Conformational analysis: crystallographic, molecular mechanics and quantum chemical studies of C—H···O hydrogen bonding in the flexible bis(nosylate) derivative of catechol
Munro, Orde Quentin; Mariah, Lynette; Acta Crystallographica Section B 60 (2004) 598–608; doi:10.1107/S0108768104019846

data_2102619
_publ_section_title
;
 Conformational analysis: crystallographic, molecular mechanics and
 quantum chemical studies of C---H&#x00B7;&#x00B7;&#x00B7;O hydrogen
 bonding in the flexible bis(nosylate) derivative of catechol
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              598
_journal_page_last               608
_journal_paper_doi               10.1107/S0108768104019846
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C18 H12 N2 O10 S2'
_chemical_formula_sum            'C18 H12 N2 O10 S2'
_chemical_formula_weight         480.42
_chemical_name_common            'catechol dinosylate'
_chemical_name_systematic
;
 2-{[(4-nitrophenoxy)sulfonyl]oxy}phenyl 4-nitrophenyl sulfate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.20(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.667(11)
_cell_length_b                   10.803(11)
_cell_length_c                   15.868(16)
_cell_measurement_reflns_used    105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      4
_cell_volume                     1900(3)
_computing_cell_refinement       'CrysAlis CCD 170 (Oxford Diffraction,2002)'
_computing_data_collection       'CrysAlis CCD 170 (Oxford Diffraction,2002)'
_computing_data_reduction        'CrysAlis RED 170 (Oxford Diffraction,2002)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2 CCD'
_diffrn_measurement_method       'omega-2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38881
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.08
_diffrn_reflns_theta_min         4.64
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.8461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.446
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0490P)^2^+2.7297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                3259
_reflns_number_total             3744
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            de5007.cif
_cod_data_source_block           lynette2
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2102619