_matrix_UB_12      -0.0374298000
_diffrn_orient_matrix_UB_13      -0.0690544000
_diffrn_orient_matrix_UB_21      0.0045869000
_diffrn_orient_matrix_UB_22      0.1055336000
_diffrn_orient_matrix_UB_23      -0.0434490000
_diffrn_orient_matrix_UB_31      0.0991877000
_diffrn_orient_matrix_UB_32      -0.0358944000
_diffrn_orient_matrix_UB_33      -0.0554708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                12865
_reflns_number_total             14093
_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_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         0.168
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.38(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         14093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.072
_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)+(0.0820P)²+0.1123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7509(12)
 0.2491(12)
2. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C14(H14), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C15(H15A,H15B), C12(H12A,H12B), C13(H13A,H13B), B1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C22(H22), C7(H7), C21(H21), C8(H8), C6(H6)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O -0.74194(13) -0.58229(12) -0.56614(10) 0.0284(3) Uani 1 1 d . . . . .
O2 O -0.68601(15) -0.46822(14) -0.66459(10) 0.0339(4) Uani 1 1 d . . . . .
N2 N -0.80163(16) -0.32865(15) -0.45234(13) 0.0303(4) Uani 1 1 d . . . . .
N1 N -0.75075(17) -0.45588(16) -0.37510(12) 0.0311(4) Uani 1 1 d . . . . .
C1 C -0.66908(17) -0.51346(16) -0.59797(13) 0.0237(4) Uani 1 1 d . . . . .
C2 C -0.57175(17) -0.49736(17) -0.54099(13) 0.0252(4) Uani 1 1 d . . . . .
H2 H -0.563665 -0.556456 -0.502976 0.030 Uiso 1 1 calc R . . . .
C4 C -0.43345(17) -0.57384(18) -0.65094(14) 0.0278(4) Uani 1 1 d . . . . .
C20 C -0.71539(18) -0.39318(18) -0.43792(14) 0.0281(4) Uani 1 1 d . . . . .
C10 C -0.84704(18) -0.59659(18) -0.61162(14) 0.0294(5) Uani 1 1 d . . . . .
H10 H -0.835647 -0.583983 -0.672888 0.035 Uiso 1 1 calc R . . . .
C3 C -0.46457(18) -0.48443(17) -0.59354(14) 0.0277(4) Uani 1 1 d . . . . .
H3A H -0.472490 -0.424089 -0.629062 0.033 Uiso 1 1 calc R . . . .
H3B H -0.403143 -0.472119 -0.554310 0.033 Uiso 1 1 calc R . . . .
C9 C -0.4646(2) -0.6736(2) -0.63321(18) 0.0400(6) Uani 1 1 d . . . . .
H9 H -0.506924 -0.687259 -0.584573 0.048 Uiso 1 1 calc R . . . .
C11 C -0.8824(2) -0.70700(19) -0.59810(17) 0.0346(5) Uani 1 1 d . . . . .
H11 H -0.886026 -0.718463 -0.536117 0.042 Uiso 1 1 calc R . . . .
C5 C -0.3709(2) -0.5571(2) -0.72418(17) 0.0400(6) Uani 1 1 d . . . . .
H5 H -0.349493 -0.490850 -0.738021 0.048 Uiso 1 1 calc R . . . .
C15 C -0.93106(19) -0.5207(2) -0.57654(17) 0.0358(5) Uani 1 1 d . . . . .
H15A H -0.906501 -0.452114 -0.590585 0.043 Uiso 1 1 calc R . . . .
H15B H -0.933010 -0.526484 -0.514605 0.043 Uiso 1 1 calc R . . . .
C22 C -0.8897(2) -0.3510(2) -0.39832(16) 0.0362(5) Uani 1 1 d . . . . .
H22 H -0.957956 -0.317233 -0.395901 0.043 Uiso 1 1 calc R . . . .
C23 C -0.8051(2) -0.2497(2) -0.51834(18) 0.0398(6) Uani 1 1 d . . . . .
H23A H -0.757611 -0.193943 -0.501902 0.060 Uiso 1 1 calc GR . . . .
H23B H -0.880415 -0.225616 -0.524800 0.060 Uiso 1 1 calc GR . . . .
H23C H -0.779502 -0.277648 -0.571713 0.060 Uiso 1 1 calc GR . . . .
C7 C -0.3703(3) -0.7359(2) -0.75904(18) 0.0433(6) Uani 1 1 d . . . . .
H7 H -0.348979 -0.789523 -0.794517 0.052 Uiso 1 1 calc R . . . .
C21 C -0.8582(2) -0.4306(2) -0.35001(15) 0.0368(5) Uani 1 1 d . . . . .
H21 H -0.900445 -0.462592 -0.307796 0.044 Uiso 1 1 calc R . . . .
C14 C -1.0490(2) -0.5366(2) -0.61163(19) 0.0418(6) Uani 1 1 d . . . . .
H14 H -1.047175 -0.525531 -0.673719 0.050 Uiso 1 1 calc R . . . .
C24 C -0.6872(2) -0.5429(2) -0.34312(16) 0.0389(6) Uani 1 1 d . . . . .
H24A H -0.697179 -0.599998 -0.380939 0.058 Uiso 1 1 calc GR . . . .
H24B H -0.713219 -0.560666 -0.286879 0.058 Uiso 1 1 calc GR . . . .
H24C H -0.609348 -0.525370 -0.340487 0.058 Uiso 1 1 calc GR . . . .
C8 C -0.4337(3) -0.7535(2) -0.6868(2) 0.0472(7) Uani 1 1 d . . . . .
H8 H -0.456118 -0.819652 -0.673815 0.057 Uiso 1 1 calc R . . . .
C17 C -0.7963(2) -0.7831(2) -0.63455(19) 0.0417(6) Uani 1 1 d . . . . .
H17 H -0.722803 -0.762074 -0.613133 0.050 Uiso 1 1 calc R . . . .
C6 C -0.3393(3) -0.6369(3) -0.77745(19) 0.0496(7) Uani 1 1 d . . . . .
H6 H -0.296763 -0.623405 -0.826035 0.059 Uiso 1 1 calc R . . . .
C12 C -1.0010(2) -0.7214(2) -0.6334(2) 0.0495(7) Uani 1 1 d . . . . .
H12A H -0.999605 -0.712598 -0.695115 0.059 Uiso 1 1 calc R . . . .
H12B H -1.025550 -0.790574 -0.621547 0.059 Uiso 1 1 calc R . . . .
C13 C -1.0843(2) -0.6467(3) -0.5949(2) 0.0527(8) Uani 1 1 d . . . . .
H13A H -1.089589 -0.658164 -0.533677 0.063 Uiso 1 1 calc R . . . .
H13B H -1.157569 -0.658488 -0.619701 0.063 Uiso 1 1 calc R . . . .
C19 C -0.8168(3) -0.8909(2) -0.6020(2) 0.0576(8) Uani 1 1 d . . . . .
H19A H -0.824964 -0.889762 -0.540860 0.086 Uiso 1 1 calc GR . . . .
H19B H -0.754690 -0.933633 -0.617228 0.086 Uiso 1 1 calc GR . . . .
H19C H -0.883857 -0.917508 -0.627511 0.086 Uiso 1 1 calc GR . . . .
C16 C -1.1289(2) -0.4591(3) -0.5723(2) 0.0556(8) Uani 1 1 d . . . . .
H16A H -1.129262 -0.466820 -0.511132 0.083 Uiso 1 1 calc GR . . . .
H16B H -1.202894 -0.470289 -0.594165 0.083 Uiso 1 1 calc GR . . . .
H16C H -1.104903 -0.391288 -0.586781 0.083 Uiso 1 1 calc GR . . . .
B1 B -0.5938(2) -0.3933(2) -0.48226(16) 0.0288(5) Uani 1 1 d . . . . .
H1A H -0.536947 -0.389000 -0.438099 0.035 Uiso 1 1 calc R . . . .
H1B H -0.586797 -0.333403 -0.518454 0.035 Uiso 1 1 calc R . . . .
C18 C -0.7896(5) -0.7823(3) -0.7321(2) 0.0787(14) Uani 1 1 d . . . . .
H18A H -0.856177 -0.812356 -0.755456 0.118 Uiso 1 1 calc GR . . . .
H18B H -0.725634 -0.820935 -0.750246 0.118 Uiso 1 1 calc GR . . . .
H18C H -0.782821 -0.713245 -0.751969 0.118 Uiso 1 1 calc GR . . . .


_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
O1 C1 1.349(3) . ?
O1 C10 1.456(3) . ?
O2 C1 1.214(3) . ?
N2 C20 1.352(3) . ?
N2 C22 1.380(3) . ?
N2 C23 1.460(3) . ?
N1 C20 1.347(3) . ?
N1 C21 1.384(3) . ?
N1 C24 1.458(3) . ?
C1 C2 1.480(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.531(3) . ?
C2 B1 1.664(3) . ?
C4 C3 1.521(3) . ?
C4 C9 1.386(4) . ?
C4 C5 1.384(3) . ?
C20 B1 1.611(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.521(3) . ?
C10 C15 1.516(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C8 1.390(4) . ?
C11 H11 0.9800 . ?
C11 C17 1.542(4) . ?
C11 C12 1.534(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.527(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.340(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C7 C6 1.379(5) . ?
C21 H21 0.9300 . ?
C14 H14 0.9800 . ?
C14 C13 1.526(4) . ?
C14 C16 1.523(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C8 H8 0.9300 . ?
C17 H17 0.9800 . ?
C17 C19 1.521(4) . ?
C17 C18 1.524(5) . ?
C6 H6 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C1 O1 C10 117.66(17) . . ?
C20 N2 C22 110.3(2) . . ?
C20 N2 C23 125.6(2) . . ?
C22 N2 C23 124.0(2) . . ?
C20 N1 C21 110.6(2) . . ?
C20 N1 C24 124.2(2) . . ?
C21 N1 C24 125.1(2) . . ?
O1 C1 C2 112.46(17) . . ?
O2 C1 O1 122.28(19) . . ?
O2 C1 C2 125.2(2) . . ?
C1 C2 H2 109.2 . . ?
C1 C2 C3 110.64(17) . . ?
C1 C2 B1 108.85(17) . . ?
C3 C2 H2 109.2 . . ?
C3 C2 B1 109.71(18) . . ?
B1 C2 H2 109.2 . . ?
C9 C4 C3 122.8(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 C9 117.4(2) . . ?
N2 C20 B1 128.1(2) . . ?
N1 C20 N2 105.23(19) . . ?
N1 C20 B1 126.6(2) . . ?
O1 C10 H10 109.5 . . ?
O1 C10 C11 107.14(19) . . ?
O1 C10 C15 108.18(18) . . ?
C11 C10 H10 109.5 . . ?
C15 C10 H10 109.5 . . ?
C15 C10 C11 112.88(19) . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 C2 115.81(18) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C4 C9 H9 119.4 . . ?
C4 C9 C8 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C11 H11 107.2 . . ?
C10 C11 C17 112.2(2) . . ?
C10 C11 C12 108.9(2) . . ?
C17 C11 H11 107.2 . . ?
C12 C11 H11 107.2 . . ?
C12 C11 C17 113.9(2) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C10 C15 H15A 108.9 . . ?
C10 C15 H15B 108.9 . . ?
C10 C15 C14 113.2(2) . . ?
H15A C15 H15B 107.8 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
N2 C22 H22 126.4 . . ?
C21 C22 N2 107.2(2) . . ?
C21 C22 H22 126.4 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 C7 H7 120.8 . . ?
C8 C7 C6 118.4(3) . . ?
C6 C7 H7 120.8 . . ?
N1 C21 H21 126.6 . . ?
C22 C21 N1 106.7(2) . . ?
C22 C21 H21 126.6 . . ?
C15 C14 H14 108.3 . . ?
C13 C14 C15 108.9(2) . . ?
C13 C14 H14 108.3 . . ?
C16 C14 C15 110.1(2) . . ?
C16 C14 H14 108.3 . . ?
C16 C14 C13 112.8(2) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
C11 C17 H17 107.0 . . ?
C19 C17 C11 111.7(2) . . ?
C19 C17 H17 107.0 . . ?
C19 C17 C18 110.3(3) . . ?
C18 C17 C11 113.5(3) . . ?
C18 C17 H17 107.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.7(2) . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 C14 111.1(2) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
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 . . ?
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 . . ?
C2 B1 H1A 109.1 . . ?
C2 B1 H1B 109.1 . . ?
C20 B1 C2 112.37(19) . . ?
C20 B1 H1A 109.1 . . ?
C20 B1 H1B 109.1 . . ?
H1A B1 H1B 107.9 . . ?
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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.783
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7509(12) 21072 12791 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2491(12) 21119 12790 nmt 0.9980 0.0206 -0.0077 -0.0208 0.9995 0.0135 0.0135
-0.0217 1.0011

_twin_special_details            
;
Component 2 rotated by 1.6272° 
 around [-0.56 -0.34 -0.76] (reciprocal) or [-0.73 -0.37 -0.58] (direct)
;
