# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Itzia Padilla-Martinez'
_publ_contact_author_email       IPADILLAMAR@IPN.MX

_publ_section_title              
;
Competition between OH***O hydrogen bonding and
multicentered halogen-dipole interactions on intramolecular three
centered hydrogen bonding formation in ethanol amides derived
from 3-acyl coumarins
;
loop_
_publ_author_name
'Itzia Padilla-Martinez'
'Efren V Garcia-Baez'
'N Alejandra Mancilla-Margalli'
;
F.J.Martinez-Martinez
;
'Luis M Morin-Sanchez'
'Ana L Peraza-Campos'
;
R.J.Santos-Contreras
;

# Attachment '1a.cif'

data_baesevx
_database_code_depnum_ccdc_archive 'CCDC 704502'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N O4'
_chemical_formula_sum            'C12 H11 N O4'
_chemical_formula_weight         233.22

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   17.372(4)
_cell_length_b                   5.1248(13)
_cell_length_c                   11.968(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.925(4)
_cell_angle_gamma                90
_cell_volume                     1034.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker SMART area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            10189
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2027
_reflns_number_gt                1641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (Farrugia, 1999)'

_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)+(0.0683P)²+0.3079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2027
_refine_ls_number_parameters     154
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.36410(9) 0.5683(3) 0.93429(14) 1.000 0.0170(5) . .
O2 O Uani 0.29743(10) 0.8874(3) 0.98714(15) 1.000 0.0215(6) . .
O11 O Uani 0.11651(10) 0.8071(4) 0.68320(14) 1.000 0.0204(5) . .
O15 O Uani 0.14687(10) 1.4318(4) 0.99491(15) 1.000 0.0274(6) . .
N12 N Uani 0.15321(12) 1.0188(4) 0.85176(17) 1.000 0.0181(7) . .
C2 C Uani 0.29830(14) 0.7251(5) 0.9143(2) 1.000 0.0168(7) . .
C3 C Uani 0.23823(14) 0.6816(5) 0.8077(2) 1.000 0.0164(7) . .
C4 C Uani 0.24874(14) 0.4939(5) 0.7346(2) 1.000 0.0164(7) . .
C5 C Uani 0.33052(14) 0.1326(5) 0.6853(2) 1.000 0.0177(7) . .
C6 C Uani 0.39792(14) -0.0171(5) 0.7148(2) 1.000 0.0187(8) . .
C7 C Uani 0.45381(14) 0.0317(5) 0.8171(2) 1.000 0.0179(7) . .
C8 C Uani 0.44247(14) 0.2285(5) 0.8901(2) 1.000 0.0179(7) . .
C9 C Uani 0.37441(14) 0.3751(5) 0.8597(2) 1.000 0.0151(7) . .
C10 C Uani 0.31737(14) 0.3327(5) 0.7576(2) 1.000 0.0156(7) . .
C11 C Uani 0.16444(14) 0.8426(5) 0.7767(2) 1.000 0.0169(7) . .
C13 C Uani 0.08418(14) 1.1860(5) 0.8316(2) 1.000 0.0199(8) . .
C14 C Uani 0.07535(15) 1.3011(6) 0.9428(2) 1.000 0.0248(8) . .
H4 H Uiso 0.20910 0.46790 0.66540 1.000 0.0200 calc R
H5 H Uiso 0.29250 0.09980 0.61510 1.000 0.0210 calc R
H6 H Uiso 0.40630 -0.15370 0.66540 1.000 0.0220 calc R
H7 H Uiso 0.50040 -0.07200 0.83710 1.000 0.0210 calc R
H8 H Uiso 0.48090 0.26200 0.95980 1.000 0.0210 calc R
H12 H Uiso 0.18940 1.03530 0.91700 1.000 0.0220 calc R
H13A H Uiso 0.03720 1.08580 0.79660 1.000 0.0240 calc R
H13B H Uiso 0.08960 1.32480 0.77890 1.000 0.0240 calc R
H14A H Uiso 0.03130 1.42290 0.92870 1.000 0.0300 calc R
H14B H Uiso 0.06490 1.16440 0.99330 1.000 0.0300 calc R
H15 H Uiso 0.14100 1.51460 1.05290 1.000 0.0410 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.370(3) . . yes
O1 C9 1.373(3) . . yes
O2 C2 1.208(3) . . yes
O11 C11 1.237(3) . . yes
O15 C14 1.417(3) . . yes
O15 H15 0.8400 . . no
N12 C13 1.446(3) . . yes
N12 C11 1.321(3) . . yes
N12 H12 0.8800 . . no
C2 C3 1.458(3) . . no
C3 C4 1.342(4) . . no
C3 C11 1.494(4) . . no
C4 C10 1.422(4) . . no
C5 C10 1.396(4) . . no
C5 C6 1.373(4) . . no
C6 C7 1.390(3) . . no
C7 C8 1.379(4) . . no
C8 C9 1.374(4) . . no
C9 C10 1.393(3) . . no
C13 C14 1.497(3) . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C13 H13A 0.9700 . . no
C13 H13B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 122.89(19) . . . yes
C14 O15 H15 110.00 . . . no
C11 N12 C13 123.0(2) . . . yes
C11 N12 H12 119.00 . . . no
C13 N12 H12 119.00 . . . no
O2 C2 C3 127.3(2) . . . yes
O1 C2 O2 115.6(2) . . . yes
O1 C2 C3 117.0(2) . . . yes
C2 C3 C4 119.9(2) . . . no
C2 C3 C11 121.6(2) . . . no
C4 C3 C11 118.5(2) . . . no
C3 C4 C10 122.0(2) . . . no
C6 C5 C10 120.5(2) . . . no
C5 C6 C7 119.8(2) . . . no
C6 C7 C8 120.9(2) . . . no
C7 C8 C9 118.5(2) . . . no
O1 C9 C8 117.4(2) . . . yes
O1 C9 C10 120.4(2) . . . yes
C8 C9 C10 122.2(2) . . . no
C4 C10 C5 124.2(2) . . . no
C4 C10 C9 117.8(2) . . . no
C5 C10 C9 118.1(2) . . . no
O11 C11 C3 119.6(2) . . . yes
O11 C11 N12 122.6(2) . . . yes
N12 C11 C3 117.8(2) . . . yes
N12 C13 C14 110.1(2) . . . yes
O15 C14 C13 108.1(2) . . . yes
C3 C4 H4 119.00 . . . no
C10 C4 H4 119.00 . . . no
C6 C5 H5 120.00 . . . no
C10 C5 H5 120.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 121.00 . . . no
C9 C8 H8 121.00 . . . no
N12 C13 H13A 110.00 . . . no
N12 C13 H13B 110.00 . . . no
C14 C13 H13A 110.00 . . . no
C14 C13 H13B 110.00 . . . no
H13A C13 H13B 108.00 . . . no
O15 C14 H14A 110.00 . . . no
O15 C14 H14B 110.00 . . . no
C13 C14 H14A 110.00 . . . no
C13 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no

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 O1 C2 O2 -179.7(2) . . . . no
C9 O1 C2 C3 -0.8(3) . . . . no
C2 O1 C9 C8 -179.1(2) . . . . no
C2 O1 C9 C10 0.9(3) . . . . no
C13 N12 C11 O11 -0.1(4) . . . . no
C11 N12 C13 C14 162.3(2) . . . . no
C13 N12 C11 C3 -180.0(2) . . . . no
O1 C2 C3 C11 -179.5(2) . . . . no
O1 C2 C3 C4 0.3(3) . . . . no
O2 C2 C3 C11 -0.7(4) . . . . no
O2 C2 C3 C4 179.1(3) . . . . no
C2 C3 C11 O11 176.9(2) . . . . no
C2 C3 C11 N12 -3.2(4) . . . . no
C4 C3 C11 O11 -2.8(4) . . . . no
C4 C3 C11 N12 177.1(2) . . . . no
C11 C3 C4 C10 179.9(2) . . . . no
C2 C3 C4 C10 0.1(4) . . . . no
C3 C4 C10 C9 0.0(4) . . . . no
C3 C4 C10 C5 179.0(2) . . . . no
C6 C5 C10 C9 0.0(4) . . . . no
C10 C5 C6 C7 -0.4(4) . . . . no
C6 C5 C10 C4 -178.9(2) . . . . no
C5 C6 C7 C8 0.3(4) . . . . no
C6 C7 C8 C9 0.3(4) . . . . no
C7 C8 C9 C10 -0.6(4) . . . . no
C7 C8 C9 O1 179.4(2) . . . . no
O1 C9 C10 C4 -0.5(4) . . . . no
O1 C9 C10 C5 -179.5(2) . . . . no
C8 C9 C10 C4 179.5(2) . . . . no
C8 C9 C10 C5 0.5(4) . . . . no
N12 C13 C14 O15 55.6(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.330(3) . 1_565 no
O1 C5 3.357(3) . 4_555 no
O1 C6 3.277(3) . 4_555 no
O2 C9 3.368(3) . 1_565 no
O2 C5 3.369(3) . 4_565 no
O2 N12 2.721(3) . . no
O2 C4 3.326(3) . 4_565 no
O11 O15 2.778(3) . 4_574 no
O11 C14 3.311(3) . 2_546 no
O15 C2 3.366(3) . 1_565 no
O15 N12 2.742(3) . . no
O15 O11 2.778(3) . 4_575 no
O15 C3 3.300(3) . 1_565 no
O1 H5 2.8800 . 4_555 no
O1 H6 2.7200 . 4_555 no
O1 H8 2.8200 . 3_667 no
O2 H12 2.0100 . . no
O2 H6 2.7600 . 4_555 no
O11 H15 1.9400 . 4_574 no
O11 H4 2.4100 . . no
O11 H13A 2.5800 . . no
O11 H13B 2.8100 . 1_545 no
O11 H14A 2.6600 . 2_546 no
O15 H12 2.4200 . . no
O15 H4 2.9100 . 4_565 no
O15 H5 2.6000 . 4_565 no
N12 O2 2.721(3) . . no
N12 O15 2.742(3) . . no
N12 C4 3.431(3) . 1_565 no
C2 O15 3.366(3) . 1_545 no
C2 C5 3.595(4) . 1_565 no
C2 C6 3.526(4) . 1_565 no
C2 C7 3.554(4) . 1_565 no
C3 C5 3.345(4) . 1_565 no
C3 C6 3.578(4) . 1_565 no
C3 O15 3.300(3) . 1_545 no
C4 O2 3.326(3) . 4_564 no
C4 N12 3.431(3) . 1_545 no
C5 C2 3.595(4) . 1_545 no
C5 C3 3.345(4) . 1_545 no
C5 O1 3.357(3) . 4_554 no
C5 O2 3.369(3) . 4_564 no
C6 C3 3.578(4) . 1_545 no
C6 C8 3.555(4) . 2_646 no
C6 C7 3.550(4) . 2_646 no
C6 C2 3.526(4) . 1_545 no
C6 O1 3.277(3) . 4_554 no
C7 C6 3.550(4) . 2_656 no
C7 O1 3.330(3) . 1_545 no
C7 C2 3.554(4) . 1_545 no
C8 C6 3.555(4) . 2_656 no
C9 O2 3.368(3) . 1_545 no
C14 O11 3.311(3) . 2_556 no
C2 H12 2.4800 . . no
C2 H5 2.9500 . 4_555 no
C4 H13B 3.0600 . 1_545 no
C6 H7 3.0400 . 2_656 no
C7 H7 2.9800 . 2_656 no
C7 H6 2.8800 . 2_656 no
C7 H8 3.0400 . 3_657 no
C8 H6 2.9200 . 2_656 no
C11 H15 2.7100 . 4_574 no
C11 H13B 2.9600 . 1_545 no
C13 H13A 3.0700 . 2_556 no
C14 H14A 3.0300 . 3_587 no
H4 O11 2.4100 . . no
H4 H5 2.5400 . . no
H4 O15 2.9100 . 4_564 no
H5 H4 2.5400 . . no
H5 O1 2.8800 . 4_554 no
H5 O15 2.6000 . 4_564 no
H5 C2 2.9500 . 4_554 no
H6 C7 2.8800 . 2_646 no
H6 C8 2.9200 . 2_646 no
H6 O1 2.7200 . 4_554 no
H6 O2 2.7600 . 4_554 no
H7 C6 3.0400 . 2_646 no
H7 C7 2.9800 . 2_646 no
H7 H8 2.5700 . 3_657 no
H8 O1 2.8200 . 3_667 no
H8 C7 3.0400 . 3_657 no
H8 H7 2.5700 . 3_657 no
H12 O2 2.0100 . . no
H12 O15 2.4200 . . no
H12 C2 2.4800 . . no
H13A O11 2.5800 . . no
H13A C13 3.0700 . 2_546 no
H13A H13B 2.5500 . 2_546 no
H13B O11 2.8100 . 1_565 no
H13B C4 3.0600 . 1_565 no
H13B C11 2.9600 . 1_565 no
H13B H13A 2.5500 . 2_556 no
H14A O11 2.6600 . 2_556 no
H14A C14 3.0300 . 3_587 no
H14A H14A 2.3700 . 3_587 no
H15 O11 1.9400 . 4_575 no
H15 C11 2.7100 . 4_575 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N12 H12 O2 0.8800 2.0100 2.721(3) 137.00 . yes
N12 H12 O15 0.8800 2.4200 2.742(3) 102.00 . yes
O15 H15 O11 0.8400 1.9400 2.778(3) 174.00 4_575 yes
C4 H4 O11 0.9500 2.4100 2.748(3) 100.00 . yes
C5 H5 O15 0.9500 2.6000 3.461(3) 151.00 4_564 yes

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.059

# Attachment '2a.cif'

data_m3mendm
_database_code_depnum_ccdc_archive 'CCDC 704503'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide hydrate
;
_chemical_name_common            
;N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide
hydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O7'
_chemical_formula_sum            'C12 H12 N2 O7'
_chemical_formula_weight         296.24

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           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                   5.0399(13)
_cell_length_b                   8.901(2)
_cell_length_c                   14.031(4)
_cell_angle_alpha                94.044(4)
_cell_angle_beta                 91.533(4)
_cell_angle_gamma                90.092(4)
_cell_volume                     627.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_ave  0.8617
_exptl_crystal_size_rad          0.2000

_exptl_special_details           
;
?
;

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6037
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2179
_reflns_number_gt                1958
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0493P)²+0.2307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2179
_refine_ls_number_parameters     191
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_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
O1 O 0.7677(3) 0.86941(17) 0.98598(10) 0.0385(4) Uani 1 1 d . . .
O2 O 0.8695(3) 0.88110(18) 0.83642(11) 0.0452(4) Uani 1 1 d . . .
O6A O 1.1000(4) 0.5949(2) 1.36723(12) 0.0674(6) Uani 1 1 d . . .
O6B O 0.7707(4) 0.7309(3) 1.41295(13) 0.0722(6) Uani 1 1 d . . .
O11 O 1.4982(3) 0.57416(18) 0.86833(10) 0.0437(4) Uani 1 1 d . . .
O15 O 1.2785(3) 0.86295(19) 0.58827(11) 0.0495(5) Uani 1 1 d D . .
H15 H 1.4238 0.9090 0.5960 0.074 Uiso 1 1 d RD . .
N6 N 0.9184(4) 0.6800(2) 1.35167(14) 0.0469(5) Uani 1 1 d . . .
N12 N 1.2769(4) 0.7093(2) 0.76323(12) 0.0392(5) Uani 1 1 d D . .
H12 H 1.1431 0.7703 0.7536 0.047 Uiso 1 1 calc RD . .
C2 C 0.9218(4) 0.8241(2) 0.90976(15) 0.0327(5) Uani 1 1 d . . .
C3 C 1.1332(4) 0.7162(2) 0.92680(14) 0.0303(5) Uani 1 1 d . . .
C4 C 1.1684(4) 0.6651(2) 1.01405(14) 0.0317(5) Uani 1 1 d . . .
H4 H 1.3060 0.5948 1.0244 0.038 Uiso 1 1 calc R . .
C5 C 1.0396(4) 0.6676(2) 1.18429(15) 0.0348(5) Uani 1 1 d . . .
H5 H 1.1747 0.5977 1.1986 0.042 Uiso 1 1 calc R . .
C6 C 0.8748(4) 0.7256(2) 1.25404(15) 0.0367(5) Uani 1 1 d . . .
C7 C 0.6712(4) 0.8255(3) 1.23569(17) 0.0419(6) Uani 1 1 d . . .
H7 H 0.5583 0.8612 1.2854 0.050 Uiso 1 1 calc R . .
C8 C 0.6346(4) 0.8720(3) 1.14544(16) 0.0410(6) Uani 1 1 d . . .
H8 H 0.4969 0.9404 1.1314 0.049 Uiso 1 1 calc R . .
C9 C 0.8032(4) 0.8169(2) 1.07503(15) 0.0329(5) Uani 1 1 d . . .
C10 C 1.0036(4) 0.7140(2) 1.09196(14) 0.0311(5) Uani 1 1 d . . .
C11 C 1.3181(4) 0.6613(2) 0.84969(14) 0.0317(5) Uani 1 1 d . . .
C13 C 1.4456(5) 0.6646(3) 0.68388(15) 0.0422(6) Uani 1 1 d . . .
H13A H 1.4747 0.5567 0.6818 0.051 Uiso 1 1 calc R . .
H13B H 1.6166 0.7143 0.6934 0.051 Uiso 1 1 calc R . .
C14 C 1.3212(5) 0.7051(3) 0.59069(16) 0.0447(6) Uani 1 1 d . . .
H14A H 1.4355 0.6715 0.5389 0.054 Uiso 1 1 calc R . .
H14B H 1.1526 0.6528 0.5806 0.054 Uiso 1 1 calc R . .
O8 O 0.7627(3) 1.0139(2) 0.59881(12) 0.0526(5) Uani 1 1 d D . .
H8A H 0.7701 1.0529 0.5460 0.079 Uiso 1 1 d RD . .
H8B H 0.9091 0.9689 0.6011 0.079 Uiso 1 1 d RD . .


_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 C9 1.372(3) . ?
O1 C2 1.376(3) . ?
O2 C2 1.202(3) . ?
O6A N6 1.213(3) . ?
O6B N6 1.216(3) . ?
O11 C11 1.230(2) . ?
O15 C14 1.424(3) . ?
O15 H15 0.8394 . ?
N6 C6 1.467(3) . ?
N12 C11 1.326(3) . ?
N12 C13 1.453(3) . ?
N12 H12 0.8800 . ?
C2 C3 1.462(3) . ?
C3 C4 1.343(3) . ?
C3 C11 1.503(3) . ?
C4 C10 1.434(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 C10 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C7 C8 1.368(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C13 C14 1.502(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O8 H8A 0.8417 . ?
O8 H8B 0.8411 . ?

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 O1 C2 123.01(16) . . ?
C14 O15 H15 109.8 . . ?
O6A N6 O6B 123.6(2) . . ?
O6A N6 C6 118.64(19) . . ?
O6B N6 C6 117.8(2) . . ?
C11 N12 C13 122.12(18) . . ?
C11 N12 H12 118.9 . . ?
C13 N12 H12 118.9 . . ?
O2 C2 O1 115.54(18) . . ?
O2 C2 C3 127.2(2) . . ?
O1 C2 C3 117.23(18) . . ?
C4 C3 C2 119.74(19) . . ?
C4 C3 C11 118.22(18) . . ?
C2 C3 C11 122.04(18) . . ?
C3 C4 C10 121.69(19) . . ?
C3 C4 H4 119.2 . . ?
C10 C4 H4 119.2 . . ?
C6 C5 C10 118.3(2) . . ?
C6 C5 H5 120.8 . . ?
C10 C5 H5 120.8 . . ?
C5 C6 C7 122.7(2) . . ?
C5 C6 N6 118.1(2) . . ?
C7 C6 N6 119.21(19) . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C8 117.10(18) . . ?
O1 C9 C10 120.20(18) . . ?
C8 C9 C10 122.7(2) . . ?
C9 C10 C5 118.46(19) . . ?
C9 C10 C4 118.12(19) . . ?
C5 C10 C4 123.38(19) . . ?
O11 C11 N12 122.74(19) . . ?
O11 C11 C3 119.62(18) . . ?
N12 C11 C3 117.64(18) . . ?
N12 C13 C14 110.95(19) . . ?
N12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O15 C14 C13 112.25(19) . . ?
O15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
O15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
H8A O8 H8B 101.6 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042

# Attachment '3a.cif'

data_aca1
_database_code_depnum_ccdc_archive 'CCDC 704504'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide
;
_chemical_name_common            
N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O5'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   6.8051(14)
_cell_length_b                   24.947(5)
_cell_length_c                   8.097(3)
_cell_angle_alpha                90
_cell_angle_beta                 123.45(2)
_cell_angle_gamma                90
_cell_volume                     1146.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker SMART area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            24974
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         35.91
_reflns_number_total             4881
_reflns_number_gt                4105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (Farrugia, 1999)'

_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)+(0.0664P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4881
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.46713(9) 0.00688(2) 0.19746(8) 1.000 0.0141(1) . .
O2 O Uani 0.57549(10) 0.07733(2) 0.10554(9) 1.000 0.0172(1) . .
O11 O Uani 0.07512(10) 0.17443(2) 0.11568(9) 1.000 0.0177(1) . .
O15 O Uani 0.60497(11) 0.20199(3) -0.10856(9) 1.000 0.0206(2) . .
O16 O Uani -0.07256(10) -0.09594(2) 0.41542(9) 1.000 0.0177(1) . .
N12 N Uani 0.33983(11) 0.16966(2) 0.02894(10) 1.000 0.0150(2) . .
C2 C Uani 0.43864(12) 0.05956(3) 0.14437(10) 1.000 0.0128(2) . .
C3 C Uani 0.25159(11) 0.08947(3) 0.14237(10) 1.000 0.0115(2) . .
C4 C Uani 0.11272(12) 0.06417(3) 0.19044(10) 1.000 0.0121(2) . .
C5 C Uani 0.01387(12) -0.01910(3) 0.30203(10) 1.000 0.0128(2) . .
C6 C Uani 0.06371(12) -0.07264(3) 0.35935(10) 1.000 0.0130(2) . .
C7 C Uani 0.24298(12) -0.09930(3) 0.35627(11) 1.000 0.0146(2) . .
C8 C Uani 0.37558(12) -0.07240(3) 0.29923(11) 1.000 0.0147(2) . .
C9 C Uani 0.32828(11) -0.01877(3) 0.24747(10) 1.000 0.0122(2) . .
C10 C Uani 0.14820(11) 0.00853(3) 0.24650(10) 1.000 0.0114(2) . .
C11 C Uani 0.21390(12) 0.14827(3) 0.09305(10) 1.000 0.0125(2) . .
C13 C Uani 0.33675(13) 0.22610(3) -0.01731(11) 1.000 0.0148(2) . .
C14 C Uani 0.56873(13) 0.23910(3) 0.00568(12) 1.000 0.0179(2) . .
C17 C Uani -0.00806(15) -0.14853(3) 0.49884(12) 1.000 0.0182(2) . .
H4 H Uiso -0.00970 0.08350 0.18690 1.000 0.0140 calc R
H5 H Uiso -0.11060 -0.00140 0.30060 1.000 0.0150 calc R
H7 H Uiso 0.27420 -0.13600 0.39340 1.000 0.0180 calc R
H8 H Uiso 0.49620 -0.09050 0.29580 1.000 0.0180 calc R
H12 H Uiso 0.43110 0.14810 0.01360 1.000 0.0180 calc R
H13A H Uiso 0.31780 0.24810 0.07190 1.000 0.0180 calc R
H13B H Uiso 0.20630 0.23330 -0.15180 1.000 0.0180 calc R
H14A H Uiso 0.56470 0.27530 -0.03940 1.000 0.0220 calc R
H14B H Uiso 0.69690 0.23660 0.14390 1.000 0.0220 calc R
H15 H Uiso 0.74710 0.19260 -0.04460 1.000 0.0310 calc R
H17A H Uiso -0.11750 -0.16060 0.53230 1.000 0.0270 calc R
H17B H Uiso 0.15010 -0.14780 0.61740 1.000 0.0270 calc R
H17C H Uiso -0.01300 -0.17300 0.40340 1.000 0.0270 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3630(10) . . yes
O1 C9 1.3741(12) . . yes
O2 C2 1.2188(13) . . yes
O11 C11 1.2418(12) . . yes
O15 C14 1.4230(12) . . yes
O16 C6 1.3668(13) . . yes
O16 C17 1.4294(11) . . yes
O15 H15 0.8400 . . no
N12 C13 1.4541(11) . . yes
N12 C11 1.3338(13) . . yes
N12 H12 0.8800 . . no
C2 C3 1.4678(13) . . no
C3 C4 1.3596(13) . . no
C3 C11 1.5047(12) . . no
C4 C10 1.4388(12) . . no
C5 C10 1.4022(13) . . no
C5 C6 1.3932(12) . . no
C6 C7 1.4017(14) . . no
C7 C8 1.3919(14) . . no
C8 C9 1.3858(12) . . no
C9 C10 1.3982(13) . . no
C13 C14 1.5192(15) . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C13 H13A 0.9700 . . no
C13 H13B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no
C17 H17A 0.9700 . . no
C17 H17B 0.9700 . . no
C17 H17C 0.9700 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 122.73(7) . . . yes
C6 O16 C17 117.35(8) . . . yes
C14 O15 H15 109.00 . . . no
C11 N12 C13 124.50(8) . . . yes
C11 N12 H12 118.00 . . . no
C13 N12 H12 118.00 . . . no
O1 C2 O2 115.85(8) . . . yes
O1 C2 C3 117.73(8) . . . yes
O2 C2 C3 126.41(7) . . . yes
C4 C3 C11 119.00(8) . . . no
C2 C3 C4 119.75(7) . . . no
C2 C3 C11 121.23(8) . . . no
C3 C4 C10 121.06(8) . . . no
C6 C5 C10 119.74(8) . . . no
O16 C6 C5 115.67(8) . . . yes
C5 C6 C7 120.23(8) . . . no
O16 C6 C7 124.10(7) . . . yes
C6 C7 C8 120.46(7) . . . no
C7 C8 C9 118.74(8) . . . no
O1 C9 C8 117.12(8) . . . yes
O1 C9 C10 120.96(7) . . . yes
C8 C9 C10 121.92(8) . . . no
C4 C10 C5 123.35(8) . . . no
C4 C10 C9 117.76(8) . . . no
C5 C10 C9 118.88(7) . . . no
O11 C11 C3 120.36(8) . . . yes
O11 C11 N12 123.45(7) . . . yes
N12 C11 C3 116.18(8) . . . yes
N12 C13 C14 107.98(7) . . . yes
O15 C14 C13 108.79(7) . . . yes
C3 C4 H4 120.00 . . . no
C10 C4 H4 119.00 . . . no
C6 C5 H5 120.00 . . . no
C10 C5 H5 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 121.00 . . . no
C9 C8 H8 121.00 . . . no
N12 C13 H13A 110.00 . . . no
N12 C13 H13B 110.00 . . . no
C14 C13 H13A 110.00 . . . no
C14 C13 H13B 110.00 . . . no
H13A C13 H13B 108.00 . . . no
O15 C14 H14A 110.00 . . . no
O15 C14 H14B 110.00 . . . no
C13 C14 H14A 110.00 . . . no
C13 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no
O16 C17 H17A 109.00 . . . no
O16 C17 H17B 110.00 . . . no
O16 C17 H17C 110.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no

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 O1 C2 O2 179.31(7) . . . . no
C9 O1 C2 C3 0.29(10) . . . . no
C2 O1 C9 C8 -179.83(7) . . . . no
C2 O1 C9 C10 -0.11(11) . . . . no
C17 O16 C6 C7 8.05(10) . . . . no
C17 O16 C6 C5 -172.28(7) . . . . no
C11 N12 C13 C14 154.94(8) . . . . no
C13 N12 C11 O11 1.79(12) . . . . no
C13 N12 C11 C3 -176.99(7) . . . . no
O2 C2 C3 C4 -179.63(7) . . . . no
O1 C2 C3 C4 -0.72(10) . . . . no
O2 C2 C3 C11 -1.24(11) . . . . no
O1 C2 C3 C11 177.67(6) . . . . no
C11 C3 C4 C10 -177.46(6) . . . . no
C2 C3 C11 O11 -171.06(7) . . . . no
C2 C3 C4 C10 0.97(10) . . . . no
C2 C3 C11 N12 7.76(10) . . . . no
C4 C3 C11 N12 -173.83(7) . . . . no
C4 C3 C11 O11 7.35(11) . . . . no
C3 C4 C10 C5 178.40(7) . . . . no
C3 C4 C10 C9 -0.78(10) . . . . no
C10 C5 C6 O16 178.51(7) . . . . no
C10 C5 C6 C7 -1.80(11) . . . . no
C6 C5 C10 C9 0.86(10) . . . . no
C6 C5 C10 C4 -178.30(7) . . . . no
O16 C6 C7 C8 -179.26(7) . . . . no
C5 C6 C7 C8 1.08(11) . . . . no
C6 C7 C8 C9 0.58(11) . . . . no
C7 C8 C9 C10 -1.55(11) . . . . no
C7 C8 C9 O1 178.18(7) . . . . no
O1 C9 C10 C4 0.33(10) . . . . no
O1 C9 C10 C5 -178.88(7) . . . . no
C8 C9 C10 C4 -179.96(7) . . . . no
C8 C9 C10 C5 0.83(11) . . . . no
N12 C13 C14 O15 52.75(8) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C5 3.3922(17) . 1_655 no
O1 O2 3.1196(14) . 3_655 no
O2 O1 3.1196(14) . 3_655 no
O2 N12 2.6768(13) . . no
O2 C4 3.3430(17) . 1_655 no
O2 C17 3.4185(16) . 3_656 no
O11 O15 2.7571(15) . 1_455 no
O15 O11 2.7571(15) . 1_655 no
O15 C13 3.2930(16) . 4_554 no
O15 C14 3.3358(16) . 4_554 no
O15 N12 2.7130(15) . . no
O16 C8 3.3821(17) . 1_455 no
O1 H5 2.5200 . 1_655 no
O2 H12 1.9600 . . no
O2 H4 2.5300 . 1_655 no
O2 H17B 2.6400 . 3_656 no
O2 H5 2.6800 . 1_655 no
O11 H13B 2.7900 . 4_555 no
O11 H4 2.4900 . . no
O11 H13A 2.6200 . . no
O11 H17A 2.7200 . 3_556 no
O11 H15 1.9200 . 1_455 no
O15 H12 2.3400 . . no
O15 H13A 2.5500 . 4_554 no
O15 H14B 2.8500 . 4_554 no
O16 H8 2.5400 . 1_455 no
N12 O2 2.6768(13) . . no
N12 O15 2.7130(15) . . no
N12 H17C 2.9400 . 3_555 no
C2 C6 3.5666(17) . 3_656 no
C2 C7 3.5168(16) . 3_656 no
C2 C5 3.3609(16) . 3_555 no
C3 C7 3.5649(17) . 3_555 no
C3 C5 3.4824(16) . 3_555 no
C3 C6 3.4167(16) . 3_555 no
C4 O2 3.3430(17) . 1_455 no
C4 C9 3.3363(16) . 3_555 no
C4 C10 3.4689(16) . 3_555 no
C4 C8 3.5043(17) . 3_555 no
C5 C5 3.4480(17) . 3_556 no
C5 C3 3.4824(16) . 3_555 no
C5 O1 3.3922(17) . 1_455 no
C5 C2 3.3609(16) . 3_555 no
C6 C2 3.5666(17) . 3_656 no
C6 C3 3.4167(16) . 3_555 no
C6 C11 3.5942(17) . 3_555 no
C7 C2 3.5168(16) . 3_656 no
C7 C11 3.4533(17) . 3_555 no
C7 C3 3.5649(17) . 3_555 no
C8 C4 3.5043(17) . 3_555 no
C8 O16 3.3821(17) . 1_655 no
C9 C10 3.5042(16) . 3_555 no
C9 C4 3.3363(16) . 3_555 no
C9 C9 3.5393(16) . 3_656 no
C10 C10 3.3627(16) . 3_555 no
C10 C4 3.4689(16) . 3_555 no
C10 C9 3.5042(16) . 3_555 no
C11 C7 3.4533(17) . 3_555 no
C11 C6 3.5942(17) . 3_555 no
C13 O15 3.2930(16) . 4_555 no
C14 O15 3.3358(16) . 4_555 no
C17 O2 3.4185(16) . 3_656 no
C2 H5 3.0100 . 1_655 no
C2 H12 2.4400 . . no
C5 H5 2.9500 . 3_556 no
C7 H17C 2.7000 . . no
C7 H17B 2.7900 . . no
C11 H15 2.9400 . 1_455 no
C13 H17C 2.9600 . 3_555 no
C14 H13A 2.9600 . 4_554 no
C17 H7 2.5100 . . no
C17 H4 2.9600 . 3_556 no
H4 O2 2.5300 . 1_455 no
H4 O11 2.4900 . . no
H4 H5 2.5500 . . no
H4 C17 2.9600 . 3_556 no
H5 O1 2.5200 . 1_455 no
H5 O2 2.6800 . 1_455 no
H5 C2 3.0100 . 1_455 no
H5 H4 2.5500 . . no
H5 C5 2.9500 . 3_556 no
H7 C17 2.5100 . . no
H7 H17B 2.4000 . . no
H7 H17C 2.2000 . . no
H7 H14A 2.4600 . 2_645 no
H8 O16 2.5400 . 1_655 no
H12 O2 1.9600 . . no
H12 O15 2.3400 . . no
H12 C2 2.4400 . . no
H13A O11 2.6200 . . no
H13A H17A 2.5500 . 2_555 no
H13A O15 2.5500 . 4_555 no
H13A C14 2.9600 . 4_555 no
H13B H17C 2.2800 . 3_555 no
H13B O11 2.7900 . 4_554 no
H14A H7 2.4600 . 2_655 no
H14B O15 2.8500 . 4_555 no
H15 O11 1.9200 . 1_655 no
H15 C11 2.9400 . 1_655 no
H17A H13A 2.5500 . 2_545 no
H17A O11 2.7200 . 3_556 no
H17B C7 2.7900 . . no
H17B H7 2.4000 . . no
H17B O2 2.6400 . 3_656 no
H17C C7 2.7000 . . no
H17C H7 2.2000 . . no
H17C N12 2.9400 . 3_555 no
H17C C13 2.9600 . 3_555 no
H17C H13B 2.2800 . 3_555 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N12 H12 O2 0.8800 1.9600 2.6768(13) 138.00 . yes
N12 H12 O15 0.8800 2.3400 2.7130(15) 106.00 . yes
O15 H15 O11 0.8400 1.9200 2.7571(15) 176.00 1_655 yes
C4 H4 O2 0.9500 2.5300 3.3430(17) 144.00 1_455 yes
C5 H5 O1 0.9500 2.5200 3.3922(17) 153.00 1_455 yes
C8 H8 O16 0.9500 2.5400 3.3821(17) 148.00 1_655 yes
C13 H13A O15 0.9700 2.5500 3.2930(16) 134.00 4_555 yes

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061

# Attachment '4a.cif'

data_alfrdosm
_database_code_depnum_ccdc_archive 'CCDC 704505'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
6-chloro-N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide
;
_chemical_name_common            
6-chloro-N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Cl N O4'
_chemical_formula_sum            'C12 H10 Cl N O4'
_chemical_formula_weight         267.66

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           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   5.3567(5)
_cell_length_b                   22.078(2)
_cell_length_c                   9.3087(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.873(2)
_cell_angle_gamma                90
_cell_volume                     1100.29(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       square
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker SMART area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            12432
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         28.33
_reflns_number_total             2629
_reflns_number_gt                2545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (Farrugia, 1999)'

_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)+(0.0423P)²+0.7991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2629
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl6 Cl Uani 0.15686(8) 0.57294(2) 1.43324(5) 1.000 0.0167(1) . .
O1 O Uani 0.7891(2) 0.56025(6) 0.93404(14) 1.000 0.0148(3) . .
O2 O Uani 0.8896(3) 0.58165(6) 0.71390(15) 1.000 0.0194(4) . .
O11 O Uani 0.2833(3) 0.70410(6) 0.67517(15) 1.000 0.0204(4) . .
O15 O Uani 0.9461(3) 0.77576(6) 0.52313(15) 1.000 0.0198(4) . .
N12 N Uani 0.6292(3) 0.66960(7) 0.56692(17) 1.000 0.0153(4) . .
C2 C Uani 0.7435(3) 0.59099(8) 0.80783(19) 1.000 0.0138(5) . .
C3 C Uani 0.5264(3) 0.63106(8) 0.80085(19) 1.000 0.0129(5) . .
C4 C Uani 0.3740(3) 0.63433(8) 0.91307(19) 1.000 0.0134(5) . .
C5 C Uani 0.2720(3) 0.60340(8) 1.16218(19) 1.000 0.0140(5) . .
C6 C Uani 0.3388(3) 0.57013(8) 1.2825(2) 1.000 0.0140(5) . .
C7 C Uani 0.5519(3) 0.53377(8) 1.2873(2) 1.000 0.0156(5) . .
C8 C Uani 0.7024(3) 0.53054(8) 1.1697(2) 1.000 0.0157(5) . .
C9 C Uani 0.6360(3) 0.56425(8) 1.0488(2) 1.000 0.0133(5) . .
C10 C Uani 0.4240(3) 0.60070(8) 1.04214(19) 1.000 0.0128(5) . .
C11 C Uani 0.4689(3) 0.67116(8) 0.67327(19) 1.000 0.0140(5) . .
C13 C Uani 0.6098(4) 0.70915(9) 0.4419(2) 1.000 0.0174(5) . .
C14 C Uani 0.8608(3) 0.73684(8) 0.4106(2) 1.000 0.0165(5) . .
H4 H Uiso 0.23030 0.65950 0.90620 1.000 0.0160 calc R
H5 H Uiso 0.12580 0.62780 1.16040 1.000 0.0170 calc R
H7 H Uiso 0.59370 0.51120 1.37150 1.000 0.0190 calc R
H8 H Uiso 0.84770 0.50580 1.17170 1.000 0.0190 calc R
H12 H Uiso 0.75280 0.64340 0.57250 1.000 0.0180 calc R
H13A H Uiso 0.49030 0.74110 0.45930 1.000 0.0210 calc R
H13B H Uiso 0.54960 0.68610 0.35910 1.000 0.0210 calc R
H14A H Uiso 0.98190 0.70480 0.39810 1.000 0.0200 calc R
H14B H Uiso 0.84690 0.75960 0.32160 1.000 0.0200 calc R
H15 H Uiso 1.05140 0.75740 0.57590 1.000 0.0300 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl6 C6 1.7355(18) . . yes
O1 C2 1.372(2) . . yes
O1 C9 1.371(2) . . yes
O2 C2 1.210(2) . . yes
O11 C11 1.232(2) . . yes
O15 C14 1.419(2) . . yes
O15 H15 0.8400 . . no
N12 C13 1.456(2) . . yes
N12 C11 1.332(2) . . yes
N12 H12 0.8800 . . no
C2 C3 1.461(2) . . no
C3 C4 1.349(2) . . no
C3 C11 1.505(2) . . no
C4 C10 1.430(2) . . no
C5 C10 1.405(2) . . no
C5 C6 1.377(3) . . no
C6 C7 1.395(2) . . no
C7 C8 1.382(3) . . no
C8 C9 1.386(3) . . no
C9 C10 1.392(2) . . no
C13 C14 1.514(3) . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C13 H13A 0.9700 . . no
C13 H13B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 122.77(13) . . . yes
C14 O15 H15 109.00 . . . no
C11 N12 C13 123.21(16) . . . yes
C11 N12 H12 118.00 . . . no
C13 N12 H12 118.00 . . . no
O1 C2 O2 115.68(15) . . . yes
O1 C2 C3 117.19(14) . . . yes
O2 C2 C3 127.14(17) . . . yes
C4 C3 C11 117.79(15) . . . no
C2 C3 C4 119.94(16) . . . no
C2 C3 C11 122.23(15) . . . no
C3 C4 C10 121.43(16) . . . no
C6 C5 C10 118.84(15) . . . no
Cl6 C6 C5 120.05(13) . . . yes
C5 C6 C7 121.58(16) . . . no
Cl6 C6 C7 118.37(14) . . . yes
C6 C7 C8 120.14(17) . . . no
C7 C8 C9 118.33(15) . . . no
O1 C9 C8 117.00(15) . . . yes
O1 C9 C10 120.71(16) . . . yes
C8 C9 C10 122.28(16) . . . no
C4 C10 C5 123.27(15) . . . no
C4 C10 C9 117.89(16) . . . no
C5 C10 C9 118.84(16) . . . no
O11 C11 C3 118.70(15) . . . yes
O11 C11 N12 124.46(17) . . . yes
N12 C11 C3 116.81(15) . . . yes
N12 C13 C14 110.82(16) . . . yes
O15 C14 C13 111.66(15) . . . yes
C3 C4 H4 119.00 . . . no
C10 C4 H4 119.00 . . . no
C6 C5 H5 121.00 . . . no
C10 C5 H5 121.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 121.00 . . . no
C9 C8 H8 121.00 . . . no
N12 C13 H13A 109.00 . . . no
N12 C13 H13B 109.00 . . . no
C14 C13 H13A 109.00 . . . no
C14 C13 H13B 109.00 . . . no
H13A C13 H13B 108.00 . . . no
O15 C14 H14A 109.00 . . . no
O15 C14 H14B 109.00 . . . no
C13 C14 H14A 109.00 . . . no
C13 C14 H14B 109.00 . . . no
H14A C14 H14B 108.00 . . . no

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 O1 C2 O2 -177.62(16) . . . . no
C9 O1 C2 C3 2.4(2) . . . . no
C2 O1 C9 C10 -0.3(2) . . . . no
C2 O1 C9 C8 179.58(15) . . . . no
C11 N12 C13 C14 133.28(18) . . . . no
C13 N12 C11 O11 2.9(3) . . . . no
C13 N12 C11 C3 -175.03(16) . . . . no
O2 C2 C3 C4 176.78(18) . . . . no
O2 C2 C3 C11 -5.3(3) . . . . no
O1 C2 C3 C11 174.74(15) . . . . no
O1 C2 C3 C4 -3.2(2) . . . . no
C4 C3 C11 N12 176.52(16) . . . . no
C2 C3 C4 C10 2.0(3) . . . . no
C4 C3 C11 O11 -1.6(2) . . . . no
C11 C3 C4 C10 -175.98(16) . . . . no
C2 C3 C11 N12 -1.5(2) . . . . no
C2 C3 C11 O11 -179.55(16) . . . . no
C3 C4 C10 C5 179.15(17) . . . . no
C3 C4 C10 C9 0.0(3) . . . . no
C6 C5 C10 C9 0.3(3) . . . . no
C10 C5 C6 Cl6 179.42(13) . . . . no
C10 C5 C6 C7 -0.4(3) . . . . no
C6 C5 C10 C4 -178.78(17) . . . . no
Cl6 C6 C7 C8 -179.68(14) . . . . no
C5 C6 C7 C8 0.1(3) . . . . no
C6 C7 C8 C9 0.2(3) . . . . no
C7 C8 C9 C10 -0.3(3) . . . . no
C7 C8 C9 O1 179.84(15) . . . . no
O1 C9 C10 C4 -1.0(2) . . . . no
O1 C9 C10 C5 179.90(15) . . . . no
C8 C9 C10 C4 179.15(16) . . . . no
C8 C9 C10 C5 0.0(3) . . . . no
N12 C13 C14 O15 -64.72(19) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl6 O2 3.0260(15) . 1_456 no
Cl6 C7 3.5787(17) . 1_455 no
Cl6 C8 3.5257(18) . 1_455 no
Cl6 C11 3.4992(18) . 1_556 no
Cl6 H12 2.9900 . 1_456 no
Cl6 H14A 3.0700 . 1_456 no
Cl6 H7 2.9000 . 3_668 no
O1 C7 3.412(2) . 3_667 no
O2 C4 3.348(2) . 1_655 no
O2 Cl6 3.0260(15) . 1_654 no
O2 N12 2.732(2) . . no
O11 C14 3.368(2) . 1_455 no
O11 O15 2.757(2) . 1_455 no
O15 C5 3.420(2) . 4_664 no
O15 O11 2.757(2) . 1_655 no
O15 N12 2.930(2) . . no
O15 C4 3.225(2) . 4_664 no
O1 H8 2.6500 . 3_767 no
O2 H8 2.6000 . 3_767 no
O2 H12 2.0200 . . no
O11 H13A 2.4700 . . no
O11 H15 1.9300 . 1_455 no
O11 H14B 2.8600 . 4_465 no
O11 H4 2.3900 . . no
O15 H4 2.3800 . 4_664 no
O15 H5 2.6500 . 4_664 no
N12 O2 2.732(2) . . no
N12 O15 2.930(2) . . no
C2 C7 3.284(2) . 3_667 no
C3 C14 3.555(2) . 4_565 no
C4 O2 3.348(2) . 1_455 no
C4 O15 3.225(2) . 4_465 no
C5 O15 3.420(2) . 4_465 no
C5 C8 3.452(2) . 1_455 no
C7 C2 3.284(2) . 3_667 no
C7 O1 3.412(2) . 3_667 no
C7 Cl6 3.5787(17) . 1_655 no
C8 C9 3.400(3) . 3_667 no
C8 C10 3.557(3) . 3_667 no
C8 C5 3.452(2) . 1_655 no
C8 Cl6 3.5257(18) . 1_655 no
C9 C8 3.400(3) . 3_667 no
C9 C9 3.303(2) . 3_667 no
C10 C8 3.557(3) . 3_667 no
C11 Cl6 3.4992(18) . 1_554 no
C14 O11 3.368(2) . 1_655 no
C14 C3 3.555(2) . 4_564 no
C2 H8 3.0600 . 3_767 no
C2 H12 2.4800 . . no
C3 H14B 2.9600 . 4_565 no
C4 H13A 2.8500 . 4_565 no
C5 H13B 2.9500 . 1_556 no
C6 H13B 2.8800 . 1_556 no
C11 H14B 2.8600 . 4_565 no
C11 H15 3.0500 . 1_455 no
C14 H4 3.0300 . 4_664 no
H4 O11 2.3900 . . no
H4 H5 2.5500 . . no
H4 O15 2.3800 . 4_465 no
H4 C14 3.0300 . 4_465 no
H5 H4 2.5500 . . no
H5 O15 2.6500 . 4_465 no
H7 Cl6 2.9000 . 3_668 no
H8 O1 2.6500 . 3_767 no
H8 O2 2.6000 . 3_767 no
H8 C2 3.0600 . 3_767 no
H12 Cl6 2.9900 . 1_654 no
H12 O2 2.0200 . . no
H12 C2 2.4800 . . no
H12 H14A 2.4700 . . no
H13A O11 2.4700 . . no
H13A C4 2.8500 . 4_564 no
H13B C5 2.9500 . 1_554 no
H13B C6 2.8800 . 1_554 no
H14A Cl6 3.0700 . 1_654 no
H14A H12 2.4700 . . no
H14B O11 2.8600 . 4_664 no
H14B C3 2.9600 . 4_564 no
H14B C11 2.8600 . 4_564 no
H14B H15 2.6000 . 4_564 no
H15 O11 1.9300 . 1_655 no
H15 C11 3.0500 . 1_655 no
H15 H14B 2.6000 . 4_565 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N12 H12 O2 0.8800 2.0200 2.732(2) 138.00 . yes
O15 H15 O11 0.8400 1.9300 2.757(2) 170.00 1_655 yes
C4 H4 O11 0.9500 2.3900 2.728(2) 100.00 . yes
C4 H4 O15 0.9500 2.3800 3.225(2) 148.00 4_465 yes
C8 H8 O2 0.9500 2.6000 3.454(2) 150.00 3_767 yes
C13 H13A O11 0.9700 2.4700 2.835(2) 102.00 . yes

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062

# Attachment '5a.cif'

data_r2garcix
_database_code_depnum_ccdc_archive 'CCDC 704506'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br N O4'
_chemical_formula_weight         312.12

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'
Br Br -0.2901 2.4595 '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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.2813(7)
_cell_length_b                   25.012(2)
_cell_length_c                   5.5283(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.459(2)
_cell_angle_gamma                90
_cell_volume                     1141.62(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.1454
_exptl_absorpt_correction_T_max  0.1686
_exptl_absorpt_correction_T_ave  0.1571
_exptl_absorpt_coefficient_mu    3.607
_exptl_crystal_size_rad          0.4000
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker SMART area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            10984
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2018
_reflns_number_gt                1913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (Farrugia, 1999)'

_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)+(0.0311P)²+6.1451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br6 Br Uani 0.44282(9) 0.70332(3) 0.64458(13) 1.000 0.0290(2) . .
O1 O Uani 0.3657(5) 0.50752(19) 1.2522(8) 1.000 0.0231(14) . .
O2 O Uani 0.2651(6) 0.42828(19) 1.3233(8) 1.000 0.0253(16) . .
O11 O Uani -0.0346(5) 0.43362(18) 0.6765(8) 1.000 0.0205(12) . .
O15 O Uani 0.1637(6) 0.2740(2) 0.7612(10) 1.000 0.0296(17) . .
N12 N Uani 0.0688(7) 0.3787(2) 0.9727(10) 1.000 0.0209(17) . .
C2 C Uani 0.2672(8) 0.4658(3) 1.1842(12) 1.000 0.0208(19) . .
C3 C Uani 0.1745(8) 0.4696(3) 0.9469(11) 1.000 0.0205(19) . .
C4 C Uani 0.1890(8) 0.5134(3) 0.8073(12) 1.000 0.0199(19) . .
C5 C Uani 0.3104(8) 0.6023(3) 0.7453(12) 1.000 0.0210(19) . .
C6 C Uani 0.4161(8) 0.6410(3) 0.8345(12) 1.000 0.023(2) . .
C7 C Uani 0.5042(8) 0.6362(3) 1.0576(12) 1.000 0.024(2) . .
C8 C Uani 0.4864(8) 0.5910(3) 1.1968(12) 1.000 0.0261(19) . .
C9 C Uani 0.3800(8) 0.5519(3) 1.1095(12) 1.000 0.020(2) . .
C10 C Uani 0.2922(8) 0.5564(3) 0.8845(12) 1.000 0.021(2) . .
C11 C Uani 0.0596(8) 0.4257(3) 0.8573(11) 1.000 0.0178(17) . .
C13 C Uani -0.0353(8) 0.3349(3) 0.8938(13) 1.000 0.025(2) . .
C14 C Uani 0.0225(9) 0.3046(3) 0.6827(14) 1.000 0.029(2) . .
H3 H Uiso 0.12890 0.51550 0.65410 1.000 0.0240 calc R
H4 H Uiso 0.25090 0.60660 0.59250 1.000 0.0250 calc R
H5 H Uiso 0.57620 0.66390 1.11430 1.000 0.0290 calc R
H7 H Uiso 0.54620 0.58690 1.34950 1.000 0.0310 calc R
H12 H Uiso 0.13940 0.37450 1.09870 1.000 0.0250 calc R
H13A H Uiso -0.14300 0.34860 0.84890 1.000 0.0300 calc R
H13B H Uiso -0.04330 0.31040 1.02840 1.000 0.0300 calc R
H14A H Uiso -0.06240 0.28090 0.61600 1.000 0.0340 calc R
H14B H Uiso 0.04850 0.32940 0.55660 1.000 0.0340 calc R
H15 H Uiso 0.19520 0.25670 0.64320 1.000 0.0450 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br6 C6 1.902(7) . . yes
O1 C2 1.359(8) . . yes
O1 C9 1.372(9) . . yes
O2 C2 1.214(9) . . yes
O11 C11 1.235(8) . . yes
O15 C14 1.436(9) . . yes
O15 H15 0.8400 . . no
N12 C13 1.441(9) . . yes
N12 C11 1.337(9) . . yes
N12 H12 0.8800 . . no
C2 C3 1.471(9) . . no
C3 C4 1.351(10) . . no
C3 C11 1.511(10) . . no
C4 C10 1.419(10) . . no
C5 C10 1.397(10) . . no
C5 C6 1.371(10) . . no
C6 C7 1.389(9) . . no
C7 C8 1.382(10) . . no
C8 C9 1.378(10) . . no
C9 C10 1.396(9) . . no
C13 C14 1.501(10) . . no
C4 H3 0.9500 . . no
C5 H4 0.9500 . . no
C7 H5 0.9500 . . no
C8 H7 0.9500 . . no
C13 H13A 0.9700 . . no
C13 H13B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 122.6(5) . . . yes
C14 O15 H15 110.00 . . . no
C11 N12 C13 120.9(6) . . . yes
C11 N12 H12 119.00 . . . no
C13 N12 H12 120.00 . . . no
O1 C2 O2 117.1(6) . . . yes
O1 C2 C3 117.2(6) . . . yes
O2 C2 C3 125.6(7) . . . yes
C4 C3 C11 118.9(6) . . . no
C2 C3 C4 119.9(6) . . . no
C2 C3 C11 121.2(6) . . . no
C3 C4 C10 121.4(6) . . . no
C6 C5 C10 118.4(6) . . . no
Br6 C6 C5 118.6(5) . . . yes
C5 C6 C7 122.4(7) . . . no
Br6 C6 C7 119.1(5) . . . yes
C6 C7 C8 119.6(7) . . . no
C7 C8 C9 118.6(6) . . . no
O1 C9 C8 117.0(6) . . . yes
O1 C9 C10 121.0(6) . . . yes
C8 C9 C10 122.0(7) . . . no
C4 C10 C5 123.1(6) . . . no
C4 C10 C9 117.8(6) . . . no
C5 C10 C9 119.1(6) . . . no
O11 C11 C3 119.4(6) . . . yes
O11 C11 N12 122.4(6) . . . yes
N12 C11 C3 118.1(6) . . . yes
N12 C13 C14 113.6(6) . . . yes
O15 C14 C13 109.6(6) . . . yes
C3 C4 H3 119.00 . . . no
C10 C4 H3 119.00 . . . no
C6 C5 H4 121.00 . . . no
C10 C5 H4 121.00 . . . no
C6 C7 H5 120.00 . . . no
C8 C7 H5 120.00 . . . no
C7 C8 H7 121.00 . . . no
C9 C8 H7 121.00 . . . no
N12 C13 H13A 109.00 . . . no
N12 C13 H13B 109.00 . . . no
C14 C13 H13A 109.00 . . . no
C14 C13 H13B 109.00 . . . no
H13A C13 H13B 108.00 . . . no
O15 C14 H14A 110.00 . . . no
O15 C14 H14B 110.00 . . . no
C13 C14 H14A 110.00 . . . no
C13 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no

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 O1 C2 O2 179.2(6) . . . . no
C9 O1 C2 C3 0.2(9) . . . . no
C2 O1 C9 C10 0.2(9) . . . . no
C2 O1 C9 C8 -178.7(6) . . . . no
C11 N12 C13 C14 81.0(8) . . . . no
C13 N12 C11 O11 -1.6(10) . . . . no
C13 N12 C11 C3 -178.9(6) . . . . no
O2 C2 C3 C4 -179.2(7) . . . . no
O2 C2 C3 C11 2.2(11) . . . . no
O1 C2 C3 C11 -178.9(6) . . . . no
O1 C2 C3 C4 -0.3(10) . . . . no
C4 C3 C11 N12 167.5(6) . . . . no
C2 C3 C4 C10 -0.1(10) . . . . no
C4 C3 C11 O11 -9.9(10) . . . . no
C11 C3 C4 C10 178.6(6) . . . . no
C2 C3 C11 N12 -13.9(9) . . . . no
C2 C3 C11 O11 168.8(6) . . . . no
C3 C4 C10 C5 180.0(7) . . . . no
C3 C4 C10 C9 0.6(10) . . . . no
C6 C5 C10 C9 0.9(10) . . . . no
C10 C5 C6 Br6 179.5(5) . . . . no
C10 C5 C6 C7 -0.4(10) . . . . no
C6 C5 C10 C4 -178.6(7) . . . . no
Br6 C6 C7 C8 -179.7(5) . . . . no
C5 C6 C7 C8 0.1(10) . . . . no
C6 C7 C8 C9 -0.4(10) . . . . no
C7 C8 C9 C10 0.9(10) . . . . no
C7 C8 C9 O1 179.8(6) . . . . no
O1 C9 C10 C4 -0.6(10) . . . . no
O1 C9 C10 C5 180.0(6) . . . . no
C8 C9 C10 C4 178.3(6) . . . . no
C8 C9 C10 C5 -1.2(10) . . . . no
N12 C13 C14 O15 71.5(7) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br6 C7 3.723(7) . 1_554 no
Br6 Br6 3.6185(11) . 4_564 no
Br6 Br6 3.6185(11) . 4_565 no
O1 O11 3.164(6) . 3_567 no
O1 C9 3.361(8) . 3_667 no
O1 C10 3.389(8) . 3_667 no
O2 N12 2.729(7) . . no
O2 C8 3.265(8) . 3_668 no
O2 C6 3.330(8) . 3_667 no
O2 C7 3.363(8) . 3_667 no
O11 C10 3.363(8) . 3_567 no
O11 C4 3.164(8) . 3_566 no
O11 C14 3.261(9) . . no
O11 C9 3.200(8) . 3_567 no
O11 C2 3.296(8) . 3_567 no
O11 O1 3.164(6) . 3_567 no
O11 C5 3.261(8) . 3_566 no
O15 O15 3.014(8) . 4_554 no
O15 C14 3.330(9) . 4_555 no
O15 N12 2.998(7) . . no
O15 O15 3.014(8) . 4_555 no
O2 H12 2.0600 . . no
O2 H7 2.3300 . 3_668 no
O11 H3 2.3100 . 3_566 no
O11 H14B 2.7900 . . no
O11 H3 2.4600 . . no
O11 H4 2.4500 . 3_566 no
O11 H13A 2.5200 . . no
O15 H5 2.7000 . 3_667 no
O15 H15 2.2400 . 4_555 no
N12 O2 2.729(7) . . no
N12 O15 2.998(7) . . no
C2 C8 3.360(10) . 3_667 no
C2 O11 3.296(8) . 3_567 no
C2 C7 3.503(10) . 3_667 no
C2 C9 3.479(9) . 3_667 no
C3 C8 3.341(10) . 3_667 no
C3 C3 3.358(10) . 3_567 no
C3 C4 3.424(9) . 3_567 no
C3 C11 3.481(10) . 3_567 no
C4 C3 3.424(9) . 3_567 no
C4 O11 3.164(8) . 3_566 no
C4 C11 3.254(10) . 3_567 no
C5 C13 3.514(10) . 3_567 no
C5 C8 3.477(9) . 1_554 no
C5 O11 3.261(8) . 3_566 no
C6 O2 3.330(8) . 3_667 no
C7 O2 3.363(8) . 3_667 no
C7 C2 3.503(10) . 3_667 no
C7 Br6 3.723(7) . 1_556 no
C8 O2 3.265(8) . 3_668 no
C8 C5 3.477(9) . 1_556 no
C8 C3 3.341(10) . 3_667 no
C8 C2 3.360(10) . 3_667 no
C9 C9 3.540(10) . 3_667 no
C9 O11 3.200(8) . 3_567 no
C9 O1 3.361(8) . 3_667 no
C9 C2 3.479(9) . 3_667 no
C10 O11 3.363(8) . 3_567 no
C10 C11 3.372(9) . 3_567 no
C10 O1 3.389(8) . 3_667 no
C11 C10 3.372(9) . 3_567 no
C11 C3 3.481(10) . 3_567 no
C11 C4 3.254(10) . 3_567 no
C13 C5 3.514(10) . 3_567 no
C14 O11 3.261(9) . . no
C14 O15 3.330(9) . 4_554 no
C2 H12 2.5500 . . no
C5 H7 3.0700 . 1_554 no
C5 H13A 2.9900 . 3_567 no
C6 H13A 2.9800 . 3_567 no
C7 H13A 3.1000 . 3_567 no
C8 H4 3.0700 . 1_556 no
C11 H14B 2.9200 . . no
C14 H13B 3.0400 . 4_554 no
H3 O11 2.4600 . . no
H3 H4 2.5300 . . no
H3 O11 2.3100 . 3_566 no
H4 C8 3.0700 . 1_554 no
H4 H3 2.5300 . . no
H4 O11 2.4500 . 3_566 no
H5 O15 2.7000 . 3_667 no
H7 C5 3.0700 . 1_556 no
H7 O2 2.3300 . 3_668 no
H12 O2 2.0600 . . no
H12 C2 2.5500 . . no
H13A O11 2.5200 . . no
H13A C5 2.9900 . 3_567 no
H13A C6 2.9800 . 3_567 no
H13A C7 3.1000 . 3_567 no
H13B C14 3.0400 . 4_555 no
H13B H14A 2.3400 . 4_555 no
H14A H13B 2.3400 . 4_554 no
H14B O11 2.7900 . . no
H14B C11 2.9200 . . no
H15 O15 2.2400 . 4_554 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N12 H12 O2 0.8800 2.0600 2.729(7) 132.00 . yes
O15 H15 O15 0.8400 2.2400 3.014(8) 152.00 4_554 yes
C4 H3 O11 0.9500 2.3100 3.164(8) 149.00 3_566 yes
C5 H4 O11 0.9500 2.4500 3.261(8) 143.00 3_566 yes
C8 H7 O2 0.9500 2.3300 3.265(8) 168.00 3_668 yes

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.601
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.108


