# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_RS-1_1'binaphthyl_280K
_database_code_depnum_ccdc_archive 'CCDC 1531186'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   21.107(2)
_cell_length_b                   6.3354(5)
_cell_length_c                   10.2009(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.090(13)
_cell_angle_gamma                90.00
_cell_volume                     1317.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    1307
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      26.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      280(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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4269
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.27
_reflns_number_total             1307
_reflns_number_gt                1013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.3534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       3.176(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1307
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46422(6) 0.1067(2) 0.74670(13) 0.0391(4) Uani 1 1 d . . .
C2 C 0.43889(7) -0.0513(2) 0.81040(16) 0.0481(4) Uani 1 1 d . . .
H2 H 0.4669 -0.1542 0.8585 0.058 Uiso 1 1 calc R . .
C3 C 0.37152(8) -0.0608(2) 0.80450(16) 0.0529(4) Uani 1 1 d . . .
H3 H 0.3556 -0.1696 0.8483 0.063 Uiso 1 1 calc R . .
C4 C 0.32974(7) 0.0880(2) 0.73520(15) 0.0487(4) Uani 1 1 d . . .
H4 H 0.2854 0.0803 0.7319 0.058 Uiso 1 1 calc R . .
C5 C 0.31049(7) 0.4127(2) 0.59476(15) 0.0483(4) Uani 1 1 d . . .
H5 H 0.2661 0.4087 0.5921 0.058 Uiso 1 1 calc R . .
C6 C 0.33333(7) 0.5695(2) 0.52853(16) 0.0507(4) Uani 1 1 d . . .
H6 H 0.3046 0.6711 0.4809 0.061 Uiso 1 1 calc R . .
C7 C 0.40013(7) 0.5784(2) 0.53194(15) 0.0473(4) Uani 1 1 d . . .
H7 H 0.4155 0.6856 0.4861 0.057 Uiso 1 1 calc R . .
C8 C 0.44262(6) 0.4305(2) 0.60209(14) 0.0407(4) Uani 1 1 d . . .
H8 H 0.4868 0.4388 0.6036 0.049 Uiso 1 1 calc R . .
C9 C 0.42092(6) 0.2648(2) 0.67267(12) 0.0368(3) Uani 1 1 d . . .
C10 C 0.35292(6) 0.2549(2) 0.66789(13) 0.0409(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0377(8) 0.0396(7) 0.0393(7) -0.0039(5) 0.0087(5) -0.0021(5)
C2 0.0485(8) 0.0431(8) 0.0520(8) 0.0030(6) 0.0117(7) -0.0028(6)
C3 0.0525(9) 0.0524(9) 0.0558(9) 0.0022(7) 0.0178(7) -0.0156(7)
C4 0.0368(7) 0.0601(9) 0.0501(8) -0.0063(7) 0.0131(6) -0.0114(6)
C5 0.0329(7) 0.0606(9) 0.0503(8) -0.0071(7) 0.0089(6) 0.0013(6)
C6 0.0418(8) 0.0541(9) 0.0529(9) 0.0015(7) 0.0066(7) 0.0097(6)
C7 0.0459(8) 0.0478(8) 0.0473(8) 0.0055(6) 0.0107(6) 0.0008(6)
C8 0.0342(7) 0.0466(8) 0.0418(7) 0.0008(6) 0.0104(5) -0.0007(5)
C9 0.0338(7) 0.0410(7) 0.0354(6) -0.0057(5) 0.0083(5) -0.0025(5)
C10 0.0341(7) 0.0486(8) 0.0400(7) -0.0089(6) 0.0095(5) -0.0045(6)

_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 1.3748(19) . ?
C1 C9 1.4316(18) . ?
C1 C1 1.494(3) 2_656 ?
C2 C3 1.409(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(2) . ?
C3 H3 0.9300 . ?
C4 C10 1.416(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(2) . ?
C5 C10 1.418(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3637(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.4150(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.4245(18) . ?

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 C9 119.02(13) . . ?
C2 C1 C1 119.44(11) . 2_656 ?
C9 C1 C1 121.52(10) . 2_656 ?
C1 C2 C3 121.56(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.27(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 120.79(13) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C6 C5 C10 121.33(13) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 120.11(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.33(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.40(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 118.15(12) . . ?
C8 C9 C1 122.74(12) . . ?
C10 C9 C1 119.11(12) . . ?
C4 C10 C5 122.08(12) . . ?
C4 C10 C9 119.24(13) . . ?
C5 C10 C9 118.68(13) . . ?

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
C9 C1 C2 C3 0.0(2) . . . . ?
C1 C1 C2 C3 -178.53(14) 2_656 . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C10 0.0(2) . . . . ?
C10 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.46(19) . . . . ?
C7 C8 C9 C1 179.71(12) . . . . ?
C2 C1 C9 C8 -178.80(12) . . . . ?
C1 C1 C9 C8 -0.3(2) 2_656 . . . ?
C2 C1 C9 C10 0.44(18) . . . . ?
C1 C1 C9 C10 178.92(12) 2_656 . . . ?
C3 C4 C10 C5 -179.99(13) . . . . ?
C3 C4 C10 C9 0.4(2) . . . . ?
C6 C5 C10 C4 -178.71(14) . . . . ?
C6 C5 C10 C9 0.9(2) . . . . ?
C8 C9 C10 C4 178.64(12) . . . . ?
C1 C9 C10 C4 -0.64(18) . . . . ?
C8 C9 C10 C5 -0.96(18) . . . . ?
C1 C9 C10 C5 179.76(11) . . . . ?
C9 C1 C1 C9 86.67(14) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.27
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_RS-1_1'binaphthyl_0_01MPa
_database_code_depnum_ccdc_archive 'CCDC 1531187'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   21.1362(19)
_cell_length_b                   6.3427(4)
_cell_length_c                   10.2203(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.098(12)
_cell_angle_gamma                90.00
_cell_volume                     1322.84(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1309
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      26.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;

_exptl_special_details           
; 
 ? 
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4303
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.28
_reflns_number_total             1309
_reflns_number_gt                1003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       2.842(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1309
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46431(7) 0.1071(2) 0.24670(13) 0.0415(4) Uani 1 1 d . . .
C2 C 0.43896(8) -0.0506(2) 0.31025(16) 0.0515(4) Uani 1 1 d . . .
H2 H 0.4669 -0.1535 0.3581 0.062 Uiso 1 1 calc R . .
C3 C 0.37161(8) -0.0601(3) 0.30463(17) 0.0572(5) Uani 1 1 d . . .
H3 H 0.3558 -0.1686 0.3485 0.069 Uiso 1 1 calc R . .
C4 C 0.32988(7) 0.0886(3) 0.23541(16) 0.0529(4) Uani 1 1 d . . .
H4 H 0.2856 0.0811 0.2323 0.063 Uiso 1 1 calc R . .
C5 C 0.31071(7) 0.4125(3) 0.09507(16) 0.0520(4) Uani 1 1 d . . .
H5 H 0.2664 0.4088 0.0926 0.062 Uiso 1 1 calc R . .
C6 C 0.33341(8) 0.5689(3) 0.02870(17) 0.0556(4) Uani 1 1 d . . .
H6 H 0.3047 0.6703 -0.0191 0.067 Uiso 1 1 calc R . .
C7 C 0.40018(8) 0.5774(2) 0.03222(16) 0.0518(4) Uani 1 1 d . . .
H7 H 0.4156 0.6844 -0.0136 0.062 Uiso 1 1 calc R . .
C8 C 0.44255(7) 0.4304(2) 0.10217(14) 0.0441(4) Uani 1 1 d . . .
H8 H 0.4867 0.4388 0.1037 0.053 Uiso 1 1 calc R . .
C9 C 0.42087(6) 0.2645(2) 0.17275(12) 0.0397(4) Uani 1 1 d . . .
C10 C 0.35305(6) 0.2548(2) 0.16800(13) 0.0445(4) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0398(8) 0.0419(7) 0.0419(7) -0.0037(5) 0.0090(6) -0.0026(5)
C2 0.0514(9) 0.0473(8) 0.0550(9) 0.0042(7) 0.0123(7) -0.0024(7)
C3 0.0559(10) 0.0581(9) 0.0598(10) 0.0019(7) 0.0189(8) -0.0171(8)
C4 0.0404(8) 0.0652(10) 0.0546(9) -0.0058(7) 0.0151(7) -0.0129(7)
C5 0.0339(7) 0.0657(10) 0.0552(9) -0.0077(7) 0.0096(6) 0.0023(6)
C6 0.0464(9) 0.0583(9) 0.0585(10) 0.0024(7) 0.0071(7) 0.0100(7)
C7 0.0481(9) 0.0525(9) 0.0536(9) 0.0054(7) 0.0113(7) 0.0017(7)
C8 0.0370(7) 0.0503(8) 0.0455(8) 0.0005(6) 0.0116(6) -0.0014(6)
C9 0.0365(7) 0.0444(7) 0.0380(7) -0.0058(6) 0.0094(6) -0.0028(6)
C10 0.0370(7) 0.0535(8) 0.0427(7) -0.0091(6) 0.0100(6) -0.0056(6)
_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
C8 C9 1.4172(19) . ?
C9 C10 1.4228(18) . ?
C1 C9 1.4316(19) . ?
C1 C2 1.3750(19) . ?
C1 C1 1.493(3) 2_655 ?
C2 C3 1.411(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(2) . ?
C3 H3 0.9300 . ?
C4 C10 1.415(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.418(2) . ?
C5 C6 1.358(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 118.11(12) . . ?
C8 C9 C1 122.57(12) . . ?
C10 C9 C1 119.31(12) . . ?
C2 C1 C9 118.79(13) . . ?
C2 C1 C1 119.49(11) . 2_655 ?
C9 C1 C1 121.71(11) . 2_655 ?
C1 C2 C3 121.67(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.20(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 120.74(14) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C4 C10 C5 122.05(13) . . ?
C4 C10 C9 119.28(13) . . ?
C5 C10 C9 118.67(13) . . ?
C6 C5 C10 121.41(14) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 119.95(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.48(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.37(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?

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
C8 C9 C1 C2 -178.80(13) . . . . ?
C10 C9 C1 C2 0.56(19) . . . . ?
C8 C8 C1 C1 -0.4(2) . . . 2_655 ?
C10 C9 C1 C1 178.94(13) . . . 2_655 ?
C9 C1 C2 C3 -0.2(2) . . . . ?
C1 C1 C2 C3 -178.66(15) 2_655 . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C10 0.0(2) . . . . ?
C3 C4 C10 C5 -179.92(14) . . . . ?
C3 C4 C10 C9 0.3(2) . . . . ?
C8 C9 C10 C4 178.80(12) . . . . ?
C1 C9 C10 C4 -0.59(19) . . . . ?
C8 C9 C10 C5 -0.99(19) . . . . ?
C1 C9 C10 C5 179.62(12) . . . . ?
C4 C10 C5 C6 -178.73(15) . . . . ?
C9 C10 C5 C6 1.1(2) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C10 C9 C8 C7 0.4(2) . . . . ?
C1 C9 C8 C7 179.73(13) . . . . ?
C9 C1 C1 C9 69.9(2) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        26.28
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_1_1'binaphthyl_3_14GPa
_database_code_depnum_ccdc_archive 'CCDC 1531205'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1,1'binaphthyl_3.14GPa 
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.707 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_RINTA01_1,1'binaphthyl_3.14GPa 
;
PROBLEM: The value of Rint is greater than 0.18...........0.209
RESPONSE: Poor quality of the data due to poor quality of measured crystal.
;
_vrf_PLAT020_1,1'binaphthyl_3.14GPa 
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.209 Report
RESPONSE: Poor quality of the data due to poor quality of measured crystal.
;
_vrf_PLAT340_1,1'binaphthyl_3.14GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01708 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
_cell_length_a                   6.6809(5)
_cell_length_b                   6.6809(5)
_cell_length_c                   26.433(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1179.84(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2730000
_cell_measurement_reflns_used    1084
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      28.83

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 3.14(2) GPa
(3140000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6986
_diffrn_reflns_av_R_equivalents  0.2095
_diffrn_reflns_av_sigmaI/netI    0.1522
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         28.83
_reflns_number_total             1084
_reflns_number_gt                450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0002P)²+0.4460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_number_reflns         1084
_refine_ls_number_parameters     92
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.1017
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.097
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.129(2) 0.9837(19) 0.0084(4) 0.059(4) Uani 1 1 d U . .
C2 C 0.319(2) 0.9600(19) -0.0159(4) 0.060(4) Uani 1 1 d U . .
H2 H 0.3515 1.0407 -0.0433 0.072 Uiso 1 1 calc R . .
C3 C 0.451(2) 0.8205(19) 0.0007(4) 0.064(4) Uani 1 1 d U . .
H3 H 0.5717 0.8071 -0.0163 0.077 Uiso 1 1 calc R . .
C4 C 0.4147(19) 0.6974(18) 0.0417(4) 0.056(3) Uani 1 1 d U . .
H4 H 0.5073 0.6019 0.0520 0.067 Uiso 1 1 calc R . .
C5 C 0.1913(19) 0.617(2) 0.1130(4) 0.063(4) Uani 1 1 d U . .
H5 H 0.2824 0.5223 0.1245 0.075 Uiso 1 1 calc R . .
C6 C 0.018(2) 0.657(2) 0.1398(4) 0.071(4) Uani 1 1 d U . .
H6 H 0.0001 0.5984 0.1714 0.085 Uiso 1 1 calc R . .
C7 C -0.125(2) 0.778(2) 0.1209(4) 0.067(4) Uani 1 1 d U . .
H7 H -0.2455 0.7908 0.1383 0.081 Uiso 1 1 calc R . .
C8 C -0.0984(18) 0.8829(18) 0.0773(4) 0.048(3) Uani 1 1 d U . .
H8 H -0.1983 0.9673 0.0652 0.057 Uiso 1 1 calc R . .
C9 C 0.0882(18) 0.8605(18) 0.0500(4) 0.051(3) Uani 1 1 d U . .
C10 C 0.2267(19) 0.724(2) 0.0677(4) 0.055(3) Uani 1 1 d 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 0.061(7) 0.061(7) 0.055(6) 0.004(5) -0.003(6) 0.005(7)
C2 0.071(8) 0.057(7) 0.051(6) 0.002(5) 0.001(6) -0.006(7)
C3 0.065(7) 0.070(8) 0.057(6) 0.000(6) -0.003(6) 0.004(7)
C4 0.060(7) 0.049(7) 0.059(6) 0.000(5) 0.004(5) 0.006(7)
C5 0.059(7) 0.067(7) 0.063(6) 0.007(6) -0.002(6) -0.003(7)
C6 0.075(8) 0.071(8) 0.066(7) 0.018(6) 0.002(6) -0.006(7)
C7 0.068(8) 0.070(8) 0.064(6) 0.007(6) -0.002(6) -0.012(7)
C8 0.044(6) 0.051(6) 0.047(5) 0.001(5) -0.009(5) -0.002(6)
C9 0.048(6) 0.054(7) 0.051(5) -0.002(5) -0.016(5) -0.008(7)
C10 0.057(7) 0.057(7) 0.052(5) -0.002(5) -0.004(5) -0.012(7)

_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 1.426(17) . ?
C1 C9 1.401(15) . ?
C1 C1 1.45(2) 7_465 ?
C2 C3 1.357(16) . ?
C3 C4 1.381(15) . ?
C4 C10 1.443(16) . ?
C5 C6 1.381(17) . ?
C5 C10 1.413(15) . ?
C6 C7 1.351(16) . ?
C7 C8 1.360(14) . ?
C8 C9 1.448(16) . ?
C9 C10 1.381(15) . ?

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 C9 117.5(11) . . ?
C2 C1 C1 122.2(10) . 7_465 ?
C9 C1 C1 120.3(12) . 7_465 ?
C1 C2 C3 120.5(11) . . ?
C4 C3 C2 123.3(13) . . ?
C3 C4 C10 116.9(12) . . ?
C6 C5 C10 118.6(13) . . ?
C5 C6 C7 121.3(12) . . ?
C6 C7 C8 121.9(13) . . ?
C7 C8 C9 118.8(12) . . ?
C10 C9 C1 121.5(11) . . ?
C10 C9 C8 118.5(11) . . ?
C1 C9 C8 120.0(11) . . ?
C9 C10 C4 120.2(11) . . ?
C9 C10 C5 120.5(12) . . ?
C4 C10 C5 119.2(12) . . ?

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
C9 C1 C2 C3 1.0(18) . . . . ?
C1 C1 C2 C3 -179.5(11) 7_465 . . . ?
C1 C2 C3 C4 -1.2(19) . . . . ?
C2 C3 C4 C10 -0.8(18) . . . . ?
C10 C5 C6 C7 7(2) . . . . ?
C5 C6 C7 C8 -7(2) . . . . ?
C6 C7 C8 C9 0.9(18) . . . . ?
C2 C1 C9 C10 1.4(17) . . . . ?
C1 C1 C9 C10 -178.2(10) 7_465 . . . ?
C2 C1 C9 C8 177.7(10) . . . . ?
C1 C1 C9 C8 -1.9(16) 7_465 . . . ?
C7 C8 C9 C10 4.0(16) . . . . ?
C7 C8 C9 C1 -172.4(11) . . . . ?
C1 C9 C10 C4 -3.4(16) . . . . ?
C8 C9 C10 C4 -179.8(11) . . . . ?
C1 C9 C10 C5 172.9(12) . . . . ?
C8 C9 C10 C5 -3.5(16) . . . . ?
C3 C4 C10 C9 3.1(16) . . . . ?
C3 C4 C10 C5 -173.3(12) . . . . ?
C6 C5 C10 C9 -1.9(18) . . . . ?
C6 C5 C10 C4 174.5(12) . . . . ?
C9 C1 C1 C9 -100.1(19) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.707
_diffrn_reflns_theta_full        28.83
_diffrn_measured_fraction_theta_full 0.707
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_045GPa
_database_code_depnum_ccdc_archive 'CCDC 1531191'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_045GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.412 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT340_RS_1,1'binaphthyl_045GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02258 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT369_RS_1,1'binaphthyl_045GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C2     -   C2_a   ..       1.58 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.89(1)
_cell_length_b                   6.204(5)
_cell_length_c                   10.011(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.14(4)
_cell_angle_gamma                90.00
_cell_volume                     1252.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       450000
_cell_measurement_reflns_used    486
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      28.67

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.45(2) GPa
(450000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3522
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         28.66
_reflns_number_total             486
_reflns_number_gt                312
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1074P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         486
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4188(7) 0.2620(7) 0.1700(7) 0.043(5) Uani 1 1 d GU . .
C1 C 0.4613(7) 0.1039(11) 0.2416(8) 0.044(5) Uani 1 1 d GU . .
C2 C 0.4368(7) -0.0602(8) 0.3088(6) 0.048(5) Uani 1 1 d GU . .
H2 H 0.4652 -0.1660 0.3567 0.057 Uiso 1 1 calc R . .
C3 C 0.3698(7) -0.0661(8) 0.3045(6) 0.056(6) Uani 1 1 d GU . .
H3 H 0.3533 -0.1758 0.3495 0.067 Uiso 1 1 calc R . .
C4 C 0.3273(7) 0.0921(11) 0.2329(7) 0.051(5) Uani 1 1 d GU . .
H4 H 0.2824 0.0882 0.2300 0.061 Uiso 1 1 calc R . .
C10 C 0.3518(7) 0.2561(8) 0.1656(6) 0.043(5) Uani 1 1 d GU . .
C5 C 0.3060(14) 0.4118(14) 0.0916(12) 0.053(5) Uani 1 1 d U . .
H5 H 0.2615 0.4048 0.0916 0.064 Uiso 1 1 calc R . .
C6 C 0.327(2) 0.568(2) 0.022(2) 0.074(7) Uani 1 1 d U . .
H6 H 0.2978 0.6652 -0.0329 0.089 Uiso 1 1 calc R . .
C7 C 0.3987(19) 0.5832(17) 0.0340(18) 0.043(5) Uani 1 1 d U . .
H7 H 0.4138 0.7003 -0.0072 0.051 Uiso 1 1 calc R . .
C8 C 0.4450(14) 0.4344(13) 0.1028(12) 0.044(5) Uani 1 1 d U . .
H8 H 0.4898 0.4446 0.1056 0.053 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
C9 0.041(13) 0.038(5) 0.053(7) 0.000(5) 0.020(9) 0.010(8)
C1 0.045(13) 0.043(3) 0.047(5) -0.013(5) 0.018(9) -0.005(8)
C2 0.050(13) 0.054(5) 0.047(6) -0.008(5) 0.025(9) -0.006(8)
C3 0.058(13) 0.056(6) 0.057(7) 0.003(5) 0.023(9) -0.008(8)
C4 0.052(13) 0.060(5) 0.043(6) -0.003(5) 0.016(8) 0.003(8)
C10 0.049(13) 0.057(6) 0.029(6) -0.005(5) 0.020(9) -0.001(9)
C5 0.054(13) 0.060(5) 0.044(6) -0.001(5) 0.012(9) 0.000(8)
C6 0.072(14) 0.071(8) 0.081(8) 0.011(6) 0.024(10) -0.002(9)
C7 0.044(13) 0.032(5) 0.046(7) 0.002(5) 0.001(9) -0.001(9)
C8 0.046(13) 0.041(4) 0.049(6) 0.006(4) 0.016(8) 0.005(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
C8 C9 1.445(19) . ?
C9 C10 1.3900 . ?
C1 C9 1.390(13) . ?
C1 C2 1.3900 . ?
C1 C1 1.58(3) 2_655 ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C10 1.3900 . ?
C4 H4 0.9300 . ?
C5 C10 1.42(2) . ?
C5 C6 1.34(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.46(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.38(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 120.0 . . ?
C8 C9 C1 119.6(13) . . ?
C10 C9 C1 120.4(12) . . ?
C2 C1 C9 120.0 . . ?
C2 C1 C1 116.4(6) . 2_655 ?
C9 C1 C1 123.5(5) . 2_655 ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C10 120.0 . . ?
C3 C4 H4 120.0 . . ?
C10 C4 H4 120.0 . . ?
C4 C10 C5 117.8(15) . . ?
C4 C10 C9 120.9(9) . . ?
C5 C10 C9 122.2(11) . . ?
C6 C5 C10 120(3) . . ?
C6 C5 H5 120.3 . . ?
C10 C5 H5 120.2 . . ?
C5 C6 C7 118(3) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 124.3(16) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 118.1 . . ?
C7 C8 C9 115(2) . . ?
C7 C8 H8 122.6 . . ?
C9 C8 H8 122.3 . . ?

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
C8 C9 C1 C2 178.8(7) . . . . ?
C10 C9 C1 C2 0.0(10) . . . . ?
C8 C8 C1 C1 -176.8(10) . . . 2_655 ?
C10 C9 C1 C1 -176.9(6) . . . 2_655 ?
C9 C1 C2 C3 0.0 . . . . ?
C1 C1 C2 C3 177.0(9) 2_655 . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C10 0.0 . . . . ?
C3 C4 C10 C5 178.8(7) . . . . ?
C3 C4 C10 C9 -0.1(9) . . . . ?
C8 C9 C10 C4 -178.7(7) . . . . ?
C1 C9 C10 C4 0.0(9) . . . . ?
C8 C9 C10 C5 2.5(11) . . . . ?
C1 C9 C10 C5 -178.8(7) . . . . ?
C4 C10 C5 C6 -177.9(9) . . . . ?
C9 C10 C5 C6 0.9(12) . . . . ?
C10 C5 C6 C7 -4.9(19) . . . . ?
C5 C6 C7 C8 6(2) . . . . ?
C6 C7 C8 C9 -3(2) . . . . ?
C10 C9 C8 C7 -1.4(13) . . . . ?
C1 C9 C8 C7 179.8(10) . . . . ?
C9 C1 C1 C9 64.2(13) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.412
_diffrn_reflns_theta_full        28.67
_diffrn_measured_fraction_theta_full 0.412
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_1_1'binaphthyl_1_53GPa
_database_code_depnum_ccdc_archive 'CCDC 1531203'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_1,1'binaphthyl_1.53GPa 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Poor quality of the data due to poor quality of measured crystal.
;
_vrf_PLAT029_1,1'binaphthyl_1.53GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.719 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT020_1,1'binaphthyl_1.53GPa 
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.224 Report
RESPONSE: Poor quality of the data due to poor quality of measured crystal.
;
_vrf_PLAT340_1,1'binaphthyl_1.53GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01575 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   6.8496(4)
_cell_length_b                   6.8496(4)
_cell_length_c                   26.691(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1252.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1530000
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      28.58


_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;

_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 1.53(2) GPa
(1530000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;


_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7536
_diffrn_reflns_av_R_equivalents  0.2240
_diffrn_reflns_av_sigmaI/netI    0.1797
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         28.58
_reflns_number_total             1145
_reflns_number_gt                465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0002P)²+0.04460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(1)
_refine_ls_number_reflns         1145
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.1095
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1673
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1280(17) 0.9893(16) 0.0080(4) 0.053(3) Uani 1 1 d U . .
C2 C 0.3108(18) 0.9580(17) -0.0154(4) 0.058(3) Uani 1 1 d U . .
H2 H 0.3427 1.0342 -0.0431 0.070 Uiso 1 1 calc R . .
C3 C 0.4405(18) 0.8245(17) 0.0002(4) 0.064(4) Uani 1 1 d U . .
H3 H 0.5582 0.8141 -0.0170 0.077 Uiso 1 1 calc R . .
C4 C 0.4087(17) 0.7017(17) 0.0403(4) 0.056(3) Uani 1 1 d U . .
H4 H 0.4989 0.6075 0.0501 0.067 Uiso 1 1 calc R . .
C5 C 0.1905(17) 0.6220(18) 0.1099(4) 0.060(3) Uani 1 1 d U . .
H5 H 0.2808 0.5304 0.1211 0.072 Uiso 1 1 calc R . .
C6 C 0.0208(17) 0.6534(18) 0.1360(4) 0.062(3) Uani 1 1 d U . .
H6 H -0.0001 0.5877 0.1661 0.074 Uiso 1 1 calc R . .
C7 C -0.1179(18) 0.7794(16) 0.1187(4) 0.057(3) Uani 1 1 d U . .
H7 H -0.2343 0.7930 0.1364 0.068 Uiso 1 1 calc R . .
C8 C -0.0898(17) 0.8852(17) 0.0765(3) 0.050(3) Uani 1 1 d U . .
H8 H -0.1859 0.9703 0.0651 0.060 Uiso 1 1 calc R . .
C9 C 0.0874(17) 0.8644(17) 0.0500(4) 0.051(3) Uani 1 1 d U . .
C10 C 0.2262(16) 0.7295(16) 0.0662(3) 0.046(3) Uani 1 1 d 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 0.051(4) 0.054(4) 0.054(4) 0.001(3) -0.002(3) 0.003(4)
C2 0.058(5) 0.058(5) 0.059(4) 0.002(3) 0.002(3) 0.000(4)
C3 0.062(5) 0.067(5) 0.064(4) -0.001(3) 0.003(3) 0.001(4)
C4 0.054(4) 0.053(4) 0.060(4) 0.001(3) -0.002(3) 0.003(4)
C5 0.057(5) 0.057(5) 0.065(4) 0.003(3) -0.007(3) -0.003(4)
C6 0.062(5) 0.060(5) 0.063(4) 0.007(3) 0.001(3) -0.001(4)
C7 0.055(4) 0.056(4) 0.058(4) 0.002(3) 0.000(3) 0.001(4)
C8 0.048(4) 0.048(4) 0.054(4) 0.000(3) -0.002(3) 0.001(4)
C9 0.050(4) 0.052(4) 0.051(4) 0.001(3) -0.009(3) -0.002(4)
C10 0.044(4) 0.047(4) 0.048(4) 0.000(3) -0.001(3) -0.001(4)

_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 1.415(15) . ?
C1 C9 1.437(14) . ?
C1 C1 1.41(2) 7_465 ?
C2 C3 1.341(15) . ?
C3 C4 1.380(14) . ?
C4 C10 1.441(14) . ?
C5 C6 1.373(15) . ?
C5 C10 1.402(13) . ?
C6 C7 1.364(14) . ?
C7 C8 1.355(13) . ?
C8 C9 1.412(15) . ?
C9 C10 1.394(14) . ?

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 C9 115.2(10) . . ?
C2 C1 C1 124.4(10) . 7_465 ?
C9 C1 C1 120.4(10) . 7_465 ?
C1 C2 C3 123.5(11) . . ?
C4 C3 C2 123.5(12) . . ?
C3 C4 C10 115.3(11) . . ?
C6 C5 C10 119.2(12) . . ?
C5 C6 C7 121.1(11) . . ?
C8 C7 C6 121.4(11) . . ?
C7 C8 C9 119.0(11) . . ?
C10 C9 C1 120.3(10) . . ?
C10 C9 C8 119.9(10) . . ?
C1 C9 C8 119.8(11) . . ?
C9 C10 C5 119.2(10) . . ?
C9 C10 C4 122.1(9) . . ?
C5 C10 C4 118.7(11) . . ?

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
C9 C1 C2 C3 -0.9(17) . . . . ?
C1 C1 C2 C3 -179.6(10) 7_465 . . . ?
C1 C2 C3 C4 0.7(19) . . . . ?
C2 C3 C4 C10 -1.8(17) . . . . ?
C10 C5 C6 C7 3.6(18) . . . . ?
C5 C6 C7 C8 -3.2(18) . . . . ?
C6 C7 C8 C9 -0.2(17) . . . . ?
C2 C1 C9 C10 2.3(15) . . . . ?
C1 C1 C9 C10 -178.9(9) 7_465 . . . ?
C2 C1 C9 C8 179.1(10) . . . . ?
C1 C1 C9 C8 -2.1(15) 7_465 . . . ?
C7 C8 C9 C10 3.0(16) . . . . ?
C7 C8 C9 C1 -173.8(10) . . . . ?
C1 C9 C10 C5 174.2(11) . . . . ?
C8 C9 C10 C5 -2.6(15) . . . . ?
C1 C9 C10 C4 -3.6(15) . . . . ?
C8 C9 C10 C4 179.6(10) . . . . ?
C6 C5 C10 C9 -0.7(16) . . . . ?
C6 C5 C10 C4 177.2(10) . . . . ?
C3 C4 C10 C9 3.2(15) . . . . ?
C3 C4 C10 C5 -174.6(10) . . . . ?
C9 C1 C1 C9 -99.4(18) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.719
_diffrn_reflns_theta_full        28.58
_diffrn_measured_fraction_theta_full 0.719
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_129GPa
_database_code_depnum_ccdc_archive 'CCDC 1531195'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_129GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.288 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT340_RS_1,1'binaphthyl_129GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02308 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT369_RS_1,1'binaphthyl_129GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C1     -   C6     ..       1.57 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.575(10)
_cell_length_b                   6.0390(9)
_cell_length_c                   9.8506(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.34(4)
_cell_angle_gamma                90.00
_cell_volume                     1180.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1290000
_cell_measurement_reflns_used    420
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      28.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 1.29(2) GPa
(1290000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3492
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         28.22
_reflns_number_total             420
_reflns_number_gt                201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1467P)²+1.6466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         420
_refine_ls_number_parameters     92
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.018
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4222(11) 0.2595(10) 0.1657(8) 0.024(3) Uani 1 1 d U . .
C1 C 0.4645(11) 0.0923(9) 0.2464(10) 0.029(3) Uani 1 1 d U . .
C2 C 0.4372(11) -0.0727(12) 0.3085(9) 0.029(3) Uani 1 1 d U . .
H2 H 0.4649 -0.1870 0.3535 0.035 Uiso 1 1 calc R . .
C3 C 0.3627(12) -0.0767(13) 0.3071(9) 0.039(3) Uani 1 1 d U . .
H3 H 0.3457 -0.1851 0.3554 0.047 Uiso 1 1 calc R . .
C4 C 0.3230(9) 0.0809(11) 0.2339(7) 0.039(3) Uani 1 1 d U . .
H4 H 0.2770 0.0734 0.2264 0.047 Uiso 1 1 calc R . .
C10 C 0.3463(13) 0.2535(11) 0.1690(8) 0.034(3) Uani 1 1 d U . .
C5 C 0.3049(9) 0.4224(11) 0.0920(7) 0.039(3) Uani 1 1 d U . .
H5 H 0.2591 0.4219 0.0869 0.047 Uiso 1 1 calc R . .
C6 C 0.3301(12) 0.5869(13) 0.0247(9) 0.038(3) Uani 1 1 d U . .
H6 H 0.3013 0.6972 -0.0224 0.046 Uiso 1 1 calc R . .
C7 C 0.4027(12) 0.5935(11) 0.0249(9) 0.034(3) Uani 1 1 d U . .
H7 H 0.4191 0.7031 -0.0234 0.041 Uiso 1 1 calc R . .
C8 C 0.4437(8) 0.4340(10) 0.0982(6) 0.031(3) Uani 1 1 d U . .
H8 H 0.4894 0.4428 0.1034 0.037 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
C9 0.025(5) 0.020(3) 0.029(3) -0.004(2) 0.008(4) 0.000(4)
C1 0.029(5) 0.028(3) 0.030(3) -0.002(3) 0.008(4) -0.002(3)
C2 0.028(5) 0.023(3) 0.034(3) 0.002(3) 0.004(4) 0.000(4)
C3 0.040(6) 0.040(3) 0.038(4) 0.003(3) 0.014(4) -0.001(4)
C4 0.039(5) 0.042(3) 0.036(3) -0.003(3) 0.008(4) -0.001(4)
C10 0.033(6) 0.033(4) 0.034(4) -0.002(3) 0.007(4) 0.002(4)
C5 0.038(5) 0.039(3) 0.039(3) -0.003(3) 0.009(3) 0.000(4)
C6 0.037(6) 0.034(3) 0.042(4) 0.004(3) 0.008(4) 0.001(4)
C7 0.035(6) 0.032(3) 0.036(4) 0.003(3) 0.011(4) -0.002(4)
C8 0.030(5) 0.029(3) 0.032(3) 0.000(2) 0.009(3) 0.001(4)

_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
C8 C9 1.380(16) . ?
C9 C10 1.57(4) . ?
C1 C9 1.429(17) . ?
C1 C1 1.44(5) 2_655 ?
C1 C2 1.37(2) . ?
C2 C3 1.53(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.335(17) . ?
C3 H3 0.9300 . ?
C4 C10 1.374(18) . ?
C4 H4 0.9300 . ?
C5 C10 1.414(16) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.49(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(16) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 118.3(12) . . ?
C8 C9 C1 125.6(19) . . ?
C10 C9 C1 115.8(13) . . ?
C2 C1 C9 125.7(11) 2_655 . ?
C2 C1 C1 119.2(15) 2_655 . ?
C9 C1 C1 120.1(18) . . ?
C1 C2 C3 122.6(10) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 117.6(14) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C10 123.5(19) . . ?
C3 C4 H4 118.2 . . ?
C10 C4 H4 118.2 . . ?
C4 C10 C5 124(2) . . ?
C4 C10 C9 119.9(13) . . ?
C5 C10 C9 115.7(13) . . ?
C6 C5 C10 122(2) . . ?
C6 C5 H5 119.0 . . ?
C10 C5 H5 119.0 . . ?
C5 C6 C7 121.7(12) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.6(13) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C9 124.4(18) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?

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
C8 C9 C1 C2 -37.4(12) . . . 2_655 ?
C10 C9 C1 C2 149.2(9) . . . 2_655 ?
C8 C8 C1 C1 180.0(8) . . . . ?
C10 C9 C1 C1 6.5(12) . . . . ?
C9 C1 C2 C3 142.5(11) 2_655 . . . ?
C1 C1 C2 C3 -5.6(13) . . . . ?
C1 C2 C3 C4 4.4(13) . . . . ?
C2 C3 C4 C10 -4.8(12) . . . . ?
C3 C4 C10 C5 -179.5(8) . . . . ?
C3 C4 C10 C9 6.2(11) . . . . ?
C8 C9 C10 C4 179.2(5) . . . . ?
C1 C9 C10 C4 -6.8(11) . . . . ?
C8 C9 C10 C5 4.5(11) . . . . ?
C1 C9 C10 C5 178.5(6) . . . . ?
C4 C10 C5 C6 -177.5(7) . . . . ?
C9 C10 C5 C6 -3.1(11) . . . . ?
C10 C5 C6 C7 1.9(12) . . . . ?
C5 C6 C7 C8 -2.0(13) . . . . ?
C6 C7 C8 C9 3.8(11) . . . . ?
C10 C9 C8 C7 -5.2(10) . . . . ?
C1 C9 C8 C7 -178.4(8) . . . . ?
C9 C1 C1 C9 72.1(17) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.288
_diffrn_reflns_theta_full        28.22
_diffrn_measured_fraction_theta_full 0.288
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_116GPa
_database_code_depnum_ccdc_archive 'CCDC 1531194'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_116GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.388 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.

;
_vrf_PLAT340_RS_1,1'binaphthyl_116GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01633 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.584(13)
_cell_length_b                   6.058(4)
_cell_length_c                   9.874(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.24(2)
_cell_angle_gamma                90.00
_cell_volume                     1188.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1160000
_cell_measurement_reflns_used    490
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      26.72

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 1.16(2) GPa
(1160000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2370
_diffrn_reflns_av_R_equivalents  0.1781
_diffrn_reflns_av_sigmaI/netI    0.1928
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         26.72
_reflns_number_total             490
_reflns_number_gt                223
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.02000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         490
_refine_ls_number_parameters     91
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.1158
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.2127
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.074
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4207(5) 0.263(2) 0.1721(11) 0.021(3) Uani 1 1 d U . .
C1 C 0.4630(5) 0.093(2) 0.2456(11) 0.027(3) Uani 1 1 d U . .
C2 C 0.4363(5) -0.069(2) 0.3126(11) 0.034(3) Uani 1 1 d U . .
H2 H 0.4649 -0.1755 0.3642 0.041 Uiso 1 1 calc R . .
C3 C 0.3668(6) -0.079(2) 0.3053(12) 0.036(4) Uani 1 1 d U . .
H3 H 0.3498 -0.1917 0.3498 0.044 Uiso 1 1 calc R . .
C4 C 0.3264(5) 0.075(2) 0.2348(11) 0.029(3) Uani 1 1 d U . .
H4 H 0.2807 0.0661 0.2303 0.034 Uiso 1 1 calc R . .
C10 C 0.3489(5) 0.255(2) 0.1647(11) 0.025(3) Uani 1 1 d U . .
C5 C 0.3077(6) 0.424(2) 0.0906(12) 0.030(3) Uani 1 1 d U . .
H5 H 0.2622 0.4234 0.0877 0.036 Uiso 1 1 calc R . .
C6 C 0.3305(5) 0.585(2) 0.0249(12) 0.033(3) Uani 1 1 d U . .
H6 H 0.3010 0.6905 -0.0248 0.039 Uiso 1 1 calc R . .
C7 C 0.4000(6) 0.596(2) 0.0300(12) 0.029(3) Uani 1 1 d U . .
H7 H 0.4166 0.7126 -0.0121 0.035 Uiso 1 1 calc R . .
C8 C 0.4422(5) 0.434(2) 0.0970(11) 0.026(3) Uani 1 1 d U . .
H8 H 0.4868 0.4354 0.0931 0.032 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
C9 0.016(6) 0.018(8) 0.027(7) -0.010(5) 0.002(5) -0.002(4)
C1 0.031(7) 0.029(8) 0.021(6) -0.006(5) 0.008(5) 0.010(5)
C2 0.042(6) 0.027(8) 0.035(7) 0.000(5) 0.013(5) 0.004(5)
C3 0.033(7) 0.034(9) 0.045(7) -0.003(6) 0.014(6) -0.002(5)
C4 0.017(6) 0.034(8) 0.039(7) -0.010(5) 0.015(6) -0.013(5)
C10 0.024(6) 0.024(8) 0.030(7) -0.016(5) 0.013(5) 0.000(5)
C5 0.024(6) 0.034(8) 0.029(7) 0.011(5) 0.000(6) -0.001(5)
C6 0.027(6) 0.022(8) 0.043(7) -0.006(5) -0.001(5) 0.003(5)
C7 0.031(6) 0.027(8) 0.030(7) -0.002(5) 0.006(5) 0.000(5)
C8 0.030(6) 0.027(8) 0.029(6) 0.004(5) 0.019(6) 0.001(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
C8 C9 1.409(15) . ?
C9 C10 1.461(15) . ?
C1 C9 1.419(16) . ?
C1 C2 1.376(15) . ?
C1 C1 1.50(2) 2_655 ?
C2 C3 1.416(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.319(15) . ?
C3 H3 0.9300 . ?
C4 C10 1.432(16) . ?
C4 H4 0.9300 . ?
C5 C10 1.408(15) . ?
C5 C6 1.320(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.420(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(15) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 116.8(10) . . ?
C8 C9 C1 124.5(10) . . ?
C10 C9 C1 118.5(12) . . ?
C2 C1 C9 119.7(11) . . ?
C2 C1 C1 119.9(9) . 2_655 ?
C9 C1 C1 120.4(8) . 2_655 ?
C1 C2 C3 122.1(11) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.1(12) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C10 123.5(11) . . ?
C3 C4 H4 118.2 . . ?
C10 C4 H4 118.2 . . ?
C4 C10 C5 125.3(11) . . ?
C4 C10 C9 117.0(10) . . ?
C5 C10 C9 117.6(12) . . ?
C6 C5 C10 123.3(12) . . ?
C6 C5 H5 118.4 . . ?
C10 C5 H5 118.4 . . ?
C5 C6 C7 120.1(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.4(13) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 122.4(11) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?

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
C8 C9 C1 C2 -178.3(10) . . . . ?
C10 C9 C1 C2 -3(2) . . . . ?
C8 C8 C1 C1 4(2) . . . 2_655 ?
C10 C9 C1 C1 179.2(9) . . . 2_655 ?
C9 C1 C2 C3 3(2) . . . . ?
C1 C1 C2 C3 -178.8(11) 2_655 . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C2 C3 C4 C10 0(2) . . . . ?
C3 C4 C10 C5 -178.8(16) . . . . ?
C3 C4 C10 C9 0.8(19) . . . . ?
C8 C9 C10 C4 176.7(10) . . . . ?
C1 C9 C10 C4 0.9(17) . . . . ?
C8 C9 C10 C5 -3.7(19) . . . . ?
C1 C9 C10 C5 -179.6(14) . . . . ?
C4 C10 C5 C6 -178.5(10) . . . . ?
C9 C10 C5 C6 2(2) . . . . ?
C10 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C6 C7 C8 C9 -5(2) . . . . ?
C10 C9 C8 C7 5.4(16) . . . . ?
C1 C9 C8 C7 -178.8(11) . . . . ?
C9 C1 C1 C9 65(3) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.388
_diffrn_reflns_theta_full        26.72
_diffrn_measured_fraction_theta_full 0.388
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_030GPa
_database_code_depnum_ccdc_archive 'CCDC 1531190'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_030GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.215 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT369_RS_1,1'binaphthyl_030GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C2     -   C2_a   ..       1.67 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT340_RS_1,1'binaphthyl_030GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03917 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.922(17)
_cell_length_b                   6.238(4)
_cell_length_c                   10.090(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.08(3)
_cell_angle_gamma                90.00
_cell_volume                     1271.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       300000
_cell_measurement_reflns_used    347
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      28.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.30(2) GPa
(300000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3544
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         28.49
_reflns_number_total             347
_reflns_number_gt                156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         347
_refine_ls_number_parameters     91
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.426(2) 0.2611(18) 0.1729(18) 0.055(6) Uani 1 1 d U . .
C1 C 0.459(2) 0.0996(11) 0.240(2) 0.044(5) Uani 1 1 d U . .
C2 C 0.4407(19) -0.0616(17) 0.3148(17) 0.047(6) Uani 1 1 d U . .
H2 H 0.4701 -0.1581 0.3691 0.057 Uiso 1 1 calc R . .
C3 C 0.363(2) -0.063(2) 0.296(2) 0.066(6) Uani 1 1 d U . .
H3 H 0.3434 -0.1757 0.3323 0.080 Uiso 1 1 calc R . .
C4 C 0.3266(14) 0.0892(13) 0.2327(12) 0.058(5) Uani 1 1 d U . .
H4 H 0.2818 0.0917 0.2297 0.069 Uiso 1 1 calc R . .
C10 C 0.3539(19) 0.2585(17) 0.1649(17) 0.034(5) Uani 1 1 d U . .
C5 C 0.3045(13) 0.4088(14) 0.0915(11) 0.057(5) Uani 1 1 d U . .
H5 H 0.2601 0.3994 0.0912 0.068 Uiso 1 1 calc R . .
C6 C 0.328(2) 0.565(2) 0.023(2) 0.079(7) Uani 1 1 d U . .
H6 H 0.2989 0.6607 -0.0317 0.095 Uiso 1 1 calc R . .
C7 C 0.3987(18) 0.5844(15) 0.0339(17) 0.042(5) Uani 1 1 d U . .
H7 H 0.4135 0.7017 -0.0068 0.051 Uiso 1 1 calc R . .
C8 C 0.4449(13) 0.4351(11) 0.1026(11) 0.041(5) Uani 1 1 d U . .
H8 H 0.4890 0.4504 0.1020 0.049 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
C9 0.053(14) 0.057(6) 0.061(8) -0.004(5) 0.027(9) 0.008(10)
C1 0.044(13) 0.040(3) 0.051(5) -0.012(5) 0.016(10) -0.002(8)
C2 0.048(13) 0.049(5) 0.048(7) -0.006(4) 0.016(9) 0.007(9)
C3 0.066(14) 0.062(7) 0.071(8) 0.005(5) 0.019(9) 0.000(9)
C4 0.059(13) 0.064(5) 0.052(6) -0.005(5) 0.018(9) -0.001(8)
C10 0.035(13) 0.043(5) 0.029(6) -0.011(5) 0.016(9) 0.004(9)
C5 0.056(13) 0.064(5) 0.052(6) 0.003(5) 0.018(9) 0.002(8)
C6 0.078(14) 0.076(8) 0.087(9) 0.009(6) 0.028(10) -0.003(9)
C7 0.043(13) 0.029(4) 0.049(7) 0.010(4) 0.001(9) 0.002(9)
C8 0.044(13) 0.036(4) 0.043(6) 0.008(4) 0.013(8) 0.002(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
C8 C9 1.407(18) . ?
C9 C10 1.49(6) . ?
C1 C9 1.31(3) . ?
C1 C2 1.367(16) . ?
C1 C1 1.68(8) 2_655 ?
C2 C3 1.59(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.28(3) . ?
C3 H3 0.9300 . ?
C4 C10 1.454(19) . ?
C4 H4 0.9300 . ?
C5 C10 1.45(3) . ?
C5 C6 1.36(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.45(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.39(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 113(2) . . ?
C8 C9 C1 133(3) . . ?
C10 C9 C1 114(2) . . ?
C2 C1 C9 132(3) . . ?
C2 C1 C1 111(3) . 2_655 ?
C9 C1 C1 116.4(18) . 2_655 ?
C1 C2 C3 111(2) . . ?
C1 C2 H2 124.3 . . ?
C3 C2 H2 124.3 . . ?
C4 C3 C2 120.6(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C10 121(3) . . ?
C3 C4 H4 119.3 . . ?
C10 C4 H4 119.3 . . ?
C4 C10 C5 113(3) . . ?
C4 C10 C9 120(2) . . ?
C5 C10 C9 126.8(14) . . ?
C6 C5 C10 114(3) . . ?
C6 C5 H5 122.8 . . ?
C10 C5 H5 122.8 . . ?
C5 C6 C7 121(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 122.7(15) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 121(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?

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
C8 C9 C1 C2 175.7(18) . . . . ?
C10 C9 C1 C2 -6(3) . . . . ?
C8 C8 C1 C1 5(3) . . . 2_655 ?
C10 C9 C1 C1 -177.1(18) . . . 2_655 ?
C9 C1 C2 C3 9(3) . . . . ?
C1 C1 C2 C3 -179.8(16) 2_655 . . . ?
C1 C2 C3 C4 -8(2) . . . . ?
C2 C3 C4 C10 5(2) . . . . ?
C3 C4 C10 C5 176.5(11) . . . . ?
C3 C4 C10 C9 -2(2) . . . . ?
C8 C9 C10 C4 -179.8(7) . . . . ?
C1 C9 C10 C4 2(2) . . . . ?
C8 C9 C10 C5 2(2) . . . . ?
C1 C9 C10 C5 -176.6(12) . . . . ?
C4 C10 C5 C6 -177.8(11) . . . . ?
C9 C10 C5 C6 1(2) . . . . ?
C10 C5 C6 C7 -5(2) . . . . ?
C5 C6 C7 C8 7(2) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C10 C9 C8 C7 -0.2(19) . . . . ?
C1 C9 C8 C7 177.8(15) . . . . ?
C9 C1 C1 C9 61(3) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.215
_diffrn_reflns_theta_full        28.49
_diffrn_measured_fraction_theta_full 0.215
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_1_1'binaphthyl_250K
_database_code_depnum_ccdc_archive 'CCDC 1531201'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31


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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.1562(4)
_cell_length_b                   7.1562(4)
_cell_length_c                   27.473(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1406.93(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    1829
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.03

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26352
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         29.03
_reflns_number_total             1829
_reflns_number_gt                1709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         1829
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1274(5) 0.9856(4) 0.00836(11) 0.0488(9) Uani 1 1 d . . .
C2 C 0.2927(5) 0.9677(5) -0.01552(13) 0.0645(11) Uani 1 1 d . . .
H2 H 0.3174 1.0442 -0.0421 0.077 Uiso 1 1 calc R . .
C3 C 0.4272(5) 0.8357(6) -0.00087(14) 0.0706(12) Uani 1 1 d . . .
H3 H 0.5387 0.8246 -0.0180 0.085 Uiso 1 1 calc R . .
C4 C 0.3948(5) 0.7250(5) 0.03817(13) 0.0624(11) Uani 1 1 d . . .
H4 H 0.4844 0.6386 0.0479 0.075 Uiso 1 1 calc R . .
C5 C 0.1881(6) 0.6321(5) 0.10573(13) 0.0664(12) Uani 1 1 d . . .
H5 H 0.2768 0.5459 0.1161 0.080 Uiso 1 1 calc R . .
C6 C 0.0267(6) 0.6502(6) 0.13087(14) 0.0729(12) Uani 1 1 d . . .
H6 H 0.0070 0.5786 0.1586 0.087 Uiso 1 1 calc R . .
C7 C -0.1097(6) 0.7750(5) 0.11552(12) 0.0630(11) Uani 1 1 d . . .
H7 H -0.2214 0.7848 0.1326 0.076 Uiso 1 1 calc R . .
C8 C -0.0804(5) 0.8826(5) 0.07562(12) 0.0529(10) Uani 1 1 d . . .
H8 H -0.1729 0.9653 0.0656 0.063 Uiso 1 1 calc R . .
C9 C 0.0897(5) 0.8713(4) 0.04875(11) 0.0432(9) Uani 1 1 d . . .
C10 C 0.2246(5) 0.7405(5) 0.06427(11) 0.0505(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.046(2) 0.054(2) 0.0464(19) -0.0032(18) -0.0018(18) -0.0006(19)
C2 0.058(3) 0.080(3) 0.055(2) 0.006(2) 0.008(2) 0.004(2)
C3 0.052(2) 0.097(3) 0.063(2) -0.014(2) 0.011(2) 0.008(3)
C4 0.050(2) 0.067(3) 0.070(2) -0.005(2) -0.004(2) 0.014(2)
C5 0.067(3) 0.063(3) 0.070(3) 0.008(2) -0.013(2) 0.006(2)
C6 0.078(3) 0.074(3) 0.067(3) 0.023(2) 0.003(2) -0.004(3)
C7 0.064(3) 0.066(3) 0.059(2) 0.014(2) 0.011(2) -0.001(2)
C8 0.050(2) 0.054(2) 0.056(2) 0.0041(19) 0.0003(19) 0.003(2)
C9 0.045(2) 0.046(2) 0.0390(17) -0.0040(17) -0.0035(17) -0.0044(19)
C10 0.052(2) 0.055(2) 0.0453(19) -0.0023(17) -0.0071(18) 0.001(2)

_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 1.359(4) . ?
C1 C9 1.405(4) . ?
C1 C1 1.507(6) 7_465 ?
C2 C3 1.407(5) . ?
C3 C4 1.353(4) . ?
C4 C10 1.418(4) . ?
C5 C6 1.352(5) . ?
C5 C10 1.403(4) . ?
C6 C7 1.389(5) . ?
C7 C8 1.356(4) . ?
C8 C9 1.426(4) . ?
C9 C10 1.410(4) . ?

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 C9 119.6(3) . . ?
C2 C1 C1 120.2(3) . 7_465 ?
C9 C1 C1 120.3(3) . 7_465 ?
C1 C2 C3 121.4(3) . . ?
C4 C3 C2 120.1(4) . . ?
C3 C4 C10 120.2(4) . . ?
C6 C5 C10 121.4(4) . . ?
C5 C6 C7 120.5(4) . . ?
C8 C7 C6 120.1(4) . . ?
C7 C8 C9 121.2(3) . . ?
C1 C9 C10 119.6(3) . . ?
C1 C9 C8 122.7(3) . . ?
C10 C9 C8 117.7(3) . . ?
C9 C10 C5 119.0(3) . . ?
C9 C10 C4 119.1(3) . . ?
C5 C10 C4 121.8(4) . . ?

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
C9 C1 C2 C3 0.4(5) . . . . ?
C1 C1 C2 C3 -179.6(3) 7_465 . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C10 0.4(5) . . . . ?
C10 C5 C6 C7 1.4(6) . . . . ?
C5 C6 C7 C8 -1.3(6) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C2 C1 C9 C10 0.6(5) . . . . ?
C1 C1 C9 C10 -179.4(3) 7_465 . . . ?
C2 C1 C9 C8 179.9(3) . . . . ?
C1 C1 C9 C8 -0.1(4) 7_465 . . . ?
C7 C8 C9 C1 -177.5(3) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C1 C9 C10 C5 177.6(3) . . . . ?
C8 C9 C10 C5 -1.7(4) . . . . ?
C1 C9 C10 C4 -1.1(5) . . . . ?
C8 C9 C10 C4 179.6(3) . . . . ?
C6 C5 C10 C9 0.2(5) . . . . ?
C6 C5 C10 C4 178.8(4) . . . . ?
C3 C4 C10 C9 0.5(5) . . . . ?
C3 C4 C10 C5 -178.1(3) . . . . ?
C9 C1 C1 C9 -101.3(5) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.03
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_1_1'binaphthyl_2_73GPa
_database_code_depnum_ccdc_archive 'CCDC 1531204'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1,1'binaphthyl_2.73GPa 
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.412 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT026_1,1'binaphthyl_2.73GPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .........   35%
RESPONSE: Due to limited acces to reciprocal lattice due to 
the specificity of the applied measuring technique and 
use of a diamond-anvil cell; Poor quality of the data due to 
poor quality of measured crystal.
;
_vrf_PLAT340_1,1'binaphthyl_2.73GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01575 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   6.7514(15)
_cell_length_b                   6.7514(15)
_cell_length_c                   26.507(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1208.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2730000
_cell_measurement_reflns_used    564
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.78

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 2.73(2) GPa
(2730000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            963
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_sigmaI/netI    0.2294
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.78
_reflns_number_total             564
_reflns_number_gt                199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0002P)²+0.04460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(1)
_refine_ls_number_reflns         564
_refine_ls_number_parameters     92
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.128
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.127(4) 0.982(4) 0.0091(8) 0.075(8) Uani 1 1 d U . .
C2 C 0.308(3) 0.961(3) -0.0142(7) 0.059(6) Uani 1 1 d U . .
H2 H 0.3400 1.0460 -0.0405 0.071 Uiso 1 1 calc R . .
C3 C 0.444(3) 0.821(3) -0.0006(6) 0.051(6) Uani 1 1 d U . .
H3 H 0.5581 0.8061 -0.0199 0.061 Uiso 1 1 calc R . .
C4 C 0.417(3) 0.701(3) 0.0406(6) 0.054(6) Uani 1 1 d U . .
H4 H 0.5136 0.6118 0.0514 0.065 Uiso 1 1 calc R . .
C5 C 0.191(3) 0.631(3) 0.1127(7) 0.061(7) Uani 1 1 d U . .
H5 H 0.2884 0.5527 0.1273 0.073 Uiso 1 1 calc R . .
C6 C 0.013(3) 0.657(4) 0.1366(7) 0.071(7) Uani 1 1 d U . .
H6 H -0.0139 0.5858 0.1658 0.086 Uiso 1 1 calc R . .
C7 C -0.124(3) 0.783(3) 0.1183(7) 0.058(6) Uani 1 1 d U . .
H7 H -0.2420 0.8028 0.1358 0.070 Uiso 1 1 calc R . .
C8 C -0.090(3) 0.883(4) 0.0746(7) 0.068(7) Uani 1 1 d U . .
H8 H -0.1875 0.9640 0.0607 0.082 Uiso 1 1 calc R . .
C9 C 0.091(4) 0.862(4) 0.0509(8) 0.075(7) Uani 1 1 d U . .
C10 C 0.224(3) 0.722(3) 0.0668(7) 0.057(6) Uani 1 1 d 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 0.069(12) 0.076(12) 0.081(11) -0.009(10) -0.006(9) 0.019(12)
C2 0.061(11) 0.055(11) 0.063(9) 0.019(8) 0.011(9) 0.009(11)
C3 0.050(10) 0.053(10) 0.048(8) -0.001(8) 0.014(8) 0.013(11)
C4 0.039(10) 0.057(11) 0.065(9) 0.014(9) 0.001(8) 0.018(11)
C5 0.061(11) 0.060(11) 0.063(9) 0.003(9) -0.026(9) -0.013(11)
C6 0.066(11) 0.077(12) 0.071(10) 0.023(9) -0.010(9) 0.010(11)
C7 0.048(10) 0.060(11) 0.066(9) -0.006(9) 0.006(8) 0.009(11)
C8 0.067(11) 0.070(12) 0.068(10) 0.021(9) -0.004(9) 0.006(11)
C9 0.065(11) 0.079(12) 0.080(11) 0.002(10) -0.011(9) 0.017(12)
C10 0.054(10) 0.062(11) 0.053(9) -0.011(8) 0.018(8) 0.040(11)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.38(3) . ?
C1 C9 1.40(3) . ?
C1 C1 1.47(4) 7_465 ?
C2 C3 1.36(3) . ?
C3 C4 1.37(2) . ?
C4 C10 1.49(2) . ?
C5 C6 1.37(3) . ?
C5 C10 1.38(2) . ?
C6 C7 1.35(2) . ?
C7 C8 1.36(2) . ?
C8 C9 1.38(3) . ?
C9 C10 1.37(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 C9 117(2) . . ?
C2 C1 C1 121(2) . 7_465 ?
C9 C1 C1 122(2) . 7_465 ?
C1 C2 C3 123(2) . . ?
C4 C3 C2 122.1(18) . . ?
C3 C4 C10 115(2) . . ?
C6 C5 C10 120(2) . . ?
C5 C6 C7 121(2) . . ?
C6 C7 C8 120(2) . . ?
C7 C8 C9 119(3) . . ?
C10 C9 C1 122(2) . . ?
C10 C9 C8 121(2) . . ?
C1 C9 C8 117(3) . . ?
C9 C10 C4 120.0(19) . . ?
C9 C10 C5 118(2) . . ?
C4 C10 C5 121(2) . . ?

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
C9 C1 C2 C3 5(4) . . . . ?
C1 C1 C2 C3 -176.1(18) 7_465 . . . ?
C1 C2 C3 C4 -6(3) . . . . ?
C2 C3 C4 C10 5(3) . . . . ?
C10 C5 C6 C7 -6(4) . . . . ?
C5 C6 C7 C8 2(3) . . . . ?
C6 C7 C8 C9 -4(3) . . . . ?
C2 C1 C9 C10 -3(4) . . . . ?
C1 C1 C9 C10 177.6(19) 7_465 . . . ?
C2 C1 C9 C8 180(2) . . . . ?
C1 C1 C9 C8 1(3) 7_465 . . . ?
C7 C8 C9 C10 10(4) . . . . ?
C7 C8 C9 C1 -173(2) . . . . ?
C1 C9 C10 C4 3(3) . . . . ?
C8 C9 C10 C4 179(2) . . . . ?
C1 C9 C10 C5 170(2) . . . . ?
C8 C9 C10 C5 -13(3) . . . . ?
C3 C4 C10 C9 -3(3) . . . . ?
C3 C4 C10 C5 -170.6(19) . . . . ?
C6 C5 C10 C9 11(3) . . . . ?
C6 C5 C10 C4 179(2) . . . . ?
C9 C1 C1 C9 -101(4) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.412
_diffrn_reflns_theta_full        27.78
_diffrn_measured_fraction_theta_full 0.412
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_RS-1_1'binaphthyl_005GPa
_database_code_depnum_ccdc_archive 'CCDC 1531188'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_005GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.309 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.

;
_vrf_PLAT026_RS_1,1'binaphthyl_005GPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         32 %     
RESPONSE: Due to limited acces to reciprocal lattice due to 
the specificity of the applied measuring technique and 
use of a diamond-anvil cell; Poor quality of the data due to 
small size of measured crystal.
;
_vrf_PLAT340_RS_1,1'binaphthyl_005GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01842 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   21.124(19)
_cell_length_b                   6.342(5)
_cell_length_c                   10.189(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.08(1)
_cell_angle_gamma                90.00
_cell_volume                     1318(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       50000
_cell_measurement_reflns_used    452
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      27.16

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.05(2) GPa
(50000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3090
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_sigmaI/netI    0.1988
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.39
_diffrn_reflns_theta_max         27.16
_reflns_number_total             452
_reflns_number_gt                143
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0818P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         452
_refine_ls_number_parameters     88
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      0.986
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4220(8) 0.2638(10) 0.1735(14) 0.043(4) Uani 1 1 d U . .
C1 C 0.4645(6) 0.1075(10) 0.2469(13) 0.041(4) Uani 1 1 d U . .
C2 C 0.4391(7) -0.0499(11) 0.3067(15) 0.061(5) Uani 1 1 d U . .
H2 H 0.4668 -0.1551 0.3528 0.073 Uiso 1 1 calc R . .
C3 C 0.3701(6) -0.0595(9) 0.3012(12) 0.066(5) Uani 1 1 d U . .
H3 H 0.3542 -0.1679 0.3452 0.079 Uiso 1 1 calc R . .
C4 C 0.3283(6) 0.0896(9) 0.2319(12) 0.067(5) Uani 1 1 d RU . .
H4 H 0.2839 0.0826 0.2273 0.080 Uiso 1 1 calc R . .
C10 C 0.3530(8) 0.2553(12) 0.1667(15) 0.059(5) Uani 1 1 d U . .
C5 C 0.3101(8) 0.4122(13) 0.0924(17) 0.075(5) Uani 1 1 d U . .
H5 H 0.2656 0.4076 0.0878 0.090 Uiso 1 1 calc R . .
C6 C 0.3341(8) 0.5667(11) 0.0289(15) 0.068(5) Uani 1 1 d U . .
H6 H 0.3057 0.6695 -0.0184 0.081 Uiso 1 1 calc R . .
C7 C 0.3998(9) 0.5765(13) 0.0323(16) 0.067(5) Uani 1 1 d U . .
H7 H 0.4146 0.6831 -0.0149 0.080 Uiso 1 1 calc R . .
C8 C 0.4439(8) 0.4308(11) 0.1047(14) 0.057(5) Uani 1 1 d U . .
H8 H 0.4882 0.4427 0.1081 0.069 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
C9 0.038(10) 0.044(4) 0.046(9) -0.002(5) 0.007(8) 0.001(5)
C1 0.032(10) 0.045(3) 0.045(9) -0.001(5) 0.007(8) -0.008(5)
C2 0.045(10) 0.072(4) 0.066(10) 0.001(5) 0.015(8) 0.000(5)
C3 0.059(10) 0.066(5) 0.073(10) 0.002(5) 0.019(9) -0.012(5)
C4 0.061(10) 0.068(4) 0.075(10) 0.001(5) 0.025(8) -0.004(5)
C10 0.048(10) 0.067(5) 0.066(10) -0.002(5) 0.024(9) -0.005(6)
C5 0.065(10) 0.083(5) 0.082(10) -0.001(6) 0.030(9) 0.002(6)
C6 0.056(10) 0.072(5) 0.074(10) 0.009(5) 0.014(9) 0.009(5)
C7 0.058(10) 0.069(5) 0.074(10) 0.011(5) 0.018(9) 0.003(6)
C8 0.054(10) 0.058(4) 0.062(9) 0.010(5) 0.018(8) 0.003(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
C8 C9 1.413(9) . ?
C9 C10 1.442(16) . ?
C1 C9 1.413(17) . ?
C1 C2 1.352(8) . ?
C1 C1 1.48(2) 2_655 ?
C2 C3 1.445(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.3586 . ?
C3 H3 0.9300 . ?
C4 C10 1.413(8) . ?
C4 H4 0.9300 . ?
C5 C10 1.424(19) . ?
C5 C6 1.344(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(19) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 117.5(11) . . ?
C8 C9 C1 122.9(12) . . ?
C10 C9 C1 119.6(8) . . ?
C2 C1 C9 119.0(11) . . ?
C2 C1 C1 119.8(11) . 2_655 ?
C9 C1 C1 121.2(7) . 2_655 ?
C1 C2 C3 121.9(11) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 119.5(8) . . ?
C3 C4 H4 120.2 . . ?
C10 C4 H4 120.2 . . ?
C4 C10 C5 120.5(13) . . ?
C4 C10 C9 119.8(12) . . ?
C5 C10 C9 119.7(8) . . ?
C6 C5 C10 119.9(13) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 121.5(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.2(9) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.2(12) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?

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
C8 C9 C1 C2 -178.2(9) . . . . ?
C10 C9 C1 C2 1.5(15) . . . . ?
C8 C8 C1 C1 -1.5(18) . . . 2_655 ?
C10 C9 C1 C1 178.3(11) . . . 2_655 ?
C9 C1 C2 C3 -1.9(15) . . . . ?
C1 C1 C2 C3 -178.7(12) 2_655 . . . ?
C1 C2 C3 C4 1.5(12) . . . . ?
C2 C3 C4 C10 -0.8(7) . . . . ?
C3 C4 C10 C5 179.4(9) . . . . ?
C3 C4 C10 C9 0.5(11) . . . . ?
C8 C9 C10 C4 179.0(9) . . . . ?
C1 C9 C10 C4 -0.8(15) . . . . ?
C8 C9 C10 C5 0.0(17) . . . . ?
C1 C9 C10 C5 -179.8(12) . . . . ?
C4 C10 C5 C6 -178.8(9) . . . . ?
C9 C10 C5 C6 0.1(19) . . . . ?
C10 C5 C6 C7 0.8(19) . . . . ?
C5 C6 C7 C8 -1.9(19) . . . . ?
C6 C7 C8 C9 2.0(18) . . . . ?
C10 C9 C8 C7 -1.1(16) . . . . ?
C1 C9 C8 C7 178.7(12) . . . . ?
C9 C1 C1 C9 70(2) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.309
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.309
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_1_1'binaphthyl_0_01MPa
_database_code_depnum_ccdc_archive 'CCDC 1531202'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.2063(2)
_cell_length_b                   7.2063(2)
_cell_length_c                   27.5057(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1428.39(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1454
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.48

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;

_exptl_special_details           
; 
 ? 
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23469
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         26.48
_reflns_number_total             1454
_reflns_number_gt                954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0360P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(1)
_refine_ls_number_reflns         1454
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1265(3) 0.9855(3) 0.00813(6) 0.0521(5) Uani 1 1 d . . .
C2 C 0.2914(3) 0.9673(3) -0.01551(7) 0.0687(6) Uani 1 1 d . . .
H2 H 0.3160 1.0431 -0.0421 0.082 Uiso 1 1 calc R . .
C3 C 0.4255(3) 0.8372(3) -0.00094(8) 0.0770(7) Uani 1 1 d . . .
H3 H 0.5365 0.8268 -0.0180 0.092 Uiso 1 1 calc R . .
C4 C 0.3928(3) 0.7270(3) 0.03801(8) 0.0706(6) Uani 1 1 d . . .
H4 H 0.4818 0.6412 0.0477 0.085 Uiso 1 1 calc R . .
C5 C 0.1881(3) 0.6342(3) 0.10562(8) 0.0733(7) Uani 1 1 d . . .
H5 H 0.2766 0.5490 0.1160 0.088 Uiso 1 1 calc R . .
C6 C 0.0281(4) 0.6515(3) 0.13098(9) 0.0808(7) Uani 1 1 d . . .
H6 H 0.0090 0.5805 0.1588 0.097 Uiso 1 1 calc R . .
C7 C -0.1084(3) 0.7755(3) 0.11548(7) 0.0717(6) Uani 1 1 d . . .
H7 H -0.2192 0.7849 0.1326 0.086 Uiso 1 1 calc R . .
C8 C -0.0803(3) 0.8832(3) 0.07530(7) 0.0560(5) Uani 1 1 d . . .
H8 H -0.1726 0.9648 0.0652 0.067 Uiso 1 1 calc R . .
C9 C 0.0891(3) 0.8718(3) 0.04869(6) 0.0471(5) Uani 1 1 d . . .
C10 C 0.2239(3) 0.7416(3) 0.06405(7) 0.0534(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0507(12) 0.0611(13) 0.0444(11) -0.0033(10) -0.0010(10) -0.0002(10)
C2 0.0616(14) 0.0881(17) 0.0564(12) 0.0086(12) 0.0082(12) 0.0072(13)
C3 0.0566(14) 0.1017(19) 0.0726(15) -0.0071(14) 0.0117(13) 0.0102(14)
C4 0.0548(14) 0.0784(16) 0.0787(15) -0.0084(14) -0.0075(13) 0.0213(13)
C5 0.0776(18) 0.0678(15) 0.0744(16) 0.0086(14) -0.0162(13) 0.0054(14)
C6 0.093(2) 0.0789(18) 0.0701(15) 0.0251(13) 0.0007(15) -0.0017(16)
C7 0.0708(16) 0.0768(16) 0.0674(14) 0.0108(13) 0.0134(12) -0.0028(14)
C8 0.0555(13) 0.0558(13) 0.0565(12) 0.0028(10) 0.0005(11) -0.0009(11)
C9 0.0484(12) 0.0494(11) 0.0436(10) -0.0037(9) -0.0058(9) -0.0026(10)
C10 0.0561(13) 0.0516(12) 0.0524(12) -0.0014(10) -0.0104(10) 0.0038(11)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.361(3) . ?
C1 C9 1.410(2) . ?
C1 C1 1.505(4) 7_465 ?
C2 C3 1.405(3) . ?
C3 C4 1.355(3) . ?
C4 C10 1.416(3) . ?
C5 C6 1.353(3) . ?
C5 C10 1.405(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.366(2) . ?
C8 C9 1.426(2) . ?
C9 C10 1.415(2) . ?

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 C9 119.25(18) . . ?
C2 C1 C1 120.84(17) . 7_465 ?
C9 C1 C1 119.91(17) . 7_465 ?
C1 C2 C3 121.9(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C10 120.4(2) . . ?
C6 C5 C10 121.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C8 C9 120.6(2) . . ?
C1 C9 C10 119.35(18) . . ?
C1 C9 C8 122.42(18) . . ?
C10 C9 C8 118.23(18) . . ?
C9 C10 C5 118.81(19) . . ?
C9 C10 C4 119.23(19) . . ?
C5 C10 C4 121.9(2) . . ?

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
C9 C1 C2 C3 0.5(3) . . . . ?
C1 C1 C2 C3 179.77(18) 7_465 . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C10 0.2(3) . . . . ?
C10 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C2 C1 C9 C10 0.2(3) . . . . ?
C1 C1 C9 C10 -179.08(15) 7_465 . . . ?
C2 C1 C9 C8 179.89(16) . . . . ?
C1 C1 C9 C8 0.6(2) 7_465 . . . ?
C7 C8 C9 C1 -177.51(17) . . . . ?
C7 C8 C9 C10 2.2(3) . . . . ?
C1 C9 C10 C5 177.54(18) . . . . ?
C8 C9 C10 C5 -2.1(3) . . . . ?
C1 C9 C10 C4 -0.7(3) . . . . ?
C8 C9 C10 C4 179.64(17) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C6 C5 C10 C4 178.6(2) . . . . ?
C3 C4 C10 C9 0.5(3) . . . . ?
C3 C4 C10 C5 -177.7(2) . . . . ?
C9 C1 C1 C9 -101.9(3) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.081
_refine_diff_density_min         -0.083
_refine_diff_density_rms         0.021
####################################################################### 
# 
# 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_1_1'binaphthyl_100K
_database_code_depnum_ccdc_archive 'CCDC 1531198'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'
_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_

_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
_cell_length_a                   7.0872(3)
_cell_length_b                   7.0872(3)
_cell_length_c                   27.477(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1380.13(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1787
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      29.11

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25896
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.11
_reflns_number_total             1787
_reflns_number_gt                1581
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0317P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(3)
_refine_ls_number_reflns         1787
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1296(3) 0.9867(3) 0.00827(8) 0.0270(6) Uani 1 1 d . . .
C2 C 0.2973(3) 0.9674(3) -0.01576(8) 0.0342(6) Uani 1 1 d . . .
H2 H 0.3225 1.0442 -0.0424 0.041 Uiso 1 1 calc R . .
C3 C 0.4325(3) 0.8337(3) -0.00099(8) 0.0359(7) Uani 1 1 d . . .
H3 H 0.5450 0.8216 -0.0181 0.043 Uiso 1 1 calc R . .
C4 C 0.3989(3) 0.7218(3) 0.03842(8) 0.0316(6) Uani 1 1 d . . .
H4 H 0.4892 0.6347 0.0483 0.038 Uiso 1 1 calc R . .
C5 C 0.1909(3) 0.6275(3) 0.10606(8) 0.0331(7) Uani 1 1 d . . .
H5 H 0.2802 0.5400 0.1163 0.040 Uiso 1 1 calc R . .
C6 C 0.0271(4) 0.6471(3) 0.13159(8) 0.0352(7) Uani 1 1 d . . .
H6 H 0.0070 0.5754 0.1595 0.042 Uiso 1 1 calc R . .
C7 C -0.1112(4) 0.7749(3) 0.11600(8) 0.0313(6) Uani 1 1 d . . .
H7 H -0.2237 0.7859 0.1332 0.038 Uiso 1 1 calc R . .
C8 C -0.0812(3) 0.8830(3) 0.07581(8) 0.0278(6) Uani 1 1 d . . .
H8 H -0.1746 0.9664 0.0657 0.033 Uiso 1 1 calc R . .
C9 C 0.0906(3) 0.8709(3) 0.04883(7) 0.0245(6) Uani 1 1 d . . .
C10 C 0.2272(3) 0.7376(3) 0.06432(7) 0.0255(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0269(14) 0.0279(14) 0.0263(13) -0.0028(11) -0.0027(11) -0.0020(12)
C2 0.0376(16) 0.0384(17) 0.0265(12) 0.0050(12) 0.0041(12) -0.0008(14)
C3 0.0277(15) 0.0472(17) 0.0328(14) -0.0098(13) 0.0051(12) 0.0008(13)
C4 0.0247(14) 0.0346(15) 0.0355(13) -0.0033(13) -0.0018(12) 0.0058(13)
C5 0.0337(17) 0.0330(15) 0.0327(14) 0.0041(13) -0.0069(12) 0.0029(14)
C6 0.0390(17) 0.0343(16) 0.0323(14) 0.0089(12) -0.0014(13) -0.0018(14)
C7 0.0302(15) 0.0305(15) 0.0331(13) 0.0026(12) 0.0065(12) -0.0018(13)
C8 0.0262(14) 0.0277(14) 0.0296(13) -0.0015(11) 0.0000(11) 0.0003(12)
C9 0.0276(14) 0.0240(13) 0.0218(11) -0.0024(11) -0.0042(11) -0.0047(12)
C10 0.0268(14) 0.0262(14) 0.0236(12) -0.0031(10) -0.0029(11) 0.0010(12)

_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 1.366(3) . ?
C1 C9 1.411(3) . ?
C1 C1 1.503(4) 7_465 ?
C2 C3 1.408(3) . ?
C3 C4 1.363(3) . ?
C4 C10 1.414(3) . ?
C5 C6 1.364(3) . ?
C5 C10 1.411(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.361(3) . ?
C8 C9 1.429(3) . ?
C9 C10 1.418(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 C9 119.6(2) . . ?
C2 C1 C1 120.5(2) . 7_465 ?
C9 C1 C1 119.9(2) . 7_465 ?
C1 C2 C3 121.3(2) . . ?
C4 C3 C2 120.1(2) . . ?
C3 C4 C10 120.3(2) . . ?
C6 C5 C10 121.1(2) . . ?
C5 C6 C7 120.3(2) . . ?
C8 C7 C6 120.2(2) . . ?
C7 C8 C9 121.4(2) . . ?
C10 C9 C1 119.4(2) . . ?
C10 C9 C8 117.8(2) . . ?
C1 C9 C8 122.8(2) . . ?
C9 C10 C5 119.2(2) . . ?
C9 C10 C4 119.3(2) . . ?
C5 C10 C4 121.5(2) . . ?

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
C9 C1 C2 C3 0.1(3) . . . . ?
C1 C1 C2 C3 -179.65(19) 7_465 . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C10 0.8(3) . . . . ?
C10 C5 C6 C7 1.5(4) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C2 C1 C9 C10 0.7(3) . . . . ?
C1 C1 C9 C10 -179.51(18) 7_465 . . . ?
C2 C1 C9 C8 179.9(2) . . . . ?
C1 C1 C9 C8 -0.3(3) 7_465 . . . ?
C7 C8 C9 C10 2.1(3) . . . . ?
C7 C8 C9 C1 -177.1(2) . . . . ?
C1 C9 C10 C5 177.4(2) . . . . ?
C8 C9 C10 C5 -1.8(3) . . . . ?
C1 C9 C10 C4 -0.8(3) . . . . ?
C8 C9 C10 C4 179.94(19) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C6 C5 C10 C4 178.2(2) . . . . ?
C3 C4 C10 C9 0.0(3) . . . . ?
C3 C4 C10 C5 -178.2(2) . . . . ?
C9 C1 C1 C9 -101.3(3) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_070GPa
_database_code_depnum_ccdc_archive 'CCDC 1531193'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_070GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.348 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT334_RS_1,1'binaphthyl_070GPa 
;
PROBLEM: Small Average Benzene  C-C Dist. C1     -C6            1.32 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT340_RS_1,1'binaphthyl_070GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01075 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.770(5)
_cell_length_b                   6.1526(14)
_cell_length_c                   9.991(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.30(2)
_cell_angle_gamma                90.00
_cell_volume                     1231.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       700000
_cell_measurement_reflns_used    532
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.70(2) GPa
(700000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1863
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         28.31
_reflns_number_total             532
_reflns_number_gt                413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1467P)²+0.06466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         532
_refine_ls_number_parameters     91
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4212(6) 0.2500(2) 0.1714(2) 0.0420(6) Uani 1 1 d U . .
C1 C 0.4662(7) 0.0965(4) 0.2450(1) 0.0360(3) Uani 1 1 d U . .
C2 C 0.4363(9) -0.0665(6) 0.3075(4) 0.0330(4) Uani 1 1 d U . .
H2 H 0.4631 -0.1804 0.3512 0.039 Uiso 1 1 calc R . .
C3 C 0.3630(2) -0.0690(2) 0.3082(1) 0.0590(6) Uani 1 1 d U . .
H3 H 0.3453 -0.1708 0.3573 0.071 Uiso 1 1 calc R . .
C4 C 0.3278(1) 0.0837(1) 0.2340(3) 0.0490(4) Uani 1 1 d U . .
H4 H 0.2822 0.0848 0.2270 0.058 Uiso 1 1 calc R . .
C10 C 0.3512(7) 0.2380(1) 0.1676(1) 0.0380(6) Uani 1 1 d U . .
C5 C 0.3079(6) 0.4194(1) 0.0918(1) 0.046(4) Uani 1 1 d U . .
H5 H 0.2630 0.4230 0.0904 0.055 Uiso 1 1 calc R . .
C6 C 0.3330(2) 0.5780(2) 0.0252(5) 0.0470(5) Uani 1 1 d U . .
H6 H 0.3046 0.6843 -0.0241 0.056 Uiso 1 1 calc R . .
C7 C 0.4010(2) 0.5860(2) 0.0294(6) 0.0510(5) Uani 1 1 d U . .
H7 H 0.4167 0.6964 -0.0169 0.061 Uiso 1 1 calc R . .
C8 C 0.4433(5) 0.4341(1) 0.0999(1) 0.0480(4) Uani 1 1 d U . .
H8 H 0.4883 0.4449 0.1030 0.057 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
C9 0.044(7) 0.043(7) 0.041(5) 0.000(4) 0.013(4) 0.000(4)
C1 0.036(6) 0.035(4) 0.036(4) 0.000(4) 0.010(4) -0.001(4)
C2 0.033(6) 0.030(4) 0.036(4) 0.005(3) 0.009(4) 0.003(4)
C3 0.058(7) 0.060(6) 0.058(6) 0.002(4) 0.014(4) -0.001(4)
C4 0.050(6) 0.049(4) 0.048(5) -0.002(4) 0.014(4) -0.002(4)
C10 0.038(7) 0.038(8) 0.039(5) 0.001(4) 0.010(4) 0.000(4)
C5 0.047(6) 0.044(4) 0.046(4) -0.004(3) 0.014(4) 0.001(4)
C6 0.046(7) 0.043(5) 0.050(6) 0.005(3) 0.012(4) 0.002(4)
C7 0.050(7) 0.049(5) 0.052(6) 0.002(4) 0.013(4) -0.002(4)
C8 0.049(6) 0.048(5) 0.047(5) 0.002(3) 0.015(4) 0.002(4)

_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
C8 C9 1.476(8) . ?
C9 C10 1.45(4) . ?
C1 C9 1.394(11) . ?
C1 C1 1.38(2) 2_655 ?
C1 C2 1.41(4) . ?
C2 C3 1.52(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.296(4) . ?
C3 H3 0.9300 . ?
C4 C10 1.322(8) . ?
C4 H4 0.9300 . ?
C5 C10 1.506(10) . ?
C5 C6 1.360(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.347(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 117.7(6) . . ?
C8 C9 C1 121.6(11) . . ?
C10 C9 C1 120.6(7) . . ?
C2 C1 C9 130.1(6) 2_655 . ?
C2 C1 C1 124(3) 2_655 . ?
C9 C1 C1 113.8(13) . . ?
C1 C2 C3 124.5(8) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 H3 123.1 . . ?
C2 C3 H3 123.1 . . ?
C3 C4 C10 125.5(6) . . ?
C3 C4 H4 117.3 . . ?
C10 C4 H4 117.3 . . ?
C4 C10 C5 121.6(6) . . ?
C4 C10 C9 121.6(6) . . ?
C5 C10 C9 116.0(7) . . ?
C6 C5 C10 121.5(10) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 121.6(6) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 122.9(9) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.7 . . ?

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
C8 C9 C1 C2 -38.6(6) . . . 2_655 ?
C10 C9 C1 C2 143.9(6) . . . 2_655 ?
C8 C8 C1 C1 179.5(3) . . . . ?
C10 C9 C1 C1 2.0(4) . . . . ?
C9 C1 C2 C3 142.7(6) 2_655 . . . ?
C1 C1 C2 C3 -5.4(4) . . . . ?
C1 C2 C3 C4 6.2(4) . . . . ?
C2 C3 C4 C10 -3.3(4) . . . . ?
C3 C4 C10 C5 -175.50(16) . . . . ?
C3 C4 C10 C9 0.4(3) . . . . ?
C8 C9 C10 C4 -177.0(3) . . . . ?
C1 C9 C10 C4 0.5(3) . . . . ?
C8 C9 C10 C5 -0.9(3) . . . . ?
C1 C9 C10 C5 176.7(2) . . . . ?
C4 C10 C5 C6 179.3(3) . . . . ?
C9 C10 C5 C6 3.3(3) . . . . ?
C10 C5 C6 C7 -3.1(5) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C6 C7 C8 C9 2.1(6) . . . . ?
C10 C9 C8 C7 -1.7(4) . . . . ?
C1 C9 C8 C7 -179.2(4) . . . . ?
C9 C1 C1 C9 69.6(3) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.348
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.348
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_010GPa
_database_code_depnum_ccdc_archive 'CCDC 1531189'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_010GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.311 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.

;
_vrf_PLAT340_RS_1,1'binaphthyl_010GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01583 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   21.064(15)
_cell_length_b                   6.305(4)
_cell_length_c                   10.165(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.11(2)
_cell_angle_gamma                90.00
_cell_volume                     1303.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       100000
_cell_measurement_reflns_used    441
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      27.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.10(2) GPa
(100000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2811
_diffrn_reflns_av_R_equivalents  0.1258
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         27.01
_reflns_number_total             441
_reflns_number_gt                193
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1346P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         441
_refine_ls_number_parameters     91
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4192(7) 0.2626(11) 0.1704(8) 0.049(4) Uani 1 1 d U . .
C1 C 0.4652(6) 0.1071(11) 0.2482(9) 0.047(4) Uani 1 1 d U . .
C2 C 0.4376(8) -0.0565(11) 0.3103(9) 0.062(4) Uani 1 1 d U . .
H2 H 0.4650 -0.1629 0.3568 0.075 Uiso 1 1 calc R . .
C3 C 0.3711(8) -0.0646(12) 0.3044(10) 0.069(4) Uani 1 1 d U . .
H3 H 0.3550 -0.1739 0.3479 0.083 Uiso 1 1 calc R . .
C4 C 0.3288(6) 0.0884(11) 0.2345(7) 0.058(3) Uani 1 1 d U . .
H4 H 0.2842 0.0821 0.2308 0.070 Uiso 1 1 calc R . .
C10 C 0.3528(7) 0.2523(11) 0.1695(8) 0.049(4) Uani 1 1 d U . .
C5 C 0.3099(7) 0.4129(11) 0.0960(7) 0.062(4) Uani 1 1 d U . .
H5 H 0.2655 0.4105 0.0938 0.075 Uiso 1 1 calc R . .
C6 C 0.3336(8) 0.5700(12) 0.0290(9) 0.062(4) Uani 1 1 d U . .
H6 H 0.3049 0.6720 -0.0192 0.074 Uiso 1 1 calc R . .
C7 C 0.3987(8) 0.5800(12) 0.0315(9) 0.061(4) Uani 1 1 d U . .
H7 H 0.4135 0.6893 -0.0143 0.073 Uiso 1 1 calc R . .
C8 C 0.4428(6) 0.4306(11) 0.1006(7) 0.057(4) Uani 1 1 d U . .
H8 H 0.4870 0.4388 0.1019 0.068 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
C9 0.052(11) 0.055(5) 0.043(4) -0.001(3) 0.016(6) 0.003(5)
C1 0.048(11) 0.045(5) 0.049(4) -0.007(3) 0.017(7) 0.001(3)
C2 0.063(11) 0.057(5) 0.063(5) 0.002(4) 0.010(7) 0.004(5)
C3 0.069(11) 0.066(5) 0.074(5) 0.008(4) 0.022(7) -0.007(5)
C4 0.062(10) 0.059(5) 0.050(4) -0.002(3) 0.008(5) -0.007(4)
C10 0.047(10) 0.051(5) 0.050(4) -0.007(4) 0.013(6) -0.001(5)
C5 0.062(11) 0.062(5) 0.057(4) -0.006(4) 0.007(5) -0.004(5)
C6 0.059(11) 0.061(5) 0.063(5) 0.009(4) 0.014(6) 0.009(5)
C7 0.063(11) 0.056(5) 0.064(5) -0.003(4) 0.016(6) -0.010(5)
C8 0.056(11) 0.059(5) 0.053(4) 0.007(3) 0.011(5) -0.006(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
C8 C9 1.434(12) . ?
C9 C10 1.398(16) . ?
C1 C9 1.457(15) . ?
C1 C2 1.411(12) . ?
C1 C1 1.46(2) 2_655 ?
C2 C3 1.388(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(15) . ?
C3 H3 0.9300 . ?
C4 C10 1.391(11) . ?
C4 H4 0.9300 . ?
C5 C10 1.431(14) . ?
C5 C6 1.369(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(14) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 120.4(9) . . ?
C8 C9 C1 119.9(12) . . ?
C10 C9 C1 119.6(7) . . ?
C2 C1 C9 116.2(11) . . ?
C2 C1 C1 121.1(9) . 2_655 ?
C9 C1 C1 122.4(6) . 2_655 ?
C1 C2 C3 122.4(9) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 120.4(8) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C10 119.9(12) . . ?
C3 C4 H4 120.1 . . ?
C10 C4 H4 120.1 . . ?
C4 C10 C5 121.0(13) . . ?
C4 C10 C9 121.3(9) . . ?
C5 C10 C9 117.7(8) . . ?
C6 C5 C10 120.6(13) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 121.2(11) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 121.2(9) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 118.8(12) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?

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
C8 C9 C1 C2 -178.1(6) . . . . ?
C10 C9 C1 C2 4.7(12) . . . . ?
C8 C8 C1 C1 -3.7(14) . . . 2_655 ?
C10 C9 C1 C1 179.1(8) . . . 2_655 ?
C9 C1 C2 C3 -3.3(12) . . . . ?
C1 C1 C2 C3 -177.7(10) 2_655 . . . ?
C1 C2 C3 C4 1.0(13) . . . . ?
C2 C3 C4 C10 -0.1(12) . . . . ?
C3 C4 C10 C5 179.9(6) . . . . ?
C3 C4 C10 C9 1.7(11) . . . . ?
C8 C9 C10 C4 178.8(6) . . . . ?
C1 C9 C10 C4 -4.1(12) . . . . ?
C8 C9 C10 C5 0.6(11) . . . . ?
C1 C9 C10 C5 177.7(7) . . . . ?
C4 C10 C5 C6 -178.0(6) . . . . ?
C9 C10 C5 C6 0.2(11) . . . . ?
C10 C5 C6 C7 -0.8(12) . . . . ?
C5 C6 C7 C8 0.7(14) . . . . ?
C6 C7 C8 C9 0.1(12) . . . . ?
C10 C9 C8 C7 -0.7(11) . . . . ?
C1 C9 C8 C7 -177.8(7) . . . . ?
C9 C1 C1 C9 74.4(17) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.311
_diffrn_reflns_theta_full        27.01
_diffrn_measured_fraction_theta_full 0.311
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_221GPa
_database_code_depnum_ccdc_archive 'CCDC 1531196'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_221GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.252 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT026_RS_1,1'binaphthyl_221GPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         38 %     
RESPONSE: Due to limited acces to reciprocal lattice due to 
the specificity of the applied measuring technique and 
use of a diamond-anvil cell; Poor quality of the data due to 
small size of measured crystal.
;
_vrf_PLAT369_RS_1,1'binaphthyl_221GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C2     -   C2_a   ..       1.58 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.41(2)
_cell_length_b                   5.934(3)
_cell_length_c                   9.683(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.49(3)
_cell_angle_gamma                90.00
_cell_volume                     1130.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2210000
_cell_measurement_reflns_used    356
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      28.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 2.21(2) GPa
(2210000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3300
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         28.39
_reflns_number_total             356
_reflns_number_gt                135
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1564P)²+0.01961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         356
_refine_ls_number_parameters     92
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      0.977
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4160(2) 0.2560(2) 0.1704(7) 0.0430(5) Uani 1 1 d U . .
C1 C 0.4610(2) 0.0880(4) 0.2471(9) 0.0350(4) Uani 1 1 d U . .
C2 C 0.4350(2) -0.0770(2) 0.3123(8) 0.0500(5) Uani 1 1 d U . .
H2 H 0.4634 -0.1875 0.3642 0.060 Uiso 1 1 calc R . .
C3 C 0.3700(2) -0.0860(2) 0.3038(8) 0.0440(5) Uani 1 1 d U . .
H3 H 0.3542 -0.2056 0.3484 0.052 Uiso 1 1 calc R . .
C4 C 0.3203(6) 0.0758(7) 0.2312(2) 0.0480(4) Uani 1 1 d U . .
H4 H 0.2744 0.0690 0.2275 0.058 Uiso 1 1 calc R . .
C10 C 0.3510(3) 0.2540(2) 0.1633(7) 0.0470(6) Uani 1 1 d U . .
C5 C 0.3059(6) 0.4248(6) 0.0899(1) 0.0420(4) Uani 1 1 d U . .
H5 H 0.2602 0.4271 0.0882 0.050 Uiso 1 1 calc R . .
C6 C 0.3350(2) 0.5880(2) 0.0210(2) 0.0470(5) Uani 1 1 d U . .
H6 H 0.3056 0.6950 -0.0332 0.056 Uiso 1 1 calc R . .
C7 C 0.3960(2) 0.6020(2) 0.0270(2) 0.0490(6) Uani 1 1 d U . .
H7 H 0.4111 0.7235 -0.0167 0.059 Uiso 1 1 calc R . .
C8 C 0.4436(6) 0.4356(6) 0.09711(1) 0.0440(4) Uani 1 1 d U . .
H8 H 0.4891 0.4401 0.0970 0.052 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
C9 0.043(7) 0.045(6) 0.040(5) -0.002(3) 0.011(4) 0.000(4)
C1 0.036(6) 0.040(4) 0.032(4) -0.003(3) 0.011(4) 0.000(4)
C2 0.049(7) 0.049(6) 0.051(6) 0.000(3) 0.012(4) 0.000(4)
C3 0.044(7) 0.043(5) 0.043(5) -0.001(3) 0.012(4) 0.000(4)
C4 0.049(6) 0.051(4) 0.046(4) -0.002(3) 0.014(4) -0.001(4)
C10 0.047(7) 0.048(6) 0.047(6) -0.001(3) 0.013(4) 0.001(4)
C5 0.043(6) 0.043(4) 0.041(4) 0.002(3) 0.012(4) 0.002(4)
C6 0.048(7) 0.045(5) 0.049(6) 0.005(3) 0.013(4) 0.001(4)
C7 0.048(7) 0.048(6) 0.050(6) 0.003(3) 0.012(4) -0.001(4)
C8 0.044(6) 0.045(4) 0.042(4) -0.002(3) 0.012(4) 0.001(4)

_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
C8 C9 1.473(8) . ?
C9 C10 1.310(8) . ?
C1 C9 1.423(7) . ?
C1 C2 1.348(7) . ?
C1 C1 1.578(7) 2_655 ?
C2 C3 1.308(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.437(9) . ?
C3 H3 0.9300 . ?
C4 C10 1.471(9) . ?
C4 H4 0.9300 . ?
C5 C10 1.425(8) . ?
C5 C6 1.396(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.234(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 119.6(5) . . ?
C8 C9 C1 118.8(5) . . ?
C10 C9 C1 121.6(4) . . ?
C2 C1 C9 126.8(5) . 2_655 ?
C2 C1 C1 118.3(4) . . ?
C9 C1 C1 121.5(4) 2_655 . ?
C1 C2 C3 121.3(5) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 125.1(5) . . ?
C4 C3 H3 117.4 . . ?
C2 C3 H3 117.4 . . ?
C3 C4 C10 111.7(9) . . ?
C3 C4 H4 124.0 . . ?
C10 C4 H4 124.0 . . ?
C4 C10 C5 116.0(7) . . ?
C4 C10 C9 122.0(5) . . ?
C5 C10 C9 122.0(6) . . ?
C6 C5 C10 115.6(9) . . ?
C6 C5 H5 122.1 . . ?
C10 C5 H5 122.1 . . ?
C5 C6 C7 125.3(5) . . ?
C5 C6 H6 117.5 . . ?
C7 C6 H6 117.5 . . ?
C8 C7 C6 121.8(5) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 115.6(8) . . ?
C7 C8 H8 122.3 . . ?
C9 C8 H8 122.3 . . ?

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
C8 C9 C1 C2 -179.1(11) . . . . ?
C10 C9 C1 C2 0(3) . . . . ?
C8 C8 C1 C1 -1(2) . . . 2_655 ?
C10 C9 C1 C1 179(2) . . . 2_655 ?
C9 C1 C2 C3 150.7(5) 2_655 . . . ?
C1 C1 C2 C3 1(3) . . . . ?
C1 C2 C3 C4 -2(3) . . . . ?
C2 C3 C4 C10 1(3) . . . . ?
C3 C4 C10 C5 -179.2(4) . . . . ?
C3 C4 C10 C9 0.5(7) . . . . ?
C8 C9 C10 C4 178.4(9) . . . . ?
C1 C9 C10 C4 -1(3) . . . . ?
C8 C9 C10 C5 -2(3) . . . . ?
C1 C9 C10 C5 178.3(11) . . . . ?
C4 C10 C5 C6 -177.6(12) . . . . ?
C9 C10 C5 C6 3(2) . . . . ?
C10 C5 C6 C7 -4.8(4) . . . . ?
C5 C6 C7 C8 5.8(3) . . . . ?
C6 C7 C8 C9 -4.3(4) . . . . ?
C10 C9 C8 C7 2.4(6) . . . . ?
C1 C9 C8 C7 -177.8(4) . . . . ?
C9 C1 C1 C9 69(3) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.252
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.252
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_055GPa
_database_code_depnum_ccdc_archive 'CCDC 1531192'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_055GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.379 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.
;
_vrf_PLAT026_RS_1,1'binaphthyl_055GPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         37 %     
RESPONSE: Due to limited acces to reciprocal lattice due to 
the specificity of the applied measuring technique and 
use of a diamond-anvil cell; Poor quality of the data due to 
small size of measured crystal.
;
_vrf_PLAT340_RS_1,1'binaphthyl_055GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03583 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT369_RS_1,1'binaphthyl_055GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C3     -   C4     ..       1.57 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.809(16)
_cell_length_b                   6.185(2)
_cell_length_c                   10.044(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.22(1)
_cell_angle_gamma                90.00
_cell_volume                     1247.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       550000
_cell_measurement_reflns_used    378
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      28.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.55(2) GPa
(550000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3491
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         28.15
_reflns_number_total             378
_reflns_number_gt                138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0942P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         378
_refine_ls_number_parameters     92
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1963
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2129
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      0.994
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4250(19) 0.263(2) 0.1656(16) 0.062(8) Uani 1 1 d U . .
C1 C 0.469(2) 0.0961(11) 0.245(2) 0.045(5) Uani 1 1 d U . .
C2 C 0.4381(16) -0.0629(15) 0.3077(10) 0.032(5) Uani 1 1 d U . .
H2 H 0.4645 -0.1748 0.3542 0.038 Uiso 1 1 calc R . .
C3 C 0.3621(18) -0.065(2) 0.3044(17) 0.083(8) Uani 1 1 d U . .
H3 H 0.3440 -0.1695 0.3505 0.100 Uiso 1 1 calc R . .
C4 C 0.3258(14) 0.0895(13) 0.2330(9) 0.055(5) Uani 1 1 d U . .
H4 H 0.2800 0.0917 0.2231 0.065 Uiso 1 1 calc R . .
C10 C 0.3560(19) 0.2559(18) 0.1697(11) 0.030(6) Uani 1 1 d U . .
C5 C 0.3062(14) 0.4133(13) 0.0943(9) 0.055(5) Uani 1 1 d U . .
H5 H 0.2614 0.3977 0.0914 0.066 Uiso 1 1 calc R . .
C6 C 0.3262(17) 0.574(2) 0.0321(14) 0.064(7) Uani 1 1 d U . .
H6 H 0.2963 0.6817 -0.0081 0.077 Uiso 1 1 calc R . .
C7 C 0.4009(16) 0.5862(18) 0.0242(11) 0.041(6) Uani 1 1 d U . .
H7 H 0.4155 0.6900 -0.0282 0.050 Uiso 1 1 calc R . .
C8 C 0.4425(13) 0.4357(11) 0.0990(7) 0.041(5) Uani 1 1 d U . .
H8 H 0.4876 0.4523 0.1054 0.049 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
C9 0.061(14) 0.056(7) 0.068(8) -0.006(5) 0.016(9) 0.002(9)
C1 0.045(13) 0.049(4) 0.041(4) -0.015(6) 0.012(10) -0.006(9)
C2 0.038(13) 0.029(4) 0.033(4) 0.001(3) 0.018(8) 0.009(8)
C3 0.081(14) 0.085(7) 0.082(8) -0.007(6) 0.017(9) -0.008(10)
C4 0.052(13) 0.058(5) 0.051(5) 0.001(4) 0.008(8) 0.011(8)
C10 0.032(13) 0.039(5) 0.021(4) 0.003(4) 0.011(8) 0.000(9)
C5 0.054(13) 0.059(5) 0.052(5) -0.001(4) 0.012(8) -0.011(8)
C6 0.063(13) 0.055(6) 0.070(7) 0.003(5) 0.011(9) 0.004(9)
C7 0.042(13) 0.039(5) 0.044(5) 0.007(4) 0.012(9) 0.001(9)
C8 0.042(12) 0.042(4) 0.039(4) 0.005(4) 0.014(8) 0.005(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
C8 C9 1.36(3) . ?
C9 C10 1.45(6) . ?
C1 C9 1.47(3) . ?
C1 C2 1.41(4) . ?
C1 C1 1.26(10) 2_655 ?
C2 C3 1.57(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.31(2) . ?
C3 H3 0.9300 . ?
C4 C10 1.44(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.48(3) . ?
C5 C6 1.30(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.58(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.36(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 115.6(19) . . ?
C8 C9 C1 128(3) . . ?
C10 C9 C1 116(3) . . ?
C2 C1 C9 116(4) . . ?
C2 C1 C1 122.9(18) . 2_655 ?
C9 C1 C1 121(3) . 2_655 ?
C1 C2 C3 124.8(17) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C4 C3 C2 116(2) . . ?
C4 C3 H3 122.0 . . ?
C2 C3 H3 122.0 . . ?
C3 C4 C10 120(3) . . ?
C3 C4 H4 119.8 . . ?
C10 C4 H4 119.8 . . ?
C4 C10 C5 112(3) . . ?
C4 C10 C9 125.9(17) . . ?
C5 C10 C9 122.2(19) . . ?
C6 C5 C10 119(3) . . ?
C6 C5 H5 120.6 . . ?
C10 C5 H5 120.6 . . ?
C5 C6 C7 120(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 115.6(19) . . ?
C8 C7 H7 122.2 . . ?
C6 C7 H7 122.2 . . ?
C7 C8 C9 127(3) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?

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
C8 C9 C1 C2 178.2(13) . . . . ?
C10 C9 C1 C2 5(2) . . . . ?
C8 C8 C1 C1 -3(3) . . . 2_655 ?
C10 C9 C1 C1 -176(2) . . . 2_655 ?
C9 C1 C2 C3 -4(2) . . . . ?
C1 C1 C2 C3 177(2) 2_655 . . . ?
C1 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 C10 -3.6(18) . . . . ?
C3 C4 C10 C5 180.0(9) . . . . ?
C3 C4 C10 C9 6(2) . . . . ?
C8 C9 C10 C4 179.5(6) . . . . ?
C1 C9 C10 C4 -7(2) . . . . ?
C8 C9 C10 C5 6(2) . . . . ?
C1 C9 C10 C5 -179.9(8) . . . . ?
C4 C10 C5 C6 179.7(10) . . . . ?
C9 C10 C5 C6 -6.0(18) . . . . ?
C10 C5 C6 C7 6.3(17) . . . . ?
C5 C6 C7 C8 -7.3(19) . . . . ?
C6 C7 C8 C9 8.2(19) . . . . ?
C10 C9 C8 C7 -8(2) . . . . ?
C1 C9 C8 C7 179.0(14) . . . . ?
C9 C1 C1 C9 70(4) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.379
_diffrn_reflns_theta_full        28.15
_diffrn_measured_fraction_theta_full 0.379
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1_1'binaphthyl_200K
_database_code_depnum_ccdc_archive 'CCDC 1531200'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.1316(2)
_cell_length_b                   7.1316(2)
_cell_length_c                   27.467(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1396.96(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1809
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      29.09

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26194
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         29.09
_reflns_number_total             1809
_reflns_number_gt                1798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0317P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(1)
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1276(4) 0.9856(4) 0.00848(9) 0.0401(8) Uani 1 1 d . . .
C2 C 0.2940(4) 0.9672(4) -0.01575(10) 0.0510(8) Uani 1 1 d . . .
H2 H 0.3187 1.0435 -0.0425 0.061 Uiso 1 1 calc R . .
C3 C 0.4290(4) 0.8345(4) -0.00095(10) 0.0562(9) Uani 1 1 d . . .
H3 H 0.5408 0.8231 -0.0181 0.067 Uiso 1 1 calc R . .
C4 C 0.3962(4) 0.7234(4) 0.03826(10) 0.0508(8) Uani 1 1 d . . .
H4 H 0.4859 0.6364 0.0480 0.061 Uiso 1 1 calc R . .
C5 C 0.1897(4) 0.6304(4) 0.10580(10) 0.0549(9) Uani 1 1 d . . .
H5 H 0.2786 0.5438 0.1162 0.066 Uiso 1 1 calc R . .
C6 C 0.0271(5) 0.6486(4) 0.13108(11) 0.0598(9) Uani 1 1 d . . .
H6 H 0.0071 0.5765 0.1588 0.072 Uiso 1 1 calc R . .
C7 C -0.1100(5) 0.7749(4) 0.11570(10) 0.0536(9) Uani 1 1 d . . .
H7 H -0.2217 0.7854 0.1330 0.064 Uiso 1 1 calc R . .
C8 C -0.0812(4) 0.8824(4) 0.07570(9) 0.0428(8) Uani 1 1 d . . .
H8 H -0.1743 0.9649 0.0656 0.051 Uiso 1 1 calc R . .
C9 C 0.0901(4) 0.8711(4) 0.04886(9) 0.0364(7) Uani 1 1 d . . .
C10 C 0.2266(4) 0.7396(4) 0.06423(9) 0.0406(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0383(17) 0.0451(18) 0.0370(16) -0.0028(15) -0.0028(15) -0.0001(15)
C2 0.050(2) 0.061(2) 0.0415(16) 0.0071(16) 0.0046(17) 0.0024(19)
C3 0.043(2) 0.074(2) 0.0517(19) -0.0112(18) 0.0094(17) 0.0068(19)
C4 0.041(2) 0.056(2) 0.0556(19) -0.0058(18) -0.0004(17) 0.0094(18)
C5 0.054(2) 0.053(2) 0.058(2) 0.0066(19) -0.0088(17) 0.0053(19)
C6 0.068(3) 0.056(2) 0.055(2) 0.0162(17) 0.0006(19) -0.004(2)
C7 0.053(2) 0.053(2) 0.0542(18) 0.0101(17) 0.0104(17) 0.000(2)
C8 0.0402(19) 0.0429(19) 0.0453(17) -0.0011(15) -0.0004(15) 0.0012(16)
C9 0.0396(18) 0.0371(17) 0.0324(15) -0.0035(14) -0.0032(14) -0.0019(16)
C10 0.0448(19) 0.0387(18) 0.0381(16) -0.0035(14) -0.0077(15) 0.0023(16)

_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 1.367(4) . ?
C1 C9 1.403(3) . ?
C1 C1 1.506(5) 7_465 ?
C2 C3 1.410(4) . ?
C3 C4 1.357(3) . ?
C4 C10 1.409(3) . ?
C5 C6 1.358(4) . ?
C5 C10 1.407(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.355(3) . ?
C8 C9 1.429(3) . ?
C9 C10 1.416(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 C9 119.6(2) . . ?
C2 C1 C1 119.9(2) . 7_465 ?
C9 C1 C1 120.5(3) . 7_465 ?
C1 C2 C3 121.1(3) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C10 120.1(3) . . ?
C6 C5 C10 121.5(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C6 120.3(3) . . ?
C7 C8 C9 121.1(3) . . ?
C10 C9 C1 119.4(3) . . ?
C10 C9 C8 118.1(3) . . ?
C1 C9 C8 122.5(3) . . ?
C9 C10 C5 118.7(3) . . ?
C9 C10 C4 119.6(3) . . ?
C5 C10 C4 121.7(3) . . ?

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
C9 C1 C2 C3 0.1(4) . . . . ?
C1 C1 C2 C3 -179.5(2) 7_465 . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C10 0.3(4) . . . . ?
C10 C5 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C8 -0.9(5) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C2 C1 C9 C10 0.8(4) . . . . ?
C1 C1 C9 C10 -179.6(2) 7_465 . . . ?
C2 C1 C9 C8 -179.7(2) . . . . ?
C1 C1 C9 C8 -0.1(4) 7_465 . . . ?
C7 C8 C9 C10 2.1(4) . . . . ?
C7 C8 C9 C1 -177.4(3) . . . . ?
C1 C9 C10 C5 177.8(3) . . . . ?
C8 C9 C10 C5 -1.7(4) . . . . ?
C1 C9 C10 C4 -1.2(4) . . . . ?
C8 C9 C10 C4 179.3(2) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C6 C5 C10 C4 179.0(3) . . . . ?
C3 C4 C10 C9 0.6(4) . . . . ?
C3 C4 C10 C5 -178.3(3) . . . . ?
C9 C1 C1 C9 -101.3(4) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        29.09
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_1_1'binaphthyl_150K
_database_code_depnum_ccdc_archive 'CCDC 1531199'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31


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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2
_symmetry_space_group_name_Hall  'P 4abw 2nw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.1071(2)
_cell_length_b                   7.1071(2)
_cell_length_c                   27.466(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1387.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1799
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      29.12

_exptl_crystal_description       tetragonal-bipyramidal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26030
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         29.12
_reflns_number_total             1799
_reflns_number_gt                1576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0317P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_number_reflns         1799
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1286(3) 0.9863(3) 0.00839(8) 0.0336(7) Uani 1 1 d . . .
C2 C 0.2952(4) 0.9671(4) -0.01571(9) 0.0425(7) Uani 1 1 d . . .
H2 H 0.3200 1.0436 -0.0424 0.051 Uiso 1 1 calc R . .
C3 C 0.4304(4) 0.8344(4) -0.00105(9) 0.0443(8) Uani 1 1 d . . .
H3 H 0.5427 0.8232 -0.0182 0.053 Uiso 1 1 calc R . .
C4 C 0.3976(4) 0.7222(4) 0.03824(9) 0.0395(7) Uani 1 1 d . . .
H4 H 0.4876 0.6350 0.0480 0.047 Uiso 1 1 calc R . .
C5 C 0.1898(4) 0.6290(4) 0.10587(9) 0.0425(8) Uani 1 1 d . . .
H5 H 0.2789 0.5419 0.1162 0.051 Uiso 1 1 calc R . .
C6 C 0.0270(4) 0.6476(4) 0.13145(10) 0.0462(8) Uani 1 1 d . . .
H6 H 0.0071 0.5759 0.1593 0.055 Uiso 1 1 calc R . .
C7 C -0.1106(4) 0.7748(4) 0.11576(9) 0.0405(7) Uani 1 1 d . . .
H7 H -0.2230 0.7853 0.1329 0.049 Uiso 1 1 calc R . .
C8 C -0.0814(4) 0.8833(4) 0.07559(8) 0.0343(7) Uani 1 1 d . . .
H8 H -0.1744 0.9666 0.0655 0.041 Uiso 1 1 calc R . .
C9 C 0.0902(4) 0.8710(3) 0.04881(8) 0.0299(6) Uani 1 1 d . . .
C10 C 0.2270(4) 0.7385(4) 0.06418(8) 0.0318(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0322(16) 0.0396(17) 0.0290(14) -0.0027(13) -0.0020(13) 0.0023(14)
C2 0.0470(19) 0.050(2) 0.0310(13) 0.0033(14) 0.0058(15) 0.0013(16)
C3 0.0338(17) 0.057(2) 0.0420(16) -0.0084(15) 0.0054(14) 0.0024(16)
C4 0.0320(17) 0.0419(18) 0.0445(16) -0.0040(15) -0.0033(14) 0.0072(15)
C5 0.043(2) 0.0423(18) 0.0426(17) 0.0057(15) -0.0088(14) 0.0020(16)
C6 0.053(2) 0.044(2) 0.0417(16) 0.0124(14) 0.0016(16) -0.0025(17)
C7 0.0384(17) 0.0402(17) 0.0430(15) 0.0060(15) 0.0076(14) -0.0032(16)
C8 0.0298(16) 0.0370(17) 0.0361(15) 0.0002(13) -0.0013(13) 0.0005(14)
C9 0.0298(15) 0.0329(15) 0.0269(13) -0.0023(12) -0.0033(12) -0.0035(14)
C10 0.0327(16) 0.0331(16) 0.0296(13) -0.0051(12) -0.0040(13) -0.0016(14)

_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 1.364(3) . ?
C1 C9 1.407(3) . ?
C1 C1 1.502(5) 7_465 ?
C2 C3 1.405(3) . ?
C3 C4 1.362(3) . ?
C4 C10 1.411(3) . ?
C5 C6 1.360(3) . ?
C5 C10 1.409(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.362(3) . ?
C8 C9 1.427(3) . ?
C9 C10 1.418(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 C9 119.5(2) . . ?
C2 C1 C1 120.2(2) . 7_465 ?
C9 C1 C1 120.3(2) . 7_465 ?
C1 C2 C3 121.5(2) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C10 120.0(3) . . ?
C6 C5 C10 121.7(3) . . ?
C5 C6 C7 119.9(3) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 C9 120.9(3) . . ?
C10 C9 C1 119.3(2) . . ?
C10 C9 C8 118.3(2) . . ?
C1 C9 C8 122.4(2) . . ?
C9 C10 C5 118.7(2) . . ?
C9 C10 C4 119.5(2) . . ?
C5 C10 C4 121.8(3) . . ?

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
C9 C1 C2 C3 -0.1(4) . . . . ?
C1 C1 C2 C3 -179.6(2) 7_465 . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C10 0.3(4) . . . . ?
C10 C5 C6 C7 1.6(4) . . . . ?
C5 C6 C7 C8 -1.4(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C2 C1 C9 C10 0.9(3) . . . . ?
C1 C1 C9 C10 -179.6(2) 7_465 . . . ?
C2 C1 C9 C8 -179.9(2) . . . . ?
C1 C1 C9 C8 -0.4(3) 7_465 . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?
C7 C8 C9 C1 -177.3(2) . . . . ?
C1 C9 C10 C5 177.5(2) . . . . ?
C8 C9 C10 C5 -1.8(3) . . . . ?
C1 C9 C10 C4 -1.1(3) . . . . ?
C8 C9 C10 C4 179.6(2) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
C6 C5 C10 C4 178.6(2) . . . . ?
C3 C4 C10 C9 0.5(4) . . . . ?
C3 C4 C10 C5 -178.1(2) . . . . ?
C9 C1 C1 C9 -101.0(4) . . 7_465 7_465 ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_RS_1_1'binaphthyl_297GPa
_database_code_depnum_ccdc_archive 'CCDC 1531197'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_RS_1,1'binaphthyl_297GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.298 Note  
RESPONSE: Due to the specificity of the applied measuring 
technique and use of a diamond-anvil cell limiting the access 
of the X-ray radiation to the measured sample, and therefore 
lowering the measured fraction of the theta angle.

;
_vrf_PLAT026_RS_1,1'binaphthyl_297GPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         36 %     
RESPONSE: Due to limited acces to reciprocal lattice due to 
the specificity of the applied measuring technique and 
use of a diamond-anvil cell; Poor quality of the data due to 
small size of measured crystal.
;
_vrf_PLAT340_RS_1,1'binaphthyl_297GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02767 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
_vrf_PLAT369_RS_1,1'binaphthyl_297GPa 
;
PROBLEM: Long    C(sp2)-C(sp2) Bond  C2     -   C2_a   ..       1.59 Ang.  
RESPONSE: Low precision of bond length due to limited access 
to reciprocal lattice due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell.
;
# end Validation Reply Form

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
1,1'-binaphthyl
;
_chemical_name_common            1,1'-binaphthyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   20.32(1)
_cell_length_b                   5.888(2)
_cell_length_c                   9.592(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.50(2)
_cell_angle_gamma                90.00
_cell_volume                     1105.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2970000
_cell_measurement_reflns_used    357
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      26.85

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 2.97(2) GPa
(2970000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_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_type  'multiwire proportional'
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2663
_diffrn_reflns_av_R_equivalents  0.1724
_diffrn_reflns_av_sigmaI/netI    0.1483
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         26.85
_reflns_number_total             357
_reflns_number_gt                127
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       2.010(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         357
_refine_ls_number_parameters     80
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2088
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.087
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.4168(10) 0.2566(10) 0.1688(9) 0.035(6) Uani 1 1 d GU . .
C1 C 0.4602(10) 0.0886(14) 0.2436(12) 0.035(5) Uani 1 1 d GU . .
C2 C 0.4344(10) -0.0849(11) 0.3121(9) 0.043(6) Uani 1 1 d GU . .
H2 H 0.4635 -0.1973 0.3621 0.051 Uiso 1 1 calc R . .
C3 C 0.3653(10) -0.0903(11) 0.3058(8) 0.043(6) Uani 1 1 d GU . .
H3 H 0.3481 -0.2063 0.3516 0.051 Uiso 1 1 calc R . .
C4 C 0.3220(10) 0.0777(16) 0.2310(11) 0.049(6) Uani 1 1 d GU . .
H4 H 0.2757 0.0741 0.2268 0.058 Uiso 1 1 calc R . .
C10 C 0.3477(10) 0.2512(12) 0.1625(8) 0.051(6) Uani 1 1 d GU . .
C5 C 0.2985(19) 0.426(2) 0.0881(14) 0.052(6) Uani 1 1 d U . .
H5 H 0.2525 0.4222 0.0858 0.063 Uiso 1 1 calc R . .
C6 C 0.328(2) 0.599(2) 0.020(2) 0.037(6) Uani 1 1 d U . .
H6 H 0.3000 0.7153 -0.0284 0.044 Uiso 1 1 calc R . .
C7 C 0.399(2) 0.596(2) 0.0257(18) 0.034(6) Uani 1 1 d U . .
H7 H 0.4194 0.7063 -0.0191 0.041 Uiso 1 1 calc R . .
C8 C 0.4320(18) 0.4351(17) 0.0953(13) 0.036(5) Uani 1 1 d U . .
H8 H 0.4780 0.4390 0.0969 0.043 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
C9 0.041(13) 0.031(6) 0.034(7) -0.006(5) 0.012(9) 0.010(8)
C1 0.038(13) 0.035(5) 0.028(5) 0.003(6) 0.002(9) 0.008(8)
C2 0.046(13) 0.047(7) 0.039(7) -0.014(5) 0.018(9) -0.012(8)
C3 0.040(13) 0.041(6) 0.049(8) 0.001(5) 0.013(9) 0.002(9)
C4 0.054(13) 0.051(6) 0.040(7) 0.001(5) 0.011(9) -0.018(8)
C10 0.058(14) 0.046(7) 0.042(8) 0.002(6) 0.001(9) -0.006(9)
C5 0.057(13) 0.051(7) 0.048(7) -0.007(5) 0.013(9) 0.019(9)
C6 0.035(14) 0.035(7) 0.045(8) -0.006(5) 0.020(10) -0.012(9)
C7 0.033(14) 0.029(6) 0.038(7) 0.005(5) 0.006(9) 0.007(9)
C8 0.035(13) 0.028(6) 0.034(6) -0.004(4) -0.007(9) 0.001(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
C8 C9 1.346(17) . ?
C9 C10 1.3900 . ?
C1 C9 1.3900 . ?
C1 C2 1.3900 . ?
C1 C1 1.59(4) 2_655 ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C10 1.3900 . ?
C4 H4 0.9300 . ?
C5 C10 1.48(3) . ?
C5 C6 1.42(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.44(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.25(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C9 C10 111.4(17) . . ?
C8 C9 C1 129(2) . . ?
C10 C9 C1 120.0 . . ?
C2 C1 C9 120.0 . . ?
C2 C1 C1 117.9(8) . 2_655 ?
C9 C1 C1 122.1(8) . 2_655 ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C10 120.0 . . ?
C3 C4 H4 120.0 . . ?
C10 C4 H4 120.0 . . ?
C4 C10 C5 117(2) . . ?
C4 C10 C9 120.0(12) . . ?
C5 C10 C9 123.4(16) . . ?
C6 C5 C10 114(3) . . ?
C6 C5 H5 122.9 . . ?
C10 C5 H5 122.9 . . ?
C5 C6 C7 121(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 115(2) . . ?
C8 C7 H7 122.7 . . ?
C6 C7 H7 122.7 . . ?
C7 C8 C9 135(3) . . ?
C7 C8 H8 112.3 . . ?
C9 C8 H8 112.3 . . ?

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
C8 C9 C1 C2 -179.3(9) . . . . ?
C10 C9 C1 C2 0.0 . . . . ?
C8 C8 C1 C1 1.7(13) . . . 2_655 ?
C10 C9 C1 C1 -179.0(14) . . . 2_655 ?
C9 C1 C2 C3 0.0 . . . . ?
C1 C1 C2 C3 179.0(13) 2_655 . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C10 0.0 . . . . ?
C3 C4 C10 C5 -178.7(9) . . . . ?
C3 C4 C10 C9 0.0(13) . . . . ?
C8 C9 C10 C4 179.4(7) . . . . ?
C1 C9 C10 C4 0.0 . . . . ?
C8 C9 C10 C5 -1.9(11) . . . . ?
C1 C9 C10 C5 178.7(8) . . . . ?
C4 C10 C5 C6 179.9(9) . . . . ?
C9 C10 C5 C6 1.2(13) . . . . ?
C10 C5 C6 C7 0(2) . . . . ?
C5 C6 C7 C8 -1(3) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C10 C9 C8 C7 1.2(19) . . . . ?
C1 C9 C8 C7 -179.4(15) . . . . ?
C9 C1 C1 C9 65.6(19) . . 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.298
_diffrn_reflns_theta_full        26.85
_diffrn_measured_fraction_theta_full 0.298
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
