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

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

data_scd0861
_database_code_depnum_ccdc_archive 'CCDC 1555680'
#Added by publCIF



_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'HELIOS optics monochromator'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2n 2ab'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 O2'
_chemical_formula_sum            'C10 H8 O2'
_chemical_formula_weight         160.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   9.490(3)
_cell_length_b                   11.322(4)
_cell_length_c                   7.377(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     792.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2635
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.37

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryostreams cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7653
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         30.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1224
_reflns_number_gt                869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.6920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1224
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.074
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67882(12) 0.34139(10) 0.59001(15) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.56241(16) 0.51130(14) 0.4607(2) 0.0117(3) Uani 1 1 d . . . . .
H5 H 0.5693 0.5799 0.3872 0.014 Uiso 1 1 calc R U . . .
C4 C 0.68611(17) 0.43936(13) 0.4797(2) 0.0123(3) Uani 1 1 d . . . . .
C3 C 0.81832(18) 0.44773(15) 0.4080(2) 0.0153(3) Uani 1 1 d . . . . .
H3 H 0.8516 0.5071 0.3278 0.018 Uiso 1 1 calc R U . . .
C2 C 0.89687(18) 0.35011(15) 0.4767(2) 0.0176(4) Uani 1 1 d . . . . .
H2 H 0.9924 0.3316 0.4508 0.021 Uiso 1 1 calc R U . . .
C1 C 0.80904(18) 0.28936(15) 0.5853(2) 0.0175(4) Uani 1 1 d . . . . .
H1 H 0.8340 0.2198 0.6499 0.021 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0134(6) 0.0131(5) 0.0179(5) 0.0016(4) 0.0018(5) 0.0010(5)
C5 0.0142(7) 0.0107(7) 0.0103(6) -0.0022(6) -0.0029(6) -0.0006(6)
C4 0.0153(8) 0.0111(7) 0.0104(6) -0.0017(6) -0.0009(6) -0.0005(6)
C3 0.0145(8) 0.0170(8) 0.0145(7) -0.0001(6) 0.0019(7) -0.0015(7)
C2 0.0138(8) 0.0200(8) 0.0190(8) -0.0043(7) 0.0002(7) 0.0030(7)
C1 0.0167(9) 0.0155(8) 0.0203(8) -0.0020(7) -0.0019(7) 0.0063(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
O1 C1 1.369(2) . ?
O1 C4 1.3776(19) . ?
C5 C5 1.343(3) 5_666 ?
C5 C4 1.436(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.365(2) . ?
C3 C2 1.426(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.345(2) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?

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
C1 O1 C4 106.61(13) . . ?
C5 C5 C4 124.81(19) 5_666 . ?
C5 C5 H5 117.6 5_666 . ?
C4 C5 H5 117.6 . . ?
C3 C4 O1 109.33(14) . . ?
C3 C4 C5 132.42(15) . . ?
O1 C4 C5 118.25(14) . . ?
C4 C3 C2 106.80(14) . . ?
C4 C3 H3 126.6 . . ?
C2 C3 H3 126.6 . . ?
C1 C2 C3 106.50(15) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 126.8 . . ?
C2 C1 O1 110.76(15) . . ?
C2 C1 H1 124.6 . . ?
O1 C1 H1 124.6 . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.065

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL scd0861_a.res in Pbcn
CELL  0.71073   9.48989  11.32185   7.37733   90.000   90.000   90.000
ZERR    4.000   0.00332   0.00447   0.00391    0.000    0.000    0.000
rem
rem  Component                Vol
rem     1.1(1)             792.64
rem
LATT 1
SYMM 1/2-X, 1/2-Y, 1/2+Z
SYMM -X, Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C  H  O
UNIT 40  32  8
ACTA
BOND $H
FMAP 2
LIST 4
TEMP -183
SIZE 0.06 0.06 0.24
L.S. 20
PLAN 5
rem  PLAT031_ALERT_4_B Refined Extinction Parameter within Range .. 1.000 Sigma
WGHT    0.039100    0.692000
FVAR       0.65436
O1    3    0.678820    0.341388    0.590015    11.00000    0.01338    0.01309 =
         0.01793    0.00163    0.00181    0.00104
C5    1    0.562411    0.511305    0.460715    11.00000    0.01424    0.01072 =
         0.01029   -0.00218   -0.00293   -0.00057
AFIX  43
H5    2    0.569336    0.579949    0.387197    11.00000   -1.20000
AFIX   0
C4    1    0.686112    0.439360    0.479680    11.00000    0.01532    0.01113 =
         0.01036   -0.00166   -0.00085   -0.00045
C3    1    0.818323    0.447728    0.407986    11.00000    0.01452    0.01703 =
         0.01450   -0.00005    0.00191   -0.00150
AFIX  43
H3    2    0.851614    0.507142    0.327771    11.00000   -1.20000
AFIX   0
C2    1    0.896873    0.350112    0.476673    11.00000    0.01378    0.01996 =
         0.01898   -0.00428    0.00023    0.00303
AFIX  43
H2    2    0.992428    0.331624    0.450817    11.00000   -1.20000
AFIX   0
C1    1    0.809042    0.289362    0.585281    11.00000    0.01675    0.01549 =
         0.02029   -0.00201   -0.00189    0.00630
AFIX  43
H1    2    0.833959    0.219847    0.649886    11.00000   -1.20000
AFIX   0
HKLF 4

REM  scd0861_a.res in Pbcn
REM R1 =  0.0615 for     869 Fo > 4sig(Fo)  and  0.0990 for all    1224 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0391      0.6920

REM Highest difference peak  0.279,  deepest hole -0.300,  1-sigma level  0.065
Q1    1   0.6154  0.4493  0.4256  11.00000  0.05    0.28
Q2    1   0.7389  0.4394  0.4124  11.00000  0.05    0.28
Q3    1   0.7578  0.4755  0.4663  11.00000  0.05    0.25
Q4    1   0.6307  0.4878  0.5034  11.00000  0.05    0.25
Q5    1   0.8059  0.2366  0.6883  11.00000  0.05    0.24
;
_shelx_res_checksum              44423

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
