#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/05/7200567.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_7200567
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 H10 Cl N O4'
_chemical_formula_sum            'C12 H10 Cl N O4'
_chemical_formula_weight         267.66
_chemical_name_common
6-chloro-N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide
_chemical_name_systematic
;
6-chloro-N-(2-hydroxyethyl)-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                 91.873(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3567(5)
_cell_length_b                   22.078(2)
_cell_length_c                   9.3087(8)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     1100.31(17)
_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 0.999
_diffrn_measured_fraction_theta_max 0.958
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12432
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.389
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.7991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                2545
_reflns_number_total             2629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b818309k.txt
_cod_data_source_block           alfrdosm
_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_cell_volume        1100.29(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7200567
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
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
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'
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_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_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
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940816
