# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_amji373
_database_code_depnum_ccdc_archive 'CCDC 1529715'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2016-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C28 H21 B F4 O2'
_chemical_formula_sum            'C28 H21 B F4 O2'
_chemical_formula_weight         476.30
_chemical_oxdiff_formula         C28H21BF4O2
_chemical_oxdiff_usercomment     'AJW f5-dibenzopentalene(Ph)(BPin)'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.1811(5)
_cell_length_b                   12.0413(9)
_cell_length_c                   12.5311(10)
_cell_angle_alpha                74.768(7)
_cell_angle_beta                 73.263(6)
_cell_angle_gamma                72.295(6)
_cell_volume                     1105.21(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      26.6290
_cell_measurement_theta_min      3.7470
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4311
_exptl_crystal_description       plate
_exptl_crystal_F_000             492.3293
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Slow evaporation of a solution in toluene'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8344
_diffrn_reflns_theta_full        29.2123
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_temperature      150.02(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8370
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   83.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601   57.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   45.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601   80.0000   21.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   36.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -57.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   55.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -19.0000  120.0000 109

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   59.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -99.0000 -180.0000 41
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0181825000
_diffrn_orient_matrix_UB_12      -0.0537585000
_diffrn_orient_matrix_UB_13      0.0396588000
_diffrn_orient_matrix_UB_21      -0.0226020000
_diffrn_orient_matrix_UB_22      -0.0301560000
_diffrn_orient_matrix_UB_23      -0.0331613000
_diffrn_orient_matrix_UB_31      0.0888195000
_diffrn_orient_matrix_UB_32      -0.0130568000
_diffrn_orient_matrix_UB_33      -0.0309007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3160
_reflns_number_total             4969
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.4045
_refine_diff_density_min         -0.4577
_refine_diff_density_rms         0.1071
_refine_ls_d_res_high            0.7281
_refine_ls_d_res_low             5.8885
_refine_ls_goodness_of_fit_ref   1.0502
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.0502
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.6160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1433
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C39(H39), C15(H15), C36(H36), C23(H23), C29(H29), C42(H42), C50(H50),
 C45(H45), C12(H12)
2.b Idealised Me refined as rotating group:
 C48(H48a,H48b,H48c), C51(H51a,H51b,H51c), C52(H52a,H52b,H52c), C53(H53a,H53b,
 H53c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.24584(19) 1.24364(13) 0.80326(12) 0.0288(4) Uani 1.000000 .
F2 F 0.27802(19) 0.98942(13) 1.23099(12) 0.0301(4) Uani 1.000000 .
F3 F 0.2963(2) 1.33986(13) 0.95921(13) 0.0320(4) Uani 1.000000 .
F4 F 0.3193(2) 1.21197(14) 1.16901(13) 0.0341(4) Uani 1.000000 .
O1 O 0.3612(2) 0.74284(15) 1.22653(15) 0.0262(4) Uani 1.000000 .
O2 O 0.1707(2) 0.67416(16) 1.17341(15) 0.0292(4) Uani 1.000000 .
C1 C 0.1799(3) 0.8520(2) 0.7806(2) 0.0214(6) Uani 1.000000 .
H53a C 0.2245(3) 0.9797(2) 0.8709(2) 0.0200(5) Uani 1.000000 .
H53b C 0.2050(3) 0.8705(2) 0.9537(2) 0.0208(5) Uani 1.000000 .
H53c C 0.2595(3) 0.9917(2) 1.0443(2) 0.0202(5) Uani 1.000000 .
C2 C 0.2510(3) 1.0491(2) 0.6553(2) 0.0214(5) Uani 1.000000 .
H48a C 0.3914(3) 1.1028(2) 0.6249(2) 0.0252(6) Uani 1.000000 .
H48b C 0.1729(3) 0.7910(2) 0.8945(2) 0.0215(6) Uani 1.000000 .
H48c C 0.1140(3) 0.6277(2) 0.8497(2) 0.0268(6) Uani 1.000000 .
C3 C 0.2162(3) 0.9704(2) 0.7657(2) 0.0220(6) Uani 1.000000 .
C4 C 0.2798(3) 1.0452(2) 1.1220(2) 0.0222(6) Uani 1.000000 .
C5 C 0.2543(3) 1.0577(2) 0.9316(2) 0.0205(5) Uani 1.000000 .
H52a C 0.1603(3) 0.7974(2) 0.7019(2) 0.0246(6) Uani 1.000000 .
H52b C 0.2323(3) 0.8722(2) 1.0557(2) 0.0211(5) Uani 1.000000 .
H52c C 0.2884(3) 1.2251(2) 0.9852(2) 0.0231(6) Uani 1.000000 .
C6 C 0.1529(3) 1.0664(2) 0.5743(2) 0.0272(6) Uani 1.000000 .
H51a C 0.2641(3) 1.1744(2) 0.9049(2) 0.0220(6) Uani 1.000000 .
H51b C 0.2972(3) 1.1610(2) 1.0921(2) 0.0233(6) Uani 1.000000 .
H51c C 0.1254(3) 0.6852(2) 0.7383(2) 0.0269(6) Uani 1.000000 .
C7 C 0.3358(3) 0.6357(2) 1.3111(2) 0.0256(6) Uani 1.000000 .
C8 C 0.1393(3) 0.6797(2) 0.9296(2) 0.0250(6) Uani 1.000000 .
C9 C 0.1979(4) 1.1320(2) 0.4661(2) 0.0312(7) Uani 1.000000 .
C10 C 0.2539(4) 0.5738(2) 1.2520(2) 0.0291(6) Uani 1.000000 .
C11 C 0.4337(4) 1.1693(2) 0.5167(2) 0.0315(7) Uani 1.000000 .
C12 C 0.3900(4) 0.4897(3) 1.1790(3) 0.0407(8) Uani 1.000000 .
C13 C 0.3398(4) 1.1825(2) 0.4372(2) 0.0320(7) Uani 1.000000 .
C14 C 0.5134(4) 0.5648(3) 1.3364(2) 0.0349(7) Uani 1.000000 .
C15 B 0.2528(4) 0.7631(3) 1.1554(2) 0.0226(6) Uani 1.000000 .
C16 C 0.2113(4) 0.6767(3) 1.4171(2) 0.0408(8) Uani 1.000000 .
C17 C 0.1115(4) 0.5148(3) 1.3297(3) 0.0468(9) Uani 1.000000 .
H39 H 0.1335(3) 0.6402(2) 1.0046(2) 0.0300(7) Uiso 1.000000 R
C18 H 0.0892(3) 0.5534(2) 0.8722(2) 0.0321(7) Uiso 1.000000 R
H15 H 0.1097(3) 0.6487(2) 0.6864(2) 0.0323(7) Uiso 1.000000 R
C19 H 0.1702(3) 0.8349(2) 0.6261(2) 0.0295(7) Uiso 1.000000 R
H36 H 0.0566(3) 1.0335(2) 0.5934(2) 0.0327(7) Uiso 1.000000 R
C20 H 0.1328(4) 1.1420(2) 0.4129(2) 0.0375(8) Uiso 1.000000 R
H23 H 0.3714(4) 1.2253(2) 0.3642(2) 0.0385(8) Uiso 1.000000 R
C21 H 0.5266(4) 1.2053(2) 0.4978(2) 0.0378(8) Uiso 1.000000 R
C22 H 0.4569(3) 1.0938(2) 0.6775(2) 0.0302(7) Uiso 1.000000 R
C23 H 0.3322(5) 0.4626(15) 1.1376(14) 0.0610(12) Uiso 1.000000 GR
C24 H 0.4739(16) 0.5306(6) 1.1265(12) 0.0610(12) Uiso 1.000000 GR
H12 H 0.450(2) 0.4228(9) 1.2267(3) 0.0610(12) Uiso 1.000000 GR
C25 H 0.5972(7) 0.5515(15) 1.2666(3) 0.0523(11) Uiso 1.000000 GR
H45 H 0.5531(12) 0.6082(8) 1.3739(15) 0.0523(11) Uiso 1.000000 GR
C26 H 0.5020(7) 0.4898(7) 1.3847(13) 0.0523(11) Uiso 1.000000 GR
H50 H 0.2599(13) 0.7262(15) 1.4419(10) 0.0613(12) Uiso 1.000000 GR
C27 H 0.0993(9) 0.7210(16) 1.4005(5) 0.0613(12) Uiso 1.000000 GR
H42 H 0.196(2) 0.6088(3) 1.4761(6) 0.0613(12) Uiso 1.000000 GR
C28 H 0.0163(13) 0.5732(4) 1.3643(13) 0.0702(13) Uiso 1.000000 GR
H29 H 0.0687(19) 0.4793(16) 1.2864(4) 0.0702(13) Uiso 1.000000 GR
B1 H 0.1593(8) 0.4545(13) 1.3877(10) 0.0702(13) Uiso 1.000000 GR


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 H51a 1.347(3) . ?
F2 C4 1.352(3) . ?
F3 H52c 1.351(3) . ?
F4 H51b 1.348(3) . ?
O1 C7 1.466(3) . ?
O1 C15 1.360(3) . ?
O2 C10 1.468(3) . ?
O2 C15 1.368(3) . ?
C1 H48b 1.417(3) . ?
C1 C3 1.498(4) . ?
C1 H52a 1.388(3) . ?
H53a H53b 1.465(3) . ?
H53a C3 1.374(3) . ?
H53a C5 1.464(3) . ?
H53b H48b 1.475(3) . ?
H53b H52b 1.366(3) . ?
H53c C4 1.370(3) . ?
H53c C5 1.433(3) . ?
H53c H52b 1.486(3) . ?
C2 H48a 1.397(4) . ?
C2 C3 1.464(3) . ?
C2 C6 1.405(3) . ?
H48a C11 1.388(4) . ?
H48b C8 1.381(4) . ?
H48c H51c 1.375(4) . ?
H48c C8 1.402(4) . ?
C4 H51b 1.386(4) . ?
C5 H51a 1.378(3) . ?
H52a H51c 1.397(4) . ?
H52b C15 1.562(4) . ?
H52c H51a 1.392(4) . ?
H52c H51b 1.370(4) . ?
C6 C9 1.387(4) . ?
C7 C10 1.559(4) . ?
C7 C14 1.520(3) . ?
C7 C16 1.519(3) . ?
C9 C13 1.386(4) . ?
C10 C12 1.522(4) . ?
C10 C17 1.516(4) . ?
C11 C13 1.376(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
C15 O1 C7 107.2(2) . . ?
C15 O2 C10 107.1(2) . . ?
C3 C1 H48b 110.0(2) . . ?
H52a C1 H48b 119.7(2) . . ?
H52a C1 C3 130.3(2) . . ?
C3 H53a H53b 110.7(2) . . ?
C5 H53a H53b 106.2(2) . . ?
C5 H53a C3 143.0(2) . . ?
H48b H53b H53a 107.1(2) . . ?
H52b H53b H53a 111.8(2) . . ?
H52b H53b H48b 140.9(2) . . ?
C5 H53c C4 119.0(2) . . ?
H52b H53c C4 131.2(2) . . ?
H52b H53c C5 109.7(2) . . ?
C3 C2 H48a 120.3(2) . . ?
C6 C2 H48a 118.2(2) . . ?
C6 C2 C3 121.3(2) . . ?
C11 H48a C2 120.4(3) . . ?
H53b H48b C1 106.0(2) . . ?
C8 H48b C1 120.9(2) . . ?
C8 H48b H53b 133.1(2) . . ?
C8 H48c H51c 120.7(3) . . ?
H53a C3 C1 106.1(2) . . ?
C2 C3 C1 123.3(2) . . ?
C2 C3 H53a 130.4(2) . . ?
H53c C4 F2 121.9(2) . . ?
H51b C4 F2 117.3(2) . . ?
H51b C4 H53c 120.8(2) . . ?
H53c C5 H53a 106.3(2) . . ?
H51a C5 H53a 134.1(2) . . ?
H51a C5 H53c 119.4(2) . . ?
H51c H52a C1 118.9(2) . . ?
H53c H52b H53b 105.8(2) . . ?
C15 H52b H53b 125.1(2) . . ?
C15 H52b H53c 128.7(2) . . ?
H51a H52c F3 119.9(2) . . ?
H51b H52c F3 119.6(2) . . ?
H51b H52c H51a 120.5(2) . . ?
C9 C6 C2 120.7(3) . . ?
C5 H51a F1 122.0(2) . . ?
H52c H51a F1 118.0(2) . . ?
H52c H51a C5 120.0(2) . . ?
C4 H51b F4 120.1(2) . . ?
H52c H51b F4 119.6(2) . . ?
H52c H51b C4 120.3(2) . . ?
H52a H51c H48c 121.2(3) . . ?
C10 C7 O1 102.89(19) . . ?
C14 C7 O1 108.3(2) . . ?
C14 C7 C10 114.8(2) . . ?
C16 C7 O1 106.9(2) . . ?
C16 C7 C10 113.3(2) . . ?
C16 C7 C14 110.0(2) . . ?
H48c C8 H48b 118.5(2) . . ?
C13 C9 C6 120.0(3) . . ?
C7 C10 O2 102.2(2) . . ?
C12 C10 O2 106.3(2) . . ?
C12 C10 C7 113.7(2) . . ?
C17 C10 O2 107.6(2) . . ?
C17 C10 C7 115.2(2) . . ?
C17 C10 C12 110.8(2) . . ?
C13 C11 H48a 120.8(3) . . ?
C11 C13 C9 119.8(3) . . ?
O2 C15 O1 113.8(2) . . ?
H52b C15 O1 124.1(2) . . ?
H52b C15 O2 121.9(2) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted in a Oxford cryosystems cold stream at 150 K'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amji333
_database_code_depnum_ccdc_archive 'CCDC 1529716'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2017-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_formula_moiety         'C30 H30 B Cl O4'
_chemical_formula_sum            'C30 H30 B Cl O4'
_chemical_formula_weight         500.85
_chemical_oxdiff_formula         'B Cl O4 C30 H30'
_chemical_oxdiff_usercomment     'Andy dichloro cyclisation'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.8844(8)
_cell_length_b                   11.0536(8)
_cell_length_c                   12.8011(9)
_cell_angle_alpha                72.871(7)
_cell_angle_beta                 85.108(6)
_cell_angle_gamma                75.762(7)
_cell_volume                     1295.40(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3601
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      27.4660
_cell_measurement_theta_min      3.9180
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.2839
_exptl_crystal_description       block
_exptl_crystal_F_000             528.5437
_exptl_crystal_recrystallization_method 'Slow evaporation of DCM solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9932
_diffrn_reflns_theta_full        28.4281
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8413
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       20.2703   57.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       20.2703   37.0000 -120.0000 105

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -99.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766   57.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766   37.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -89.00    5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -57.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega  -18.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -99.0000 -180.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0374179000
_diffrn_orient_matrix_UB_12      -0.0641751000
_diffrn_orient_matrix_UB_13      0.0258677000
_diffrn_orient_matrix_UB_21      0.0234051000
_diffrn_orient_matrix_UB_22      -0.0087233000
_diffrn_orient_matrix_UB_23      -0.0518038000
_diffrn_orient_matrix_UB_31      0.0594489000
_diffrn_orient_matrix_UB_32      0.0238867000
_diffrn_orient_matrix_UB_33      0.0031133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3925
_reflns_number_total             5488
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3517
_refine_diff_density_min         -0.3809
_refine_diff_density_rms         0.0749
_refine_ls_d_res_high            0.7465
_refine_ls_d_res_low             6.3144
_refine_ls_goodness_of_fit_ref   1.0457
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.0457
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.3430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1396
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C12(H12), C22(H22), C26(H26), C25(H25), C21(H21), C11(H11),
 C10(H10), C28(H28), C19(H19), C9(H9), C18(H18)
2.b Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C30(H30a,H30b,H30c), C6(H6a,H6b,H6c), C2(H2a,H2b,H2c),
 C5(H5a,H5b,H5c), C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl 0.26452(7) 0.34289(6) 0.80664(5) 0.0479(2) Uani 1.000000 .
O1 O 0.26486(16) -0.23128(14) 1.26550(12) 0.0343(4) Uani 1.000000 .
O2 O 0.07302(16) -0.10811(15) 1.32718(12) 0.0344(4) Uani 1.000000 .
O3 O 0.37747(17) -0.43293(15) 0.88495(14) 0.0408(4) Uani 1.000000 .
O4 O 0.47515(17) -0.15370(16) 0.60755(13) 0.0409(4) Uani 1.000000 .
C1 C 0.1398(4) -0.3973(3) 1.3080(2) 0.0622(9) Uani 1.000000 .
H1a H 0.0597(13) -0.3395(5) 1.2682(14) 0.0933(13) Uiso 1.000000 GR
H1b H 0.2033(8) -0.4354(17) 1.2591(14) 0.0933(13) Uiso 1.000000 GR
H1c H 0.111(2) -0.4647(13) 1.3650(3) 0.0933(13) Uiso 1.000000 GR
C2 C 0.3346(3) -0.4116(3) 1.4263(2) 0.0597(8) Uani 1.000000 .
H2a H 0.3910(11) -0.4660(13) 1.3852(6) 0.0895(12) Uiso 1.000000 GR
H2b H 0.3897(12) -0.3610(3) 1.4453(13) 0.0895(12) Uiso 1.000000 GR
H2c H 0.3006(3) -0.4650(13) 1.4918(8) 0.0895(12) Uiso 1.000000 GR
C3 C 0.2122(3) -0.3214(2) 1.35800(18) 0.0354(5) Uani 1.000000 .
C4 C 0.1105(2) -0.2283(2) 1.41613(17) 0.0315(5) Uani 1.000000 .
C5 C -0.0226(3) -0.2701(3) 1.4614(2) 0.0487(7) Uani 1.000000 .
H5a H -0.0787(9) -0.2076(9) 1.4954(13) 0.0731(10) Uiso 1.000000 GR
H5b H -0.0736(9) -0.2753(17) 1.4029(3) 0.0731(10) Uiso 1.000000 GR
H5c H 0.0001(3) -0.3538(8) 1.5144(11) 0.0731(10) Uiso 1.000000 GR
C6 C 0.1789(3) -0.1948(3) 1.50164(19) 0.0460(6) Uani 1.000000 .
H6a H 0.2644(9) -0.1709(16) 1.4725(5) 0.0690(10) Uiso 1.000000 GR
H6b H 0.1173(8) -0.1233(11) 1.5220(10) 0.0690(10) Uiso 1.000000 GR
H6c H 0.1986(17) -0.2690(6) 1.5648(6) 0.0690(10) Uiso 1.000000 GR
C7 C 0.1793(2) 0.0061(2) 1.14780(16) 0.0261(5) Uani 1.000000 .
C8 C 0.1395(2) 0.1418(2) 1.15327(17) 0.0269(5) Uani 1.000000 .
C9 C 0.0805(2) 0.1908(2) 1.23890(18) 0.0330(5) Uani 1.000000 .
H9 H 0.0563(2) 0.1359(2) 1.30435(18) 0.0396(6) Uiso 1.000000 R
C10 C 0.0583(2) 0.3237(2) 1.22487(19) 0.0368(5) Uani 1.000000 .
H10 H 0.0174(2) 0.3582(2) 1.28115(19) 0.0442(7) Uiso 1.000000 R
C11 C 0.0962(2) 0.4052(2) 1.12824(19) 0.0376(6) Uani 1.000000 .
H11 H 0.0827(2) 0.4936(2) 1.12109(19) 0.0451(7) Uiso 1.000000 R
C12 C 0.1542(2) 0.3569(2) 1.04184(18) 0.0310(5) Uani 1.000000 .
H12 H 0.1794(2) 0.4124(2) 0.97718(18) 0.0371(6) Uiso 1.000000 R
C13 C 0.1741(2) 0.2249(2) 1.05273(17) 0.0266(5) Uani 1.000000 .
C14 C 0.2296(2) 0.14241(19) 0.97852(16) 0.0248(4) Uani 1.000000 .
C15 C 0.2309(2) 0.00598(19) 1.04581(16) 0.0250(4) Uani 1.000000 .
C16 C 0.2687(2) 0.1794(2) 0.87231(17) 0.0274(5) Uani 1.000000 .
C17 C 0.3217(2) 0.0971(2) 0.79849(16) 0.0277(5) Uani 1.000000 .
C18 C 0.4581(2) 0.0862(2) 0.75883(17) 0.0315(5) Uani 1.000000 .
H18 H 0.5128(2) 0.1357(2) 0.77492(17) 0.0378(6) Uiso 1.000000 R
C19 C 0.5139(2) 0.0030(2) 0.69578(17) 0.0338(5) Uani 1.000000 .
H19 H 0.6062(2) -0.0052(2) 0.67160(17) 0.0405(6) Uiso 1.000000 R
C20 C 0.4313(2) -0.0685(2) 0.66868(17) 0.0320(5) Uani 1.000000 .
C21 C 0.2929(2) -0.0536(2) 0.70428(17) 0.0324(5) Uani 1.000000 .
H21 H 0.2364(2) -0.0990(2) 0.68452(17) 0.0388(6) Uiso 1.000000 R
C22 C 0.2388(2) 0.0277(2) 0.76853(17) 0.0298(5) Uani 1.000000 .
H22 H 0.1462(2) 0.0364(2) 0.79213(17) 0.0358(6) Uiso 1.000000 R
C23 C 0.6202(3) -0.1831(2) 0.5798(2) 0.0452(6) Uani 1.000000 .
H23a H 0.6374(4) -0.2440(13) 0.5373(12) 0.0678(9) Uiso 1.000000 GR
H23b H 0.6468(5) -0.1047(4) 0.5380(12) 0.0678(9) Uiso 1.000000 GR
H23c H 0.6738(3) -0.2204(15) 0.6455(2) 0.0678(9) Uiso 1.000000 GR
C24 C 0.2756(2) -0.11255(19) 1.00797(16) 0.0241(4) Uani 1.000000 .
C25 C 0.4132(2) -0.1574(2) 0.97779(16) 0.0269(5) Uani 1.000000 .
H25 H 0.4805(2) -0.1146(2) 0.98506(16) 0.0323(6) Uiso 1.000000 R
C26 C 0.4522(2) -0.2643(2) 0.93716(17) 0.0290(5) Uani 1.000000 .
H26 H 0.5446(2) -0.2932(2) 0.91755(17) 0.0348(6) Uiso 1.000000 R
C27 C 0.3512(2) -0.3280(2) 0.92601(17) 0.0298(5) Uani 1.000000 .
C28 C 0.2141(2) -0.2868(2) 0.95896(17) 0.0300(5) Uani 1.000000 .
H28 H 0.1472(2) -0.3307(2) 0.95323(17) 0.0360(6) Uiso 1.000000 R
C29 C 0.1773(2) -0.1811(2) 1.00006(17) 0.0273(5) Uani 1.000000 .
H29 H 0.0857(2) -0.1549(2) 1.02290(17) 0.0328(6) Uiso 1.000000 R
C30 C 0.5085(3) -0.4627(2) 0.8313(2) 0.0422(6) Uani 1.000000 .
H30a H 0.5175(8) -0.3896(6) 0.7704(8) 0.0633(9) Uiso 1.000000 GR
H30b H 0.5826(3) -0.4815(15) 0.8817(4) 0.0633(9) Uiso 1.000000 GR
H30c H 0.5137(7) -0.5371(10) 0.8057(12) 0.0633(9) Uiso 1.000000 GR
B1 B 0.1718(3) -0.1140(2) 1.24690(19) 0.0269(5) Uani 1.000000 .


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
Cl1 C16 1.746(2) . ?
O1 C3 1.456(2) . ?
O1 B1 1.361(3) . ?
O2 C4 1.462(2) . ?
O2 B1 1.360(3) . ?
O3 C27 1.370(2) . ?
O3 C30 1.425(3) . ?
O4 C20 1.365(3) . ?
O4 C23 1.428(3) . ?
C1 C3 1.522(3) . ?
C2 C3 1.515(3) . ?
C3 C4 1.561(3) . ?
C4 C5 1.514(3) . ?
C4 C6 1.510(3) . ?
C7 C8 1.476(3) . ?
C7 C15 1.361(3) . ?
C7 B1 1.555(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.414(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.486(3) . ?
C14 C15 1.498(3) . ?
C14 C16 1.351(3) . ?
C15 C24 1.483(3) . ?
C16 C17 1.477(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.393(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.390(3) . ?
C21 C22 1.376(3) . ?
C24 C25 1.391(3) . ?
C24 C29 1.397(3) . ?
C25 C26 1.385(3) . ?
C26 C27 1.393(3) . ?
C27 C28 1.391(3) . ?
C28 C29 1.377(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
B1 O1 C3 107.48(17) . . ?
B1 O2 C4 107.69(17) . . ?
C30 O3 C27 117.49(17) . . ?
C23 O4 C20 117.62(17) . . ?
C1 C3 O1 105.28(18) . . ?
C2 C3 O1 108.8(2) . . ?
C2 C3 C1 110.6(2) . . ?
C4 C3 O1 102.69(16) . . ?
C4 C3 C1 113.9(2) . . ?
C4 C3 C2 114.75(19) . . ?
C3 C4 O2 102.40(16) . . ?
C5 C4 O2 107.95(18) . . ?
C5 C4 C3 115.03(19) . . ?
C6 C4 O2 106.18(17) . . ?
C6 C4 C3 113.95(19) . . ?
C6 C4 C5 110.45(19) . . ?
C15 C7 C8 108.45(18) . . ?
B1 C7 C8 123.96(19) . . ?
B1 C7 C15 127.4(2) . . ?
C9 C8 C7 129.7(2) . . ?
C13 C8 C7 109.19(18) . . ?
C13 C8 C9 121.1(2) . . ?
C10 C9 C8 118.6(2) . . ?
C11 C10 C9 120.8(2) . . ?
C12 C11 C10 120.9(2) . . ?
C13 C12 C11 119.4(2) . . ?
C12 C13 C8 119.1(2) . . ?
C14 C13 C8 107.19(17) . . ?
C14 C13 C12 133.66(19) . . ?
C15 C14 C13 105.28(17) . . ?
C16 C14 C13 128.69(19) . . ?
C16 C14 C15 126.01(19) . . ?
C14 C15 C7 109.80(18) . . ?
C24 C15 C7 124.00(18) . . ?
C24 C15 C14 126.16(18) . . ?
C14 C16 Cl1 120.15(17) . . ?
C17 C16 Cl1 111.41(14) . . ?
C17 C16 C14 128.42(19) . . ?
C18 C17 C16 119.67(18) . . ?
C22 C17 C16 121.68(19) . . ?
C22 C17 C18 118.6(2) . . ?
C19 C18 C17 121.06(19) . . ?
C20 C19 C18 119.8(2) . . ?
C19 C20 O4 124.9(2) . . ?
C21 C20 O4 115.80(18) . . ?
C21 C20 C19 119.3(2) . . ?
C22 C21 C20 120.57(19) . . ?
C21 C22 C17 120.5(2) . . ?
C25 C24 C15 122.05(17) . . ?
C29 C24 C15 119.68(18) . . ?
C29 C24 C25 118.26(19) . . ?
C26 C25 C24 121.45(18) . . ?
C27 C26 C25 119.2(2) . . ?
C26 C27 O3 124.2(2) . . ?
C28 C27 O3 115.82(18) . . ?
C28 C27 C26 119.99(19) . . ?
C29 C28 C27 120.01(18) . . ?
C28 C29 C24 121.0(2) . . ?
O2 B1 O1 113.51(19) . . ?
C7 B1 O1 124.5(2) . . ?
C7 B1 O2 121.9(2) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted in a Oxford Cryostystems cryo probe at 150 K'
_olex2_submission_special_instructions 'No special instructions were received'
