The crystal structure of 2,4-dihydroxybenzoic acid–nicotinamide–methanol (1/1/1), C15H18N2O6
Dai, Bencai; Zhou, Yang; Chen, Jin; Liu, Changchun; Shen, Zhihao; Tang, Junming; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 1413–1415; doi:10.1515/ncrs-2020-0341

data_8105481
_publ_section_title
;
 The crystal structure of 2,4-dihydroxybenzoic
 acid--nicotinamide--methanol (1/1/1), C15H18N2O6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1413
_journal_page_last               1415
_journal_paper_doi               10.1515/ncrs-2020-0341
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C2 H6 O, C6 H6 N2 O, C7 H6 O4'
_chemical_formula_sum            'C15 H18 N2 O6'
_chemical_formula_weight         322.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                79.223(2)
_cell_angle_beta                 82.086(3)
_cell_angle_gamma                65.182(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4217(18)
_cell_length_b                   7.7021(18)
_cell_length_c                   15.362(4)
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      3.262
_cell_volume                     781.2(3)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 2009 [1])'
_computing_data_reduction        'SAINT v7.34A (Bruker, 2009[1])'
_computing_molecular_graphics    'Diamond (Brandenburg, et al., 2012 [5])'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009[4])'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008 [2])'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015 [3])'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.705
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.9442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0668P)^2^+0.1822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2225
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2020-0341_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105481
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-C14 = O6-C14'
 1.47 with sigma of 0.01
 C14-C15 = C14'-C15'
 1.52 with sigma of 0.01
 C15-O6 = C15'-O6
 2.41 with sigma of 0.02
3. Rigid bond restraints
 O6, C14, C15, C14', C15'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O6) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14')
\\sim Ueq, Uanis(C15') \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(C14')=Sof(H14C)=Sof(H14D)=Sof(C15')=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
6.a Riding coordinates:
 O6(H6)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14'(H14C,H14D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C5(H5A), C9(H9), C11(H11), C12(H12)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15'(H15D,H15E,H15F)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5)
;