# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# 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. 
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data_shelx
_audit_block_doi                 10.5517/cc1413mx
_database_code_depnum_ccdc_archive 'CCDC 1043758'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-methoxy-1-naphtaldehyde
_chemical_name_common            ?
_chemical_formula_moiety         '(C12 H10 O2)0.6, (C12H10 O3)0.4'
_chemical_formula_sum            'C12 H10 O2.40'
_chemical_melting_point          ?

_exptl_crystal_description       rectangle
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         192.60

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.074(2)
_cell_length_b                   3.9014(4)
_cell_length_c                   17.001(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.532(11)
_cell_angle_gamma                90
_cell_volume                     936.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3606
_cell_measurement_theta_min      1.55
_cell_measurement_theta_max      26.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             405
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            11041
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.1455
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1660
_reflns_number_gt                823
_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)+(0.0663P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    heteroxyz
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1660
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
C1 C 0.5595(2) 0.5012(8) 0.71074(18) 0.0575(8) Uani 1 1 d . . . . .
C2 C 0.6471(2) 0.6449(8) 0.7527(2) 0.0604(9) Uani 1 1 d . . . . .
H2 H 0.6821 0.7336 0.7204 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6865(2) 0.6665(8) 0.8391(2) 0.0638(9) Uani 1 1 d . . . . .
H3 H 0.7473 0.7660 0.8651 0.077 Uiso 1 1 calc R U . . .
C4 C 0.6374(2) 0.5438(8) 0.88669(18) 0.0573(8) Uani 1 1 d . . . . .
C5 C 0.5464(2) 0.3912(8) 0.84839(18) 0.0557(8) Uani 1 1 d . . . . .
C6 C 0.4956(2) 0.2611(8) 0.8976(2) 0.0639(9) Uani 1 1 d . . . . .
H6 H 0.5226 0.2735 0.9571 0.077 Uiso 1 1 calc R U . . .
C7 C 0.4085(3) 0.1183(9) 0.8609(2) 0.0733(10) Uani 1 1 d . . . . .
H7 H 0.3750 0.0325 0.8947 0.088 Uiso 1 1 calc R U . . .
C8 C 0.3689(2) 0.0977(9) 0.7748(2) 0.0719(10) Uani 1 1 d . . . . .
H8 H 0.3080 -0.0024 0.7499 0.086 Uiso 1 1 calc R U . . .
C9 C 0.4157(2) 0.2192(8) 0.7237(2) 0.0633(9) Uani 1 1 d . . . . .
H9 H 0.3869 0.2020 0.6644 0.076 Uiso 1 1 calc R U . . .
C10 C 0.5066(2) 0.3695(7) 0.75972(18) 0.0529(8) Uani 1 1 d . . . . .
C11 C 0.5277(3) 0.4952(10) 0.6196(2) 0.0700(10) Uani 1 1 d . . . . .
C12 C 0.7585(3) 0.7184(11) 1.0144(2) 0.0894(12) Uani 1 1 d . . . . .
H12A H 0.8074 0.6079 0.9975 0.134 Uiso 1 1 calc R U . . .
H12B H 0.7748 0.6953 1.0752 0.134 Uiso 1 1 calc R U . . .
H12C H 0.7546 0.9619 0.9994 0.134 Uiso 1 1 calc R U . . .
O1 O 0.45379(19) 0.3740(8) 0.57199(15) 0.0951(9) Uani 1 1 d . . . . .
O2 O 0.66827(16) 0.5564(7) 0.97169(14) 0.0777(8) Uani 1 1 d . . . . .
O3 O 0.5937(4) 0.6452(17) 0.5904(3) 0.0689(17) Uani 0.4 1 d . . P A 2
H3A H 0.572(4) 0.65(2) 0.537(6) 0.103 Uiso 0.4 1 calc R U P A 2
H11 H 0.5697 0.5918 0.5947 0.083 Uiso 0.6 1 d . U P B 1


_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 1.380(4) . ?
C1 C10 1.435(4) . ?
C1 C11 1.453(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.360(4) . ?
C3 H3 0.9500 . ?
C4 O2 1.355(3) . ?
C4 C5 1.426(4) . ?
C5 C6 1.412(4) . ?
C5 C10 1.416(4) . ?
C6 C7 1.359(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(4) . ?
C9 H9 0.9500 . ?
C11 O1 1.220(4) . ?
C11 O3 1.388(6) . ?
C11 H11 0.955(4) . ?
C12 O2 1.443(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O3 H3A 0.85(10) . ?

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 C10 118.1(3) . . ?
C2 C1 C11 117.1(3) . . ?
C10 C1 C11 124.8(3) . . ?
C1 C2 C3 123.4(3) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O2 C4 C3 124.5(3) . . ?
O2 C4 C5 114.7(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C10 119.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C10 C5 C4 119.5(3) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 118.0(3) . . ?
C5 C10 C1 118.8(3) . . ?
C9 C10 C1 123.2(3) . . ?
O1 C11 O3 122.0(4) . . ?
O1 C11 C1 126.6(3) . . ?
O3 C11 C1 111.4(3) . . ?
O1 C11 H11 116.9(3) . . ?
C1 C11 H11 116.4(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 O2 C12 117.5(3) . . ?
C11 O3 H3A 109.5 . . ?

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
C10 C1 C2 C3 0.4(5) . . . . ?
C11 C1 C2 C3 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 O2 -178.8(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
O2 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
O2 C4 C5 C10 179.0(2) . . . . ?
C3 C4 C5 C10 -0.4(4) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C6 C5 C10 C9 0.7(4) . . . . ?
C4 C5 C10 C9 -179.4(3) . . . . ?
C6 C5 C10 C1 -179.6(3) . . . . ?
C4 C5 C10 C1 0.3(4) . . . . ?
C8 C9 C10 C5 -0.4(4) . . . . ?
C8 C9 C10 C1 180.0(3) . . . . ?
C2 C1 C10 C5 -0.2(4) . . . . ?
C11 C1 C10 C5 179.8(3) . . . . ?
C2 C1 C10 C9 179.4(3) . . . . ?
C11 C1 C10 C9 -0.6(5) . . . . ?
C2 C1 C11 O1 178.5(4) . . . . ?
C10 C1 C11 O1 -1.5(5) . . . . ?
C2 C1 C11 O3 -0.8(5) . . . . ?
C10 C1 C11 O3 179.2(4) . . . . ?
C3 C4 O2 C12 1.5(4) . . . . ?
C5 C4 O2 C12 -177.9(3) . . . . ?

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 H3A O1 0.85 1.76 2.599(5) 170.9 3_666

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.042

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

_chemical_properties_physical    'Air-sensitive, Oxygen-sensitive'
