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_7240464
_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            'C8 H12 B2 F8 N2 O2'
_chemical_formula_weight         341.82
_chemical_melting_point          484.0(10)
_chemical_name_systematic
;
Methyl2,6-dinitrobenzoate bis HBF4 salt
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 94.379(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1001(4)
_cell_length_b                   10.8475(7)
_cell_length_c                   16.4165(11)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2360
_cell_measurement_theta_min      4.1030
_cell_volume                     1260.68(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.855
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6957
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.372
_diffrn_reflns_theta_min         3.047
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.3349
_exptl_crystal_size_mid          0.1509
_exptl_crystal_size_min          0.1331
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.2125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2368
_reflns_number_total             2966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00495b2.cif
_cod_data_source_block           bf4absH
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '483-485' was changed to
'484.0(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/n'
_cod_database_code               7240464
_shelxl_version_number           2014-3
_shelx_res_checksum              84236