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_4507979
_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         'C13 H18 N2 O5'
_chemical_formula_sum            'C13 H18 N2 O5'
_chemical_formula_weight         282.29
_chemical_melting_point          144.5(5)
_chemical_name_systematic
; 
 tert-butyl (2-((4-nitrophenyl)amino)ethyl) carbonate 
;
_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                 94.3870(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.90070(10)
_cell_length_b                   16.0041(2)
_cell_length_c                   7.37630(10)
_cell_measurement_reflns_used    2021
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.07
_cell_measurement_theta_min      4.64
_cell_volume                     1400.77(3)
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3944
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.8806
_exptl_absorpt_correction_T_min  0.8119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Majewski, Borek & Minor,2003)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0572
_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^)+(0.1007P)^2^+0.3545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                2021
_reflns_number_total             2402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4005714_si_002.cif
_cod_data_source_block           5B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '144-145' was changed to '144.5(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               4507979