# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_anisole_new
_database_code_depnum_ccdc_archive 'CCDC 1875315'
loop_
_audit_author_name
_audit_author_address
'Michael Probert'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2018-10-25 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        methoxybenzene
_chemical_formula_moiety         'C7 H8 O'
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   13.700(4)
_cell_length_b                   5.4468(8)
_cell_length_c                   7.8567(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.401(18)
_cell_angle_gamma                90
_cell_volume                     580.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    986
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.53
_cell_measurement_theta_min      3.60
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.8456.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_preparation       
'Crystal grown inside diamond anvil cell at high pressure'
_exptl_crystal_recrystallization_method 
'Crystal grown inside diamond anvil cell at high pressure'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.392
_diffrn_reflns_Laue_measured_fraction_max 0.392
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2664
_diffrn_reflns_point_group_measured_fraction_full 0.392
_diffrn_reflns_point_group_measured_fraction_max 0.392
_diffrn_reflns_theta_full        18.131
_diffrn_reflns_theta_max         18.131
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.392
_diffrn_measured_fraction_theta_max 0.392
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   'Bruker TXS with Helios Optics'
_diffrn_special_details          
;
Sample grown in a diamond anvil cell from
the pure liquid
;
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                231
_reflns_number_total             326
_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       'SAINT V8.38A (Bruker AXS Inc, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.088
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         326
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.048
_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)+(0.0223P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0898
_refine_special_details          
;
Rigu instruction maintained throughout due
to low completeness imposed by diamond
anvil cell collection
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6), C4(H4), C7(H7)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.8907(7) 0.4839(7) 0.5559(5) 0.066(3) Uani 1 1 d . U . . .
C5 C 0.6678(9) 0.6932(11) 0.3119(7) 0.063(4) Uani 1 1 d . U . . .
H5 H 0.649412 0.820780 0.235215 0.075 Uiso 1 1 calc R . . . .
C8 C 0.7250(9) 0.3077(10) 0.5275(7) 0.058(4) Uani 1 1 d . U . . .
H8 H 0.744859 0.177237 0.600766 0.069 Uiso 1 1 calc R . . . .
C6 C 0.5950(7) 0.5201(8) 0.3466(5) 0.066(3) Uani 1 1 d . U . . .
H6 H 0.528801 0.534478 0.300205 0.079 Uiso 1 1 calc R . . . .
C1 C 0.9313(8) 0.2770(9) 0.6506(6) 0.085(4) Uani 1 1 d . U . . .
H1A H 0.916301 0.130993 0.583369 0.127 Uiso 1 1 calc GR . . . .
H1B H 0.903464 0.264265 0.755560 0.127 Uiso 1 1 calc GR . . . .
H1C H 1.001544 0.295576 0.677013 0.127 Uiso 1 1 calc GR . . . .
C4 C 0.7587(9) 0.6776(10) 0.3843(6) 0.059(4) Uani 1 1 d . U . . .
H4 H 0.802287 0.801075 0.363207 0.071 Uiso 1 1 calc R . . . .
C3 C 0.7943(9) 0.4854(10) 0.4919(6) 0.054(4) Uani 1 1 d . U . . .
C7 C 0.6307(9) 0.3281(9) 0.4551(6) 0.061(4) Uani 1 1 d . U . . .
H7 H 0.586533 0.207375 0.478677 0.073 Uiso 1 1 calc R . . . .

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
O2 0.085(11) 0.055(2) 0.058(2) 0.0120(17) 0.009(3) 0.002(4)
C5 0.104(12) 0.046(3) 0.039(3) 0.006(3) 0.013(4) 0.005(5)
C8 0.094(12) 0.047(3) 0.034(3) 0.006(2) 0.018(4) 0.000(5)
C6 0.100(12) 0.056(3) 0.043(2) -0.003(2) 0.011(4) 0.002(4)
C1 0.126(15) 0.074(4) 0.052(3) 0.015(2) 0.008(5) 0.016(5)
C4 0.099(12) 0.040(3) 0.040(3) 0.002(2) 0.013(4) -0.008(5)
C3 0.085(11) 0.048(3) 0.033(3) 0.002(2) 0.021(4) 0.009(4)
C7 0.098(12) 0.042(3) 0.044(3) 0.000(2) 0.016(4) -0.005(5)

_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
O2 C1 1.419(8) . ?
O2 C3 1.343(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.428(12) . ?
C5 C4 1.294(16) . ?
C8 H8 0.9300 . ?
C8 C3 1.411(15) . ?
C8 C7 1.339(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.389(10) . ?
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
C3 O2 C1 119.3(7) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(6) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C3 119.6(7) . . ?
C5 C6 H6 122.6 . . ?
C7 C6 C5 114.9(9) . . ?
C7 C6 H6 122.6 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C4 H4 118.4 . . ?
C5 C4 C3 123.1(10) . . ?
C3 C4 H4 118.4 . . ?
O2 C3 C8 125.1(7) . . ?
O2 C3 C4 118.1(9) . . ?
C4 C3 C8 116.8(11) . . ?
C8 C7 C6 123.6(8) . . ?
C8 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?

_iucr_refine_instructions_details 
;
TITL test_a.res in P2(1)/c
    anisole_new.res
    created by SHELXL-2016/6 at 12:32:23 on 24-Oct-2018
REM Old TITL test in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.253, Rweak 0.011, Alpha 0.062, Orientation as input
REM Formula found by SHELXT: C12
CELL 0.56086 13.6995 5.4468 7.8567 90 98.401 90
ZERR 4 0.0037 0.0008 0.0011 0 0.018 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 28 32 4
RIGU

L.S. 4
PLAN  3
SIZE 0.1 0.25 0.25
TEMP 23
BOND $H
list 4
fmap 2
acta
more -3
OMIT -6 1 3
OMIT -8 0 6
OMIT -4 2 1
OMIT -4 1 2
OMIT -8 1 5
OMIT -6 1 4
REM <olex2.extras>
REM <HklSrc "%./anisole_new_0m.hkl">
REM </olex2.extras>

WGHT    0.022300    0.450500
FVAR       1.32088
O2    3    0.890665    0.483916    0.555874    11.00000    0.08505    0.05524 =
         0.05799    0.01204    0.00909    0.00214
C5    1    0.667817    0.693250    0.311923    11.00000    0.10386    0.04584 =
         0.03925    0.00587    0.01281    0.00451
AFIX  43
H5    2    0.649412    0.820780    0.235215    11.00000   -1.20000
AFIX   0
C8    1    0.725036    0.307733    0.527468    11.00000    0.09446    0.04727 =
         0.03415    0.00580    0.01834    0.00040
AFIX  43
H8    2    0.744859    0.177237    0.600766    11.00000   -1.20000
AFIX   0
C6    1    0.595004    0.520104    0.346588    11.00000    0.09983    0.05570 =
         0.04269   -0.00270    0.01081    0.00206
AFIX  43
H6    2    0.528801    0.534478    0.300205    11.00000   -1.20000
AFIX   0
C1    1    0.931278    0.276953    0.650614    11.00000    0.12638    0.07409 =
         0.05171    0.01481    0.00758    0.01585
AFIX 137
H1A   2    0.916301    0.130993    0.583369    11.00000   -1.50000
H1B   2    0.903464    0.264265    0.755560    11.00000   -1.50000
H1C   2    1.001544    0.295576    0.677013    11.00000   -1.50000
AFIX   0
C4    1    0.758695    0.677643    0.384270    11.00000    0.09925    0.03962 =
         0.03987    0.00187    0.01258   -0.00813
AFIX  43
H4    2    0.802287    0.801075    0.363207    11.00000   -1.20000
AFIX   0
C3    1    0.794274    0.485360    0.491897    11.00000    0.08471    0.04759 =
         0.03319    0.00160    0.02077    0.00936
C7    1    0.630675    0.328090    0.455136    11.00000    0.09758    0.04205 =
         0.04447    0.00030    0.01628   -0.00535
AFIX  43
H7    2    0.586533    0.207375    0.478677    11.00000   -1.20000
AFIX   0
HKLF 4




REM  test_a.res in P2(1)/c
REM R1 =  0.0362 for     231 Fo > 4sig(Fo)  and  0.0616 for all     326 data
REM     74 parameters refined using     51 restraints

END  
     
WGHT      0.0223      0.4505 

REM Highest difference peak  0.094,  deepest hole -0.088,  1-sigma level  0.025
Q1    1   0.6578  1.0515  0.3436  11.00000  0.05    0.09
Q2    1   0.9403  0.0723  0.5669  11.00000  0.05    0.09
Q3    1   0.8542  0.8681  0.4030  11.00000  0.05    0.08

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0362 for 231 Fo > 4sig(Fo) and 0.0616 for all 2878 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.09, deepest hole -0.09
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0616
  REM R1_gt = 0.0362
  REM wR_ref = 0.0898
  REM GOOF = 1.133
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2878
  REM Reflections_gt = 231
  REM Parameters = n/a
  REM Hole = -0.09
  REM Peak = 0.09
  REM Flack = n/a

  
;
_olex2_exptl_crystal_mounting_method 
;
Crystal mounted onto diffractometer using
custom grip for diamond anvil cell into standard
goniometer head
;
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_anisole_new         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.392 Why?  
RESPONSE: data collection limited in coverage due to collection
within a diamond anvil cell at high pressure
;
_vrf_PLAT088_anisole_new         
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.41 Note  
RESPONSE: data collection limited in coverage due to collection
within a diamond anvil cell at high pressure
;
_vrf_PLAT340_anisole_new         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: limited angular resolution of data available due to diamond
anvil cell contraints and small organic sample measured at room temperature
;
_vrf_PLAT911_anisole_new         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        279 Report
RESPONSE: data collection limited in coverage due to collection
within a diamond anvil cell at high pressure
;
_vrf_REFNR01_anisole_new         
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: data collection limited in coverage due to collection
within a diamond anvil cell at high pressure
;
_vrf_THETM01_anisole_new         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: data collection limited in coverage due to collection
within a diamond anvil cell at high pressure
;
####################################################################### 
# 
# 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_anisole_lt
_database_code_depnum_ccdc_archive 'CCDC 1875316'
loop_
_audit_author_name
_audit_author_address
'Michael Probert'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2018-10-25 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        methoxybenzene
_chemical_formula_moiety         'C7 H8 O'
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13
_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'
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/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                   13.6132(7)
_cell_length_b                   14.5917(8)
_cell_length_c                   6.2617(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.935(2)
_cell_angle_gamma                90
_cell_volume                     1237.16(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    224.0
_cell_measurement_theta_max      66.75
_cell_measurement_theta_min      4.45
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.1300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1733 before and 0.1013 after correction.
The Ratio of minimum to maximum transmission is 0.1727.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
_exptl_crystal_preparation       
;
Crystal grown inside capillary in-situ on
diffractmeter through cryogenic control
;
_exptl_crystal_recrystallization_method 
'Grown from pure liquid at low temperature'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17860
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        66.741
_diffrn_reflns_theta_max         66.741
_diffrn_reflns_theta_min         3.264
_diffrn_ambient_temperature      224.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_collimation    'focussed source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Bruker TXS with Helios Optics'
_diffrn_source_type              
;
'Incoatec microfocus 3.0 (Cu) X-ray Source'
;
_diffrn_special_details          
;
Crystal grown at low temperature 
from pure liquid
;
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1896
_reflns_number_total             2126
_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       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.103
_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)+(0.0929P)²+0.1289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C8'(H8'), C4'(H4'), C4(H4), C7(H7), C5(H5), C6(H6), C7'(H7'),
 C5'(H5'), C6'(H6')
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1'(H1'A,H1'B,H1'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2' O 0.64480(7) 0.63748(6) 0.63317(15) 0.0521(3) Uani 1 1 d . . . . .
O2 O 0.14199(7) 0.62505(6) 0.65050(15) 0.0537(3) Uani 1 1 d . . . . .
C3' C 0.74049(9) 0.62697(7) 0.72066(19) 0.0407(3) Uani 1 1 d . . . . .
C3 C 0.23959(9) 0.62566(7) 0.7296(2) 0.0416(3) Uani 1 1 d . . . . .
C8 C 0.31279(10) 0.67329(8) 0.6380(2) 0.0463(4) Uani 1 1 d . . . . .
H8 H 0.297186 0.708560 0.513500 0.056 Uiso 1 1 calc R . . . .
C8' C 0.81162(10) 0.57792(8) 0.6256(2) 0.0484(4) Uani 1 1 d . . . . .
H8' H 0.795975 0.548789 0.492550 0.058 Uiso 1 1 calc R . . . .
C4' C 0.76447(10) 0.66997(8) 0.9161(2) 0.0453(3) Uani 1 1 d . . . . .
H4' H 0.716078 0.703150 0.980121 0.054 Uiso 1 1 calc R . . . .
C4 C 0.26334(10) 0.57417(8) 0.9139(2) 0.0485(4) Uani 1 1 d . . . . .
H4 H 0.213659 0.542183 0.976507 0.058 Uiso 1 1 calc R . . . .
C7 C 0.40946(10) 0.66816(9) 0.7328(2) 0.0513(4) Uani 1 1 d . . . . .
H7 H 0.459311 0.700565 0.671778 0.062 Uiso 1 1 calc R . . . .
C5 C 0.35986(11) 0.56991(9) 1.0054(2) 0.0549(4) Uani 1 1 d . . . . .
H5 H 0.375748 0.535108 1.130504 0.066 Uiso 1 1 calc R . . . .
C6 C 0.43346(11) 0.61665(10) 0.9137(2) 0.0550(4) Uani 1 1 d . . . . .
H6 H 0.499348 0.613092 0.975114 0.066 Uiso 1 1 calc R . . . .
C7' C 0.90651(10) 0.57266(9) 0.7308(2) 0.0562(4) Uani 1 1 d . . . . .
H7' H 0.955034 0.539180 0.668015 0.067 Uiso 1 1 calc R . . . .
C5' C 0.85922(11) 0.66424(9) 1.0173(2) 0.0535(4) Uani 1 1 d . . . . .
H5' H 0.875328 0.693670 1.149797 0.064 Uiso 1 1 calc R . . . .
C6' C 0.93077(11) 0.61510(10) 0.9236(3) 0.0577(4) Uani 1 1 d . . . . .
H6' H 0.995387 0.611043 0.992165 0.069 Uiso 1 1 calc R . . . .
C1 C 0.11449(11) 0.67573(12) 0.4604(2) 0.0649(5) Uani 1 1 d . . . . .
H1A H 0.148493 0.651307 0.344144 0.097 Uiso 1 1 calc GR . . . .
H1B H 0.132471 0.739540 0.483779 0.097 Uiso 1 1 calc GR . . . .
H1C H 0.043713 0.670996 0.423306 0.097 Uiso 1 1 calc GR . . . .
C1' C 0.61637(11) 0.59410(13) 0.4330(2) 0.0668(5) Uani 1 1 d . . . . .
H1'A H 0.654822 0.618978 0.324497 0.100 Uiso 1 1 calc GR . . . .
H1'B H 0.546734 0.605016 0.391326 0.100 Uiso 1 1 calc GR . . . .
H1'C H 0.628150 0.528692 0.446566 0.100 Uiso 1 1 calc GR . . . .

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
O2' 0.0470(6) 0.0572(6) 0.0503(6) -0.0064(4) -0.0028(4) 0.0020(4)
O2 0.0435(6) 0.0541(6) 0.0619(6) 0.0064(4) -0.0017(4) -0.0002(4)
C3' 0.0443(7) 0.0341(6) 0.0433(7) 0.0025(5) 0.0026(5) -0.0034(5)
C3 0.0425(7) 0.0348(6) 0.0470(7) -0.0030(5) 0.0011(5) 0.0027(5)
C8 0.0500(8) 0.0401(7) 0.0486(7) 0.0054(5) 0.0041(6) 0.0026(5)
C8' 0.0546(8) 0.0408(7) 0.0504(7) -0.0056(5) 0.0085(6) -0.0027(5)
C4' 0.0514(7) 0.0367(7) 0.0475(7) -0.0032(5) 0.0038(5) 0.0006(5)
C4 0.0557(8) 0.0391(7) 0.0511(8) 0.0036(5) 0.0067(6) 0.0000(5)
C7 0.0462(8) 0.0445(8) 0.0631(8) 0.0013(6) 0.0059(6) -0.0006(5)
C5 0.0650(9) 0.0478(8) 0.0496(8) 0.0074(6) -0.0045(6) 0.0063(6)
C6 0.0485(8) 0.0508(8) 0.0629(9) -0.0031(6) -0.0075(6) 0.0058(6)
C7' 0.0489(8) 0.0475(8) 0.0733(9) -0.0030(6) 0.0117(7) 0.0028(6)
C5' 0.0594(8) 0.0462(8) 0.0522(8) -0.0042(5) -0.0063(6) -0.0043(6)
C6' 0.0459(8) 0.0517(8) 0.0731(10) 0.0007(7) -0.0050(7) -0.0018(6)
C1 0.0545(9) 0.0681(10) 0.0679(10) 0.0110(7) -0.0144(7) 0.0037(7)
C1' 0.0587(9) 0.0859(12) 0.0526(8) -0.0123(7) -0.0096(7) -0.0045(8)

_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
O2' C3' 1.3685(15) . ?
O2' C1' 1.4218(16) . ?
O2 C3 1.3691(15) . ?
O2 C1 1.4183(17) . ?
C3' C8' 1.3868(18) . ?
C3' C4' 1.3841(17) . ?
C3 C8 1.3869(18) . ?
C3 C4 1.3869(18) . ?
C8 H8 0.9400 . ?
C8 C7 1.3885(18) . ?
C8' H8' 0.9400 . ?
C8' C7' 1.3901(19) . ?
C4' H4' 0.9400 . ?
C4' C5' 1.3793(19) . ?
C4 H4 0.9400 . ?
C4 C5 1.3794(19) . ?
C7 H7 0.9400 . ?
C7 C6 1.3707(19) . ?
C5 H5 0.9400 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9400 . ?
C7' H7' 0.9400 . ?
C7' C6' 1.366(2) . ?
C5' H5' 0.9400 . ?
C5' C6' 1.387(2) . ?
C6' H6' 0.9400 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' H1'C 0.9700 . ?

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
C3' O2' C1' 117.65(11) . . ?
C3 O2 C1 117.53(11) . . ?
O2' C3' C8' 124.33(12) . . ?
O2' C3' C4' 115.53(11) . . ?
C4' C3' C8' 120.14(12) . . ?
O2 C3 C8 124.44(12) . . ?
O2 C3 C4 115.57(11) . . ?
C8 C3 C4 120.00(12) . . ?
C3 C8 H8 120.5 . . ?
C3 C8 C7 119.08(12) . . ?
C7 C8 H8 120.5 . . ?
C3' C8' H8' 120.6 . . ?
C3' C8' C7' 118.74(13) . . ?
C7' C8' H8' 120.6 . . ?
C3' C4' H4' 119.9 . . ?
C5' C4' C3' 120.16(12) . . ?
C5' C4' H4' 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.99(12) . . ?
C5 C4 H4 120.0 . . ?
C8 C7 H7 119.4 . . ?
C6 C7 C8 121.14(13) . . ?
C6 C7 H7 119.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.32(12) . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.46(13) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8' C7' H7' 119.3 . . ?
C6' C7' C8' 121.44(13) . . ?
C6' C7' H7' 119.3 . . ?
C4' C5' H5' 120.0 . . ?
C4' C5' C6' 120.08(13) . . ?
C6' C5' H5' 120.0 . . ?
C7' C6' C5' 119.44(13) . . ?
C7' C6' H6' 120.3 . . ?
C5' C6' H6' 120.3 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2' C1' H1'A 109.5 . . ?
O2' C1' H1'B 109.5 . . ?
O2' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?

_iucr_refine_instructions_details 
;
TITL anisole_lt_a.res in P2(1)/c
    anisole_lt.res
    created by SHELXL-2016/6 at 12:32:44 on 24-Oct-2018
REM Old TITL anisole_lt in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.151, Rweak 0.009, Alpha 0.054, Orientation as input
REM Formula found by SHELXT: C14 O2
CELL 1.54178 13.6132 14.5917 6.2617 90 95.935 90
ZERR 8 0.0007 0.0008 0.0003 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 56 64 8

L.S. 4
PLAN  20
SIZE 0.1 0.08 0.07
TEMP -49.15
BOND $H
list 4
fmap 2
acta
more -3
OMIT 7 10 2
OMIT -6 0 4
OMIT 1 7 6
OMIT 4 15 1
REM <olex2.extras>
REM <HklSrc "%./anisole_lt.hkl">
REM </olex2.extras>

WGHT    0.092900    0.128900
FVAR       1.57191
O2'   3    0.644800    0.637482    0.633166    11.00000    0.04701    0.05719 =
         0.05033   -0.00639   -0.00282    0.00200
O2    3    0.141990    0.625048    0.650499    11.00000    0.04350    0.05412 =
         0.06190    0.00636   -0.00171   -0.00022
C3'   1    0.740486    0.626966    0.720660    11.00000    0.04435    0.03408 =
         0.04332    0.00245    0.00261   -0.00342
C3    1    0.239587    0.625656    0.729612    11.00000    0.04249    0.03478 =
         0.04695   -0.00300    0.00111    0.00271
C8    1    0.312794    0.673290    0.638010    11.00000    0.05004    0.04009 =
         0.04857    0.00540    0.00413    0.00259
AFIX  43
H8    2    0.297186    0.708560    0.513500    11.00000   -1.20000
AFIX   0

C8'   1    0.811623    0.577923    0.625611    11.00000    0.05462    0.04076 =
         0.05036   -0.00564    0.00852   -0.00273
AFIX  43
H8'   2    0.795975    0.548789    0.492550    11.00000   -1.20000
AFIX   0
C4'   1    0.764472    0.669967    0.916133    11.00000    0.05139    0.03672 =
         0.04750   -0.00315    0.00381    0.00059
AFIX  43
H4'   2    0.716078    0.703150    0.980121    11.00000   -1.20000
AFIX   0

C4    1    0.263336    0.574172    0.913918    11.00000    0.05568    0.03910 =
         0.05111    0.00357    0.00674    0.00001
AFIX  43
H4    2    0.213659    0.542183    0.976507    11.00000   -1.20000
AFIX   0
C7    1    0.409463    0.668157    0.732775    11.00000    0.04621    0.04450 =
         0.06311    0.00127    0.00592   -0.00056
AFIX  43
H7    2    0.459311    0.700565    0.671778    11.00000   -1.20000
AFIX   0
C5    1    0.359861    0.569911    1.005369    11.00000    0.06501    0.04776 =
         0.04963    0.00744   -0.00450    0.00628
AFIX  43
H5    2    0.375748    0.535108    1.130504    11.00000   -1.20000
AFIX   0
C6    1    0.433462    0.616652    0.913733    11.00000    0.04851    0.05083 =
         0.06287   -0.00307   -0.00753    0.00583
AFIX  43
H6    2    0.499348    0.613092    0.975114    11.00000   -1.20000
AFIX   0

C7'   1    0.906507    0.572663    0.730838    11.00000    0.04888    0.04745 =
         0.07334   -0.00300    0.01170    0.00285
AFIX  43
H7'   2    0.955034    0.539180    0.668015    11.00000   -1.20000
AFIX   0
C5'   1    0.859217    0.664243    1.017259    11.00000    0.05944    0.04617 =
         0.05222   -0.00425   -0.00630   -0.00426
AFIX  43
H5'   2    0.875328    0.693670    1.149797    11.00000   -1.20000
AFIX   0
C6'   1    0.930767    0.615104    0.923595    11.00000    0.04594    0.05165 =
         0.07307    0.00068   -0.00497   -0.00179
AFIX  43
H6'   2    0.995387    0.611043    0.992165    11.00000   -1.20000
AFIX   0

C1    1    0.114494    0.675728    0.460411    11.00000    0.05451    0.06808 =
         0.06790    0.01098   -0.01437    0.00370
AFIX 137
H1A   2    0.148493    0.651307    0.344144    11.00000   -1.50000
H1B   2    0.132471    0.739540    0.483779    11.00000   -1.50000
H1C   2    0.043713    0.670996    0.423306    11.00000   -1.50000
AFIX   0

C1'   1    0.616368    0.594095    0.432987    11.00000    0.05871    0.08591 =
         0.05265   -0.01228   -0.00963   -0.00453
AFIX 137
H1'A  2    0.654822    0.618978    0.324497    11.00000   -1.50000
H1'B  2    0.546734    0.605016    0.391326    11.00000   -1.50000
H1'C  2    0.628150    0.528692    0.446566    11.00000   -1.50000
AFIX   0
HKLF 4




REM  anisole_lt_a.res in P2(1)/c
REM R1 =  0.0511 for    1896 Fo > 4sig(Fo)  and  0.0544 for all    2126 data
REM    147 parameters refined using      0 restraints

END  
     
WGHT      0.0929      0.1289 

REM Highest difference peak  0.172,  deepest hole -0.201,  1-sigma level  0.042
Q1    1   0.4234  0.5615  1.1877  11.00000  0.05    0.17
Q2    1   0.9241  0.6825  1.1843  11.00000  0.05    0.15
Q3    1   0.6183  0.7003  0.6150  11.00000  0.05    0.14
Q4    1   0.7883  0.5838  0.4573  11.00000  0.05    0.14
Q5    1   0.0684  0.6722  0.3150  11.00000  0.05    0.13
Q6    1   0.7376  0.6190  0.8634  11.00000  0.05    0.13
Q7    1   0.2345  0.6246  0.8588  11.00000  0.05    0.13
Q8    1   0.3626  0.6355  0.6395  11.00000  0.05    0.13
Q9    1   0.7728  0.6749  0.7633  11.00000  0.05    0.13
Q10   1   0.7243  0.5433  0.8168  11.00000  0.05    0.12
Q11   1   0.8640  0.6111  0.6493  11.00000  0.05    0.12
Q12   1  -0.0109  0.6994  0.2168  11.00000  0.05    0.12
Q13   1   0.1732  0.6627  0.7747  11.00000  0.05    0.12
Q14   1   0.8199  0.6982  0.9168  11.00000  0.05    0.11
Q15   1   0.4114  0.6079  0.7555  11.00000  0.05    0.11
Q16   1   0.7001  0.6794  0.7526  11.00000  0.05    0.11
Q17   1   0.9454  0.6621  0.6537  11.00000  0.05    0.11
Q18   1   0.2846  0.6730  0.7593  11.00000  0.05    0.11
Q19   1   0.6961  0.7017  0.5990  11.00000  0.05    0.11
Q20   1   0.1422  0.6436  0.8078  11.00000  0.05    0.10

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0511 for 1896 Fo > 4sig(Fo) and 0.0544 for all 18231 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.17, deepest hole -0.20
  REM Mean Shift 0, Max Shift -0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0544
  REM R1_gt = 0.0511
  REM wR_ref = 0.1557
  REM GOOF = 1.103
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 18231
  REM Reflections_gt = 1896
  REM Parameters = n/a
  REM Hole = -0.20
  REM Peak = 0.17
  REM Flack = n/a

  
;
_olex2_exptl_crystal_mounting_method Capillary
_olex2_submission_special_instructions 'No special instructions were received'
