# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_an1molt
_database_code_depnum_ccdc_archive 'CCDC 1995829'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2020-04-09 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_audit_creation_date             2015-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        3-Butyl-2-hydroxy-1-naphthaldehyde
_chemical_formula_moiety         'C15 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_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'

_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                   12.3890(5)
_cell_length_b                   12.5456(4)
_cell_length_c                   7.5297(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.928(4)
_cell_angle_gamma                90
_cell_volume                     1152.81(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1886
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5170
_cell_measurement_theta_min      4.2470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4219
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3887 -178.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   19.0000   60.0000 125
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0238325000
_diffrn_orient_matrix_UB_12      0.0462614000
_diffrn_orient_matrix_UB_13      0.0311769000
_diffrn_orient_matrix_UB_21      0.0515934000
_diffrn_orient_matrix_UB_22      0.0145084000
_diffrn_orient_matrix_UB_23      0.0506389000
_diffrn_orient_matrix_UB_31      0.0121657000
_diffrn_orient_matrix_UB_32      0.0290670000
_diffrn_orient_matrix_UB_33      -0.0749190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1680
_reflns_number_total             2233
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.003
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.02198(8) 0.36952(8) 0.17380(14) 0.0204(3) Uani 1 1 d . . . . .
H1 H -0.0323 0.3362 0.1986 0.031 Uiso 1 1 calc GR . . . .
O2 O -0.09269(8) 0.21205(9) 0.23505(14) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.10044(11) 0.30005(12) 0.15002(17) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.08425(11) 0.19016(12) 0.16052(18) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.16957(11) 0.11849(12) 0.12885(18) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.15944(12) 0.00600(12) 0.12649(18) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.0927 -0.0257 0.1452 0.022 Uiso 1 1 calc R . . . .
C5 C 0.24442(12) -0.05771(12) 0.09768(18) 0.0204(4) Uani 1 1 d . . . . .
H5 H 0.2361 -0.1330 0.0979 0.025 Uiso 1 1 calc R . . . .
C6 C 0.34336(12) -0.01326(13) 0.06795(18) 0.0206(4) Uani 1 1 d . . . . .
H6 H 0.4022 -0.0582 0.0496 0.025 Uiso 1 1 calc R . . . .
C7 C 0.35488(12) 0.09470(13) 0.06542(18) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.4217 0.1245 0.0429 0.024 Uiso 1 1 calc R . . . .
C8 C 0.26951(11) 0.16293(12) 0.09557(17) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.28132(11) 0.27579(11) 0.09077(18) 0.0159(3) Uani 1 1 d . . . . .
H9 H 0.3488 0.3042 0.0685 0.019 Uiso 1 1 calc R . . . .
C10 C 0.20090(11) 0.34491(12) 0.11643(18) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.21063(11) 0.46445(12) 0.11141(19) 0.0174(3) Uani 1 1 d . . . . .
H11A H 0.1980 0.4931 0.2286 0.021 Uiso 1 1 calc R . . . .
H11B H 0.1514 0.4920 0.0174 0.021 Uiso 1 1 calc R . . . .
C12 C 0.31871(12) 0.50769(12) 0.07457(18) 0.0165(3) Uani 1 1 d . . . . .
H12A H 0.3322 0.4801 -0.0428 0.020 Uiso 1 1 calc R . . . .
H12B H 0.3786 0.4820 0.1692 0.020 Uiso 1 1 calc R . . . .
C13 C 0.32008(12) 0.62911(12) 0.0708(2) 0.0206(4) Uani 1 1 d . . . . .
H13A H 0.2576 0.6547 -0.0192 0.025 Uiso 1 1 calc R . . . .
H13B H 0.3103 0.6565 0.1903 0.025 Uiso 1 1 calc R . . . .
C14 C 0.42584(12) 0.67377(13) 0.0245(2) 0.0250(4) Uani 1 1 d . . . . .
H14A H 0.4347 0.6490 -0.0956 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.4880 0.6493 0.1138 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.4230 0.7518 0.0253 0.038 Uiso 1 1 calc GR . . . .
C15 C -0.01634(12) 0.15318(13) 0.21166(19) 0.0197(4) Uani 1 1 d . . . . .
H15 H -0.0244 0.0787 0.2285 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3405(16) . ?
O2 C15 1.2365(17) . ?
C1 C2 1.397(2) . ?
C1 C10 1.4277(19) . ?
C2 C3 1.4387(19) . ?
C2 C15 1.4429(18) . ?
C3 C4 1.417(2) . ?
C3 C8 1.4190(19) . ?
C4 C5 1.369(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.362(2) . ?
C7 C8 1.409(2) . ?
C8 C9 1.424(2) . ?
C9 C10 1.3596(19) . ?
C10 C11 1.5055(19) . ?
C11 C12 1.5140(19) . ?
C12 C13 1.5238(19) . ?
C13 C14 1.5199(19) . ?

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
O1 C1 C2 121.30(12) . . ?
O1 C1 C10 116.21(13) . . ?
C2 C1 C10 122.48(13) . . ?
C1 C2 C3 119.37(12) . . ?
C1 C2 C15 118.12(13) . . ?
C3 C2 C15 122.44(13) . . ?
C4 C3 C2 123.96(12) . . ?
C4 C3 C8 117.86(13) . . ?
C8 C3 C2 118.17(13) . . ?
C5 C4 C3 120.98(13) . . ?
C4 C5 C6 120.78(14) . . ?
C7 C6 C5 119.68(14) . . ?
C6 C7 C8 121.22(14) . . ?
C3 C8 C9 119.45(13) . . ?
C7 C8 C3 119.45(14) . . ?
C7 C8 C9 121.10(13) . . ?
C10 C9 C8 123.32(13) . . ?
C1 C10 C11 118.24(12) . . ?
C9 C10 C1 117.15(13) . . ?
C9 C10 C11 124.61(13) . . ?
C10 C11 C12 116.02(12) . . ?
C11 C12 C13 112.00(12) . . ?
C14 C13 C12 112.68(12) . . ?
O2 C15 C2 124.27(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.77 2.5218(14) 148.1 .

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
O1 C1 C2 C3 178.19(11) . . . . ?
O1 C1 C2 C15 -4.7(2) . . . . ?
O1 C1 C10 C9 -179.58(11) . . . . ?
O1 C1 C10 C11 0.29(18) . . . . ?
C1 C2 C3 C4 -176.44(13) . . . . ?
C1 C2 C3 C8 2.70(19) . . . . ?
C1 C2 C15 O2 5.1(2) . . . . ?
C1 C10 C11 C12 -179.77(12) . . . . ?
C2 C1 C10 C9 1.3(2) . . . . ?
C2 C1 C10 C11 -178.80(13) . . . . ?
C2 C3 C4 C5 -179.19(12) . . . . ?
C2 C3 C8 C7 179.53(12) . . . . ?
C2 C3 C8 C9 -1.32(19) . . . . ?
C3 C2 C15 O2 -177.88(13) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C8 C9 C10 -0.1(2) . . . . ?
C4 C3 C8 C7 -1.28(19) . . . . ?
C4 C3 C8 C9 177.87(13) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C6 C7 C8 C9 -179.26(13) . . . . ?
C7 C8 C9 C10 179.04(13) . . . . ?
C8 C3 C4 C5 1.7(2) . . . . ?
C8 C9 C10 C1 0.1(2) . . . . ?
C8 C9 C10 C11 -179.72(13) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C1 C2 C3 -2.8(2) . . . . ?
C10 C1 C2 C15 174.30(12) . . . . ?
C10 C11 C12 C13 179.58(12) . . . . ?
C11 C12 C13 C14 -177.05(12) . . . . ?
C15 C2 C3 C4 6.6(2) . . . . ?
C15 C2 C3 C8 -174.24(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-03
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
####################################################################### 
# 
# 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_an3cult
_database_code_depnum_ccdc_archive 'CCDC 1995830'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2020-04-09 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_audit_creation_date             2016-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        3-Butyl-7-fluoro-2-hydroxy-1-naphthaldehyde
_chemical_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.37471(14)
_cell_length_b                   19.0645(3)
_cell_length_c                   9.32895(18)
_cell_angle_alpha                90
_cell_angle_beta                 111.872(2)
_cell_angle_gamma                90
_cell_volume                     1217.19(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.3120
_cell_measurement_theta_min      5.6040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3701
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.975
_diffrn_reflns_theta_min         4.639
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   33.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  118.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega -108.00    1.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -19.0000 -120.0000 109
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1640809000
_diffrn_orient_matrix_UB_12      0.0335222000
_diffrn_orient_matrix_UB_13      -0.1382161000
_diffrn_orient_matrix_UB_21      0.0801803000
_diffrn_orient_matrix_UB_22      0.0734493000
_diffrn_orient_matrix_UB_23      0.0593051000
_diffrn_orient_matrix_UB_31      0.1315137000
_diffrn_orient_matrix_UB_32      -0.0028893000
_diffrn_orient_matrix_UB_33      -0.0952124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             2115
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0814
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F -0.16156(8) 0.65358(3) 0.07805(6) 0.02227(17) Uani 1 1 d . . . . .
O1 O 0.46619(11) 0.69602(4) 0.76406(8) 0.02256(19) Uani 1 1 d . . . . .
O2 O 0.54644(10) 0.56786(4) 0.83671(8) 0.01974(18) Uani 1 1 d . . . . .
H2 H 0.5513 0.6116 0.8478 0.030 Uiso 1 1 calc GR . . . .
C1 C 0.35080(14) 0.67615(5) 0.63641(11) 0.0180(2) Uani 1 1 d . . . . .
H1 H 0.2814 0.7109 0.5637 0.022 Uiso 1 1 calc R . . . .
C2 C 0.31490(13) 0.60340(5) 0.59091(10) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.41852(14) 0.55157(5) 0.69561(11) 0.0149(2) Uani 1 1 d . . . . .
C4 C 0.39621(14) 0.47868(5) 0.65938(11) 0.0150(2) Uani 1 1 d . . . . .
C5 C 0.26930(14) 0.46083(5) 0.51490(11) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.2536 0.4125 0.4880 0.018 Uiso 1 1 calc R . . . .
C6 C 0.15954(13) 0.51062(5) 0.40276(11) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.03110(14) 0.48834(5) 0.25523(11) 0.0167(2) Uani 1 1 d . . . . .
H7 H 0.0192 0.4397 0.2314 0.020 Uiso 1 1 calc R . . . .
C8 C -0.07661(14) 0.53570(5) 0.14580(11) 0.0175(2) Uani 1 1 d . . . . .
H8 H -0.1626 0.5208 0.0466 0.021 Uiso 1 1 calc R . . . .
C9 C -0.05470(14) 0.60651(5) 0.18613(11) 0.0168(2) Uani 1 1 d . . . . .
C10 C 0.06638(14) 0.63157(5) 0.32647(11) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.0747 0.6805 0.3476 0.019 Uiso 1 1 calc R . . . .
C11 C 0.17908(13) 0.58318(5) 0.43969(10) 0.0140(2) Uani 1 1 d . . . . .
C12 C 0.51298(14) 0.42664(5) 0.78029(11) 0.0166(2) Uani 1 1 d . . . . .
H12A H 0.4785 0.4324 0.8725 0.020 Uiso 1 1 calc R . . . .
H12B H 0.6534 0.4381 0.8113 0.020 Uiso 1 1 calc R . . . .
C13 C 0.48329(14) 0.34994(5) 0.73064(11) 0.0176(2) Uani 1 1 d . . . . .
H13A H 0.3434 0.3378 0.7004 0.021 Uiso 1 1 calc R . . . .
H13B H 0.5186 0.3435 0.6390 0.021 Uiso 1 1 calc R . . . .
C14 C 0.60507(16) 0.30016(6) 0.85768(12) 0.0244(2) Uani 1 1 d . . . . .
H14A H 0.7434 0.3153 0.8962 0.029 Uiso 1 1 calc R . . . .
H14B H 0.5596 0.3025 0.9449 0.029 Uiso 1 1 calc R . . . .
C15 C 0.59117(19) 0.22476(6) 0.80096(16) 0.0341(3) Uani 1 1 d . . . . .
H15A H 0.6450 0.2216 0.7197 0.051 Uiso 1 1 calc GR . . . .
H15B H 0.4540 0.2101 0.7595 0.051 Uiso 1 1 calc GR . . . .
H15C H 0.6656 0.1941 0.8871 0.051 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.3605(11) . ?
O1 C1 1.2372(13) . ?
O2 C3 1.3393(12) . ?
C1 C2 1.4459(14) . ?
C2 C3 1.3993(13) . ?
C2 C11 1.4454(13) . ?
C3 C4 1.4251(14) . ?
C4 C5 1.3670(14) . ?
C4 C12 1.5081(13) . ?
C5 C6 1.4212(14) . ?
C6 C7 1.4144(14) . ?
C6 C11 1.4199(14) . ?
C7 C8 1.3726(14) . ?
C8 C9 1.3946(14) . ?
C9 C10 1.3669(14) . ?
C10 C11 1.4154(13) . ?
C12 C13 1.5249(13) . ?
C13 C14 1.5228(13) . ?
C14 C15 1.5219(16) . ?

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
O1 C1 C2 124.14(9) . . ?
C3 C2 C1 118.67(9) . . ?
C3 C2 C11 119.52(9) . . ?
C11 C2 C1 121.79(9) . . ?
O2 C3 C2 121.60(9) . . ?
O2 C3 C4 115.84(9) . . ?
C2 C3 C4 122.56(9) . . ?
C3 C4 C12 118.74(9) . . ?
C5 C4 C3 116.92(9) . . ?
C5 C4 C12 124.34(9) . . ?
C4 C5 C6 123.54(9) . . ?
C7 C6 C5 120.46(9) . . ?
C7 C6 C11 119.96(9) . . ?
C11 C6 C5 119.58(9) . . ?
C8 C7 C6 121.22(9) . . ?
C7 C8 C9 117.34(9) . . ?
F1 C9 C8 117.49(8) . . ?
F1 C9 C10 118.08(9) . . ?
C10 C9 C8 124.43(9) . . ?
C9 C10 C11 118.65(9) . . ?
C6 C11 C2 117.86(9) . . ?
C10 C11 C2 123.73(9) . . ?
C10 C11 C6 118.40(9) . . ?
C4 C12 C13 115.23(8) . . ?
C14 C13 C12 112.64(8) . . ?
C15 C14 C13 111.97(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 1.80 2.5457(9) 147.6 .

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
F1 C9 C10 C11 -179.70(7) . . . . ?
O1 C1 C2 C3 -1.14(15) . . . . ?
O1 C1 C2 C11 -179.63(9) . . . . ?
O2 C3 C4 C5 -178.74(8) . . . . ?
O2 C3 C4 C12 0.89(13) . . . . ?
C1 C2 C3 O2 1.19(14) . . . . ?
C1 C2 C3 C4 -178.42(8) . . . . ?
C1 C2 C11 C6 177.29(8) . . . . ?
C1 C2 C11 C10 -2.12(14) . . . . ?
C2 C3 C4 C5 0.89(14) . . . . ?
C2 C3 C4 C12 -179.49(8) . . . . ?
C3 C2 C11 C6 -1.18(13) . . . . ?
C3 C2 C11 C10 179.41(8) . . . . ?
C3 C4 C5 C6 -0.81(14) . . . . ?
C3 C4 C12 C13 -178.80(8) . . . . ?
C4 C5 C6 C7 179.86(8) . . . . ?
C4 C5 C6 C11 -0.27(14) . . . . ?
C4 C12 C13 C14 180.00(8) . . . . ?
C5 C4 C12 C13 0.80(14) . . . . ?
C5 C6 C7 C8 179.72(8) . . . . ?
C5 C6 C11 C2 1.27(13) . . . . ?
C5 C6 C11 C10 -179.29(8) . . . . ?
C6 C7 C8 C9 -0.19(14) . . . . ?
C7 C6 C11 C2 -178.86(8) . . . . ?
C7 C6 C11 C10 0.58(13) . . . . ?
C7 C8 C9 F1 -179.86(8) . . . . ?
C7 C8 C9 C10 0.08(15) . . . . ?
C8 C9 C10 C11 0.36(15) . . . . ?
C9 C10 C11 C2 178.73(8) . . . . ?
C9 C10 C11 C6 -0.68(13) . . . . ?
C11 C2 C3 O2 179.71(8) . . . . ?
C11 C2 C3 C4 0.11(14) . . . . ?
C11 C6 C7 C8 -0.14(14) . . . . ?
C12 C4 C5 C6 179.59(8) . . . . ?
C12 C13 C14 C15 -173.71(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-13
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloromethane and hexane'
