#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/05/7200566.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_7200566
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         'C13 H13 N O5'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24
_chemical_name_common
N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide
_chemical_name_systematic
;
N-(2-hydroxyethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 123.45(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8051(14)
_cell_length_b                   24.947(5)
_cell_length_c                   8.097(3)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     1146.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 1997) and WINGX-2003 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device       'Bruker SMART area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24974
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.91
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0378
_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)+(0.0664P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                4105
_reflns_number_total             4881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b818309k.txt
_cod_data_source_block           aca1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7200566
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
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
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_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_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_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
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1715837
