4-Chloro-3-nitrocoumarin: an unusual non-bonding C—Cl···O=C interaction
Fujii, Isao; Mano, Yoshihiro; Hirayama, Noriaki; Acta Crystallographica Section E 61 (2005) o1456–o1458; doi:10.1107/S1600536805011943

data_2205780
_publ_section_title
;
 4-Chloro-3-nitrocoumarin: an unusual non-bonding
 C---Cl&#x00B7;&#x00B7;&#x00B7;O=C interaction
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1456
_journal_page_last               o1458
_journal_paper_doi               10.1107/S1600536805011943
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H4 Cl N O4 '
_chemical_formula_moiety         'C9 H4 Cl N O4 '
_chemical_formula_sum            'C9 H4 Cl N O4'
_chemical_formula_weight         225.59
_chemical_name_common            4-chloro-3-nitrocoumarin
_chemical_name_systematic        '4-chloro-3-nitro-2H- chromen-2-one'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 114.119(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5110(4)
_cell_length_b                   13.5260(10)
_cell_length_c                   8.6612(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297.2
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      30.0
_cell_volume                     910.03(10)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1988)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR88 (Burla <i>et al.</i>, 1989)'
_diffrn_ambient_temperature      24
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2084
_diffrn_reflns_theta_full        74.86
_diffrn_reflns_theta_max         74.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.713
_exptl_absorpt_correction_T_max  0.478
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North <i>et al.</i>, 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             456.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.43
_refine_ls_extinction_coef       0.39(6)
_refine_ls_extinction_method     'type 2 Gaussian isotropic (Zachariasen, 1967)'
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1876
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.157(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                1727
_reflns_number_total             1876
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ob6503.cif
_cod_data_source_block           I
_cod_original_cell_volume        910.00(10)
_cod_original_formula_sum        'C9 H4 Cl N O4 '
_cod_database_code               2205780
_cod_database_fobs_code          2205780