N-H···O Hydrogen Bonding to the Alkoxy Oxygen of a Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate and Its Derivatives.
Wallis, John D.; Garner, Alun Christopher; Yang, Songjie; CrystEngComm  (2020) –; doi:10.1039/D0CE00495B

data_7240463
_publ_section_title
;
 N-H&#x00B7;&#x00B7;&#x00B7;O Hydrogen Bonding to the Alkoxy Oxygen of a
 Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate
 and Its Derivatives.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00495B
_journal_year                    2020
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_chemical_melting_point          425.0(10)
_chemical_name_systematic
;
Methyl 2-tosylamino-6-aminobenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-04-01 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.360(3)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   9.7212(3)
_cell_length_b                   35.4733(12)
_cell_length_c                   26.2238(10)
_cell_measurement_reflns_used    9346
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.9900
_cell_measurement_theta_min      3.5280
_cell_volume                     8968.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            56001
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        28.500
_diffrn_reflns_theta_max         30.963
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             4032
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1273
_refine_ls_number_reflns         24833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.3682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14496
_reflns_number_total             24833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00495b2.cif
_cod_data_source_block           fabs150MXA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '424-426' was changed to
'425.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240463
_shelxl_version_number           2014-3
_shelx_res_checksum              57876