# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_diphenylanthracene_TTCE_solvate_0p5_GPa
_database_code_depnum_ccdc_archive 'CCDC 1442973'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
9,10-Diphenylanthracene 1,1,2,2-tetrachloroethane solvate
;
_chemical_formula_moiety         'C26 H18, 2(C2 H2 Cl4)'
_chemical_formula_sum            'C30 H22 Cl8'
_chemical_formula_weight         666.07

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.7874(3)
_cell_length_b                   12.0308(7)
_cell_length_c                   13.8215(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.964(3)
_cell_angle_gamma                90
_cell_volume                     1411.65(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    845
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      16.8

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             676

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V.2008/1
SHADE (Parsons, 2004)
;
# The following data are from Sadabs: 
_exptl_absorpt_correction_T_min  0.7447
_exptl_absorpt_correction_T_max  0.8616


_exptl_special_details           
;
High-pressure crystallisation and data collection in a Be-containing 
diamond-anvil cell. Data collected with the DAC in three orientations
;

_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08

_exptl_absorpt_coefficient_mu    0.819

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker AXS APEX II'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_reflns_number            8102
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_reduction_process 
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;



_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         17.284
_diffrn_reflns_theta_full        17.284
_diffrn_measured_fraction_theta_max 0.754
_diffrn_measured_fraction_theta_full 0.754
_diffrn_reflns_Laue_measured_fraction_max 0.754
_diffrn_reflns_Laue_measured_fraction_full 0.754
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_point_group_measured_fraction_full 0.754
_reflns_number_total             650
_reflns_number_gt                504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement subject to GRADE restraints on bond length and angles. 
RIGU enhanced rigid-body restraints on ADPs were used.

The following ALERTS wre generated using checkCIF/PLATON


REFNR01_ALERT_3_A  Ratio of reflections to parameters is < 6 for a
            centrosymmetric structure
            sine(theta)/lambda                0.4180
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   3.7791
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4180
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......0.754 Note  
PLAT088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.01 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ............... 0.0136 Ang.  
Alert level C

Alerts due to high-pressure data collected in a Be-containing DAC. The data 
to parameter ratio was actually increased through the use of restraints.


PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of    C1CL Check 

Noted, restraints used during refinement. No further action taken.

;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+6.5542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         650
_refine_ls_number_parameters     172
_refine_ls_number_restraints     172
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7056(5) 0.7084(3) 0.8763(3) 0.0965(15) Uani 1 1 d D U . . .
Cl2 Cl 0.9894(4) 0.8390(4) 0.9517(3) 0.1109(18) Uani 1 1 d D U . . .
Cl3 Cl 0.8761(5) 0.8666(3) 1.1577(3) 0.0992(15) Uani 1 1 d D U . . .
Cl4 Cl 0.6632(4) 0.9442(4) 0.9732(3) 0.1142(17) Uani 1 1 d D U . . .
C1CL C 0.8402(14) 0.7618(11) 0.9860(9) 0.075(4) Uani 1 1 d D U . . .
H1CL H 0.8891 0.6993 1.0281 0.090 Uiso 1 1 calc R U . . .
C2CL C 0.7509(14) 0.8275(11) 1.0405(9) 0.082(4) Uani 1 1 d D U . . .
H2CL H 0.6669 0.7805 1.0531 0.098 Uiso 1 1 calc R U . . .
C1 C 0.8262(9) 0.4511(8) 1.0386(7) 0.032(3) Uani 1 1 d D U . . .
H1 H 0.8642 0.4079 0.9942 0.038 Uiso 1 1 calc R U . . .
C2 C 0.9278(10) 0.4917(9) 1.1213(7) 0.037(3) Uani 1 1 d D U . . .
H2 H 1.0347 0.4764 1.1327 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8753(10) 0.5561(9) 1.1899(7) 0.039(3) Uani 1 1 d D U . . .
H3 H 0.9471 0.5829 1.2469 0.047 Uiso 1 1 calc R U . . .
C4 C 0.7200(9) 0.5800(8) 1.1742(7) 0.037(3) Uani 1 1 d D U . . .
H4 H 0.6870 0.6240 1.2203 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6065(8) 0.5390(8) 1.0886(6) 0.025(3) Uani 1 1 d D U . . .
C6 C 0.6611(9) 0.4732(8) 1.0177(7) 0.025(3) Uani 1 1 d D U . . .
C7 C 0.4458(9) 0.5660(8) 1.0689(6) 0.026(3) Uani 1 1 d D U . . .
C8 C 0.3896(10) 0.6352(8) 1.1420(7) 0.032(3) Uani 1 1 d D U . . .
C9 C 0.3618(12) 0.7481(8) 1.1274(7) 0.045(3) Uani 1 1 d D U . . .
H9 H 0.3806 0.7820 1.0712 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3067(13) 0.8115(9) 1.1945(8) 0.065(4) Uani 1 1 d D U . . .
H10 H 0.2909 0.8875 1.1840 0.078 Uiso 1 1 calc R U . . .
C11 C 0.2757(12) 0.7622(10) 1.2765(8) 0.059(4) Uani 1 1 d D U . . .
H11 H 0.2375 0.8048 1.3213 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3005(12) 0.6505(10) 1.2932(8) 0.051(4) Uani 1 1 d D U . . .
H12 H 0.2789 0.6172 1.3489 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3581(10) 0.5875(8) 1.2263(7) 0.039(3) Uani 1 1 d D U . . .
H13 H 0.3760 0.5120 1.2381 0.047 Uiso 1 1 calc R U . . .

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
Cl1 0.169(4) 0.051(3) 0.062(3) -0.0024(18) 0.017(2) -0.013(3)
Cl2 0.078(2) 0.158(5) 0.109(4) 0.044(3) 0.045(2) 0.015(2)
Cl3 0.150(3) 0.081(4) 0.059(3) -0.0122(19) 0.014(2) -0.011(3)
Cl4 0.104(3) 0.092(4) 0.128(4) -0.018(2) -0.003(3) 0.054(3)
C1CL 0.105(8) 0.068(9) 0.057(8) 0.010(5) 0.032(6) 0.023(6)
C2CL 0.088(8) 0.083(10) 0.075(8) -0.013(6) 0.024(6) 0.015(6)
C1 0.035(5) 0.037(8) 0.030(7) 0.008(5) 0.017(5) 0.006(5)
C2 0.036(6) 0.039(9) 0.037(8) 0.010(5) 0.013(5) 0.005(5)
C3 0.038(5) 0.046(9) 0.033(7) -0.003(5) 0.007(5) -0.003(5)
C4 0.039(5) 0.030(8) 0.040(7) -0.007(5) 0.010(4) -0.003(5)
C5 0.029(5) 0.019(7) 0.030(7) -0.002(4) 0.015(4) -0.004(4)
C6 0.029(5) 0.023(7) 0.027(7) 0.005(4) 0.017(5) 0.000(5)
C7 0.032(5) 0.023(7) 0.029(7) 0.001(4) 0.020(5) -0.001(4)
C8 0.033(6) 0.040(7) 0.023(7) -0.005(4) 0.010(5) 0.008(5)
C9 0.055(7) 0.042(7) 0.042(8) -0.003(5) 0.018(6) 0.012(6)
C10 0.087(9) 0.055(8) 0.061(9) -0.013(5) 0.034(7) 0.019(6)
C11 0.055(8) 0.075(9) 0.050(9) -0.021(6) 0.020(7) 0.009(7)
C12 0.057(7) 0.073(9) 0.034(8) -0.010(5) 0.027(6) 0.004(7)
C13 0.038(6) 0.056(8) 0.027(7) -0.002(5) 0.016(5) 0.004(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
Cl1 C1CL 1.785(12) . ?
Cl2 C1CL 1.769(12) . ?
Cl3 C2CL 1.771(12) . ?
Cl4 C2CL 1.748(13) . ?
C1CL C2CL 1.454(15) . ?
C1 C2 1.347(9) . ?
C1 C6 1.429(8) . ?
C2 C3 1.393(10) . ?
C3 C4 1.356(9) . ?
C4 C5 1.424(9) . ?
C5 C7 1.405(8) . ?
C5 C6 1.436(9) . ?
C6 C7 1.399(10) 3_667 ?
C7 C6 1.399(10) 3_667 ?
C7 C8 1.489(10) . ?
C8 C9 1.386(8) . ?
C8 C13 1.388(8) . ?
C9 C10 1.381(9) . ?
C10 C11 1.368(11) . ?
C11 C12 1.372(11) . ?
C12 C13 1.388(8) . ?

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
C2CL C1CL Cl2 113.0(10) . . ?
C2CL C1CL Cl1 108.0(8) . . ?
Cl2 C1CL Cl1 109.6(7) . . ?
C1CL C2CL Cl4 112.5(10) . . ?
C1CL C2CL Cl3 109.1(8) . . ?
Cl4 C2CL Cl3 111.0(7) . . ?
C2 C1 C6 121.3(8) . . ?
C1 C2 C3 121.1(8) . . ?
C4 C3 C2 120.4(8) . . ?
C3 C4 C5 121.3(8) . . ?
C7 C5 C4 122.3(7) . . ?
C7 C5 C6 119.4(7) . . ?
C4 C5 C6 118.2(7) . . ?
C7 C6 C1 122.2(7) 3_667 . ?
C7 C6 C5 120.1(7) 3_667 . ?
C1 C6 C5 117.7(7) . . ?
C6 C7 C5 120.5(7) 3_667 . ?
C6 C7 C8 120.1(7) 3_667 . ?
C5 C7 C8 119.4(8) . . ?
C9 C8 C13 117.5(7) . . ?
C9 C8 C7 121.8(8) . . ?
C13 C8 C7 120.7(9) . . ?
C10 C9 C8 121.5(9) . . ?
C11 C10 C9 119.8(10) . . ?
C10 C11 C12 120.5(9) . . ?
C11 C12 C13 119.5(9) . . ?
C8 C13 C12 121.3(9) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049

_shelx_res_file                  
;

    dpa_solvate.res created by SHELXL-2014/7

REM Solution 1  R1  0.201,  Alpha = 0.0877  in P2(1)/c
REM C15 Cl4
TITL solvate in P2(1)/c
CELL  0.71073   8.7874  12.0308  13.8215   90.000  104.964   90.000
ZERR    2.00   0.0003   0.0007   0.0008   0.000   0.003   0.000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C H CL
REM SFAC cnt 0 0 0 0 0 0 0 0 0 0 0 0 0 0.1 ! centroid dummy
UNIT 60 44 16
OMIT 0 4 1
TEMP 23.000
L.S. 10
BOND
LIST 6
FMAP 2
PLAN 10
mpla 6 c8 > c13
mpla 14 c1 > c7 c1_$1 c2_$1 c3_$1 c4_$1 c5_$1 c6_$1 c7_$1

OMIT -1 6 9
OMIT 1 5 9
OMIT -2 7 8
OMIT -1 5 8
OMIT 4 2 5
OMIT -2 8 4
OMIT -6 5 1
OMIT -7 1 1
OMIT 0 8 3
OMIT -5 5 8
OMIT -5 0 8

eqiv $1 1-x, 1-y, 2-z
REM dfix 1.390 0.001 c5 c7 c7 c6_$1
REM flat c5 c6 c7 c5_$1 c6_$1 c7_$1
REM sadi 0.001 cnt1 c5 cnt1 c6 cnt1 c7 cnt1 c5_$1 cnt1 c6_$1 cnt1 c7_$1

+grade-XXX_solvent.dfix
+grade-XXX_dpa.dfix
rigu
acta
WGHT    0.059700    6.554200
FVAR       1.99740
CL1   3    0.705590    0.708355    0.876255    11.00000    0.16947    0.05082 =
         0.06225   -0.00241    0.01708   -0.01255
CL2   3    0.989437    0.839022    0.951682    11.00000    0.07764    0.15787 =
         0.10886    0.04407    0.04511    0.01540
CL3   3    0.876099    0.866578    1.157742    11.00000    0.15014    0.08096 =
         0.05948   -0.01221    0.01435   -0.01075
CL4   3    0.663239    0.944173    0.973235    11.00000    0.10405    0.09192 =
         0.12840   -0.01818   -0.00282    0.05390
C1CL  1    0.840201    0.761813    0.985978    11.00000    0.10525    0.06829 =
         0.05685    0.00952    0.03204    0.02345
AFIX  13
H1CL  2    0.889053    0.699301    1.028148    11.00000   -1.20000
AFIX   0
C2CL  1    0.750862    0.827542    1.040511    11.00000    0.08849    0.08309 =
         0.07524   -0.01303    0.02379    0.01489
AFIX  13
H2CL  2    0.666933    0.780504    1.053067    11.00000   -1.20000
AFIX   0
C1    1    0.826157    0.451108    1.038581    11.00000    0.03455    0.03654 =
         0.03001    0.00777    0.01720    0.00631
AFIX  43
H1    2    0.864213    0.407864    0.994190    11.00000   -1.20000
AFIX   0
C2    1    0.927777    0.491683    1.121266    11.00000    0.03642    0.03879 =
         0.03669    0.00999    0.01254    0.00505
AFIX  43
H2    2    1.034710    0.476446    1.132682    11.00000   -1.20000
AFIX   0
C3    1    0.875285    0.556086    1.189935    11.00000    0.03817    0.04576 =
         0.03321   -0.00250    0.00696   -0.00295
AFIX  43
H3    2    0.947130    0.582854    1.246865    11.00000   -1.20000
AFIX   0
C4    1    0.720048    0.579961    1.174237    11.00000    0.03943    0.03028 =
         0.04023   -0.00711    0.01033   -0.00326
AFIX  43
H4    2    0.687031    0.623994    1.220267    11.00000   -1.20000
AFIX   0
C5    1    0.606486    0.538953    1.088647    11.00000    0.02940    0.01903 =
         0.03036   -0.00233    0.01532   -0.00354
C6    1    0.661108    0.473163    1.017705    11.00000    0.02931    0.02315 =
         0.02681    0.00460    0.01750   -0.00021

C7    1    0.445807    0.565958    1.068898    11.00000    0.03206    0.02299 =
         0.02869    0.00115    0.02009   -0.00142
C8    1    0.389582    0.635195    1.142027    11.00000    0.03323    0.04048 =
         0.02262   -0.00460    0.00970    0.00809
C9    1    0.361761    0.748118    1.127448    11.00000    0.05476    0.04162 =
         0.04170   -0.00279    0.01804    0.01197
AFIX  43
H9    2    0.380588    0.781985    1.071169    11.00000   -1.20000
AFIX   0
C10   1    0.306749    0.811517    1.194517    11.00000    0.08699    0.05499 =
         0.06093   -0.01254    0.03385    0.01942
AFIX  43
H10   2    0.290856    0.887455    1.183967    11.00000   -1.20000
AFIX   0
C11   1    0.275714    0.762230    1.276530    11.00000    0.05499    0.07474 =
         0.05009   -0.02142    0.02031    0.00889
AFIX  43
H11   2    0.237529    0.804767    1.321315    11.00000   -1.20000
AFIX   0
C12   1    0.300516    0.650480    1.293194    11.00000    0.05667    0.07288 =
         0.03362   -0.00988    0.02746    0.00428
AFIX  43
H12   2    0.278905    0.617152    1.348888    11.00000   -1.20000
AFIX   0
C13   1    0.358130    0.587539    1.226262    11.00000    0.03792    0.05612 =
         0.02745   -0.00188    0.01629    0.00434
AFIX  43
H13   2    0.376003    0.511961    1.238095    11.00000   -1.20000
REM CNT1 4 0.499999 0.500000 1.000000 10.00000 0.02651
REM Cnt1 was created from: C6, C5, C7, C61, C51, C71,
AFIX   0
HKLF 4

REM  solvate in P2(1)/c
REM R1 =  0.0515 for     504 Fo > 4sig(Fo)  and  0.0738 for all     650 data
REM    172 parameters refined using    172 restraints

END

WGHT      0.0597      6.5542

REM Highest difference peak  0.367,  deepest hole -0.252,  1-sigma level  0.049
Q1    1   0.7209  0.8589  1.1378  11.00000  0.05    0.37
Q2    1   0.6632  0.7746  0.9378  11.00000  0.05    0.25
Q3    1   0.9497  0.8362  1.0563  11.00000  0.05    0.25
Q4    1   0.8404  0.7352  0.8767  11.00000  0.05    0.20
Q5    1   0.8021  1.0013  0.9763  11.00000  0.05    0.20
Q6    1   0.9035  0.9225  0.9569  11.00000  0.05    0.17
Q7    1   0.4690  0.5407  1.2617  11.00000  0.05    0.14
Q8    1   0.3623  0.7162  1.3417  11.00000  0.05    0.14
Q9    1   0.4277  0.7813  1.0575  11.00000  0.05    0.14
Q10   1   1.0925  0.4387  1.1805  11.00000  0.05    0.13
;
_shelx_res_checksum              50489
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,1,2,2-tetrachloroethane'
####################################################################### 
# 
# 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_diphenylanthracene_0p5_GPa
_database_code_depnum_ccdc_archive 'CCDC 1442974'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        9,10-Diphenylanthracene
_chemical_formula_moiety         'C26 H18'
_chemical_formula_sum            'C26 H18'
_chemical_formula_weight         330.40

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'

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

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

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

_cell_length_a                   10.4702(9)
_cell_length_b                   13.3923(10)
_cell_length_c                   12.0158(11)
_cell_angle_alpha                90
_cell_angle_beta                 89.931(8)
_cell_angle_gamma                90
_cell_volume                     1684.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    525
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      24.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             696

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V.2008/1
SHADE (Parsons, 2004)
;
# The following data are from Sadabs: 
_exptl_absorpt_correction_T_min  0.7939
_exptl_absorpt_correction_T_max  0.8838


_exptl_special_details           
;
High-pressure data collection in a Be-free diamond-anvil cell.
Data collected with the DAC in two orientations.
;

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08

_exptl_absorpt_coefficient_mu    0.074


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker AXS APEX II'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_reflns_number            6071
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_reduction_process 
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_theta_min         2.469
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.603
_diffrn_measured_fraction_theta_full 0.607
_diffrn_reflns_Laue_measured_fraction_max 0.603
_diffrn_reflns_Laue_measured_fraction_full 0.607
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_point_group_measured_fraction_full 0.607
_reflns_number_total             937
_reflns_number_gt                765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'known coordinates'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement subject to GRADE restraints on bond length and angles. 
RIGU enhanced rigid-body restraints on ADPs were used.

The following ALERTS wre generated using checkCIF/PLATON

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....0.607 Note  

Alert due to high-pressure data collected in a DAC.


PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg   89.93 Degree

Non-standard setting used to facilitate comparison with the published 
ambient-pressure structure
;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+1.0420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'known coordinates'
_atom_sites_solution_secondary   'known coordinates'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0090(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         937
_refine_ls_number_parameters     119
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0297(2) 0.13045(14) -0.03601(19) 0.0363(7) Uani 1 1 d D U . . .
H1 H 0.0342 0.0735 -0.0801 0.044 Uiso 1 1 calc R U . . .
C2 C -0.0828(2) 0.15499(14) 0.0125(2) 0.0429(8) Uani 1 1 d D U . . .
H2 H -0.1544 0.1154 0.0005 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1318(2) 0.27734(12) 0.04793(17) 0.0284(7) Uani 1 1 d D U . . .
C4 C 0.0100(2) 0.29940(14) 0.09736(19) 0.0354(7) Uani 1 1 d D U . . .
H4 H 0.0016 0.3559 0.1417 0.042 Uiso 1 1 calc R U . . .
C3 C -0.0921(2) 0.24008(15) 0.0809(2) 0.0441(8) Uani 1 1 d D U . . .
H3 H -0.1694 0.2554 0.1150 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2392(2) 0.33720(12) 0.06684(17) 0.0277(7) Uani 1 1 d D U . . .
C6 C 0.1413(2) 0.18985(12) -0.02105(18) 0.0279(6) Uani 1 1 d D U . . .
C8 C 0.2272(2) 0.42933(13) 0.1366(2) 0.0288(7) Uani 1 1 d D U . . .
C9 C 0.2884(2) 0.43775(15) 0.2376(2) 0.0409(7) Uani 1 1 d D U . . .
H9 H 0.3389 0.3853 0.2628 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2764(3) 0.52290(16) 0.3024(2) 0.0495(9) Uani 1 1 d D U . . .
H10 H 0.3194 0.5280 0.3698 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1995(3) 0.60018(16) 0.2655(2) 0.0469(8) Uani 1 1 d D U . . .
H11 H 0.1899 0.6572 0.3089 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1377(2) 0.59321(14) 0.1657(2) 0.0412(8) Uani 1 1 d D U . . .
H12 H 0.0863 0.6455 0.1415 0.049 Uiso 1 1 calc R U . . .
C13 C 0.1513(2) 0.50836(14) 0.10023(19) 0.0339(7) Uani 1 1 d D U . . .
H13 H 0.1097 0.5043 0.0320 0.041 Uiso 1 1 calc R U . . .

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
C1 0.0393(17) 0.0281(12) 0.0417(17) -0.0013(8) -0.0010(14) -0.0054(8)
C2 0.0319(17) 0.0427(14) 0.054(2) -0.0024(10) 0.0013(16) -0.0125(9)
C5 0.0335(16) 0.0271(12) 0.0245(16) 0.0038(7) -0.0018(13) -0.0026(8)
C4 0.0371(17) 0.0354(13) 0.0337(17) -0.0023(8) 0.0023(14) -0.0023(8)
C3 0.0350(18) 0.0418(14) 0.055(2) -0.0026(10) 0.0109(16) -0.0048(9)
C7 0.0353(16) 0.0260(12) 0.0220(15) 0.0023(7) -0.0037(13) -0.0030(7)
C6 0.0317(16) 0.0254(12) 0.0266(15) 0.0034(7) -0.0035(13) -0.0028(7)
C8 0.0281(16) 0.0316(13) 0.0267(16) -0.0003(8) -0.0020(13) -0.0047(8)
C9 0.048(2) 0.0410(14) 0.0340(18) -0.0047(9) -0.0100(16) 0.0040(9)
C10 0.060(2) 0.0529(17) 0.035(2) -0.0107(10) -0.0127(18) -0.0003(11)
C11 0.053(2) 0.0436(16) 0.045(2) -0.0120(10) 0.0037(17) -0.0015(10)
C12 0.0389(18) 0.0349(13) 0.0497(19) -0.0032(9) 0.0050(16) 0.0043(9)
C13 0.0305(17) 0.0391(14) 0.0322(17) -0.0011(8) -0.0042(14) -0.0008(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
C1 C2 1.354(3) . ?
C1 C6 1.425(3) . ?
C2 C3 1.408(3) . ?
C5 C7 1.400(3) . ?
C5 C4 1.436(3) . ?
C5 C6 1.439(3) . ?
C4 C3 1.347(3) . ?
C7 C6 1.414(3) 7 ?
C7 C8 1.497(3) . ?
C6 C7 1.414(3) 7 ?
C8 C9 1.377(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.384(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.389(3) . ?

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
C2 C1 C6 121.53(18) . . ?
C1 C2 C3 120.5(2) . . ?
C7 C5 C4 121.86(17) . . ?
C7 C5 C6 120.32(16) . . ?
C4 C5 C6 117.81(18) . . ?
C3 C4 C5 121.49(18) . . ?
C4 C3 C2 120.54(18) . . ?
C5 C7 C6 120.08(16) . 7 ?
C5 C7 C8 119.73(16) . . ?
C6 C7 C8 120.19(18) 7 . ?
C7 C6 C1 122.23(17) 7 . ?
C7 C6 C5 119.57(18) 7 . ?
C1 C6 C5 118.12(16) . . ?
C9 C8 C13 118.71(19) . . ?
C9 C8 C7 121.46(19) . . ?
C13 C8 C7 119.8(2) . . ?
C8 C9 C10 121.3(2) . . ?
C11 C10 C9 119.2(3) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C13 120.3(2) . . ?
C12 C13 C8 120.1(3) . . ?

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029

_shelx_res_file                  
;

    dpantr5kbar.res created by SHELXL-2014/7


TITL sad in C2/c
CELL 0.71073  10.4702  13.3923  12.0158  90.000  89.931  90.000
ZERR    4.00   0.0009   0.0010   0.0011   0.000   0.008   0.000
LATT  7
SYMM -X, Y, 0.5-Z
SFAC C H
UNIT 104 72
OMIT -5 11 4

OMIT -1 11 3
OMIT -4 10 5
OMIT -1 13 4
OMIT -5 9 6
OMIT -3 11 2
OMIT 2 4 7
OMIT 3 3 4
OMIT 4 6 7

TEMP 23.000
l.s. 10
list 6
fmap 2
plan -10
acta
rigu

+grade-XXX_dpa.dfix
eqiv $1 1/2-x, 1/2-y, -z
mpla 6 c8 > c13
mpla 14 c1 > c7 c1_$1 c2_$1 c3_$1 c4_$1 c5_$1 c6_$1 c7_$1

rem AFIX  66
WGHT    0.041100    1.042000
EXTI    0.009010
FVAR       0.58816
C1    1    0.029696    0.130450   -0.036014    11.00000    0.03928    0.02806 =
         0.04165   -0.00126   -0.00098   -0.00539
AFIX  43
H1    2    0.034250    0.073493   -0.080120    11.00000   -1.20000
AFIX   0
C2    1   -0.082769    0.154993    0.012472    11.00000    0.03195    0.04271 =
         0.05403   -0.00240    0.00133   -0.01248
AFIX  43
H2    2   -0.154403    0.115379    0.000512    11.00000   -1.20000
AFIX   0
C5    1    0.131766    0.277341    0.047933    11.00000    0.03354    0.02706 =
         0.02448    0.00384   -0.00176   -0.00261
C4    1    0.010050    0.299398    0.097364    11.00000    0.03710    0.03536 =
         0.03371   -0.00229    0.00230   -0.00232
AFIX  43
H4    2    0.001559    0.355909    0.141742    11.00000   -1.20000
AFIX   0
C3    1   -0.092112    0.240077    0.080900    11.00000    0.03497    0.04175 =
         0.05547   -0.00258    0.01093   -0.00476
AFIX  43
H3    2   -0.169442    0.255433    0.114997    11.00000   -1.20000
AFIX   0
rem AFIX   0
C7    1    0.239193    0.337201    0.066836    11.00000    0.03526    0.02595 =
         0.02201    0.00231   -0.00374   -0.00301
C6    1    0.141263    0.189852   -0.021046    11.00000    0.03170    0.02539 =
         0.02657    0.00338   -0.00347   -0.00284
rem AFIX  66
C8    1    0.227184    0.429334    0.136633    11.00000    0.02812    0.03161 =
         0.02669   -0.00026   -0.00199   -0.00470
C9    1    0.288440    0.437752    0.237588    11.00000    0.04777    0.04097 =
         0.03399   -0.00473   -0.00996    0.00404
AFIX  43
H9    2    0.338879    0.385275    0.262793    11.00000   -1.20000
AFIX   0
C10   1    0.276390    0.522896    0.302357    11.00000    0.06024    0.05289 =
         0.03532   -0.01071   -0.01273   -0.00034
AFIX  43
H10   2    0.319430    0.528029    0.369775    11.00000   -1.20000
AFIX   0
C11   1    0.199542    0.600180    0.265496    11.00000    0.05254    0.04364 =
         0.04451   -0.01196    0.00368   -0.00146
AFIX  43
H11   2    0.189922    0.657189    0.308898    11.00000   -1.20000
AFIX   0
C12   1    0.137719    0.593208    0.165699    11.00000    0.03886    0.03495 =
         0.04966   -0.00319    0.00499    0.00426
AFIX  43
H12   2    0.086332    0.645504    0.141503    11.00000   -1.20000
AFIX   0
C13   1    0.151274    0.508364    0.100226    11.00000    0.03049    0.03913 =
         0.03221   -0.00109   -0.00421   -0.00076
AFIX  43
H13   2    0.109672    0.504274    0.032037    11.00000   -1.20000
rem AFIX   0
REM #####
AFIX   0
HKLF 4

REM  sad in C2/c
REM R1 =  0.0365 for     765 Fo > 4sig(Fo)  and  0.0485 for all     937 data
REM    119 parameters refined using    128 restraints

END

WGHT      0.0406      1.1734

REM Highest difference peak  0.117,  deepest hole -0.129,  1-sigma level  0.029
Q1    1   0.1117  0.2495 -0.0134  11.00000  0.05    0.12
Q2    1   0.1571  0.2138  0.0471  11.00000  0.05    0.11
Q3    1   0.4005  0.3990  0.2496  11.00000  0.05    0.11
Q4    1   0.1822  0.3028  0.0560  11.00000  0.05    0.10
Q5    1  -0.0993  0.3261 -0.0128  11.00000  0.05    0.10
Q6    1   0.0918  0.2680  0.0964  11.00000  0.05    0.10
Q7    1  -0.0477  0.1885  0.0775  11.00000  0.05    0.10
Q8    1   0.3410  0.6031  0.1799  11.00000  0.05    0.10
Q9    1   0.0266  0.3515 -0.0377  11.00000  0.05    0.09
Q10   1   0.0689  0.6588  0.0956  11.00000  0.05    0.09
;
_shelx_res_checksum              76237
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,1,2,2-tetrachloroethane'
####################################################################### 
# 
# 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_diphenylanthracene_3_GPa
_database_code_depnum_ccdc_archive 'CCDC 1442975'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        9,10-Diphenylanthracene
_chemical_formula_moiety         'C26 H18'
_chemical_formula_sum            'C26 H18'
_chemical_formula_weight         330.40

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'

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

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

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

_cell_length_a                   10.041(2)
_cell_length_b                   13.150(2)
_cell_length_c                   11.378(2)
_cell_angle_alpha                90
_cell_angle_beta                 88.483(17)
_cell_angle_gamma                90
_cell_volume                     1501.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    638
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      20.3

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             696

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V.2008/1
SHADE (Parsons, 2004)
;
# The following data are from Sadabs: 
_exptl_absorpt_correction_T_min  0.5255
_exptl_absorpt_correction_T_max  0.8837


_exptl_special_details           
;
High-pressure data collection in a Be-containing diamond-anvil cell.
;

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.083

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker AXS APEX II'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_reflns_number            1704
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_reduction_process 
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10

_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         19.779
_diffrn_reflns_theta_full        19.779
_diffrn_measured_fraction_theta_max 0.614
_diffrn_measured_fraction_theta_full 0.614
_diffrn_reflns_Laue_measured_fraction_max 0.614
_diffrn_reflns_Laue_measured_fraction_full 0.614
_diffrn_reflns_point_group_measured_fraction_max 0.614
_diffrn_reflns_point_group_measured_fraction_full 0.614
_reflns_number_total             422
_reflns_number_gt                308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .



_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'known coordinates'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Data cut to 1.05 Angstrom. Refinement subject to GRADE restraints on
bond length and angles. RIGU enhanced rigid-body restraints on ADPs
were used.

The following ALERTS wre generated using checkCIF/PLATON

REFNR01_ALERT_3_A  Ratio of reflections to parameters is < 6 for a
            centrosymmetric structure
            sine(theta)/lambda                0.4761
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   3.5462
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4761
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.614 Note  
PLAT088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.77 Note  
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ............... 0.0089 Ang.  

Alerts due to high-pressure data collected in a Be-containing DAC. Data
were cut to 1.05 Angstrom. The data to parameter ratio was actually 
increased through the use of restraints.

PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.750 Sigma 

All crystals checked in our laboratory showed extinction at both ambient and
high-pressure conditions.

PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg   88.48 Degree

Non-standard setting used to facilitate comparison with the published 
ambient-pressure structure
;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1051P)²+0.8554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'known coordinates'
_atom_sites_solution_secondary   'known coordinates'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         422
_refine_ls_number_parameters     119
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0200(6) 0.1301(4) -0.0379(6) 0.035(2) Uani 1 1 d D U . . .
H1 H 0.0252 0.0718 -0.0841 0.042 Uiso 1 1 calc R U . . .
C2 C -0.0970(7) 0.1559(4) 0.0132(6) 0.042(3) Uani 1 1 d D U . . .
H2 H -0.1711 0.1151 0.0015 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1236(6) 0.2791(4) 0.0496(6) 0.032(2) Uani 1 1 d D U . . .
C4 C -0.0035(7) 0.3030(4) 0.0995(6) 0.033(2) Uani 1 1 d D U . . .
H4 H -0.0132 0.3618 0.1442 0.039 Uiso 1 1 calc R U . . .
C3 C -0.1104(8) 0.2434(4) 0.0841(6) 0.040(2) Uani 1 1 d D U . . .
H3 H -0.1921 0.2596 0.1197 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2383(7) 0.3377(4) 0.0694(6) 0.032(2) Uani 1 1 d D U . . .
C6 C 0.1365(7) 0.1900(4) -0.0230(6) 0.032(2) Uani 1 1 d D U . . .
C8 C 0.2247(7) 0.4322(4) 0.1409(6) 0.034(2) Uani 1 1 d D U . . .
C9 C 0.2923(7) 0.4431(4) 0.2439(6) 0.042(2) Uani 1 1 d D U . . .
H9 H 0.3452 0.3899 0.2695 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2834(7) 0.5309(4) 0.3102(6) 0.051(2) Uani 1 1 d D U . . .
H10 H 0.3324 0.5382 0.3779 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2000(8) 0.6078(5) 0.2737(6) 0.044(3) Uani 1 1 d D U . . .
H11 H 0.1899 0.6661 0.3194 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1323(7) 0.5994(4) 0.1713(6) 0.042(3) Uani 1 1 d D U . . .
H12 H 0.0786 0.6525 0.1466 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1440(6) 0.5118(4) 0.1050(5) 0.038(2) Uani 1 1 d D U . . .
H13 H 0.0975 0.5059 0.0357 0.046 Uiso 1 1 calc R U . . .

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
C1 0.041(5) 0.021(4) 0.042(6) 0.001(3) -0.003(4) -0.001(3)
C2 0.034(5) 0.034(4) 0.057(6) -0.004(3) -0.003(5) -0.007(3)
C5 0.034(5) 0.020(4) 0.041(5) 0.004(3) -0.003(4) 0.002(3)
C4 0.038(5) 0.021(4) 0.041(5) 0.000(3) -0.004(4) -0.003(3)
C3 0.033(5) 0.033(4) 0.055(6) -0.002(3) -0.002(4) -0.002(3)
C7 0.039(5) 0.021(3) 0.035(5) 0.003(3) -0.002(4) -0.002(3)
C6 0.033(5) 0.024(4) 0.040(5) 0.004(3) -0.001(4) -0.004(3)
C8 0.035(5) 0.023(3) 0.046(5) 0.004(3) -0.002(4) 0.000(3)
C9 0.049(6) 0.027(4) 0.050(5) 0.001(3) -0.012(4) 0.006(3)
C10 0.066(7) 0.037(4) 0.050(5) -0.005(3) -0.009(5) 0.006(3)
C11 0.053(6) 0.032(4) 0.046(6) -0.011(3) 0.001(4) 0.001(3)
C12 0.055(7) 0.027(4) 0.044(5) 0.002(3) 0.000(5) 0.004(3)
C13 0.040(6) 0.023(4) 0.052(5) -0.006(3) -0.010(4) 0.002(3)

_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
C1 C2 1.340(7) . ?
C1 C6 1.424(8) . ?
C2 C3 1.409(7) . ?
C5 C7 1.409(7) . ?
C5 C4 1.418(7) . ?
C5 C6 1.436(7) . ?
C4 C3 1.345(8) . ?
C7 C6 1.399(8) 7 ?
C7 C8 1.489(7) . ?
C6 C7 1.399(8) 7 ?
C8 C9 1.376(7) . ?
C8 C13 1.392(7) . ?
C9 C10 1.381(7) . ?
C10 C11 1.383(9) . ?
C11 C12 1.368(9) . ?
C12 C13 1.381(6) . ?

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
C2 C1 C6 121.4(5) . . ?
C1 C2 C3 121.6(6) . . ?
C7 C5 C4 123.0(5) . . ?
C7 C5 C6 118.5(5) . . ?
C4 C5 C6 118.5(5) . . ?
C3 C4 C5 122.1(5) . . ?
C4 C3 C2 119.1(6) . . ?
C6 C7 C5 121.8(5) 7 . ?
C6 C7 C8 119.5(6) 7 . ?
C5 C7 C8 118.7(5) . . ?
C7 C6 C1 122.9(5) 7 . ?
C7 C6 C5 119.7(5) 7 . ?
C1 C6 C5 117.2(5) . . ?
C9 C8 C13 118.4(5) . . ?
C9 C8 C7 120.8(5) . . ?
C13 C8 C7 120.8(7) . . ?
C8 C9 C10 121.7(6) . . ?
C9 C10 C11 118.6(7) . . ?
C12 C11 C10 121.0(6) . . ?
C11 C12 C13 119.7(6) . . ?
C12 C13 C8 120.6(6) . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.043

_shelx_res_file                  
;

    dpantr30kbar.res created by SHELXL-2014/7


TITL sad in C2/c
CELL 0.71073  10.0410  13.1498  11.3778  90.000  88.483  90.000
ZERR    4.00   0.0021   0.0021   0.0021   0.000   0.017   0.000
LATT  7
SYMM -X, Y, 0.5-Z
SFAC C H
UNIT 104 72

OMIT 6 6 2
OMIT 6 4 0
OMIT -3 3 7
omit -5 1 2

OMIT -5 5 8
OMIT 2 6 3
OMIT 1 5 9
OMIT -3 1 9
OMIT 5 7 2
OMIT -8 6 2

TEMP 23.000
l.s. 10
list 6
fmap 2
plan -10
acta
rigu

+grade-XXX_dpa.dfix
eqiv $1 1/2-x, 1/2-y, -z
mpla 6 c8 > c13
mpla 14 c1 > c7 c1_$1 c2_$1 c3_$1 c4_$1 c5_$1 c6_$1 c7_$1

rem AFIX  66
WGHT    0.105100    0.855400
EXTI    0.011367
FVAR       0.63208
C1    1    0.020006    0.130116   -0.037896    11.00000    0.04097    0.02115 =
         0.04210    0.00094   -0.00255   -0.00092
AFIX  43
H1    2    0.025229    0.071826   -0.084076    11.00000   -1.20000
AFIX   0
C2    1   -0.096970    0.155911    0.013154    11.00000    0.03411    0.03408 =
         0.05667   -0.00412   -0.00259   -0.00698
AFIX  43
H2    2   -0.171101    0.115100    0.001488    11.00000   -1.20000
AFIX   0
C5    1    0.123620    0.279074    0.049587    11.00000    0.03369    0.02037 =
         0.04107    0.00354   -0.00304    0.00247
C4    1   -0.003477    0.303007    0.099454    11.00000    0.03757    0.02062 =
         0.04064   -0.00021   -0.00435   -0.00290
AFIX  43
H4    2   -0.013192    0.361840    0.144225    11.00000   -1.20000
AFIX   0
C3    1   -0.110406    0.243350    0.084074    11.00000    0.03279    0.03285 =
         0.05467   -0.00175   -0.00168   -0.00172
AFIX  43
H3    2   -0.192065    0.259578    0.119743    11.00000   -1.20000
AFIX   0
rem AFIX   0
C7    1    0.238332    0.337739    0.069377    11.00000    0.03947    0.02122 =
         0.03489    0.00345   -0.00157   -0.00198
C6    1    0.136495    0.190032   -0.022964    11.00000    0.03327    0.02375 =
         0.04049    0.00406   -0.00141   -0.00412
rem AFIX  66
C8    1    0.224713    0.432191    0.140914    11.00000    0.03499    0.02252 =
         0.04592    0.00431   -0.00165    0.00043
C9    1    0.292260    0.443052    0.243868    11.00000    0.04940    0.02678 =
         0.04968    0.00063   -0.01164    0.00614
AFIX  43
H9    2    0.345219    0.389865    0.269458    11.00000   -1.20000
AFIX   0
C10   1    0.283412    0.530919    0.310164    11.00000    0.06594    0.03740 =
         0.05013   -0.00493   -0.00914    0.00613
AFIX  43
H10   2    0.332440    0.538230    0.377858    11.00000   -1.20000
AFIX   0
C11   1    0.200028    0.607803    0.273664    11.00000    0.05305    0.03209 =
         0.04555   -0.01134    0.00090    0.00060
AFIX  43
H11   2    0.189870    0.666064    0.319363    11.00000   -1.20000
AFIX   0
C12   1    0.132272    0.599412    0.171326    11.00000    0.05514    0.02728 =
         0.04421    0.00198   -0.00002    0.00387
AFIX  43
H12   2    0.078594    0.652479    0.146561    11.00000   -1.20000
AFIX   0
C13   1    0.143993    0.511781    0.105027    11.00000    0.03968    0.02344 =
         0.05228   -0.00596   -0.00983    0.00161
AFIX  43
H13   2    0.097509    0.505886    0.035735    11.00000   -1.20000
rem AFIX   0
REM #####
AFIX   0
HKLF 4

REM  sad in C2/c
REM R1 =  0.0528 for     308 Fo > 4sig(Fo)  and  0.0816 for all     422 data
REM    119 parameters refined using    128 restraints

END

WGHT      0.1050      0.8553

REM Highest difference peak  0.122,  deepest hole -0.159,  1-sigma level  0.043
Q1    1   0.1266  0.4348  0.2332  11.00000  0.05    0.12
Q2    1   0.0935  0.0861 -0.1706  11.00000  0.05    0.12
Q3    1  -0.0592  0.3546  0.2368  11.00000  0.05    0.12
Q4    1  -0.0379  0.2787 -0.0454  11.00000  0.05    0.11
Q5    1  -0.0962  0.3336  0.1996  11.00000  0.05    0.11
Q6    1  -0.1369  0.3299 -0.0554  11.00000  0.05    0.11
Q7    1  -0.0677  0.2887  0.1821  11.00000  0.05    0.11
Q8    1   0.0937  0.2432  0.1173  11.00000  0.05    0.10
Q9    1   0.1272  0.6060  0.3815  11.00000  0.05    0.10
Q10   1   0.0577  0.1882  0.0172  11.00000  0.05    0.10
;
_shelx_res_checksum              68279



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,1,2,2-tetrachloroethane'
