#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:23:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180336 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/05/7200565.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7200565
loop_
_publ_author_name
'Santos-Contreras, Rocío J.'
'Martínez-Martínez, Francisco J.'
'Mancilla-Margalli, N. Alejandra'
'Peraza-Campos, Ana L.'
'Morín-Sánchez, Luis M.'
'García-Báez, Efrén V.'
'Padilla-Martínez, Itzia I.'
_publ_section_title
;
 Competition between OH⋯O and multiple halogen--dipole
 interactions on the formation of intramolecular three-centred hydrogen
 bond in 3-acyl coumarins
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1451
_journal_paper_doi               10.1039/b818309k
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H12 N2 O7'
_chemical_formula_sum            'C12 H12 N2 O7'
_chemical_formula_weight         296.24
_chemical_name_common
;N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide
hydrate
;
_chemical_name_systematic
;
N-(2-hydroxyethyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide hydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.044(4)
_cell_angle_beta                 91.533(4)
_cell_angle_gamma                90.092(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0399(13)
_cell_length_b                   8.901(2)
_cell_length_c                   14.031(4)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     627.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6037
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8614
_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_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          0.2000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.030(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.243
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.2307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                1958
_reflns_number_total             2179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b818309k.txt
_cod_data_source_block           m3mendm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               7200565
#BEGIN Tags that were not found in dictionaries:
_exptl_absorpt_correction_t_ave  0.8617
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
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 . . ?
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 . ?
