Different packing motifs in the crystal structures of three mol­ecular salts containing the 2-amino-5-carb­oxy­anilinium cation: C₇H₉N₂O₂⁺·Cl⁻, C₇H₉N₂O₂⁺·Br⁻ and C₇H₉N₂O₂⁺·NO₃⁻·H₂O

The title mol­ecular salts containing the same cation accompanied by different simple anions show quite different inter­molecular connectivities.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.093
• Data-to-parameter ratio = 14.7

Structure: II

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 26.1

Structure: III

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.149
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00671 Ang.
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N1       - H1N      .       0.74 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H4N      .     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H5N      .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4N      ..BR1      .       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5N      ..BR1      .       2.98 Ang.

Alert level G
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00671 Ang.
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N1       - H1N      .       0.74 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H4N      .     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2       --H5N      .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4N      ..BR1      .       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5N      ..BR1      .       2.98 Ang.

Alert level G
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.37 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00543 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku, 2017); cell refinement: CrysAlis PRO (Rigaku, 2017); data reduction: CrysAlis PRO (Rigaku, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Amino-5-carboxyanilinium chloride (I)

Crystal data

C7H9N2O2^+·Cl^−	F(000) = 784
Mr = 188.61	Dx = 1.531 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.0521 (6) Å	Cell parameters from 8736 reflections
b = 8.0469 (2) Å	θ = 2.9–30.1°
c = 7.2511 (2) Å	µ = 0.43 mm^−1
β = 91.309 (2)°	T = 100 K
V = 1636.38 (7) Å^3	Plate, brown
Z = 8	0.41 × 0.26 × 0.04 mm

Data collection

Rigaku Mercury CCD diffractometer	1765 reflections with I > 2σ(I)
ω scans	Rint = 0.035
Absorption correction: gaussian (CrysAlisPRO; Rigaku, 2017)	θmax = 27.5°, θmin = 2.6°
Tmin = 0.624, Tmax = 1.000	h = −36→36
13456 measured reflections	k = −10→10
1865 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 2.8134P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.002
1865 reflections	Δρmax = 0.45 e Å^−3
127 parameters	Δρmin = −0.27 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.42198 (5)	0.7087 (2)	0.6424 (2)	0.0132 (3)
C2	0.37721 (5)	0.7561 (2)	0.7037 (2)	0.0124 (3)
H2	0.3696	0.8704	0.7173	0.015*
C3	0.34405 (5)	0.6353 (2)	0.7443 (2)	0.0115 (3)
C4	0.35376 (5)	0.46541 (19)	0.7258 (2)	0.0118 (3)
C5	0.39962 (5)	0.4200 (2)	0.6688 (2)	0.0132 (3)
H5	0.4077	0.3058	0.6586	0.016*
C6	0.43292 (6)	0.5395 (2)	0.6276 (2)	0.0139 (3)
H6	0.4636	0.5067	0.5887	0.017*
C7	0.45674 (6)	0.8354 (2)	0.5858 (2)	0.0150 (3)
N1	0.29675 (5)	0.68573 (18)	0.8047 (2)	0.0126 (3)
H1N	0.2945 (7)	0.797 (3)	0.818 (3)	0.015*
H2N	0.2748 (7)	0.653 (3)	0.717 (3)	0.015*
H3N	0.2895 (7)	0.641 (3)	0.914 (3)	0.015*
N2	0.31909 (5)	0.34702 (18)	0.7525 (2)	0.0158 (3)
H4N	0.3282 (7)	0.246 (3)	0.768 (3)	0.019*
H5N	0.2970 (8)	0.371 (3)	0.817 (3)	0.019*
O1	0.44480 (5)	0.98914 (17)	0.6117 (2)	0.0226 (3)
H1O	0.4634 (9)	1.042 (3)	0.570 (3)	0.027*
O2	0.49517 (4)	0.79238 (15)	0.51547 (18)	0.0203 (3)
Cl1	0.22232 (2)	0.53660 (4)	0.51641 (5)	0.01266 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0110 (7)	0.0134 (8)	0.0153 (7)	−0.0017 (6)	0.0015 (5)	0.0010 (6)
C2	0.0130 (7)	0.0109 (7)	0.0132 (7)	−0.0002 (6)	0.0004 (5)	0.0004 (6)
C3	0.0107 (7)	0.0131 (7)	0.0108 (7)	0.0007 (6)	0.0011 (5)	−0.0002 (6)
C4	0.0128 (7)	0.0123 (8)	0.0104 (7)	−0.0010 (5)	−0.0002 (5)	0.0013 (5)
C5	0.0144 (7)	0.0107 (7)	0.0145 (7)	0.0019 (6)	0.0011 (5)	0.0001 (6)
C6	0.0111 (7)	0.0150 (8)	0.0157 (8)	0.0012 (6)	0.0019 (6)	0.0003 (6)
C7	0.0129 (7)	0.0141 (8)	0.0180 (8)	−0.0013 (6)	0.0015 (6)	0.0014 (6)
N1	0.0124 (6)	0.0106 (7)	0.0149 (7)	0.0001 (5)	0.0032 (5)	0.0008 (5)
N2	0.0144 (7)	0.0094 (7)	0.0236 (7)	0.0003 (5)	0.0050 (5)	0.0014 (6)
O1	0.0181 (6)	0.0132 (6)	0.0370 (8)	−0.0040 (5)	0.0096 (5)	0.0020 (5)
O2	0.0130 (5)	0.0189 (6)	0.0294 (7)	−0.0015 (5)	0.0074 (5)	0.0026 (5)
Cl1	0.0148 (2)	0.0094 (2)	0.0138 (2)	0.00125 (12)	0.00239 (14)	0.00038 (12)

Geometric parameters (Å, º)

C1—C2	1.395 (2)	C5—H5	0.9500
C1—C6	1.401 (2)	C6—H6	0.9500
C1—C7	1.475 (2)	C7—O2	1.252 (2)
C2—C3	1.382 (2)	C7—O1	1.296 (2)
C2—H2	0.9500	N1—H1N	0.90 (2)
C3—C4	1.401 (2)	N1—H2N	0.91 (2)
C3—N1	1.4640 (19)	N1—H3N	0.90 (2)
C4—N2	1.378 (2)	N2—H4N	0.86 (2)
C4—C5	1.408 (2)	N2—H5N	0.81 (2)
C5—C6	1.378 (2)	O1—H1O	0.74 (3)
C2—C1—C6	119.38 (14)	C5—C6—H6	119.6
C2—C1—C7	120.35 (15)	C1—C6—H6	119.6
C6—C1—C7	120.22 (14)	O2—C7—O1	123.41 (15)
C3—C2—C1	119.42 (15)	O2—C7—C1	120.19 (15)
C3—C2—H2	120.3	O1—C7—C1	116.40 (14)
C1—C2—H2	120.3	C3—N1—H1N	111.9 (13)
C2—C3—C4	122.18 (14)	C3—N1—H2N	108.2 (12)
C2—C3—N1	119.22 (14)	H1N—N1—H2N	108.3 (18)
C4—C3—N1	118.59 (14)	C3—N1—H3N	112.1 (13)
N2—C4—C3	121.45 (14)	H1N—N1—H3N	106.6 (19)
N2—C4—C5	120.93 (15)	H2N—N1—H3N	109.6 (18)
C3—C4—C5	117.53 (14)	C4—N2—H4N	117.6 (14)
C6—C5—C4	120.72 (15)	C4—N2—H5N	118.0 (16)
C6—C5—H5	119.6	H4N—N2—H5N	112 (2)
C4—C5—H5	119.6	C7—O1—H1O	107.7 (19)
C5—C6—C1	120.73 (14)
C6—C1—C2—C3	−1.6 (2)	C3—C4—C5—C6	−2.0 (2)
C7—C1—C2—C3	175.73 (14)	C4—C5—C6—C1	0.3 (2)
C1—C2—C3—C4	−0.1 (2)	C2—C1—C6—C5	1.5 (2)
C1—C2—C3—N1	−178.67 (14)	C7—C1—C6—C5	−175.82 (15)
C2—C3—C4—N2	−174.64 (15)	C2—C1—C7—O2	−173.60 (15)
N1—C3—C4—N2	3.9 (2)	C6—C1—C7—O2	3.7 (2)
C2—C3—C4—C5	1.9 (2)	C2—C1—C7—O1	5.8 (2)
N1—C3—C4—C5	−179.57 (13)	C6—C1—C7—O1	−176.96 (16)
N2—C4—C5—C6	174.58 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.74 (3)	1.88 (3)	2.6169 (18)	170 (3)
N1—H1N···Cl1^ii	0.90 (2)	2.32 (2)	3.1578 (14)	153.4 (17)
N1—H2N···Cl1	0.91 (2)	2.25 (2)	3.1576 (15)	172.1 (18)
N1—H3N···Cl1^iii	0.90 (2)	2.49 (2)	3.1722 (14)	132.9 (16)
N2—H4N···Cl1^iv	0.86 (2)	2.72 (2)	3.2382 (15)	120.3 (17)
N2—H5N···Cl1^iii	0.81 (2)	2.68 (2)	3.4852 (15)	176 (2)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x, −y+1, z+1/2; (iv) −x+1/2, y−1/2, −z+3/2.

2-Amino-5-carboxyanilinium bromide (II)

Crystal data

C7H9N2O2^+·Br^−	F(000) = 464
Mr = 233.07	Dx = 1.857 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1190 (7) Å	Cell parameters from 8521 reflections
b = 11.0708 (5) Å	θ = 3.4–30.1°
c = 6.3795 (3) Å	µ = 4.89 mm^−1
β = 103.047 (6)°	T = 100 K
V = 833.82 (8) Å^3	Lath, pale brown
Z = 4	0.25 × 0.12 × 0.04 mm

Data collection

Rigaku Mercury CCD diffractometer	3031 reflections with I > 2σ(I)
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlisPRO; Rigaku, 2017)	h = −15→15
Tmin = 0.538, Tmax = 1.000	k = −14→14
3343 measured reflections	l = −8→8
3343 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 2.9863P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.001
3343 reflections	Δρmax = 1.01 e Å^−3
128 parameters	Δρmin = −0.69 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a two-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5791 (4)	0.3232 (4)	0.3020 (7)	0.0114 (9)
C2	0.6253 (4)	0.4394 (4)	0.3348 (7)	0.0105 (8)
H2	0.5781	0.5085	0.3035	0.013*
C3	0.7405 (4)	0.4520 (4)	0.4131 (7)	0.0093 (8)
C4	0.8130 (4)	0.3529 (4)	0.4643 (7)	0.0110 (9)
C5	0.7646 (4)	0.2369 (4)	0.4251 (7)	0.0113 (9)
H5	0.8119	0.1677	0.4535	0.014*
C6	0.6494 (4)	0.2226 (4)	0.3460 (7)	0.0122 (9)
H6	0.6181	0.1438	0.3216	0.015*
C7	0.4558 (4)	0.3082 (4)	0.2165 (7)	0.0107 (9)
N1	0.7876 (4)	0.5748 (3)	0.4373 (8)	0.0110 (8)
H1N	0.816 (5)	0.593 (5)	0.352 (10)	0.013*
H2N	0.729 (5)	0.627 (5)	0.409 (9)	0.013*
H3N	0.815 (5)	0.590 (5)	0.569 (10)	0.013*
N2	0.9285 (4)	0.3686 (4)	0.5425 (7)	0.0155 (9)
H4N	0.959 (5)	0.304 (6)	0.578 (9)	0.019*
H5N	0.951 (5)	0.420 (6)	0.635 (10)	0.019*
O1	0.3992 (3)	0.4115 (3)	0.1817 (6)	0.0167 (7)
H1O	0.334 (6)	0.400 (5)	0.130 (10)	0.020*
O2	0.4107 (3)	0.2098 (3)	0.1823 (6)	0.0161 (7)
Br1	0.86980 (4)	0.61815 (4)	−0.03325 (7)	0.01281 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.011 (2)	0.009 (2)	0.013 (2)	−0.0010 (16)	0.0028 (17)	0.0006 (16)
C2	0.013 (2)	0.009 (2)	0.010 (2)	0.0014 (16)	0.0034 (16)	−0.0008 (16)
C3	0.014 (2)	0.005 (2)	0.010 (2)	−0.0009 (16)	0.0047 (17)	−0.0012 (16)
C4	0.013 (2)	0.012 (2)	0.008 (2)	0.0008 (17)	0.0021 (16)	0.0011 (16)
C5	0.014 (2)	0.011 (2)	0.010 (2)	0.0028 (17)	0.0048 (17)	0.0011 (17)
C6	0.016 (2)	0.009 (2)	0.012 (2)	−0.0017 (16)	0.0033 (18)	−0.0015 (17)
C7	0.010 (2)	0.011 (2)	0.012 (2)	0.0009 (16)	0.0032 (17)	0.0000 (17)
N1	0.0112 (19)	0.0086 (18)	0.013 (2)	−0.0019 (15)	0.0034 (16)	−0.0003 (16)
N2	0.010 (2)	0.015 (2)	0.020 (2)	0.0019 (17)	0.0002 (16)	0.0013 (17)
O1	0.0083 (16)	0.0094 (15)	0.029 (2)	0.0007 (12)	−0.0025 (14)	0.0008 (13)
O2	0.0118 (15)	0.0097 (15)	0.0247 (19)	−0.0020 (13)	−0.0001 (14)	−0.0012 (13)
Br1	0.0108 (2)	0.0136 (2)	0.0130 (2)	−0.00047 (18)	0.00053 (16)	−0.00011 (17)

Geometric parameters (Å, º)

C1—C6	1.391 (6)	C5—H5	0.9500
C1—C2	1.400 (6)	C6—H6	0.9500
C1—C7	1.479 (6)	C7—O2	1.216 (5)
C2—C3	1.379 (6)	C7—O1	1.326 (5)
C2—H2	0.9500	N1—H1N	0.73 (6)
C3—C4	1.398 (6)	N1—H2N	0.90 (6)
C3—N1	1.468 (5)	N1—H3N	0.85 (6)
C4—N2	1.387 (6)	N2—H4N	0.81 (7)
C4—C5	1.410 (6)	N2—H5N	0.82 (6)
C5—C6	1.383 (6)	O1—H1O	0.79 (7)
C6—C1—C2	119.9 (4)	C5—C6—H6	119.9
C6—C1—C7	120.4 (4)	C1—C6—H6	119.9
C2—C1—C7	119.7 (4)	O2—C7—O1	123.2 (4)
C3—C2—C1	119.1 (4)	O2—C7—C1	122.8 (4)
C3—C2—H2	120.5	O1—C7—C1	114.0 (4)
C1—C2—H2	120.5	C3—N1—H1N	114 (5)
C2—C3—C4	122.4 (4)	C3—N1—H2N	107 (4)
C2—C3—N1	118.1 (4)	H1N—N1—H2N	99 (6)
C4—C3—N1	119.5 (4)	C3—N1—H3N	111 (4)
N2—C4—C3	121.1 (4)	H1N—N1—H3N	122 (6)
N2—C4—C5	121.6 (4)	H2N—N1—H3N	101 (5)
C3—C4—C5	117.3 (4)	C4—N2—H4N	110 (4)
C6—C5—C4	120.9 (4)	C4—N2—H5N	119 (5)
C6—C5—H5	119.5	H4N—N2—H5N	111 (6)
C4—C5—H5	119.5	C7—O1—H1O	111 (4)
C5—C6—C1	120.3 (4)
C6—C1—C2—C3	−0.7 (6)	C3—C4—C5—C6	−2.1 (7)
C7—C1—C2—C3	−179.5 (4)	C4—C5—C6—C1	0.5 (7)
C1—C2—C3—C4	−1.0 (7)	C2—C1—C6—C5	1.0 (7)
C1—C2—C3—N1	177.4 (4)	C7—C1—C6—C5	179.8 (4)
C2—C3—C4—N2	179.9 (4)	C6—C1—C7—O2	0.4 (7)
N1—C3—C4—N2	1.5 (7)	C2—C1—C7—O2	179.2 (4)
C2—C3—C4—C5	2.4 (7)	C6—C1—C7—O1	−179.9 (4)
N1—C3—C4—C5	−176.0 (4)	C2—C1—C7—O1	−1.1 (6)
N2—C4—C5—C6	−179.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1^i	0.79 (7)	2.42 (7)	3.199 (3)	169 (6)
N1—H1N···Br1	0.73 (6)	2.70 (7)	3.404 (5)	163 (6)
N1—H2N···O2^ii	0.90 (6)	1.90 (6)	2.787 (5)	168 (5)
N1—H3N···Br1^iii	0.85 (6)	2.49 (6)	3.333 (5)	171 (5)
N2—H4N···Br1^iv	0.81 (7)	2.98 (7)	3.705 (5)	150 (5)
N2—H5N···Br1^v	0.82 (6)	2.98 (6)	3.513 (4)	125 (5)
C2—H2···O2^ii	0.95	2.23	3.024 (5)	140

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y, z+1; (iv) −x+2, y−1/2, −z+1/2; (v) −x+2, −y+1, −z+1.

2-Amino-5-carboxyanilinium nitrate monohydrate (III)

Crystal data

C7H9N2O2^+·NO3^−·H2O	F(000) = 244
Mr = 233.19	Dx = 1.630 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 3.8899 (3) Å	Cell parameters from 3653 reflections
b = 9.8238 (6) Å	θ = 2.7–30.8°
c = 12.5799 (9) Å	µ = 0.14 mm^−1
β = 98.673 (7)°	T = 100 K
V = 475.22 (6) Å^3	Slab, colourless
Z = 2	0.20 × 0.10 × 0.05 mm

Data collection

Rigaku Mercury CCD diffractometer	2100 reflections with I > 2σ(I)
ω scans	Rint = 0.067
Absorption correction: multi-scan (CrysAlisPRO; Rigaku, 2017)	θmax = 27.5°, θmin = 2.6°
Tmin = 0.861, Tmax = 1.000	h = −5→5
10770 measured reflections	k = −12→12
2157 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.3934P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.005
2157 reflections	Δρmax = 0.48 e Å^−3
155 parameters	Δρmin = −0.37 e Å^−3
1 restraint

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2205 (11)	0.5688 (5)	0.4736 (3)	0.0120 (8)
C2	0.2777 (10)	0.4617 (5)	0.4062 (3)	0.0121 (8)
H2	0.4231	0.3880	0.4334	0.014*
C3	0.1240 (10)	0.4617 (4)	0.2997 (3)	0.0120 (8)
C4	−0.0999 (11)	0.5677 (4)	0.2573 (3)	0.0124 (8)
C5	−0.1462 (11)	0.6769 (4)	0.3255 (3)	0.0128 (8)
H5	−0.2878	0.7516	0.2982	0.015*
C6	0.0082 (11)	0.6778 (4)	0.4303 (3)	0.0121 (8)
H6	−0.0277	0.7530	0.4748	0.014*
C7	0.3867 (11)	0.5736 (4)	0.5864 (3)	0.0127 (8)
N1	0.1979 (10)	0.3534 (4)	0.2274 (3)	0.0137 (8)
H1N	−0.0055	0.3198	0.1919	0.016*
H2N	0.3174	0.2856	0.2661	0.016*
H3N	0.3279	0.3871	0.1790	0.016*
N2	−0.2843 (11)	0.5597 (4)	0.1542 (3)	0.0167 (8)
H4N	−0.198 (16)	0.524 (6)	0.097 (5)	0.020*
H5N	−0.358 (16)	0.637 (6)	0.136 (4)	0.020*
O1	0.5752 (9)	0.4650 (3)	0.6185 (2)	0.0182 (7)
H1O	0.685 (15)	0.469 (7)	0.685 (5)	0.022*
O2	0.3588 (8)	0.6720 (3)	0.6453 (2)	0.0156 (7)
N3	0.9275 (9)	0.4263 (4)	0.8918 (3)	0.0147 (8)
O3	0.9624 (10)	0.4968 (4)	0.8102 (3)	0.0234 (8)
O4	1.0903 (8)	0.4593 (4)	0.9805 (2)	0.0210 (7)
O5	0.7311 (10)	0.3252 (4)	0.8821 (3)	0.0263 (8)
O6	0.6514 (8)	0.2329 (3)	1.0947 (3)	0.0181 (7)
H2O	0.6684	0.2566	1.0297	0.022*
H3O	0.6328	0.1351	1.0976	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0129 (19)	0.0080 (18)	0.0155 (19)	−0.0052 (15)	0.0033 (14)	0.0015 (16)
C2	0.0105 (17)	0.0076 (18)	0.019 (2)	0.0003 (16)	0.0059 (14)	0.0019 (16)
C3	0.0133 (19)	0.0064 (18)	0.0172 (19)	−0.0016 (17)	0.0055 (14)	−0.0018 (16)
C4	0.015 (2)	0.0084 (19)	0.015 (2)	0.0014 (16)	0.0058 (15)	0.0003 (17)
C5	0.015 (2)	0.0044 (18)	0.020 (2)	0.0005 (16)	0.0043 (15)	0.0006 (17)
C6	0.0125 (19)	0.0046 (17)	0.021 (2)	−0.0010 (15)	0.0076 (15)	0.0000 (16)
C7	0.013 (2)	0.0098 (19)	0.015 (2)	−0.0043 (16)	0.0020 (15)	0.0000 (17)
N1	0.0137 (17)	0.0123 (18)	0.0148 (17)	0.0055 (14)	0.0014 (13)	−0.0014 (14)
N2	0.023 (2)	0.0115 (18)	0.0151 (18)	0.0049 (15)	0.0003 (14)	0.0008 (15)
O1	0.0250 (17)	0.0146 (16)	0.0134 (14)	0.0011 (14)	−0.0017 (12)	0.0004 (13)
O2	0.0183 (16)	0.0123 (15)	0.0159 (14)	−0.0029 (12)	0.0017 (11)	−0.0030 (13)
N3	0.0165 (17)	0.0137 (18)	0.0137 (17)	0.0016 (14)	0.0021 (13)	−0.0029 (14)
O3	0.0313 (19)	0.0206 (17)	0.0176 (16)	−0.0073 (14)	0.0010 (13)	0.0017 (14)
O4	0.0226 (16)	0.0222 (18)	0.0176 (15)	−0.0014 (14)	0.0012 (12)	−0.0029 (13)
O5	0.032 (2)	0.0202 (18)	0.0268 (19)	−0.0136 (16)	0.0056 (15)	−0.0046 (15)
O6	0.0214 (16)	0.0113 (14)	0.0223 (16)	0.0000 (13)	0.0061 (13)	−0.0008 (12)

Geometric parameters (Å, º)

C1—C2	1.391 (6)	C7—O1	1.323 (6)
C1—C6	1.410 (6)	N1—H1N	0.9100
C1—C7	1.469 (5)	N1—H2N	0.9100
C2—C3	1.382 (5)	N1—H3N	0.9100
C2—H2	0.9500	N2—H4N	0.91 (6)
C3—C4	1.409 (6)	N2—H5N	0.83 (6)
C3—N1	1.457 (5)	O1—H1O	0.88 (6)
C4—N2	1.386 (5)	N3—O4	1.240 (5)
C4—C5	1.402 (6)	N3—O5	1.247 (5)
C5—C6	1.363 (6)	N3—O3	1.262 (5)
C5—H5	0.9500	O6—H2O	0.8625
C6—H6	0.9500	O6—H3O	0.9644
C7—O2	1.232 (5)
C2—C1—C6	118.5 (4)	O2—C7—O1	123.0 (4)
C2—C1—C7	121.7 (4)	O2—C7—C1	122.7 (4)
C6—C1—C7	119.7 (4)	O1—C7—C1	114.3 (4)
C3—C2—C1	120.3 (4)	C3—N1—H1N	109.5
C3—C2—H2	119.8	C3—N1—H2N	109.5
C1—C2—H2	119.8	H1N—N1—H2N	109.5
C2—C3—C4	121.3 (4)	C3—N1—H3N	109.5
C2—C3—N1	120.5 (4)	H1N—N1—H3N	109.5
C4—C3—N1	118.2 (4)	H2N—N1—H3N	109.5
N2—C4—C5	121.3 (4)	C4—N2—H4N	124 (4)
N2—C4—C3	121.0 (4)	C4—N2—H5N	108 (4)
C5—C4—C3	117.6 (4)	H4N—N2—H5N	107 (5)
C6—C5—C4	121.2 (4)	C7—O1—H1O	115 (4)
C6—C5—H5	119.4	O4—N3—O5	121.2 (4)
C4—C5—H5	119.4	O4—N3—O3	119.0 (4)
C5—C6—C1	121.0 (4)	O5—N3—O3	119.8 (4)
C5—C6—H6	119.5	H2O—O6—H3O	108.8
C1—C6—H6	119.5
C6—C1—C2—C3	−1.1 (6)	C3—C4—C5—C6	−2.7 (6)
C7—C1—C2—C3	−178.4 (4)	C4—C5—C6—C1	0.1 (6)
C1—C2—C3—C4	−1.6 (6)	C2—C1—C6—C5	1.8 (6)
C1—C2—C3—N1	176.7 (4)	C7—C1—C6—C5	179.2 (4)
C2—C3—C4—N2	−172.5 (4)	C2—C1—C7—O2	174.8 (4)
N1—C3—C4—N2	9.2 (6)	C6—C1—C7—O2	−2.5 (6)
C2—C3—C4—C5	3.4 (6)	C2—C1—C7—O1	−3.7 (6)
N1—C3—C4—C5	−174.9 (4)	C6—C1—C7—O1	179.0 (4)
N2—C4—C5—C6	173.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6^i	0.91	1.87	2.764 (5)	165
N1—H2N···O2^ii	0.91	1.91	2.808 (5)	168
N1—H3N···N2^iii	0.91	2.32	3.094 (6)	143
N1—H3N···O6^iv	0.91	2.33	2.862 (5)	118
N2—H4N···O4^i	0.91 (6)	2.07 (6)	2.972 (5)	169 (5)
N2—H5N···O5^v	0.83 (6)	2.34 (7)	3.129 (5)	159 (6)
O1—H1O···O3	0.88 (6)	1.79 (6)	2.662 (5)	170 (6)
O6—H2O···O5	0.86	2.02	2.884 (5)	176
O6—H3O···O3^vi	0.96	2.26	2.920 (5)	125
O6—H3O···O4^vi	0.96	2.33	3.068 (5)	133
C2—H2···O2^ii	0.95	2.54	3.285 (5)	135

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, y−1/2, −z+1; (iii) x+1, y, z; (iv) x, y, z−1; (v) −x, y+1/2, −z+1; (vi) −x+2, y−1/2, −z+2.