Competition between OH⋯O and multiple halogen–dipole interactions on the formation of intramolecular three-centred hydrogen bond in 3-acyl coumarins
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.; CrystEngComm 11 (2009) 1451–; doi:10.1039/b818309k

data_7200566
_publ_section_title
;
 Competition between OH&#x22EF;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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0664P)^2^+0.2343P] where P=(Fo^2^+2Fc^2^)/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