# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

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

data_UM3320
_database_code_depnum_ccdc_archive 'CCDC 1957217'
loop_
_audit_author_name
_audit_author_address
butyrolactone
;University of Maryland College Park
United States of America
;
_audit_update_record             
;
2019-10-02 deposited with the CCDC.	2020-02-19 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2015 & ZCIF'
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
3-([1,1'-biphenyl]-4-yl)dihydrofuran-2(3H)-one
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.2309(7)
_cell_length_b                   7.4169(8)
_cell_length_c                   13.0054(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.1686(18)
_cell_angle_gamma                90
_cell_volume                     601.03(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3426
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      30.7

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS (Krause et al, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8759
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3504
_reflns_number_gt                3114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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       'Apex2 (Bruker, 2010)'
_computing_cell_refinement       'Apex2, Saint'
_computing_data_reduction        'Apex2, Saint'
_computing_structure_solution    'ShelXT-2014 (Sheldrick, 2015a)'
_computing_structure_refinement  'ShelXL-2015 (Sheldrick, 2015c)'
_computing_molecular_graphics    'Olex2 (Dolomanov, 2009)'
_computing_publication_material  'Apex2, SHELXL-2015, Platon (Spek, 2015)'
_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)+(0.0090P)²+0.2443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3504 # 1886 w/o Fiedel pairs
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.4025(3) 0.7044(3) 0.09860(12) 0.0419(4) Uani 1 1 d . . . . .
C2 C 0.5568(3) 0.6086(3) 0.09369(14) 0.0284(4) Uani 1 1 d . . . . .
O3 O 0.7320(2) 0.6562(2) 0.03879(11) 0.0342(4) Uani 1 1 d . . . . .
C4 C 0.8910(4) 0.5119(3) 0.04036(18) 0.0334(5) Uani 1 1 d . . . . .
H4A H 0.874(4) 0.449(4) -0.025(2) 0.044(7) Uiso 1 1 d . . . . .
H4B H 1.036(4) 0.564(4) 0.0444(18) 0.035(7) Uiso 1 1 d . . . . .
C5 C 0.8327(3) 0.3963(3) 0.13235(16) 0.0294(4) Uani 1 1 d . . . . .
H5A H 0.904(3) 0.437(3) 0.1944(18) 0.029(6) Uiso 1 1 d . . . . .
H5B H 0.875(4) 0.260(4) 0.1230(18) 0.038(7) Uiso 1 1 d . . . . .
C6 C 0.5895(3) 0.4225(3) 0.14136(14) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.516(3) 0.345(3) 0.0931(17) 0.027(6) Uiso 1 1 d . . . . .
C7 C 0.4942(3) 0.4068(2) 0.24762(13) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.3109(3) 0.3045(3) 0.26506(14) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.247(4) 0.234(3) 0.2067(17) 0.027(6) Uiso 1 1 d . . . . .
C9 C 0.2160(3) 0.2968(3) 0.36181(15) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.089(4) 0.231(3) 0.3716(17) 0.032(6) Uiso 1 1 d . . . . .
C10 C 0.3023(3) 0.3915(2) 0.44541(13) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.4914(3) 0.4883(3) 0.42787(15) 0.0253(4) Uani 1 1 d . . . . .
H11 H 0.558(4) 0.551(4) 0.4839(19) 0.035(7) Uiso 1 1 d . . . . .
C12 C 0.5854(3) 0.4961(3) 0.33130(16) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.713(4) 0.565(3) 0.3220(18) 0.035(7) Uiso 1 1 d . . . . .
C13 C 0.2008(3) 0.3882(2) 0.54925(14) 0.0198(3) Uani 1 1 d . . . . .
C14 C -0.0044(3) 0.3150(3) 0.56447(16) 0.0252(4) Uani 1 1 d . . . . .
H14 H -0.086(3) 0.272(3) 0.5038(17) 0.026(6) Uiso 1 1 d . . . . .
C15 C -0.0935(3) 0.3052(3) 0.66208(16) 0.0291(4) Uani 1 1 d . . . . .
H15 H -0.236(4) 0.258(4) 0.6708(18) 0.039(7) Uiso 1 1 d . . . . .
C16 C 0.0181(4) 0.3690(3) 0.74686(16) 0.0302(4) Uani 1 1 d . . . . .
H16 H -0.044(3) 0.358(3) 0.8143(17) 0.025(6) Uiso 1 1 d . . . . .
C17 C 0.2198(4) 0.4441(3) 0.73316(16) 0.0303(4) Uani 1 1 d . . . . .
H17 H 0.305(4) 0.478(3) 0.7936(19) 0.033(6) Uiso 1 1 d . . . . .
C18 C 0.3098(3) 0.4536(3) 0.63577(15) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.455(4) 0.492(4) 0.6291(19) 0.035(7) Uiso 1 1 d . . . . .


_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.


 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

 - 2.5677 (0.0049) x +  6.6854 (0.0029) y -  1.7141 (0.0105) z =  1.1448 (0.0073)

 * -0.0064 (0.0014)  C13
 *  0.0048 (0.0015)  C14
 *  0.0008 (0.0016)  C15
 * -0.0048 (0.0016)  C16
 *  0.0030 (0.0016)  C17
 *  0.0026 (0.0015)  C18
   -0.0667 (0.0029)  C10

 Rms deviation of fitted atoms =   0.0041


  3.4503 (0.0041) x -  5.9484 (0.0036) y +  2.8919 (0.0096) z =  0.0187 (0.0046)

 Angle to previous plane (with approximate esd) = 11.218 ( 0.099 )

 * -0.0172 (0.0014)  C7
 *  0.0095 (0.0014)  C8
 *  0.0076 (0.0014)  C9
 * -0.0169 (0.0014)  C10
 *  0.0093 (0.0016)  C11
 *  0.0078 (0.0015)  C12
   -0.0469 (0.0029)  C13
   -0.0890 (0.0031)  C6

 Rms deviation of fitted atoms =   0.0121


  2.4990 (0.0048) x +  3.1651 (0.0068) y +  10.5265 (0.0080) z =  4.2924 (0.0044)

 Angle to previous plane (with approximate esd) = 86.480 ( 0.064 )

 * -0.0193 (0.0011)  O1
 *  0.0118 (0.0017)  C2
 *  0.0221 (0.0014)  O3
 * -0.0208 (0.0011)  C4
 *  0.0061 (0.0007)  C6
    0.4361 (0.0031)  C5

 Rms deviation of fitted atoms =   0.0172
;

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 C2 1.197(3) . ?
C2 O3 1.353(2) . ?
C2 C6 1.527(3) . ?
O3 C4 1.459(3) . ?
C4 C5 1.517(3) . ?
C4 H4A 0.98(3) . ?
C4 H4B 0.98(3) . ?
C5 C6 1.533(3) . ?
C5 H5A 0.97(2) . ?
C5 H5B 1.05(3) . ?
C6 C7 1.510(2) . ?
C6 H6 0.96(2) . ?
C7 C8 1.391(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.393(3) . ?
C8 H8 1.00(2) . ?
C9 C10 1.400(3) . ?
C9 H9 0.94(2) . ?
C10 C11 1.399(3) . ?
C10 C13 1.493(2) . ?
C11 C12 1.388(3) . ?
C11 H11 0.96(3) . ?
C12 H12 0.95(2) . ?
C13 C18 1.400(3) . ?
C13 C14 1.403(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.99(2) . ?
C15 C16 1.385(3) . ?
C15 H15 0.96(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.96(2) . ?
C17 C18 1.388(3) . ?
C17 H17 0.98(2) . ?
C18 H18 0.95(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
O1 C2 O3 121.5(2) . . ?
O1 C2 C6 128.4(2) . . ?
O3 C2 C6 110.06(17) . . ?
C2 O3 C4 110.51(16) . . ?
O3 C4 C5 105.17(16) . . ?
O3 C4 H4A 105.6(16) . . ?
C5 C4 H4A 113.1(16) . . ?
O3 C4 H4B 109.4(15) . . ?
C5 C4 H4B 113.8(14) . . ?
H4A C4 H4B 109(2) . . ?
C4 C5 C6 103.16(17) . . ?
C4 C5 H5A 111.9(14) . . ?
C6 C5 H5A 110.3(13) . . ?
C4 C5 H5B 113.1(13) . . ?
C6 C5 H5B 112.1(13) . . ?
H5A C5 H5B 106(2) . . ?
C7 C6 C2 112.88(16) . . ?
C7 C6 C5 116.85(16) . . ?
C2 C6 C5 102.38(17) . . ?
C7 C6 H6 111.3(13) . . ?
C2 C6 H6 102.3(14) . . ?
C5 C6 H6 109.9(13) . . ?
C8 C7 C12 117.72(17) . . ?
C8 C7 C6 121.11(16) . . ?
C12 C7 C6 121.17(16) . . ?
C7 C8 C9 121.37(18) . . ?
C7 C8 H8 119.1(13) . . ?
C9 C8 H8 119.5(13) . . ?
C8 C9 C10 121.19(18) . . ?
C8 C9 H9 120.3(14) . . ?
C10 C9 H9 118.5(14) . . ?
C11 C10 C9 116.89(16) . . ?
C11 C10 C13 121.01(16) . . ?
C9 C10 C13 122.09(15) . . ?
C12 C11 C10 121.77(18) . . ?
C12 C11 H11 118.9(15) . . ?
C10 C11 H11 119.3(15) . . ?
C11 C12 C7 120.97(18) . . ?
C11 C12 H12 119.4(15) . . ?
C7 C12 H12 119.6(14) . . ?
C18 C13 C14 117.45(18) . . ?
C18 C13 C10 121.03(16) . . ?
C14 C13 C10 121.49(16) . . ?
C15 C14 C13 121.05(19) . . ?
C15 C14 H14 120.4(13) . . ?
C13 C14 H14 118.6(13) . . ?
C16 C15 C14 120.56(19) . . ?
C16 C15 H15 119.5(15) . . ?
C14 C15 H15 119.9(14) . . ?
C15 C16 C17 119.22(19) . . ?
C15 C16 H16 119.7(13) . . ?
C17 C16 H16 121.1(13) . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.3(14) . . ?
C18 C17 H17 119.9(14) . . ?
C17 C18 C13 121.29(19) . . ?
C17 C18 H18 118.9(15) . . ?
C13 C18 H18 119.3(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 O3 C4 -176.6(2) . . . . ?
C6 C2 O3 C4 1.9(2) . . . . ?
C2 O3 C4 C5 -19.8(2) . . . . ?
O3 C4 C5 C6 28.8(2) . . . . ?
O1 C2 C6 C7 -38.8(3) . . . . ?
O3 C2 C6 C7 142.84(16) . . . . ?
O1 C2 C6 C5 -165.3(2) . . . . ?
O3 C2 C6 C5 16.4(2) . . . . ?
C4 C5 C6 C7 -150.78(18) . . . . ?
C4 C5 C6 C2 -26.9(2) . . . . ?
C2 C6 C7 C8 108.5(2) . . . . ?
C5 C6 C7 C8 -133.2(2) . . . . ?
C2 C6 C7 C12 -70.7(2) . . . . ?
C5 C6 C7 C12 47.6(3) . . . . ?
C12 C7 C8 C9 2.5(3) . . . . ?
C6 C7 C8 C9 -176.72(18) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 -2.2(3) . . . . ?
C8 C9 C10 C13 178.75(18) . . . . ?
C9 C10 C11 C12 2.4(3) . . . . ?
C13 C10 C11 C12 -178.57(19) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C6 C7 C12 C11 176.9(2) . . . . ?
C11 C10 C13 C18 -11.6(3) . . . . ?
C9 C10 C13 C18 167.4(2) . . . . ?
C11 C10 C13 C14 170.3(2) . . . . ?
C9 C10 C13 C14 -10.7(3) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
C10 C13 C14 C15 177.10(18) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
C10 C13 C18 C17 -177.32(18) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036


_diffrn_radiation_monochromator  graphite
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0302051
_diffrn_orient_matrix_UB_12      -0.1321729
_diffrn_orient_matrix_UB_13      -0.0045866
_diffrn_orient_matrix_UB_21      0.0008765
_diffrn_orient_matrix_UB_22      -0.0082530
_diffrn_orient_matrix_UB_23      0.0767455
_diffrn_orient_matrix_UB_31      -0.1576189
_diffrn_orient_matrix_UB_32      0.0252972
_diffrn_orient_matrix_UB_33      0.0010755
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_detector                 'CCD area detector'
