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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zyf_IOH_160919_2_2
_database_code_depnum_ccdc_archive 'CCDC 1526446'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C14 H16 B F I N O5, C3 H6 O'
_chemical_formula_sum            'C17 H22 B F I N O6'
_chemical_formula_weight         493.09
_chemical_oxdiff_formula         'C11 H10 N O'
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
C 0.01920 0.00962 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 0.00963 0.00408 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'
F 0.07537 0.05506 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'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'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'
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'
O 0.05239 0.03377 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'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   17.3516(3)
_cell_length_b                   11.2310(2)
_cell_length_c                   10.6444(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.1114(19)
_cell_angle_gamma                90
_cell_volume                     1992.86(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5155
_cell_measurement_theta_max      71.9860
_cell_measurement_theta_min      2.6380
_exptl_absorpt_coefficient_mu    13.004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.6433
_exptl_crystal_F_000             986.6074
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7761
_diffrn_reflns_theta_full        67.0784
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         2.65
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9674
_diffrn_measured_fraction_theta_max 0.9674
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  69.00   1.00    2.00    --   44.40 -37.00  30.00   95
  2  ω     31.00  91.00   1.00    5.00    --  100.00 -94.00   0.00   60
  3  ω     79.00 108.00   1.00    5.00    --  100.00-125.00-180.00   29
  4  ω     74.00 168.00   1.00    5.00    --  100.00  61.00  30.00   94
  5  ω    126.00 166.00   1.00    5.00    --  100.00  77.00  60.00   40
  6  ω     99.00 170.00   1.00    5.00    --  100.00  61.00  90.00   71
  7  ω     69.00 116.00   1.00    5.00    --  100.00  77.00  60.00   47
  8  ω    -67.00 -26.00   1.00    2.00    --  -44.40 -57.00   0.00   41
  9  ω   -106.00 -81.00   1.00    2.00    --  -44.40-125.00  60.00   25
 10  ω   -111.00 -86.00   1.00    2.00    --  -44.40 -57.00   0.00   25
 11  ω   -117.00 -74.00   1.00    2.00    --  -44.40-125.00-150.00   43
 12  ω   -101.00 -56.00   1.00    5.00    --  -90.00 125.00-150.00   45
 13  ω   -102.00 -75.00   1.00    5.00    --  -90.00  61.00-120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376291000
_diffrn_orient_matrix_UB_12      -0.0954929000
_diffrn_orient_matrix_UB_13      -0.0685811000
_diffrn_orient_matrix_UB_21      -0.0588421000
_diffrn_orient_matrix_UB_22      -0.0931995000
_diffrn_orient_matrix_UB_23      0.0261011000
_diffrn_orient_matrix_UB_31      -0.0605666000
_diffrn_orient_matrix_UB_32      0.0312479000
_diffrn_orient_matrix_UB_33      -0.1316223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                3147
_reflns_number_total             3447
_reflns_odcompleteness_completeness 96.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'SIR2008 (Burla et al., 2007)'
_refine_diff_density_max         3.6026
_refine_diff_density_min         -1.7467
_refine_diff_density_rms         0.2292
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             16.6701
_refine_ls_goodness_of_fit_ref   1.0517
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.0517
_refine_ls_shift/su_max          3.4534
_refine_ls_shift/su_mean         0.0637
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1802P)²+3.8146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2355
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11b,H11a,H11c), C18(H18a,H18b,H18c), C25(H25a,H25b,H25c), C2(H2a,H2b,H2c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_primary     direct
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
I1 I 0.67987(3) 0.71612(4) 1.01110(5) 0.0463(3) Uani 1.000000 .
O1 O 0.3938(3) 0.5537(5) 0.8394(5) 0.0410(12) Uani 1.000000 .
O2 O 0.5238(3) 0.5806(4) 0.8555(4) 0.0355(10) Uani 1.000000 .
O3 O 0.5885(3) 0.5642(4) 0.6832(4) 0.0356(11) Uani 1.000000 .
O4 O 0.7384(3) 0.4182(5) 0.8005(5) 0.0424(12) Uani 1.000000 .
C5 C 0.5692(5) 0.3573(6) 0.6570(6) 0.0326(14) Uani 1.000000 .
O6 O 0.5915(3) 0.4863(4) 0.4901(4) 0.0394(11) Uani 1.000000 .
N7 N 0.5576(3) 0.3856(4) 0.7884(5) 0.0287(11) Uani 1.000000 .
C8 C 0.9460(9) 0.6853(15) 0.9945(13) 0.083(3) Uani 1.000000 .
C9 C 0.6762(4) 0.5427(6) 0.9195(6) 0.0326(14) Uani 1.000000 .
C10 C 0.4561(4) 0.5165(6) 0.8286(6) 0.0329(15) Uani 1.000000 .
C11 C 0.5991(5) 0.2945(6) 0.8890(7) 0.0368(16) Uani 1.000000 .
O12 O 0.7822(5) 1.1458(8) 1.0812(7) 0.080(2) Uani 1.000000 .
C13 C 0.5842(4) 0.4744(6) 0.5993(6) 0.0323(14) Uani 1.000000 .
C14 C 0.4709(4) 0.3929(6) 0.7836(7) 0.0340(14) Uani 1.000000 .
F15 F 1.0501(5) 0.6349(10) 1.1830(8) 0.113(3) Uani 1.000000 .
C16 C 0.7457(5) 0.5343(7) 0.8576(7) 0.0397(16) Uani 1.000000 .
C17 C 0.8270(6) 0.5537(10) 0.9474(10) 0.060(2) Uani 1.000000 .
C18 C 0.7891(7) 1.117(2) 0.8643(11) 0.107(6) Uani 1.000000 .
C19 C 0.8709(7) 0.6550(12) 0.9227(15) 0.084(4) Uani 1.000000 .
C20 C 0.8009(5) 1.0845(10) 1.0002(8) 0.054(2) Uani 1.000000 .
C21 C 0.8551(6) 0.4795(14) 1.0480(10) 0.075(4) Uani 1.000000 .
C22 C 0.9714(5) 0.6128(10) 1.0994(10) 0.060(2) Uani 1.000000 .
C23 C 0.9365(9) 0.5106(15) 1.1335(12) 0.092(4) Uani 1.000000 .
B24 B 0.5902(5) 0.5243(6) 0.8161(7) 0.0317(16) Uani 1.000000 .
C25 C 0.8419(18) 0.9722(13) 1.044(2) 0.148(10) Uani 1.000000 .
C2 C 0.9914(12) 0.7851(19) 0.968(2) 0.128(8) Uani 1.000000 .
H21 H 0.8264(6) 0.4139(14) 1.0636(10) 0.090(4) Uiso 1.000000 R
H23 H 0.9624(9) 0.4644(15) 1.2052(12) 0.110(5) Uiso 1.000000 R
H19 H 0.8461(7) 0.7036(12) 0.8523(15) 0.101(5) Uiso 1.000000 R
H4 H 0.741(6) 0.4230(12) 0.725(3) 0.0637(18) Uiso 1.000000 GR
H5a H 0.6146(5) 0.3042(6) 0.6663(6) 0.0392(17) Uiso 1.000000 R
H5b H 0.5217(5) 0.3192(6) 0.6015(6) 0.0392(17) Uiso 1.000000 R
H9 H 0.6834(4) 0.4813(6) 0.9872(6) 0.0391(17) Uiso 1.000000 R
H11b H 0.576(3) 0.2175(11) 0.864(3) 0.055(2) Uiso 1.000000 GR
H11a H 0.6552(8) 0.292(4) 0.894(4) 0.055(2) Uiso 1.000000 GR
H11c H 0.593(3) 0.316(3) 0.9728(14) 0.055(2) Uiso 1.000000 GR
H14a H 0.4377(4) 0.3792(6) 0.6951(7) 0.0408(17) Uiso 1.000000 R
H14b H 0.4579(4) 0.3333(6) 0.8404(7) 0.0408(17) Uiso 1.000000 R
H16 H 0.7369(5) 0.5931(7) 0.7871(7) 0.0477(19) Uiso 1.000000 R
H18a H 0.746(6) 1.071(9) 0.8100(16) 0.160(9) Uiso 1.000000 GR
H18b H 0.776(9) 1.200(3) 0.853(3) 0.160(9) Uiso 1.000000 GR
H18c H 0.838(3) 1.103(13) 0.840(4) 0.160(9) Uiso 1.000000 GR
H25a H 0.883(9) 0.960(10) 1.000(17) 0.222(15) Uiso 1.000000 GR
H25b H 0.866(12) 0.975(8) 1.136(4) 0.222(15) Uiso 1.000000 GR
H25c H 0.804(3) 0.908(3) 1.02(2) 0.222(15) Uiso 1.000000 GR
H2a H 1.042(4) 0.758(3) 0.961(17) 0.193(11) Uiso 1.000000 GR
H2b H 0.962(5) 0.822(10) 0.887(9) 0.193(11) Uiso 1.000000 GR
H2c H 1.000(9) 0.842(8) 1.038(9) 0.193(11) 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
I1 C9 2.171(6) . ?
O1 C10 1.193(9) . ?
O2 C10 1.339(9) . ?
O2 B24 1.475(9) . ?
O3 C13 1.335(8) . ?
O3 B24 1.476(8) . ?
O4 C16 1.429(9) . ?
O4 H4 0.8200 . ?
C5 N7 1.501(8) . ?
C5 C13 1.505(9) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
O6 C13 1.211(8) . ?
N7 C11 1.510(8) . ?
N7 C14 1.494(9) . ?
N7 B24 1.656(9) . ?
C8 C19 1.358(19) . ?
C8 C22 1.353(19) . ?
C8 C2 1.44(2) . ?
C9 C16 1.530(10) . ?
C9 B24 1.602(11) . ?
C9 H9 0.9800 . ?
C10 C14 1.514(9) . ?
C11 H11b 0.9600 . ?
C11 H11a 0.9600 . ?
C11 H11c 0.9600 . ?
O12 C20 1.215(12) . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
F15 C22 1.430(12) . ?
C16 C17 1.485(13) . ?
C16 H16 0.9800 . ?
C17 C19 1.433(16) . ?
C17 C21 1.338(17) . ?
C18 C20 1.450(14) . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C19 H19 0.9300 . ?
C20 C25 1.46(2) . ?
C21 C23 1.494(18) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(19) . ?
C23 H23 0.9300 . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 0.9600 . ?
C2 H2a 0.9600 . ?
C2 H2b 0.9600 . ?
C2 H2c 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
B24 O2 C10 114.7(5) . . ?
B24 O3 C13 113.2(5) . . ?
H4 O4 C16 109.5 . . ?
C13 C5 N7 106.2(5) . . ?
H5a C5 N7 110.5(3) . . ?
H5a C5 C13 110.5(4) . . ?
H5b C5 N7 110.5(4) . . ?
H5b C5 C13 110.5(4) . . ?
H5b C5 H5a 108.7 . . ?
C11 N7 C5 110.9(5) . . ?
C14 N7 C5 111.9(5) . . ?
C14 N7 C11 109.9(5) . . ?
B24 N7 C5 103.7(5) . . ?
B24 N7 C11 116.0(5) . . ?
B24 N7 C14 104.2(5) . . ?
C22 C8 C19 110.8(14) . . ?
C2 C8 C19 125.1(16) . . ?
C2 C8 C22 124.0(15) . . ?
C16 C9 I1 108.7(5) . . ?
B24 C9 I1 109.3(4) . . ?
B24 C9 C16 113.0(5) . . ?
H9 C9 I1 108.58(17) . . ?
H9 C9 C16 108.6(4) . . ?
H9 C9 B24 108.6(3) . . ?
O2 C10 O1 123.8(6) . . ?
C14 C10 O1 126.1(7) . . ?
C14 C10 O2 110.2(6) . . ?
H11b C11 N7 109.5 . . ?
H11a C11 N7 109.5 . . ?
H11a C11 H11b 109.5 . . ?
H11c C11 N7 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H11c C11 H11a 109.5 . . ?
C5 C13 O3 111.8(5) . . ?
O6 C13 O3 123.8(6) . . ?
O6 C13 C5 124.4(6) . . ?
C10 C14 N7 107.3(6) . . ?
H14a C14 N7 110.2(3) . . ?
H14a C14 C10 110.2(4) . . ?
H14b C14 N7 110.2(3) . . ?
H14b C14 C10 110.2(3) . . ?
H14b C14 H14a 108.5 . . ?
C9 C16 O4 104.5(6) . . ?
C17 C16 O4 111.4(7) . . ?
C17 C16 C9 115.9(6) . . ?
H16 C16 O4 108.3(4) . . ?
H16 C16 C9 108.3(4) . . ?
H16 C16 C17 108.3(5) . . ?
C19 C17 C16 117.2(11) . . ?
C21 C17 C16 119.6(10) . . ?
C21 C17 C19 123.2(11) . . ?
H18a C18 C20 109.5 . . ?
H18b C18 C20 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C20 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C17 C19 C8 124.8(15) . . ?
H19 C19 C8 117.6(10) . . ?
H19 C19 C17 117.6(8) . . ?
C18 C20 O12 124.9(11) . . ?
C25 C20 O12 117.8(11) . . ?
C25 C20 C18 117.2(12) . . ?
C23 C21 C17 114.5(13) . . ?
H21 C21 C17 122.7(7) . . ?
H21 C21 C23 122.7(8) . . ?
F15 C22 C8 116.4(11) . . ?
C23 C22 C8 130.2(11) . . ?
C23 C22 F15 113.0(11) . . ?
C22 C23 C21 116.1(12) . . ?
H23 C23 C21 121.9(8) . . ?
H23 C23 C22 121.9(7) . . ?
O3 B24 O2 109.5(5) . . ?
N7 B24 O2 101.5(5) . . ?
N7 B24 O3 101.5(5) . . ?
C9 B24 O2 113.7(5) . . ?
C9 B24 O3 112.7(6) . . ?
C9 B24 N7 116.8(5) . . ?
H25a C25 C20 109.5 . . ?
H25b C25 C20 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C20 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
H2a C2 C8 109.5 . . ?
H2b C2 C8 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 C8 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 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 13.281
_oxdiff_exptl_absorpt_empirical_full_min 0.396
####################################################################### 
# 
# 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_zyf_170608_2
_database_code_depnum_ccdc_archive 'CCDC 1956104'
loop_
_audit_author_name
_audit_author_address
Br-OH-BMIDA
;University of South China
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C14 H17 B Br N O5'
_chemical_formula_sum            'C14 H17 B Br N O5'
_chemical_formula_weight         370.02
_chemical_oxdiff_formula         'C11 H10 N O'
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
C 0.01920 0.00962 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 0.00963 0.00408 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'
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'
O 0.05239 0.03377 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'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   21.4754(5)
_cell_length_b                   6.47129(11)
_cell_length_c                   24.0236(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.374(3)
_cell_angle_gamma                90
_cell_volume                     3041.05(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2560
_cell_measurement_theta_min      4.0300
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6162
_exptl_crystal_description       needle
_exptl_crystal_F_000             1503.0215
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6092
_diffrn_reflns_theta_full        67.0742
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.04
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  78.00   1.00    5.00    --   44.52  57.00-120.00   57
  2  ω     79.00 111.00   1.00    5.00    --   44.52  57.00-120.00   32
  3  ω     86.00 168.00   1.00   12.00    --  100.00  30.00 -30.00   82
  4  ω     77.00 106.00   1.00    5.00    --   44.52 125.00  90.00   29
  5  ω     28.00 126.00   1.00   12.00    --  100.00 -30.00 -30.00   98
  6  ω     82.00  96.00   1.00   12.00    --  100.00 -94.00   0.00   14
  7  ω     81.00 121.00   1.00   12.00    --  100.00 -77.00   0.00   40
  8  ω     60.00 120.00   1.00   12.00    --  100.00-125.00   0.00   60
  9  ω     26.00  52.00   1.00   12.00    --  100.00 -94.00   0.00   26
 10  ω     27.00  73.00   1.00   12.00    --  100.00 -77.00   0.00   46
 11  ω    -69.00  19.00   1.00    5.00    --  -44.52  57.00-180.00   88
 12  ω   -151.00 -96.00   1.00   12.00    --  -90.00-125.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0126162000
_diffrn_orient_matrix_UB_12      -0.2344901000
_diffrn_orient_matrix_UB_13      -0.0087173000
_diffrn_orient_matrix_UB_21      0.0656365000
_diffrn_orient_matrix_UB_22      -0.0404716000
_diffrn_orient_matrix_UB_23      0.0579296000
_diffrn_orient_matrix_UB_31      -0.0416781000
_diffrn_orient_matrix_UB_32      0.0074981000
_diffrn_orient_matrix_UB_33      0.0390074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2563
_reflns_number_total             2719
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.4472
_refine_diff_density_min         -0.5750
_refine_diff_density_rms         0.0778
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             10.9412
_refine_ls_goodness_of_fit_ref   1.0609
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.0609
_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)+(0.0459P)²+2.3241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0753
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C15(H15), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C20(H20c,H20b,H20a)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_primary     direct
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
Br1 Br 0.052897(10) 0.73508(3) 0.038188(9) 0.01641(10) Uani 1.000000 .
O1 O 0.21356(8) 0.7175(2) 0.12100(6) 0.0172(3) Uani 1.000000 .
O2 O 0.24271(7) 0.4623(2) 0.06110(6) 0.0206(3) Uani 1.000000 .
O3 O 0.20863(8) 0.8248(3) 0.20763(7) 0.0247(3) Uani 1.000000 .
O5 O 0.16834(8) 0.9163(3) -0.00028(7) 0.0279(4) Uani 1.000000 .
O6 O 0.32442(9) 0.2210(3) 0.09396(9) 0.0345(4) Uani 1.000000 .
N7 N 0.17856(8) 0.3648(3) 0.11999(7) 0.0143(3) Uani 1.000000 .
C8 C 0.27625(11) 0.3055(4) 0.09711(10) 0.0216(4) Uani 1.000000 .
C9 C 0.12155(10) 0.5983(3) 0.01517(9) 0.0164(4) Uani 1.000000 .
C10 C 0.19937(10) 0.6926(3) 0.16910(9) 0.0170(4) Uani 1.000000 .
C11 C 0.04397(12) 0.9676(4) -0.10492(10) 0.0241(5) Uani 1.000000 .
C12 C 0.12199(11) 0.2142(3) 0.09006(10) 0.0190(4) Uani 1.000000 .
C13 C 0.13608(12) 0.7315(3) -0.03080(10) 0.0200(5) Uani 1.000000 .
C14 C -0.04301(11) 0.8384(4) -0.20032(9) 0.0239(5) Uani 1.000000 .
C15 C -0.01302(12) 0.9988(4) -0.15963(10) 0.0267(5) Uani 1.000000 .
C16 C 0.04346(10) 0.6100(3) -0.13005(9) 0.0188(4) Uani 1.000000 .
C17 C -0.01344(11) 0.6426(4) -0.18424(9) 0.0214(5) Uani 1.000000 .
C18 C 0.16983(10) 0.4818(3) 0.16973(9) 0.0171(4) Uani 1.000000 .
C19 C 0.07276(12) 0.7722(3) -0.08962(10) 0.0188(5) Uani 1.000000 .
C20 C -0.10468(12) 0.8738(5) -0.25966(10) 0.0336(6) Uani 1.000000 .
C21 C 0.24626(12) 0.2538(3) 0.14214(11) 0.0204(5) Uani 1.000000 .
B22 B 0.18797(11) 0.5461(4) 0.07614(10) 0.0156(4) Uani 1.000000 .
H16 H 0.06269(10) 0.4755(3) -0.12039(9) 0.0225(5) Uiso 1.000000 R
H17 H -0.03280(11) 0.5294(4) -0.21104(9) 0.0257(6) Uiso 1.000000 R
H15 H -0.03192(12) 1.1336(4) -0.16939(10) 0.0320(6) Uiso 1.000000 R
H11 H 0.06324(12) 1.0804(4) -0.07796(10) 0.0290(6) Uiso 1.000000 R
H5 H 0.1882(13) 0.973(2) -0.0198(7) 0.0419(6) Uiso 1.000000 GR
H9 H 0.10160(10) 0.4646(3) -0.00529(9) 0.0197(5) Uiso 1.000000 R
H12a H 0.1221(5) 0.1116(14) 0.12012(19) 0.0284(7) Uiso 1.000000 GR
H12b H 0.07816(13) 0.2876(5) 0.0737(6) 0.0284(7) Uiso 1.000000 GR
H12c H 0.1285(4) 0.1444(17) 0.0566(5) 0.0284(7) Uiso 1.000000 GR
H13 H 0.16972(12) 0.6552(3) -0.04206(10) 0.0241(6) Uiso 1.000000 R
H18a H 0.12088(10) 0.4921(3) 0.16175(9) 0.0205(5) Uiso 1.000000 R
H18b H 0.19469(10) 0.4133(3) 0.20969(9) 0.0205(5) Uiso 1.000000 R
H20c H -0.1416(4) 0.935(3) -0.25111(12) 0.0505(9) Uiso 1.000000 GR
H20b H -0.0925(3) 0.968(2) -0.2856(4) 0.0505(9) Uiso 1.000000 GR
H20a H -0.1200(6) 0.7416(6) -0.2808(4) 0.0505(9) Uiso 1.000000 GR
H21a H 0.27690(12) 0.3014(3) 0.18364(11) 0.0244(6) Uiso 1.000000 R
H21b H 0.23961(12) 0.1028(3) 0.14339(11) 0.0244(6) Uiso 1.000000 R


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
Br1 C9 1.9841(19) . ?
O1 C10 1.321(3) . ?
O1 B22 1.485(3) . ?
O2 C8 1.335(3) . ?
O2 B22 1.469(2) . ?
O3 C10 1.215(3) . ?
O5 C13 1.424(3) . ?
O5 H5 0.8400 . ?
O6 C8 1.200(3) . ?
N7 C12 1.490(3) . ?
N7 C18 1.490(2) . ?
N7 C21 1.508(3) . ?
N7 B22 1.644(3) . ?
C8 C21 1.507(3) . ?
C9 C13 1.531(3) . ?
C9 B22 1.603(3) . ?
C9 H9 1.0000 . ?
C10 C18 1.508(3) . ?
C11 C15 1.392(3) . ?
C11 C19 1.389(3) . ?
C11 H11 0.9500 . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 C19 1.526(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.389(4) . ?
C14 C17 1.398(4) . ?
C14 C20 1.510(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 C19 1.391(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C20 H20c 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20a 0.9800 . ?
C21 H21a 0.9900 . ?
C21 H21b 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
B22 O1 C10 113.21(16) . . ?
B22 O2 C8 113.19(16) . . ?
H5 O5 C13 109.5 . . ?
C18 N7 C12 111.81(15) . . ?
C21 N7 C12 109.52(16) . . ?
C21 N7 C18 112.39(15) . . ?
B22 N7 C12 116.66(15) . . ?
B22 N7 C18 103.93(14) . . ?
B22 N7 C21 102.15(14) . . ?
O6 C8 O2 123.7(2) . . ?
C21 C8 O2 110.95(17) . . ?
C21 C8 O6 125.4(2) . . ?
C13 C9 Br1 110.23(14) . . ?
B22 C9 Br1 108.82(12) . . ?
B22 C9 C13 114.09(17) . . ?
H9 C9 Br1 107.83(6) . . ?
H9 C9 C13 107.83(11) . . ?
H9 C9 B22 107.83(11) . . ?
O3 C10 O1 123.8(2) . . ?
C18 C10 O1 111.65(17) . . ?
C18 C10 O3 124.54(19) . . ?
C19 C11 C15 120.2(2) . . ?
H11 C11 C15 119.88(14) . . ?
H11 C11 C19 119.88(14) . . ?
H12a C12 N7 109.5 . . ?
H12b C12 N7 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 N7 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C9 C13 O5 107.57(16) . . ?
C19 C13 O5 112.96(18) . . ?
C19 C13 C9 113.33(18) . . ?
H13 C13 O5 107.57(12) . . ?
H13 C13 C9 107.57(11) . . ?
H13 C13 C19 107.57(11) . . ?
C17 C14 C15 117.2(2) . . ?
C20 C14 C15 121.5(2) . . ?
C20 C14 C17 121.3(2) . . ?
C14 C15 C11 121.9(2) . . ?
H15 C15 C11 119.06(14) . . ?
H15 C15 C14 119.06(13) . . ?
C19 C16 C17 120.7(2) . . ?
H16 C16 C17 119.65(13) . . ?
H16 C16 C19 119.65(13) . . ?
C16 C17 C14 121.4(2) . . ?
H17 C17 C14 119.29(14) . . ?
H17 C17 C16 119.29(13) . . ?
C10 C18 N7 105.01(15) . . ?
H18a C18 N7 110.74(10) . . ?
H18a C18 C10 110.74(11) . . ?
H18b C18 N7 110.74(10) . . ?
H18b C18 C10 110.74(11) . . ?
H18b C18 H18a 108.8 . . ?
C13 C19 C11 122.1(2) . . ?
C16 C19 C11 118.6(2) . . ?
C16 C19 C13 119.31(19) . . ?
H20c C20 C14 109.5 . . ?
H20b C20 C14 109.5 . . ?
H20b C20 H20c 109.5 . . ?
H20a C20 C14 109.5 . . ?
H20a C20 H20c 109.5 . . ?
H20a C20 H20b 109.5 . . ?
C8 C21 N7 106.05(17) . . ?
H21a C21 N7 110.52(11) . . ?
H21a C21 C8 110.52(12) . . ?
H21b C21 N7 110.52(10) . . ?
H21b C21 C8 110.52(12) . . ?
H21b C21 H21a 108.7 . . ?
O2 B22 O1 111.11(16) . . ?
N7 B22 O1 100.05(14) . . ?
N7 B22 O2 102.51(16) . . ?
C9 B22 O1 115.42(17) . . ?
C9 B22 O2 110.71(15) . . ?
C9 B22 N7 115.94(16) . . ?

_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 7.616
_oxdiff_exptl_absorpt_empirical_full_min 0.501
