Crystal Structures and Density Functional Theory Calculations ofo- andp-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and Aromatic Interactions on Dimerization Energy
Helttunen, Kaisa; Lehtovaara, Lauri; Häkkinen, Hannu; Nissinen, Maija; Crystal Growth & Design 13 (2013) 3603–; doi:10.1021/cg4005714

data_4507975
_publ_section_title
;
 Crystal Structures and Density Functional Theory Calculations ofo-
 andp-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and
 Aromatic Interactions on Dimerization Energy
;
_journal_issue                   8
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3603
_journal_paper_doi               10.1021/cg4005714
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C15 H16 N2 O5 S'
_chemical_formula_sum            'C15 H16 N2 O5 S'
_chemical_formula_weight         336.36
_chemical_melting_point          123.5(5)
_chemical_name_systematic
; 
 2-((2-nitrophenyl)amino)ethyl 
4-methylbenzenesulfonate 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.729(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9887(4)
_cell_length_b                   27.0768(19)
_cell_length_c                   7.0718(5)
_cell_measurement_reflns_used    2219
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.50
_cell_measurement_theta_min      3.26
_cell_volume                     1524.48(17)
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 1997)'
_computing_data_collection       'COLLECT 2000'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3944
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.50
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    2.150
_exptl_absorpt_correction_T_max  0.8137
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Majewski, Borek & Minor,2003) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0488P)^2^+0.7129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2219
_reflns_number_total             2630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4005714_si_002.cif
_cod_data_source_block           2A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '123-124' was changed to '123.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4507975