Meta Nitration of Thiacalixarenes
Ondrej Kundrat; Jan Kroupa; Stanislav Böhm; Jan Budka; Vaclav Eigner; Pavel Lhotak; Journal of Organic Chemistry 75 (2010) 8372–8375; doi:10.1021/jo1013492

data_4025861
_publ_contact_author_address
; 
 Department of Organic Chemistry, 
 Prague Institute of Chemical Technology,
 Technicka 6,
 166 28 Prague 6,
 Czech Republic.
;
_publ_contact_author_email       lhotakp@vscht.cz
_publ_contact_author_fax         '+44 1865 000000'
_publ_contact_author_name        'Pavel Lhot\'ak'
_publ_contact_author_phone       '+42 0220 445055'
_publ_section_title
;
 Meta Nitration of Thiacalixarenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8372
_journal_page_last               8375
_journal_paper_doi               10.1021/jo1013492
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H38 N2 O8 S4'
_chemical_formula_sum            'C36 H38 N2 O8 S4'
_chemical_formula_weight         754.97
_chemical_name_systematic
'4,18-Dinitro-25,26,27,28-tetrapropoxythiacalix[4]arene 1,3-alternate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2400(10)
_cell_length_b                   21.3709(14)
_cell_length_c                   16.9596(11)
_cell_measurement_reflns_used    11479
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     3711.4(5)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7537
_diffrn_reflns_theta_full        75.410
_diffrn_reflns_theta_max         78.552
_diffrn_reflns_theta_min         4.789
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.10
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.391
_exptl_crystal_size_min          0.348
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.67
_refine_ls_abs_structure_details 'Flack (1983), 3169 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9463
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7537
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0896
_refine_ls_shift/su_max          0.0020730
_refine_ls_shift/su_mean         9.9108992
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.15P)^2^ +11.79P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2361
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2361
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                6968
_reflns_number_total             7537
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.30
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.0946
_oxford_refine_ls_scale          3.21(6)
_oxford_reflns_number_all        7537
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo1013492_si_001_2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4025861