#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/35/4513562.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4513562
loop_
_publ_author_name
'Ganduri, Ramesh'
'Cherukuvada, Suryanarayan'
'Guru Row, Tayur N.'
_publ_section_title
;
 Multicomponent Adducts of Pyridoxine: An Evaluation of the Formation of
 Eutectics and Molecular Salts
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3474
_journal_paper_doi               10.1021/acs.cgd.5b00546
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.448(4)
_cell_angle_beta                 77.839(5)
_cell_angle_gamma                76.928(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6720(5)
_cell_length_b                   9.7266(5)
_cell_length_c                   12.2504(6)
_cell_measurement_temperature    100(2)
_cell_volume                     739.51(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13139
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.2363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2874
_reflns_number_total             3396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            PN-PCBA.cif
_cod_data_source_block           PN-PCBA
_cod_database_code               4513562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4945(2) 0.56351(15) 0.77947(11) 0.0142(3) Uani 1 1 d .
C2 C 0.3485(2) 0.67017(14) 0.82628(11) 0.0142(3) Uani 1 1 d .
C3 C 0.4002(2) 0.73402(14) 0.90520(11) 0.0129(3) Uani 1 1 d .
C4 C 0.5961(2) 0.68163(14) 0.94107(11) 0.0124(3) Uani 1 1 d .
C5 C 0.7329(2) 0.57330(14) 0.89550(11) 0.0136(3) Uani 1 1 d .
H5 H 0.8616 0.5370 0.9195 0.016 Uiso 1 1 calc R
C6 C 0.6582(2) 0.74700(15) 1.02576(11) 0.0148(3) Uani 1 1 d .
H6A H 0.6797 0.8447 0.9902 0.018 Uiso 1 1 calc R
H6B H 0.5472 0.7514 1.0909 0.018 Uiso 1 1 calc R
C7 C 0.2543(2) 0.85608(15) 0.95323(12) 0.0161(3) Uani 1 1 d .
H7A H 0.2165 0.8232 1.0351 0.019 Uiso 1 1 calc R
H7B H 0.3276 0.9357 0.9406 0.019 Uiso 1 1 calc R
C8 C 0.4519(2) 0.49883(16) 0.68915(12) 0.0199(3) Uani 1 1 d .
H8A H 0.5706 0.4281 0.6685 0.030 Uiso 1 1 calc R
H8B H 0.4258 0.5736 0.6230 0.030 Uiso 1 1 calc R
H8C H 0.3320 0.4535 0.7184 0.030 Uiso 1 1 calc R
C9 C 0.9429(2) 0.74638(15) 1.30163(11) 0.0135(3) Uani 1 1 d .
C10 C 0.8711(2) 0.81751(15) 1.40393(11) 0.0136(3) Uani 1 1 d .
C11 C 0.8962(2) 0.73548(15) 1.51361(12) 0.0166(3) Uani 1 1 d .
H11 H 0.9522 0.6373 1.5237 0.020 Uiso 1 1 calc R
C12 C 0.8377(2) 0.80035(16) 1.60719(11) 0.0174(3) Uani 1 1 d .
H12 H 0.8536 0.7457 1.6800 0.021 Uiso 1 1 calc R
C13 C 0.7549(2) 0.94807(16) 1.59156(11) 0.0153(3) Uani 1 1 d .
C14 C 0.7286(2) 1.03086(15) 1.48261(12) 0.0160(3) Uani 1 1 d .
H14 H 0.6737 1.1292 1.4724 0.019 Uiso 1 1 calc R
C15 C 0.7854(2) 0.96449(15) 1.38992(11) 0.0149(3) Uani 1 1 d .
H15 H 0.7661 1.0187 1.3175 0.018 Uiso 1 1 calc R
C16 C 0.6959(2) 1.01477(17) 1.69012(12) 0.0202(3) Uani 1 1 d .
N1 N 0.67982(19) 0.51975(12) 0.81565(9) 0.0137(3) Uani 1 1 d .
N2 N 0.6507(2) 1.06473(16) 1.76927(12) 0.0290(3) Uani 1 1 d .
O1 O 0.84397(16) 0.66260(11) 1.06291(9) 0.0183(2) Uani 1 1 d .
O2 O 0.06816(16) 0.90744(11) 0.90377(9) 0.0179(2) Uani 1 1 d .
O3 O 0.16188(16) 0.70880(11) 0.78934(9) 0.0189(2) Uani 1 1 d .
O4 O 1.02913(17) 0.61581(11) 1.32118(8) 0.0195(2) Uani 1 1 d .
O5 O 0.91201(16) 0.82101(10) 1.20396(8) 0.0174(2) Uani 1 1 d .
H1 H 0.791(3) 0.456(2) 0.7754(17) 0.039(5) Uiso 1 1 d .
H1A H 0.875(3) 0.710(2) 1.1075(17) 0.034(5) Uiso 1 1 d .
H2 H 0.073(3) 0.993(2) 0.8660(17) 0.039(6) Uiso 1 1 d .
H3 H 0.088(4) 0.787(3) 0.824(2) 0.061(7) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 118.42(12)
N1 C1 C8 119.29(13)
C2 C1 C8 122.28(13)
O3 C2 C1 116.49(12)
O3 C2 C3 123.25(13)
C1 C2 C3 120.24(13)
C2 C3 C4 118.48(12)
C2 C3 C7 122.74(12)
C4 C3 C7 118.78(12)
C5 C4 C3 119.40(12)
C5 C4 C6 120.28(12)
C3 C4 C6 120.29(12)
N1 C5 C4 119.94(13)
N1 C5 H5 120.0
C4 C5 H5 120.0
O1 C6 C4 110.07(11)
O1 C6 H6A 109.6
C4 C6 H6A 109.6
O1 C6 H6B 109.6
C4 C6 H6B 109.6
H6A C6 H6B 108.2
O2 C7 C3 113.58(11)
O2 C7 H7A 108.9
C3 C7 H7A 108.9
O2 C7 H7B 108.9
C3 C7 H7B 108.9
H7A C7 H7B 107.7
C1 C8 H8A 109.5
C1 C8 H8B 109.5
H8A C8 H8B 109.5
C1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O4 C9 O5 124.66(13)
O4 C9 C10 116.68(12)
O5 C9 C10 118.67(12)
C15 C10 C11 119.40(13)
C15 C10 C9 120.91(12)
C11 C10 C9 119.68(12)
C12 C11 C10 120.19(13)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 119.74(13)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C14 120.55(12)
C12 C13 C16 119.15(13)
C14 C13 C16 120.29(13)
C15 C14 C13 119.18(13)
C15 C14 H14 120.4
C13 C14 H14 120.4
C14 C15 C10 120.93(13)
C14 C15 H15 119.5
C10 C15 H15 119.5
N2 C16 C13 178.60(17)
C1 N1 C5 123.40(12)
C1 N1 H1 118.9(11)
C5 N1 H1 117.1(11)
C6 O1 H1A 104.9(13)
C7 O2 H2 107.0(14)
C2 O3 H3 105.4(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3435(18)
C1 C2 1.400(2)
C1 C8 1.5046(18)
C2 O3 1.3553(17)
C2 C3 1.4065(19)
C3 C4 1.4100(19)
C3 C7 1.5133(19)
C4 C5 1.379(2)
C4 C6 1.5114(18)
C5 N1 1.3563(17)
C5 H5 0.9300
C6 O1 1.4168(17)
C6 H6A 0.9700
C6 H6B 0.9700
C7 O2 1.4297(17)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 O4 1.2554(17)
C9 O5 1.2651(16)
C9 C10 1.5204(19)
C10 C15 1.396(2)
C10 C11 1.4019(19)
C11 C12 1.3887(19)
C11 H11 0.9300
C12 C13 1.398(2)
C12 H12 0.9300
C13 C14 1.3984(19)
C13 C16 1.4530(19)
C14 C15 1.3878(19)
C14 H14 0.9300
C15 H15 0.9300
C16 N2 1.1466(19)
N1 H1 0.99(2)
O1 H1A 0.88(2)
O2 H2 0.85(2)
O3 H3 0.95(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139148167
