# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20230530_0m_tw
_database_code_depnum_ccdc_archive 'CCDC 2267832'
loop_
_audit_author_name
_audit_author_address
'Guoyan Li'
;University of Jinan
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_audit_creation_date             2023-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 B O3'
_chemical_formula_sum            'C7 H7 B O3'
_chemical_formula_weight         149.94
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.889(2)
_cell_length_b                   13.249(8)
_cell_length_c                   14.043(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.986(9)
_cell_angle_gamma                90
_cell_volume                     723.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1566
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1591
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1258
_reflns_number_total             1591
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    ?
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.154
_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)+(0.1200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1929
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.076) H2(0.069) H6(0.063) H7(0.071) H8(0.058)
 Fixed X: H1(0.415927) H2(0.697355) H6(0.97179) H7(0.310604) H8(0.492312)
 Fixed Y: H1(0.667065) H2(0.785979) H6(0.841715) H7(0.508899) H8(0.468736)
 Fixed Z: H1(0.018224) H2(0.112691) H6(0.242999) H7(0.079382) H8(0.231852)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.9774(5) 0.61490(11) 0.44148(9) 0.0609(5) Uani 1 1 d . . . . .
O2 O 0.7539(5) 0.46112(11) 0.38669(11) 0.0618(5) Uani 1 1 d . . . . .
O3 O 1.0449(5) 0.78965(12) 0.36181(12) 0.0703(6) Uani 1 1 d . . . . .
C1 C 0.4870(6) 0.6511(2) 0.08033(14) 0.0633(7) Uani 1 1 d . . . . .
H1 H 0.415927 0.667065 0.018224 0.076 Uiso 1 1 calc R U . . .
C2 C 0.6558(6) 0.72208(19) 0.13718(14) 0.0571(6) Uani 1 1 d . . . . .
H2 H 0.697355 0.785979 0.112691 0.069 Uiso 1 1 calc R U . . .
C3 C 0.7653(5) 0.69956(14) 0.23085(12) 0.0417(5) Uani 1 1 d . . . . .
C4 C 0.7068(5) 0.60231(13) 0.26905(12) 0.0390(5) Uani 1 1 d . . . . .
C6 C 0.9389(6) 0.78442(15) 0.27985(15) 0.0525(5) Uani 1 1 d . . . . .
H6 H 0.971790 0.841715 0.242999 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4258(6) 0.55695(19) 0.11675(14) 0.0590(6) Uani 1 1 d . . . . .
H7 H 0.310604 0.508899 0.079382 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5349(5) 0.53323(16) 0.20894(13) 0.0482(5) Uani 1 1 d . . . . .
H8 H 0.492312 0.468736 0.231852 0.058 Uiso 1 1 calc R U . . .
B1 B 0.8193(6) 0.55983(16) 0.37129(13) 0.0435(5) Uani 1 1 d . . . . .
H1D H 1.005(7) 0.680(2) 0.423(2) 0.079(8) Uiso 1 1 d . . . . .
H2D H 0.800(8) 0.444(3) 0.440(3) 0.106(12) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.1047(14) 0.0398(8) 0.0371(7) 0.0036(5) -0.0160(7) -0.0068(7)
O2 0.1007(13) 0.0408(8) 0.0429(8) 0.0055(6) -0.0130(8) -0.0064(7)
O3 0.1056(14) 0.0442(8) 0.0599(10) 0.0012(7) -0.0146(9) -0.0105(8)
C1 0.0631(14) 0.0919(17) 0.0343(9) 0.0057(10) -0.0064(8) 0.0214(12)
C2 0.0633(14) 0.0645(14) 0.0437(11) 0.0169(9) 0.0030(9) 0.0189(10)
C3 0.0432(10) 0.0455(10) 0.0365(8) 0.0032(7) 0.0032(7) 0.0118(8)
C4 0.0423(10) 0.0408(9) 0.0342(8) -0.0023(6) 0.0024(7) 0.0079(7)
C6 0.0623(13) 0.0374(10) 0.0579(12) 0.0092(8) 0.0040(9) 0.0041(9)
C7 0.0537(12) 0.0797(16) 0.0429(10) -0.0138(10) -0.0074(8) 0.0071(11)
C8 0.0503(11) 0.0527(11) 0.0415(10) -0.0055(8) 0.0000(8) 0.0049(9)
B1 0.0560(13) 0.0388(10) 0.0356(9) 0.0019(7) -0.0002(8) 0.0038(9)

_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 B1 1.357(2) . ?
O1 H1D 0.91(3) . ?
O2 B1 1.351(3) . ?
O2 H2D 0.79(4) . ?
O3 C6 1.211(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(4) . ?
C1 C7 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(2) . ?
C3 C4 1.417(3) . ?
C3 C6 1.470(3) . ?
C4 C8 1.399(3) . ?
C4 B1 1.589(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9300 . ?

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 H1D 111.3(18) . . ?
B1 O2 H2D 113(3) . . ?
C2 C1 H1 120.4 . . ?
C7 C1 H1 120.4 . . ?
C7 C1 C2 119.17(18) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 120.11(19) . . ?
C2 C3 C6 113.36(18) . . ?
C4 C3 C6 126.53(17) . . ?
C3 C4 B1 128.40(16) . . ?
C8 C4 C3 116.48(17) . . ?
C8 C4 B1 115.10(18) . . ?
O3 C6 C3 128.63(18) . . ?
O3 C6 H6 115.7 . . ?
C3 C6 H6 115.7 . . ?
C1 C7 H7 119.9 . . ?
C1 C7 C8 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C4 C8 H8 118.6 . . ?
C7 C8 C4 122.7(2) . . ?
C7 C8 H8 118.6 . . ?
O1 B1 C4 124.72(18) . . ?
O2 B1 O1 119.17(16) . . ?
O2 B1 C4 116.10(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C6 -179.92(19) . . . . ?
C1 C7 C8 C4 0.6(3) . . . . ?
C2 C1 C7 C8 -0.6(3) . . . . ?
C2 C3 C4 C8 -0.6(3) . . . . ?
C2 C3 C4 B1 177.76(17) . . . . ?
C2 C3 C6 O3 175.8(2) . . . . ?
C3 C4 C8 C7 0.0(3) . . . . ?
C3 C4 B1 O1 4.1(3) . . . . ?
C3 C4 B1 O2 -174.88(19) . . . . ?
C4 C3 C6 O3 -4.7(4) . . . . ?
C6 C3 C4 C8 179.94(18) . . . . ?
C6 C3 C4 B1 -1.7(3) . . . . ?
C7 C1 C2 C3 0.1(3) . . . . ?
C8 C4 B1 O1 -177.57(19) . . . . ?
C8 C4 B1 O2 3.5(3) . . . . ?
B1 C4 C8 C7 -178.53(18) . . . . ?

_shelx_res_file                  
;
TITL 20230530_0m_a.res in P2(1)/c
    20230530_0m_tw.res
    created by SHELXL-2016/6 at 16:47:19 on 30-May-2023
CELL 0.71073 3.8886 13.2489 14.0433 90.000 91.986 90.000
ZERR 4.00 0.0024 0.0082 0.0086 0.000 0.009 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H O  B
UNIT 28 28 12 4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP 23.000
ACTA
L.S. 4
FMAP 2
SIZE 0.19 0.16 0.15
PLAN -2 0 0.00
OMIT  -1   3  11
OMIT     3   3   4
OMIT    -1   0  16
OMIT     0   4   5
OMIT     3   4   4
OMIT    -1   2  12
OMIT    -1   2  11
OMIT     0   5   6
OMIT -1   1  15
OMIT     1   5   6
OMIT     3   2   4
OMIT    -1   0  12
OMIT    -1   1   3
OMIT     0   6   8
OMIT    -3  11   4
OMIT    -3   7   8
OMIT     -3  11   3
OMIT    -3  11   5
OMIT    -1   1  11
HTAB
BOND $H
CONF
WGHT    0.120000
BASF   0.13325
FVAR      33.13803
O1    3    0.977448    0.614900    0.441481    11.00000    0.10467    0.03978 =
         0.03711    0.00359   -0.01604   -0.00683
O2    3    0.753939    0.461124    0.386687    11.00000    0.10069    0.04082 =
         0.04287    0.00554   -0.01303   -0.00638
O3    3    1.044859    0.789653    0.361814    11.00000    0.10559    0.04419 =
         0.05989    0.00119   -0.01458   -0.01049
C1    1    0.486991    0.651124    0.080328    11.00000    0.06308    0.09193 =
         0.03435    0.00569   -0.00638    0.02137
AFIX  43
H1    2    0.415927    0.667065    0.018224    11.00000   -1.20000
AFIX   0
C2    1    0.655798    0.722080    0.137175    11.00000    0.06325    0.06449 =
         0.04371    0.01695    0.00297    0.01891
AFIX  43
H2    2    0.697355    0.785979    0.112691    11.00000   -1.20000
AFIX   0
C3    1    0.765284    0.699564    0.230848    11.00000    0.04325    0.04553 =
         0.03649    0.00320    0.00315    0.01179
C4    1    0.706761    0.602308    0.269051    11.00000    0.04225    0.04076 =
         0.03418   -0.00231    0.00242    0.00793
C6    1    0.938925    0.784423    0.279851    11.00000    0.06229    0.03738 =
         0.05787    0.00916    0.00395    0.00410
AFIX  43
H6    2    0.971790    0.841715    0.242999    11.00000   -1.20000
AFIX   0
C7    1    0.425783    0.556946    0.116749    11.00000    0.05366    0.07974 =
         0.04291   -0.01383   -0.00736    0.00715
AFIX  43
H7    2    0.310604    0.508899    0.079382    11.00000   -1.20000
AFIX   0
C8    1    0.534949    0.533233    0.208941    11.00000    0.05035    0.05266 =
         0.04151   -0.00555    0.00004    0.00490
AFIX  43
H8    2    0.492312    0.468736    0.231852    11.00000   -1.20000
REM #####
REM #####
AFIX   0
B1    4    0.819278    0.559828    0.371294    11.00000    0.05602    0.03885 =
         0.03555    0.00191   -0.00021    0.00380
H1D   2    1.005449    0.680030    0.423342    11.00000    0.07856
H2D   2    0.799511    0.444211    0.439911    11.00000    0.10649
HKLF 5




REM  20230530_0m_a.res in P2(1)/c
REM R1 =  0.0562 for    1258 Fo > 4sig(Fo)  and  0.0685 for all    1591 data
REM    109 parameters refined using      0 restraints

END

WGHT      0.0934      0.1380

REM Instructions for potential hydrogen bonds
HTAB O1 O3
EQIV $1 -x+2, -y+1, -z+1
HTAB O2 O1_$1

REM Highest difference peak  0.243,  deepest hole -0.201,  1-sigma level  0.048
Q1    1   0.7992  0.5908  0.3179  11.00000  0.05    0.24
Q2    1   0.7304  0.7016  0.1797  11.00000  0.05    0.24
;
_shelx_res_checksum              50502
_shelx_SHELXL_version_number     2016/6
_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_2_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2267833'
loop_
_audit_author_name
_audit_author_address
'Guoyan Li'
;University of Jinan
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 B O3'
_chemical_formula_weight         149.94

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   22.750(7)
_cell_length_b                   3.8166(11)
_cell_length_c                   17.211(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.691(4)
_cell_angle_gamma                90
_cell_volume                     1463.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1499
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.828
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1499
_reflns_number_gt                1210
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0867P)²+0.3383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1499
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57221(7) 0.8721(5) 0.51754(9) 0.0542(5) Uani 1 1 d . . . . .
H1 H 0.604199 0.783475 0.539104 0.081 Uiso 1 1 calc R U . . .
O2 O 0.50966(6) 0.9038(5) 0.39296(9) 0.0551(5) Uani 1 1 d . . . . .
H2 H 0.487326 0.970955 0.421801 0.083 Uiso 1 1 calc R U . . .
O3 O 0.65827(7) 0.3159(6) 0.14611(9) 0.0658(6) Uani 1 1 d . . . . .
C1 C 0.61276(8) 0.6648(5) 0.39512(12) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.59993(9) 0.6183(5) 0.31291(12) 0.0375(5) Uani 1 1 d . . . . .
H2A H 0.562095 0.677191 0.284066 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64282(9) 0.4852(6) 0.27331(11) 0.0367(5) Uani 1 1 d . . . . .
C4 C 0.69975(9) 0.3968(5) 0.31562(13) 0.0379(5) Uani 1 1 d . . . . .
H4 H 0.728429 0.307625 0.289377 0.046 Uiso 1 1 calc R U . . .
C5 C 0.71326(9) 0.4426(6) 0.39700(13) 0.0424(5) Uani 1 1 d . . . . .
H5 H 0.751188 0.384984 0.425761 0.051 Uiso 1 1 calc R U . . .
C6 C 0.67008(9) 0.5749(6) 0.43570(12) 0.0396(5) Uani 1 1 d . . . . .
H6 H 0.679765 0.604262 0.490449 0.047 Uiso 1 1 calc R U . . .
C7 C 0.62605(10) 0.4344(7) 0.18767(13) 0.0510(6) Uani 1 1 d . . . . .
H7 H 0.587345 0.498497 0.162892 0.061 Uiso 1 1 calc R U . . .
B1 B 0.56304(11) 0.8175(7) 0.43735(14) 0.0382(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0434(9) 0.0865(13) 0.0358(8) -0.0020(8) 0.0154(7) 0.0173(8)
O2 0.0386(8) 0.0885(14) 0.0400(8) -0.0087(9) 0.0124(7) 0.0158(8)
O3 0.0524(10) 0.1098(16) 0.0377(8) -0.0162(10) 0.0149(8) 0.0085(10)
C1 0.0321(10) 0.0371(10) 0.0344(10) -0.0004(8) 0.0107(9) -0.0005(8)
C2 0.0309(10) 0.0465(12) 0.0362(10) -0.0035(9) 0.0091(8) 0.0012(9)
C3 0.0363(10) 0.0433(10) 0.0319(11) -0.0014(9) 0.0105(9) -0.0002(10)
C4 0.0322(10) 0.0428(11) 0.0421(11) -0.0014(10) 0.0153(9) 0.0020(8)
C5 0.0329(11) 0.0527(13) 0.0413(12) 0.0012(11) 0.0066(9) 0.0054(10)
C6 0.0398(11) 0.0494(13) 0.0291(10) -0.0027(9) 0.0061(9) 0.0018(9)
C7 0.0409(12) 0.0741(18) 0.0383(12) -0.0045(11) 0.0088(10) 0.0059(11)
B1 0.0363(12) 0.0447(13) 0.0365(12) -0.0015(10) 0.0145(10) 0.0012(11)

_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 B1 1.369(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.338(3) . ?
O2 H2 0.8200 . ?
O3 C7 1.211(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.397(3) . ?
C1 B1 1.575(3) . ?
C2 C3 1.394(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.393(3) . ?
C3 C7 1.459(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
C6 C1 C2 117.33(18) . . ?
C6 C1 B1 123.17(19) . . ?
C2 C1 B1 119.50(19) . . ?
C3 C2 C1 121.22(19) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C4 C3 C2 120.10(19) . . ?
C4 C3 C7 121.41(19) . . ?
C2 C3 C7 118.48(19) . . ?
C5 C4 C3 119.42(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.87(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 122.07(19) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O3 C7 C3 125.5(2) . . ?
O3 C7 H7 117.2 . . ?
C3 C7 H7 117.2 . . ?
O2 B1 O1 118.24(19) . . ?
O2 B1 C1 118.76(19) . . ?
O1 B1 C1 123.0(2) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.051

_shelx_res_file                  
;
TITL 2_0m_4_a.res in C2/c
    2_0m_4.res
    created by SHELXL-2016/6 at 10:32:55 on 09-May-2019
REM Old TITL 2_0m_4 in C2/c
REM SHELXT solution in C2/c
REM R1 0.199, Rweak 0.016, Alpha 0.051, Orientation as input
REM Formula found by SHELXT: C8 O3
CELL 0.71073 22.7501 3.8166 17.2105 90 101.691 90
ZERR 8 0.0065 0.0011 0.005 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H B O
UNIT 56 56 8 24

L.S. 4
PLAN  20
SIZE 0.19 0.15 0.12
TEMP 23
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\2_0m_4.hkl">
REM </olex2.extras>

WGHT    0.086700    0.338300
FVAR       0.49280
O1    4    0.572206    0.872079    0.517539    11.00000    0.04343    0.08653 =
         0.03582   -0.00202    0.01538    0.01725
AFIX 147
H1    2    0.604199    0.783475    0.539104    11.00000   -1.50000
AFIX   0
O2    4    0.509657    0.903773    0.392962    11.00000    0.03862    0.08848 =
         0.03995   -0.00866    0.01245    0.01577
AFIX 147
H2    2    0.487326    0.970955    0.421801    11.00000   -1.50000
AFIX   0
O3    4    0.658274    0.315909    0.146114    11.00000    0.05244    0.10978 =
         0.03770   -0.01621    0.01488    0.00853
C1    1    0.612756    0.664769    0.395119    11.00000    0.03210    0.03706 =
         0.03445   -0.00036    0.01068   -0.00046
C2    1    0.599935    0.618296    0.312914    11.00000    0.03089    0.04647 =
         0.03620   -0.00349    0.00911    0.00115
AFIX  43
H2A   2    0.562095    0.677191    0.284066    11.00000   -1.20000
AFIX   0
C3    1    0.642820    0.485242    0.273309    11.00000    0.03634    0.04326 =
         0.03192   -0.00142    0.01048   -0.00024
C4    1    0.699749    0.396761    0.315621    11.00000    0.03221    0.04281 =
         0.04207   -0.00137    0.01533    0.00203
AFIX  43
H4    2    0.728429    0.307625    0.289377    11.00000   -1.20000
AFIX   0
C5    1    0.713258    0.442606    0.397001    11.00000    0.03287    0.05266 =
         0.04133    0.00116    0.00657    0.00535
AFIX  43
H5    2    0.751188    0.384984    0.425761    11.00000   -1.20000
AFIX   0
C6    1    0.670076    0.574857    0.435699    11.00000    0.03981    0.04937 =
         0.02915   -0.00275    0.00606    0.00179
AFIX  43
H6    2    0.679765    0.604262    0.490449    11.00000   -1.20000
AFIX   0
C7    1    0.626053    0.434435    0.187667    11.00000    0.04094    0.07408 =
         0.03833   -0.00453    0.00879    0.00592
AFIX  43
H7    2    0.587345    0.498497    0.162892    11.00000   -1.20000
AFIX   0
B1    3    0.563042    0.817486    0.437350    11.00000    0.03629    0.04466 =
         0.03654   -0.00149    0.01454    0.00119
HKLF 5




REM  2_0m_4_a.res in C2/c
REM R1 =  0.0439 for    1210 Fo > 4sig(Fo)  and  0.0585 for all    1499 data
REM    102 parameters refined using      0 restraints

END

WGHT      0.0799      0.1253

REM Highest difference peak  0.211,  deepest hole -0.184,  1-sigma level  0.051
Q1    1   0.5894  0.7501  0.4198  11.00000  0.05    0.21
Q2    1   0.5677  0.3614  0.1670  11.00000  0.05    0.21
Q3    1   0.5107  0.6329  0.2466  11.00000  0.05    0.18
Q4    1   0.7403  0.7818  0.5061  11.00000  0.05    0.17
Q5    1   0.5898  0.7895  0.1643  11.00000  0.05    0.16
Q6    1   0.5820  0.2199  0.3174  11.00000  0.05    0.16
Q7    1   0.6970  0.0520  0.1615  11.00000  0.05    0.16
Q8    1   0.7097  0.4553  0.3616  11.00000  0.05    0.15
Q9    1   0.5067  0.9101  0.2643  11.00000  0.05    0.15
Q10   1   0.5934  0.7508  0.0927  11.00000  0.05    0.15
Q11   1   0.6615  0.1180  0.1020  11.00000  0.05    0.15
Q12   1   0.4900  1.3517  0.4238  11.00000  0.05    0.15
Q13   1   0.6763  0.3740  0.5067  11.00000  0.05    0.15
Q14   1   0.6910  0.7776  0.3633  11.00000  0.05    0.14
Q15   1   0.4694  1.1407  0.3420  11.00000  0.05    0.14
Q16   1   0.6559  0.2009  0.1454  11.00000  0.05    0.14
Q17   1   0.5568  1.2133  0.5374  11.00000  0.05    0.13
Q18   1   0.6933  0.5826  0.3989  11.00000  0.05    0.13
Q19   1   0.7191  0.1041  0.2250  11.00000  0.05    0.13
Q20   1   0.6183  0.4717  0.2915  11.00000  0.05    0.13
;
_shelx_res_checksum              60463
