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

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

data_2marb_0m
_database_code_depnum_ccdc_archive 'CCDC 1480785'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 Bis(2-hydroxy-4-methoxyphenyl)methanone
;
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         'C15 H14 O5'
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   3.8416(3)
_cell_length_b                   25.1212(16)
_cell_length_c                   12.9636(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.567(2)
_cell_angle_gamma                90.00
_cell_volume                     1249.80(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2774
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.41

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12538
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.35
_reflns_number_total             3107
_reflns_number_gt                1898
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0768P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3107
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
O2 O -0.0087(4) 0.48082(6) 0.77575(11) 0.0194(4) Uani 1 1 d . . .
O3 O 0.0302(4) 0.24320(6) 0.32574(11) 0.0259(4) Uani 1 1 d . . .
O5 O -0.4090(4) 0.42277(6) 0.44246(11) 0.0221(4) Uani 1 1 d . . .
O1 O 0.1131(4) 0.10176(5) 0.56938(11) 0.0216(4) Uani 1 1 d . . .
O4 O -0.2460(5) 0.33003(6) 0.38819(11) 0.0280(4) Uani 1 1 d . . .
C6 C -0.1001(5) 0.26085(8) 0.50354(16) 0.0158(5) Uani 1 1 d . . .
C10 C 0.0846(6) 0.39291(8) 0.72494(16) 0.0172(5) Uani 1 1 d . . .
H10 H 0.1993 0.3872 0.7887 0.021 Uiso 1 1 calc R . .
C4 C -0.0807(6) 0.18532(8) 0.62049(16) 0.0171(5) Uani 1 1 d . . .
H4 H -0.1183 0.1709 0.6852 0.021 Uiso 1 1 calc R . .
C11 C -0.0552(6) 0.44302(8) 0.70091(16) 0.0156(5) Uani 1 1 d . . .
C1 C 0.0042(6) 0.22668(8) 0.42462(15) 0.0169(5) Uani 1 1 d . . .
C5 C -0.1502(5) 0.23799(8) 0.60105(16) 0.0169(5) Uani 1 1 d . . .
H5 H -0.2324 0.2592 0.6535 0.020 Uiso 1 1 calc R . .
C2 C 0.0912(5) 0.17407(8) 0.44541(16) 0.0170(5) Uani 1 1 d . . .
H2 H 0.1792 0.1528 0.3940 0.020 Uiso 1 1 calc R . .
C12 C -0.2192(5) 0.45217(8) 0.60580(15) 0.0165(5) Uani 1 1 d . . .
H12 H -0.3085 0.4857 0.5894 0.020 Uiso 1 1 calc R . .
C9 C 0.0531(6) 0.35238(8) 0.65509(16) 0.0163(5) Uani 1 1 d . . .
H9 H 0.1502 0.3194 0.6718 0.020 Uiso 1 1 calc R . .
C8 C -0.1233(5) 0.35924(8) 0.55788(16) 0.0148(5) Uani 1 1 d . . .
C3 C 0.0467(5) 0.15347(8) 0.54256(16) 0.0160(5) Uani 1 1 d . . .
C017 C -0.1579(6) 0.53229(8) 0.75483(17) 0.0216(5) Uani 1 1 d . . .
H01A H -0.0628 0.5467 0.6936 0.032 Uiso 1 1 calc R . .
H01B H -0.1046 0.5556 0.8121 0.032 Uiso 1 1 calc R . .
H01C H -0.4061 0.5290 0.7448 0.032 Uiso 1 1 calc R . .
C13 C -0.2499(6) 0.41099(8) 0.53486(16) 0.0164(5) Uani 1 1 d . . .
C19 C 0.2452(6) 0.06758(8) 0.49181(18) 0.0232(6) Uani 1 1 d . . .
H19A H 0.2810 0.0325 0.5198 0.035 Uiso 1 1 calc R . .
H19B H 0.4625 0.0814 0.4697 0.035 Uiso 1 1 calc R . .
H19C H 0.0806 0.0659 0.4339 0.035 Uiso 1 1 calc R . .
C7 C -0.1620(6) 0.31751(8) 0.48084(16) 0.0182(5) Uani 1 1 d . . .
H888 H -0.078(8) 0.2786(11) 0.323(2) 0.066(10) Uiso 1 1 d . . .
H887 H -0.369(9) 0.3897(12) 0.397(2) 0.083(11) Uiso 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
O2 0.0257(9) 0.0160(8) 0.0162(8) -0.0008(6) -0.0045(7) 0.0010(7)
O3 0.0423(11) 0.0227(9) 0.0130(8) 0.0003(7) 0.0067(8) 0.0039(8)
O5 0.0320(10) 0.0189(8) 0.0147(8) 0.0002(7) -0.0061(7) 0.0038(7)
O1 0.0290(10) 0.0153(8) 0.0204(9) -0.0015(7) 0.0003(7) 0.0035(7)
O4 0.0491(12) 0.0202(9) 0.0141(9) 0.0007(7) -0.0030(8) 0.0067(8)
C6 0.0165(12) 0.0156(11) 0.0153(11) -0.0003(9) -0.0005(9) 0.0008(9)
C10 0.0149(11) 0.0222(12) 0.0144(11) 0.0031(9) -0.0007(9) -0.0008(9)
C4 0.0183(12) 0.0195(11) 0.0136(11) 0.0020(9) 0.0010(9) -0.0004(9)
C11 0.0133(11) 0.0186(12) 0.0153(11) -0.0002(9) 0.0033(9) -0.0036(9)
C1 0.0164(11) 0.0200(12) 0.0142(11) -0.0007(9) 0.0003(9) -0.0022(9)
C5 0.0166(11) 0.0200(12) 0.0140(11) -0.0046(9) -0.0003(9) -0.0010(9)
C2 0.0149(11) 0.0194(12) 0.0168(11) -0.0070(9) 0.0007(9) -0.0011(9)
C12 0.0178(12) 0.0131(10) 0.0188(12) 0.0035(9) 0.0017(9) 0.0010(9)
C9 0.0138(11) 0.0161(11) 0.0190(11) 0.0049(9) 0.0013(9) 0.0016(9)
C8 0.0145(11) 0.0155(11) 0.0147(11) 0.0028(9) 0.0020(9) -0.0011(9)
C3 0.0120(11) 0.0152(11) 0.0206(11) -0.0012(9) -0.0030(9) 0.0003(9)
C017 0.0240(13) 0.0166(12) 0.0241(13) -0.0026(10) -0.0027(10) 0.0021(10)
C13 0.0156(12) 0.0207(12) 0.0127(11) 0.0031(9) -0.0002(9) -0.0009(9)
C19 0.0247(13) 0.0172(12) 0.0275(13) -0.0049(10) -0.0020(11) 0.0036(10)
C7 0.0175(12) 0.0202(12) 0.0170(11) 0.0017(10) 0.0033(9) 0.0031(9)

_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
O2 C11 1.364(2) . ?
O2 C017 1.435(2) . ?
O3 C1 1.355(2) . ?
O5 C13 1.353(3) . ?
O1 C3 1.366(2) . ?
O1 C19 1.432(2) . ?
O4 C7 1.269(2) . ?
C6 C1 1.407(3) . ?
C6 C5 1.409(3) . ?
C6 C7 1.471(3) . ?
C10 C9 1.364(3) . ?
C10 C11 1.398(3) . ?
C4 C5 1.371(3) . ?
C4 C3 1.395(3) . ?
C11 C12 1.379(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.379(3) . ?
C12 C13 1.386(3) . ?
C9 C8 1.414(3) . ?
C8 C13 1.415(3) . ?
C8 C7 1.451(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
C11 O2 C017 117.03(16) . . ?
C3 O1 C19 117.35(16) . . ?
C1 C6 C5 117.27(19) . . ?
C1 C6 C7 119.58(19) . . ?
C5 C6 C7 123.12(19) . . ?
C9 C10 C11 120.1(2) . . ?
C5 C4 C3 119.49(19) . . ?
O2 C11 C12 124.06(19) . . ?
O2 C11 C10 115.58(18) . . ?
C12 C11 C10 120.34(19) . . ?
O3 C1 C2 116.64(19) . . ?
O3 C1 C6 122.42(19) . . ?
C2 C1 C6 120.93(19) . . ?
C4 C5 C6 121.66(19) . . ?
C3 C2 C1 119.77(19) . . ?
C11 C12 C13 119.4(2) . . ?
C10 C9 C8 121.7(2) . . ?
C9 C8 C13 116.50(19) . . ?
C9 C8 C7 123.76(19) . . ?
C13 C8 C7 119.66(19) . . ?
O1 C3 C2 124.05(19) . . ?
O1 C3 C4 115.40(18) . . ?
C2 C3 C4 120.53(19) . . ?
O5 C13 C12 116.49(19) . . ?
O5 C13 C8 121.66(19) . . ?
C12 C13 C8 121.8(2) . . ?
O4 C7 C8 119.10(19) . . ?
O4 C7 C6 117.46(19) . . ?
C8 C7 C6 123.42(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.073
