The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
Dekić, Vidoslav S.; Rodić, Marko V.; Radulović, Niko S.; Ristić, Milenko N.; Dekić, Biljana R.; Gurešić, Dejan M.; Ristić, Novica R.; Zeitschrift für Kristallographie - New Crystal Structures 235 (2019) 225–227; doi:10.1515/ncrs-2019-0592

data_8105066
_publ_section_title
;
 The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one,
 C16H12N2O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              225
_journal_page_last               227
_journal_paper_doi               10.1515/ncrs-2019-0592
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C16 H12 N2 O4'
_chemical_formula_sum            'C16 H12 N2 O4'
_chemical_formula_weight         296.28
_chemical_name_common            ' 3-nitro-4-(<i>p</i>-tolylamino)-coumarin'
_chemical_name_systematic
' 3-nitro-4-(<i>p</i>-tolylamino)-2<i>H</i>-chromen-2-one'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                99.292(4)
_cell_angle_beta                 109.607(4)
_cell_angle_gamma                96.771(4)
_cell_formula_units_Z            4
_cell_length_a                   10.7105(5)
_cell_length_b                   11.2685(5)
_cell_length_c                   13.0145(6)
_cell_measurement_reflns_used    4463
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1970
_cell_measurement_theta_min      3.0230
_cell_volume                     1435.01(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 [1]'
_computing_data_collection       'CrysAlisPro 1.171.40.53 [1]'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 [1]'
_computing_molecular_graphics    'PLATON [4]'
_computing_publication_material  'PLATON [4]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT-2018/2 [2]'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00  23.00   1.00   25.00    --  -16.35 -99.00-180.00   48
  2  \w    -25.00  56.00   1.00   25.00    --   17.37 -99.00   0.00   81
  3  \w    -50.00  34.00   1.00   25.00    --   17.37 -57.00  30.00   84
  4  \w    -50.00  44.00   1.00   25.00    --   17.37 -77.00-120.00   94
  5  \w     -2.00  87.00   1.00   25.00    --   17.37  37.00-180.00   89
  6  \w     32.00  57.00   1.00   25.00    --   17.37-178.00-150.00   25
  7  \w     -2.00  87.00   1.00   25.00    --   17.37  37.00   0.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0035943000
_diffrn_orient_matrix_UB_12      0.0106986000
_diffrn_orient_matrix_UB_13      0.0562325000
_diffrn_orient_matrix_UB_21      -0.0501211000
_diffrn_orient_matrix_UB_22      0.0368192000
_diffrn_orient_matrix_UB_23      -0.0129527000
_diffrn_orient_matrix_UB_31      -0.0509177000
_diffrn_orient_matrix_UB_32      -0.0523684000
_diffrn_orient_matrix_UB_33      -0.0133972000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type
'Enhance (Mo) X-ray Source (Oxford Diffraction)'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 
Analytical numeric absorption correction using a multifaceted crystal 
   model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.2797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4398
_reflns_number_total             5870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0592_suppl.cif
_cod_data_source_block           VD-H-7_2273
_cod_database_code               8105066
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.988
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;