# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_ax65m
_database_code_depnum_ccdc_archive 'CCDC 1048680'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"'Ethyl 6,8-dichloro-2-hydroxy-2-(pyridin-4-yl)-2H-chromene-3-carboxylate'"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 Cl2 N O4'
_chemical_formula_sum            'C17 H13 Cl2 N O4'
_chemical_formula_weight         366.18

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7181(13)
_cell_length_b                   8.3117(14)
_cell_length_c                   14.132(2)
_cell_angle_alpha                99.319(3)
_cell_angle_beta                 103.875(2)
_cell_angle_gamma                106.460(3)
_cell_volume                     817.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3682
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8407
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7594
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2869
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0615P)²+0.5634P] 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         2869
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
C1 C 0.4876(4) 0.9712(4) 0.2379(2) 0.0443(7) Uani 1 1 d . . .
C2 C 0.6325(5) 1.1038(4) 0.3107(3) 0.0588(9) Uani 1 1 d . . .
H2A H 0.6790 1.2119 0.2983 0.071 Uiso 1 1 calc R . .
C3 C 0.7068(5) 1.0728(5) 0.4021(2) 0.0644(10) Uani 1 1 d . . .
C4 C 0.6408(4) 0.9166(4) 0.4235(2) 0.0565(8) Uani 1 1 d . . .
H4 H 0.6928 0.8998 0.4861 0.068 Uiso 1 1 calc R . .
C5 C 0.4941(4) 0.7826(4) 0.35010(19) 0.0401(6) Uani 1 1 d . . .
C6 C 0.4170(3) 0.8101(3) 0.25675(19) 0.0360(6) Uani 1 1 d . . .
C7 C 0.1984(3) 0.5061(3) 0.18883(18) 0.0313(5) Uani 1 1 d . . .
C8 C 0.2903(3) 0.4816(4) 0.29113(18) 0.0349(6) Uani 1 1 d . . .
C9 C 0.4236(4) 0.6110(4) 0.36348(19) 0.0407(6) Uani 1 1 d . . .
H9 H 0.4729 0.5894 0.4251 0.049 Uiso 1 1 calc R . .
C10 C -0.0115(3) 0.4793(3) 0.17081(18) 0.0289(5) Uani 1 1 d . . .
C11 C -0.0712(4) 0.5471(4) 0.2473(2) 0.0466(7) Uani 1 1 d . . .
H11 H 0.0151 0.6033 0.3106 0.056 Uiso 1 1 calc R . .
C12 C -0.2585(4) 0.5315(4) 0.2299(2) 0.0517(8) Uani 1 1 d . . .
H12 H -0.2957 0.5783 0.2828 0.062 Uiso 1 1 calc R . .
C13 C -0.3305(4) 0.3887(4) 0.0682(2) 0.0429(7) Uani 1 1 d . . .
H13 H -0.4194 0.3340 0.0055 0.051 Uiso 1 1 calc R . .
C14 C -0.1454(3) 0.3973(3) 0.07884(19) 0.0356(6) Uani 1 1 d . . .
H14 H -0.1119 0.3486 0.0249 0.043 Uiso 1 1 calc R . .
C15 C 0.2305(4) 0.3054(4) 0.3088(2) 0.0433(7) Uani 1 1 d . . .
C16 C 0.0156(5) 0.0165(4) 0.2354(3) 0.0561(8) Uani 1 1 d . . .
H16A H -0.0497 -0.0005 0.2855 0.067 Uiso 1 1 calc R . .
H16B H 0.1216 -0.0257 0.2503 0.067 Uiso 1 1 calc R . .
C17 C -0.1165(5) -0.0777(5) 0.1324(3) 0.0745(11) Uani 1 1 d . . .
H17A H -0.2168 -0.0302 0.1172 0.112 Uiso 1 1 calc R . .
H17B H -0.1693 -0.1982 0.1301 0.112 Uiso 1 1 calc R . .
H17C H -0.0484 -0.0652 0.0840 0.112 Uiso 1 1 calc R . .
Cl1 Cl 0.39258(12) 1.00569(11) 0.12213(7) 0.0622(3) Uani 1 1 d . . .
Cl2 Cl 0.89525(19) 1.24092(17) 0.49063(8) 0.1170(5) Uani 1 1 d . . .
H2O H 0.339(5) 0.421(4) 0.120(2) 0.048(9) Uiso 1 1 d . . .
N1 N -0.3900(3) 0.4530(3) 0.14139(19) 0.0439(6) Uani 1 1 d . . .
O1 O 0.2743(2) 0.6870(2) 0.18324(13) 0.0440(5) Uani 1 1 d . . .
O2 O 0.2248(3) 0.4056(2) 0.11088(13) 0.0381(5) Uani 1 1 d . . .
O3 O 0.3090(4) 0.2650(3) 0.38046(18) 0.0741(7) Uani 1 1 d . . .
O4 O 0.0813(3) 0.1971(3) 0.23576(16) 0.0500(5) Uani 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
C1 C2 1.380(4) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.730(3) . ?
C2 C3 1.379(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(5) . ?
C3 Cl2 1.744(3) . ?
C4 C5 1.395(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 C9 1.436(4) . ?
C6 O1 1.344(3) . ?
C7 O2 1.363(3) . ?
C7 O1 1.474(3) . ?
C7 C10 1.523(3) . ?
C7 C8 1.523(3) . ?
C8 C9 1.331(4) . ?
C8 C15 1.486(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(4) . ?
C10 C14 1.375(3) . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.331(4) . ?
C12 H12 0.9300 . ?
C13 N1 1.324(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.199(3) . ?
C15 O4 1.320(3) . ?
C16 O4 1.440(4) . ?
C16 C17 1.495(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O2 H2O 0.83(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
C2 C1 C6 120.7(3) . . ?
C2 C1 Cl1 119.7(2) . . ?
C6 C1 Cl1 119.6(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 Cl2 120.2(3) . . ?
C2 C3 Cl2 117.4(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C9 123.0(3) . . ?
C6 C5 C9 117.1(2) . . ?
O1 C6 C1 117.8(2) . . ?
O1 C6 C5 122.7(2) . . ?
C1 C6 C5 119.5(2) . . ?
O2 C7 O1 106.81(19) . . ?
O2 C7 C10 110.4(2) . . ?
O1 C7 C10 102.15(18) . . ?
O2 C7 C8 113.3(2) . . ?
O1 C7 C8 111.4(2) . . ?
C10 C7 C8 112.09(19) . . ?
C9 C8 C15 119.5(2) . . ?
C9 C8 C7 122.3(2) . . ?
C15 C8 C7 118.1(2) . . ?
C8 C9 C5 122.6(2) . . ?
C8 C9 H9 118.7 . . ?
C5 C9 H9 118.7 . . ?
C11 C10 C14 117.6(2) . . ?
C11 C10 C7 119.5(2) . . ?
C14 C10 C7 122.8(2) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C11 123.6(3) . . ?
N1 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
N1 C13 C14 124.4(3) . . ?
N1 C13 H13 117.8 . . ?
C14 C13 H13 117.8 . . ?
C10 C14 C13 118.6(2) . . ?
C10 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
O3 C15 O4 123.5(3) . . ?
O3 C15 C8 124.2(3) . . ?
O4 C15 C8 112.2(2) . . ?
O4 C16 C17 106.8(3) . . ?
O4 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O4 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C12 116.1(2) . . ?
C6 O1 C7 123.66(19) . . ?
C7 O2 H2O 111(2) . . ?
C15 O4 C16 119.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
