# Electronic Supplementary Material (ESI) for ChemComm.
# 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_jk093
_database_code_depnum_ccdc_archive 'CCDC 1531717'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        '4-(hydroxymethyl)coumarin 7-benzoate'
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 O5'
_chemical_formula_sum            'C17 H12 O5'
_exptl_crystal_recrystallization_method 
'slow evaporation from hexane/methylene chloride'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      93(2)
_chemical_formula_weight         296.27

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1640(4)
_cell_length_b                   9.2165(5)
_cell_length_c                   10.1606(5)
_cell_angle_alpha                85.162(4)
_cell_angle_beta                 82.217(4)
_cell_angle_gamma                81.222(5)
_cell_volume                     655.52(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3049
_cell_measurement_theta_min      2.9450
_cell_measurement_theta_max      29.0520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015).
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model. Empirical absorption correction using 
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'enhance (Mo) X-ray source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8284
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2901
_reflns_number_gt                2365
_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       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
'WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)'
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0840P)²+0.0190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.79157(16) 0.44374(12) 0.87166(10) 0.0175(3) Uani 1 1 d . . . . .
O2 O 0.77669(15) 0.36403(11) 0.67445(10) 0.0139(3) Uani 1 1 d . . . . .
O3 O 0.77354(17) 0.91599(11) 0.57624(11) 0.0158(3) Uani 1 1 d . . . . .
O4 O 0.66338(16) 0.17885(12) 0.27398(11) 0.0172(3) Uani 1 1 d . . . . .
O5 O 0.96975(16) 0.07077(13) 0.24764(11) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.7839(2) 0.47749(16) 0.75451(14) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.7826(2) 0.62380(16) 0.68984(14) 0.0126(3) Uani 1 1 d . . . . .
H2 H 0.790575 0.702976 0.741966 0.015 Uiso 1 1 calc R U . . .
C3 C 0.7704(2) 0.65230(15) 0.55816(14) 0.0113(3) Uani 1 1 d . . . . .
C4 C 0.7542(2) 0.53151(15) 0.47829(14) 0.0118(3) Uani 1 1 d . . . . .
C5 C 0.7333(2) 0.54837(16) 0.34166(14) 0.0131(3) Uani 1 1 d . . . . .
H5 H 0.733620 0.642713 0.296140 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7122(2) 0.42994(17) 0.27274(15) 0.0154(3) Uani 1 1 d . . . . .
H6 H 0.699834 0.441666 0.180386 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7095(2) 0.29339(16) 0.34174(15) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.7327(2) 0.26920(16) 0.47498(15) 0.0139(3) Uani 1 1 d . . . . .
H8 H 0.733479 0.174161 0.519278 0.017 Uiso 1 1 calc R U . . .
C9 C 0.7550(2) 0.39087(16) 0.54168(14) 0.0119(3) Uani 1 1 d . . . . .
C10 C 0.7700(2) 0.80412(15) 0.49011(14) 0.0127(3) Uani 1 1 d . . . . .
H10A H 0.882252 0.802654 0.421409 0.015 Uiso 1 1 calc R U . . .
H10B H 0.654878 0.828856 0.444095 0.015 Uiso 1 1 calc R U . . .
C11 C 0.8061(2) 0.07115(16) 0.23125(14) 0.0128(3) Uani 1 1 d . . . . .
C12 C 0.7333(2) -0.04185(15) 0.16424(13) 0.0127(3) Uani 1 1 d . . . . .
C13 C 0.5395(2) -0.05116(16) 0.17458(14) 0.0137(3) Uani 1 1 d . . . . .
H13 H 0.449585 0.017338 0.223512 0.016 Uiso 1 1 calc R U . . .
C14 C 0.4785(2) -0.16125(16) 0.11289(14) 0.0144(3) Uani 1 1 d . . . . .
H14 H 0.346756 -0.169247 0.120659 0.017 Uiso 1 1 calc R U . . .
C15 C 0.6111(2) -0.26005(16) 0.03952(14) 0.0152(3) Uani 1 1 d . . . . .
H15 H 0.568819 -0.333969 -0.004088 0.018 Uiso 1 1 calc R U . . .
C16 C 0.8046(2) -0.25132(16) 0.02964(14) 0.0161(3) Uani 1 1 d . . . . .
H16 H 0.893974 -0.319305 -0.020197 0.019 Uiso 1 1 calc R U . . .
C17 C 0.8669(2) -0.14295(16) 0.09282(14) 0.0144(3) Uani 1 1 d . . . . .
H17 H 0.999031 -0.137420 0.087644 0.017 Uiso 1 1 calc R U . . .
H3 H 0.883(3) 0.901(2) 0.607(2) 0.029(6) 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.
;

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 1.2111(18) . ?
O2 C9 1.3761(18) . ?
O2 C1 1.3890(16) . ?
O3 C10 1.4127(16) . ?
O3 H3 0.87(2) . ?
O4 C11 1.3647(18) . ?
O4 C7 1.4102(16) . ?
O5 C11 1.2055(19) . ?
C1 C2 1.449(2) . ?
C2 C3 1.354(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4588(18) . ?
C3 C10 1.507(2) . ?
C4 C9 1.397(2) . ?
C4 C5 1.410(2) . ?
C5 C6 1.3829(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(2) . ?
C8 C9 1.3981(19) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.4841(18) . ?
C12 C13 1.393(2) . ?
C12 C17 1.402(2) . ?
C13 C14 1.3892(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 H17 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
C9 O2 C1 121.47(11) . . ?
C10 O3 H3 108.5(14) . . ?
C11 O4 C7 118.37(11) . . ?
O1 C1 O2 116.48(13) . . ?
O1 C1 C2 126.53(12) . . ?
O2 C1 C2 116.99(12) . . ?
C3 C2 C1 122.68(12) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 118.82(13) . . ?
C2 C3 C10 122.94(12) . . ?
C4 C3 C10 118.24(12) . . ?
C9 C4 C5 117.86(12) . . ?
C9 C4 C3 118.06(13) . . ?
C5 C4 C3 124.06(13) . . ?
C6 C5 C4 121.14(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.43(13) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 123.19(13) . . ?
C8 C7 O4 119.21(13) . . ?
C6 C7 O4 117.33(13) . . ?
C7 C8 C9 116.99(13) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
O2 C9 C4 121.79(12) . . ?
O2 C9 C8 115.85(13) . . ?
C4 C9 C8 122.35(13) . . ?
O3 C10 C3 114.50(11) . . ?
O3 C10 H10A 108.6 . . ?
C3 C10 H10A 108.6 . . ?
O3 C10 H10B 108.6 . . ?
C3 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O5 C11 O4 122.84(12) . . ?
O5 C11 C12 125.62(13) . . ?
O4 C11 C12 111.54(12) . . ?
C13 C12 C17 120.57(13) . . ?
C13 C12 C11 121.69(13) . . ?
C17 C12 C11 117.70(14) . . ?
C14 C13 C12 119.58(13) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.87(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.60(13) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.86(13) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 119.49(14) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?

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 O2 C1 O1 175.64(12) . . . . ?
C9 O2 C1 C2 -4.7(2) . . . . ?
O1 C1 C2 C3 -178.82(15) . . . . ?
O2 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C10 -179.64(13) . . . . ?
C2 C3 C4 C9 -0.9(2) . . . . ?
C10 C3 C4 C9 179.86(13) . . . . ?
C2 C3 C4 C5 177.47(13) . . . . ?
C10 C3 C4 C5 -1.7(2) . . . . ?
C9 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C6 -177.76(13) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C8 -2.0(2) . . . . ?
C5 C6 C7 O4 171.98(13) . . . . ?
C11 O4 C7 C8 -79.93(17) . . . . ?
C11 O4 C7 C6 105.81(16) . . . . ?
C6 C7 C8 C9 1.6(2) . . . . ?
O4 C7 C8 C9 -172.32(12) . . . . ?
C1 O2 C9 C4 5.1(2) . . . . ?
C1 O2 C9 C8 -174.47(12) . . . . ?
C5 C4 C9 O2 179.33(13) . . . . ?
C3 C4 C9 O2 -2.2(2) . . . . ?
C5 C4 C9 C8 -1.1(2) . . . . ?
C3 C4 C9 C8 177.40(13) . . . . ?
C7 C8 C9 O2 179.62(13) . . . . ?
C7 C8 C9 C4 0.0(2) . . . . ?
C2 C3 C10 O3 -3.1(2) . . . . ?
C4 C3 C10 O3 176.04(12) . . . . ?
C7 O4 C11 O5 -0.9(2) . . . . ?
C7 O4 C11 C12 179.00(12) . . . . ?
O5 C11 C12 C13 165.77(15) . . . . ?
O4 C11 C12 C13 -14.09(19) . . . . ?
O5 C11 C12 C17 -12.3(2) . . . . ?
O4 C11 C12 C17 167.86(12) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -178.33(13) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 -1.0(2) . . . . ?
C13 C12 C17 C16 1.3(2) . . . . ?
C11 C12 C17 C16 179.42(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O5 0.87(2) 1.98(2) 2.7561(16) 148(2) 2_766

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.073


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

