# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_bsme
_database_code_depnum_ccdc_archive 'CCDC 1520613'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C13 H12 O2'
_chemical_formula_sum            'C13 H12 O2'
_chemical_formula_weight         200.24
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'
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'

_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                   7.8751(9)
_cell_length_b                   8.2320(4)
_cell_length_c                   8.8523(12)
_cell_angle_alpha                73.986(8)
_cell_angle_beta                 73.564(11)
_cell_angle_gamma                83.983(8)
_cell_volume                     528.84(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.3080
_cell_measurement_theta_min      3.0470
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.2574
_exptl_crystal_description       block
_exptl_crystal_F_000             212.1121
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11929
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         32.75
_diffrn_reflns_theta_min         2.48
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9262
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 119.00   0.50    5.00    --   29.89  54.00 -90.00  376
  2  ω    -69.00 119.00   0.50    5.00    --   29.89  54.00 -90.00  376
  3  ω    -69.00 119.00   0.50    5.00    --   29.89  54.00  30.00  376
  4  ω    -69.00 119.00   0.50    5.00    --   29.89  54.00 150.00  376
  5  ω    -69.00  91.00   0.50    5.00    --   29.89  54.00-150.00  320
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0514496000
_diffrn_orient_matrix_UB_12      -0.0001568000
_diffrn_orient_matrix_UB_13      0.0800172000
_diffrn_orient_matrix_UB_21      -0.0761617000
_diffrn_orient_matrix_UB_22      0.0252835000
_diffrn_orient_matrix_UB_23      -0.0294057000
_diffrn_orient_matrix_UB_31      -0.0194445000
_diffrn_orient_matrix_UB_32      -0.0860418000
_diffrn_orient_matrix_UB_33      0.0144776000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1897
_reflns_number_total             3626
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.7218
_refine_diff_density_min         -0.3509
_refine_diff_density_rms         0.1009
_refine_ls_d_res_high            0.6568
_refine_ls_d_res_low             8.2028
_refine_ls_goodness_of_fit_ref   1.4669
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0969
_refine_ls_restrained_S_all      1.4669
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2396
_refine_ls_wR_factor_ref         0.2917
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00B(H00B), C008(H008), C009(H009),
 C00A(H00A)
2.c Idealised Me refined as rotating group:
 C00F(H00f,H00g,H00h)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_primary     dual
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
O001 O 0.64899(19) 0.79387(19) 0.19492(16) 0.0673(5) Uani 1.000000 .
O002 O 0.2431(2) 0.54825(18) 0.68157(18) 0.0699(5) Uani 1.000000 .
C003 C 0.5107(3) 0.7023(2) 0.6204(2) 0.0539(5) Uani 1.000000 .
C004 C 0.3686(3) 0.7263(2) 0.4112(2) 0.0542(5) Uani 1.000000 .
C005 C 0.6154(3) 0.8021(2) 0.4790(2) 0.0554(5) Uani 1.000000 .
C006 C 0.3576(2) 0.6465(2) 0.5852(2) 0.0533(5) Uani 1.000000 .
C007 C 0.5327(3) 0.8328(2) 0.3368(2) 0.0563(5) Uani 1.000000 .
C008 C 0.2483(3) 0.6998(2) 0.3406(2) 0.0575(5) Uani 1.000000 .
C009 C 0.2413(3) 0.7727(3) 0.1744(3) 0.0611(5) Uani 1.000000 .
C00A C 0.1145(3) 0.7332(3) 0.1181(3) 0.0632(5) Uani 1.000000 .
C00B C 0.5564(3) 0.6618(3) 0.7674(3) 0.0673(6) Uani 1.000000 .
C00C C 0.7750(3) 0.8594(3) 0.4801(3) 0.0677(6) Uani 1.000000 .
C00D C 0.8210(3) 0.8167(3) 0.6260(3) 0.0765(7) Uani 1.000000 .
C00E C 0.7123(4) 0.7225(3) 0.7685(3) 0.0760(7) Uani 1.000000 .
C00F C 0.0952(3) 0.8043(4) -0.0500(3) 0.0767(7) Uani 1.000000 .
H00C H 0.8485(3) 0.9243(3) 0.3855(3) 0.0812(7) Uiso 1.000000 R
H00D H 0.9281(3) 0.8525(3) 0.6285(3) 0.0918(8) Uiso 1.000000 R
H00E H 0.7447(4) 0.7000(3) 0.8656(3) 0.0912(8) Uiso 1.000000 R
H00B H 0.4840(3) 0.5958(3) 0.8619(3) 0.0808(7) Uiso 1.000000 R
H001 H 0.682(3) 0.6942(11) 0.2172(10) 0.1009(7) Uiso 1.000000 GR
H007 H 0.4951(3) 0.9521(2) 0.3084(2) 0.0675(6) Uiso 1.000000 R
H008 H 0.1591(3) 0.6259(2) 0.4062(2) 0.0690(6) Uiso 1.000000 R
H009 H 0.3266(3) 0.8489(3) 0.1050(3) 0.0733(6) Uiso 1.000000 R
H00A H 0.0320(3) 0.6553(3) 0.1897(3) 0.0759(7) Uiso 1.000000 R
H00f H 0.1895(17) 0.880(2) -0.1124(8) 0.1151(10) Uiso 1.000000 GR
H00g H 0.100(3) 0.7141(4) -0.1006(10) 0.1151(10) Uiso 1.000000 GR
H00h H -0.0165(13) 0.865(2) -0.0456(3) 0.1151(10) 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
O001 C007 1.425(3) . ?
O001 H001 0.8200 . ?
O002 C006 1.238(2) . ?
C003 C005 1.383(3) . ?
C003 C006 1.472(3) . ?
C003 C00B 1.390(3) . ?
C004 C006 1.480(3) . ?
C004 C007 1.520(3) . ?
C004 C008 1.337(3) . ?
C005 C007 1.525(3) . ?
C005 C00C 1.391(3) . ?
C007 H007 0.9800 . ?
C008 C009 1.442(3) . ?
C008 H008 0.9300 . ?
C009 C00A 1.338(3) . ?
C009 H009 0.9300 . ?
C00A C00F 1.486(3) . ?
C00A H00A 0.9300 . ?
C00B C00E 1.377(3) . ?
C00B H00B 0.9300 . ?
C00C C00D 1.382(3) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.383(4) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00f 0.9600 . ?
C00F H00g 0.9600 . ?
C00F H00h 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
H001 O001 C007 109.5 . . ?
C006 C003 C005 109.58(17) . . ?
C00B C003 C005 121.9(2) . . ?
C00B C003 C006 128.44(19) . . ?
C007 C004 C006 108.84(16) . . ?
C008 C004 C006 121.95(18) . . ?
C008 C004 C007 129.21(18) . . ?
C007 C005 C003 111.61(17) . . ?
C00C C005 C003 119.8(2) . . ?
C00C C005 C007 128.54(18) . . ?
C003 C006 O002 126.68(17) . . ?
C004 C006 O002 126.10(18) . . ?
C004 C006 C003 107.19(16) . . ?
C004 C007 O001 114.40(16) . . ?
C005 C007 O001 113.86(16) . . ?
C005 C007 C004 102.62(15) . . ?
H007 C007 O001 108.55(10) . . ?
H007 C007 C004 108.55(10) . . ?
H007 C007 C005 108.55(9) . . ?
C009 C008 C004 127.4(2) . . ?
H008 C008 C004 116.31(12) . . ?
H008 C008 C009 116.31(12) . . ?
C00A C009 C008 121.4(2) . . ?
H009 C009 C008 119.30(12) . . ?
H009 C009 C00A 119.30(14) . . ?
C00F C00A C009 125.1(2) . . ?
H00A C00A C009 117.47(14) . . ?
H00A C00A C00F 117.47(14) . . ?
C00E C00B C003 117.9(2) . . ?
H00B C00B C003 121.05(13) . . ?
H00B C00B C00E 121.05(15) . . ?
C00D C00C C005 117.9(2) . . ?
H00C C00C C005 121.04(13) . . ?
H00C C00C C00D 121.04(14) . . ?
C00E C00D C00C 122.0(2) . . ?
H00D C00D C00C 119.02(14) . . ?
H00D C00D C00E 119.02(14) . . ?
C00D C00E C00B 120.4(2) . . ?
H00E C00E C00B 119.82(15) . . ?
H00E C00E C00D 119.82(14) . . ?
H00f C00F C00A 109.5 . . ?
H00g C00F C00A 109.5 . . ?
H00g C00F H00f 109.5 . . ?
H00h C00F C00A 109.5 . . ?
H00h C00F H00f 109.5 . . ?
H00h C00F H00g 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.594
_oxdiff_exptl_absorpt_empirical_full_min 0.587
####################################################################### 
# 
# 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_BS06OMediph
_database_code_depnum_ccdc_archive 'CCDC 1520308'
_audit_update_record             
;
2016-12-01 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_formula_moiety         '0.5(C25 H20 O3)'
_chemical_formula_sum            'C12.5 H10 O1.5'
_chemical_formula_weight         184.22
_chemical_absolute_configuration unk
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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   10.1899(4)
_cell_length_b                   13.3377(5)
_cell_length_c                   14.4940(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969.88(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3051
_cell_measurement_theta_max      22.7140
_cell_measurement_theta_min      2.5940
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2422
_exptl_crystal_F_000             776.3947
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15325
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.81
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9174
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 116.00   0.50    5.00    --   29.89  54.00-120.00  370
  2  ω     -6.00 114.00   0.50    5.00    --   29.89  54.00 120.00  240
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.852
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                3790
_reflns_number_total             6671
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2753
_refine_diff_density_min         -0.2001
_refine_diff_density_rms         0.0526
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_d_res_high            0.6568
_refine_ls_d_res_low             7.2470
_refine_ls_goodness_of_fit_ref   1.0529
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     254
_refine_ls_number_reflns         6671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.0529
_refine_ls_shift/su_max          0.0384
_refine_ls_shift/su_mean         0.0016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1979
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00S(H00a,H00b,H00f)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
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
O001 O -0.52700(17) -0.94222(12) -0.31317(14) 0.0714(5) Uani 1.000000 .
O002 O -0.60611(16) -0.62721(12) -0.19042(13) 0.0710(5) Uani 1.000000 .
H002 H -0.577(2) -0.5708(10) -0.181(2) 0.1064(7) Uiso 1.000000 GR
O003 O -0.12206(18) -0.67557(13) -0.06831(14) 0.0769(5) Uani 1.000000 .
C004 C -0.40277(18) -0.72145(15) -0.21141(14) 0.0482(4) Uani 1.000000 .
C005 C -0.39370(19) -0.82444(14) -0.22711(14) 0.0496(4) Uani 1.000000 .
C006 C -0.3090(2) -0.67275(16) -0.15931(15) 0.0548(5) Uani 1.000000 .
H006 H -0.3139(2) -0.60384(16) -0.15017(15) 0.0658(6) Uiso 1.000000 R
C007 C -0.5060(2) -0.85769(15) -0.28259(14) 0.0535(5) Uani 1.000000 .
C008 C -0.59150(19) -0.76895(15) -0.29624(15) 0.0521(5) Uani 1.000000 .
C009 C -0.9242(2) -0.69564(17) -0.37817(15) 0.0536(5) Uani 1.000000 .
C00A C -1.0059(2) -0.60434(16) -0.36857(15) 0.0543(5) Uani 1.000000 .
C00B C -0.2075(2) -0.72795(17) -0.12076(15) 0.0562(5) Uani 1.000000 .
C00C C -0.1981(2) -0.83125(17) -0.13654(17) 0.0597(5) Uani 1.000000 .
H00C H -0.1294(2) -0.86760(17) -0.11069(17) 0.0716(6) Uiso 1.000000 R
C00D C -0.5244(2) -0.67713(15) -0.25517(16) 0.0524(5) Uani 1.000000 .
H00D H -0.4993(2) -0.63073(15) -0.30454(16) 0.0628(6) Uiso 1.000000 R
C00E C -0.7104(2) -0.77591(16) -0.33551(16) 0.0568(5) Uani 1.000000 .
H00E H -0.7359(2) -0.83785(16) -0.35886(16) 0.0681(6) Uiso 1.000000 R
C00F C -0.9878(2) -0.78466(16) -0.41976(14) 0.0534(5) Uani 1.000000 .
C00G C -0.2902(2) -0.87911(16) -0.19024(16) 0.0582(5) Uani 1.000000 .
H00G H -0.2832(2) -0.94749(16) -0.20175(16) 0.0698(6) Uiso 1.000000 R
C00H C -0.8009(2) -0.69339(17) -0.34379(17) 0.0591(5) Uani 1.000000 .
H00H H -0.7711(2) -0.63145(17) -0.32307(17) 0.0709(6) Uiso 1.000000 R
C00I C -1.1174(2) -0.80739(18) -0.39417(17) 0.0622(6) Uani 1.000000 .
H00I H -1.1623(2) -0.76499(18) -0.35415(17) 0.0746(7) Uiso 1.000000 R
C00J C -1.0774(2) -0.56677(19) -0.44168(17) 0.0651(6) Uani 1.000000 .
H00J H -1.0735(2) -0.59858(19) -0.49871(17) 0.0781(7) Uiso 1.000000 R
C00K C -0.9248(2) -0.84752(18) -0.48205(16) 0.0631(6) Uani 1.000000 .
H00K H -0.8405(2) -0.83239(18) -0.50218(16) 0.0757(7) Uiso 1.000000 R
C00L C -1.1550(3) -0.4821(2) -0.4311(2) 0.0773(7) Uani 1.000000 .
H00L H -1.2022(3) -0.4572(2) -0.4810(2) 0.0927(9) Uiso 1.000000 R
C00M C -1.1789(3) -0.8921(2) -0.42786(19) 0.0752(7) Uani 1.000000 .
H00M H -1.2647(3) -0.9065(2) -0.41045(19) 0.0902(8) Uiso 1.000000 R
C00N C -1.0133(3) -0.5542(2) -0.28333(18) 0.0696(6) Uani 1.000000 .
H00N H -0.9656(3) -0.5774(2) -0.23300(18) 0.0835(7) Uiso 1.000000 R
C00O C -1.1623(3) -0.4351(2) -0.3471(2) 0.0848(8) Uani 1.000000 .
H00O H -1.2155(3) -0.3791(2) -0.3396(2) 0.1017(10) Uiso 1.000000 R
C00P C -1.1132(3) -0.9551(2) -0.4873(2) 0.0832(8) Uani 1.000000 .
H00P H -1.1539(3) -1.0128(2) -0.5091(2) 0.0998(10) Uiso 1.000000 R
C00Q C -0.9876(3) -0.9326(2) -0.51415(19) 0.0760(7) Uani 1.000000 .
H00Q H -0.9439(3) -0.9752(2) -0.55461(19) 0.0912(9) Uiso 1.000000 R
C00R C -1.0912(3) -0.4709(2) -0.2748(2) 0.0877(9) Uani 1.000000 .
H00R H -1.0955(3) -0.4382(2) -0.2182(2) 0.1052(10) Uiso 1.000000 R
C00S C -0.0208(4) -0.7278(2) -0.0209(3) 0.1113(13) Uani 1.000000 .
H00a H 0.0399(17) -0.755(2) -0.0648(3) 0.167(2) Uiso 1.000000 GR
H00b H 0.024(2) -0.6823(6) 0.0194(17) 0.167(2) Uiso 1.000000 GR
H00f H -0.0585(4) -0.7811(16) 0.0148(18) 0.167(2) 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
O001 C007 1.230(3) . ?
O002 H002 0.8200 . ?
O002 C00D 1.420(3) . ?
O003 C00B 1.351(3) . ?
O003 C00S 1.422(3) . ?
C004 C005 1.395(3) . ?
C004 C006 1.380(3) . ?
C004 C00D 1.512(3) . ?
C005 C007 1.467(3) . ?
C005 C00G 1.389(3) . ?
C006 H006 0.9300 . ?
C006 C00B 1.387(3) . ?
C007 C008 1.483(3) . ?
C008 C00D 1.524(3) . ?
C008 C00E 1.342(3) . ?
C009 C00A 1.482(3) . ?
C009 C00F 1.481(3) . ?
C009 C00H 1.351(3) . ?
C00A C00J 1.380(3) . ?
C00A C00N 1.407(3) . ?
C00B C00C 1.400(3) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.376(3) . ?
C00D H00D 0.9800 . ?
C00E H00E 0.9300 . ?
C00E C00H 1.441(3) . ?
C00F C00I 1.405(3) . ?
C00F C00K 1.389(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.381(3) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.387(4) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.383(3) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.371(4) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.377(4) . ?
C00N H00N 0.9300 . ?
C00N C00R 1.370(4) . ?
C00O H00O 0.9300 . ?
C00O C00R 1.361(4) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.371(5) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00a 0.9600 . ?
C00S H00b 0.9600 . ?
C00S H00f 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
C00D O002 H002 109.5 . . ?
C00S O003 C00B 119.1(2) . . ?
C006 C004 C005 120.44(18) . . ?
C00D C004 C005 111.76(17) . . ?
C00D C004 C006 127.78(18) . . ?
C007 C005 C004 109.59(18) . . ?
C00G C005 C004 120.28(19) . . ?
C00G C005 C007 130.11(19) . . ?
H006 C006 C004 120.43(12) . . ?
C00B C006 C004 119.13(19) . . ?
C00B C006 H006 120.43(13) . . ?
C005 C007 O001 127.6(2) . . ?
C008 C007 O001 125.51(19) . . ?
C008 C007 C005 106.87(17) . . ?
C00D C008 C007 109.00(16) . . ?
C00E C008 C007 122.1(2) . . ?
C00E C008 C00D 128.80(19) . . ?
C00F C009 C00A 116.80(17) . . ?
C00H C009 C00A 118.0(2) . . ?
C00H C009 C00F 125.1(2) . . ?
C00J C00A C009 121.5(2) . . ?
C00N C00A C009 120.2(2) . . ?
C00N C00A C00J 118.2(2) . . ?
C006 C00B O003 115.7(2) . . ?
C00C C00B O003 123.8(2) . . ?
C00C C00B C006 120.5(2) . . ?
H00C C00C C00B 119.94(12) . . ?
C00G C00C C00B 120.1(2) . . ?
C00G C00C H00C 119.94(13) . . ?
C004 C00D O002 112.74(18) . . ?
C008 C00D O002 111.82(16) . . ?
C008 C00D C004 102.56(15) . . ?
H00D C00D O002 109.84(11) . . ?
H00D C00D C004 109.84(11) . . ?
H00D C00D C008 109.84(11) . . ?
H00E C00E C008 117.95(14) . . ?
C00H C00E C008 124.1(2) . . ?
C00H C00E H00E 117.95(13) . . ?
C00I C00F C009 118.5(2) . . ?
C00K C00F C009 123.12(19) . . ?
C00K C00F C00I 118.4(2) . . ?
C00C C00G C005 119.47(19) . . ?
H00G C00G C005 120.27(12) . . ?
H00G C00G C00C 120.27(13) . . ?
C00E C00H C009 127.5(2) . . ?
H00H C00H C009 116.25(14) . . ?
H00H C00H C00E 116.25(12) . . ?
H00I C00I C00F 119.67(14) . . ?
C00M C00I C00F 120.7(2) . . ?
C00M C00I H00I 119.67(16) . . ?
H00J C00J C00A 119.62(14) . . ?
C00L C00J C00A 120.8(2) . . ?
C00L C00J H00J 119.62(17) . . ?
H00K C00K C00F 119.98(13) . . ?
C00Q C00K C00F 120.0(2) . . ?
C00Q C00K H00K 119.98(16) . . ?
H00L C00L C00J 119.95(17) . . ?
C00O C00L C00J 120.1(3) . . ?
C00O C00L H00L 119.95(17) . . ?
H00M C00M C00I 120.02(16) . . ?
C00P C00M C00I 120.0(3) . . ?
C00P C00M H00M 120.02(17) . . ?
H00N C00N C00A 120.13(14) . . ?
C00R C00N C00A 119.7(3) . . ?
C00R C00N H00N 120.13(18) . . ?
H00O C00O C00L 120.18(17) . . ?
C00R C00O C00L 119.6(3) . . ?
C00R C00O H00O 120.18(17) . . ?
H00P C00P C00M 120.06(17) . . ?
C00Q C00P C00M 119.9(3) . . ?
C00Q C00P H00P 120.06(18) . . ?
C00P C00Q C00K 121.0(3) . . ?
H00Q C00Q C00K 119.48(16) . . ?
H00Q C00Q C00P 119.48(18) . . ?
C00O C00R C00N 121.5(3) . . ?
H00R C00R C00N 119.23(18) . . ?
H00R C00R C00O 119.23(17) . . ?
H00a C00S O003 109.5 . . ?
H00b C00S O003 109.5 . . ?
H00b C00S H00a 109.5 . . ?
H00f C00S O003 109.5 . . ?
H00f C00S H00a 109.5 . . ?
H00f C00S H00b 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
;
