Synthesis and crystal structure of 1-hy­droxy-8-methyl-9H-carbazole-2-carbaldehyde

Two crystallographically independent mol­ecules are present in the asymmetric unit. O—H...O, N—H...O and C—H...O hydrogen bonds form rings and chains and π–π stacks further connect mol­ecules in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.146
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1 Check

Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      7.113 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      41.96 Check

Alert level G
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.75 mm
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C1 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3       ..C14              3.02 Ang.
                                                      x,y,z  =      1_555 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

1-Hydroxy-8-methyl-9H-carbazole-2-carbaldehyde

Crystal data

C14H11NO2	F(000) = 944
Mr = 225.24	Dx = 1.389 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.290 (5) Å	Cell parameters from 7327 reflections
b = 3.9052 (7) Å	θ = 2.2–31.3°
c = 20.264 (3) Å	µ = 0.09 mm^−1
β = 105.817 (2)°	T = 296 K
V = 2154.0 (6) Å^3	Needle, brown
Z = 8	0.75 × 0.19 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer	5344 independent reflections
Radiation source: fine-focus sealed tube	4453 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −37→37
Tmin = 0.830, Tmax = 0.991	k = −5→5
19760 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: mixed
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 1.1713P] where P = (Fo^2 + 2Fc^2)/3
5344 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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	0.60695 (8)	0.8782 (6)	0.79934 (10)	0.0305 (4)
H1A	0.586381	0.993978	0.822872	0.046*
H1B	0.636607	1.007032	0.804205	0.046*
H1C	0.614950	0.654265	0.818701	0.046*
C2	0.58026 (7)	0.8460 (5)	0.72475 (10)	0.0225 (4)
C3	0.53306 (7)	0.9707 (5)	0.69748 (11)	0.0269 (4)
H3	0.517561	1.081062	0.726518	0.032*
C4	0.50767 (7)	0.9371 (5)	0.62778 (11)	0.0278 (4)
H4	0.475869	1.021909	0.611961	0.033*
C5	0.52935 (6)	0.7800 (5)	0.58267 (10)	0.0239 (4)
H5	0.512575	0.758554	0.536525	0.029*
C6	0.57725 (6)	0.6531 (5)	0.60773 (9)	0.0190 (3)
C7	0.60179 (6)	0.6862 (5)	0.67805 (9)	0.0187 (3)
C8	0.69229 (6)	0.2303 (5)	0.61767 (9)	0.0186 (3)
C9	0.65285 (6)	0.4087 (4)	0.62986 (8)	0.0171 (3)
C10	0.61009 (6)	0.4752 (5)	0.57646 (8)	0.0173 (3)
C11	0.60642 (6)	0.3678 (5)	0.50886 (9)	0.0213 (4)
H11	0.578573	0.416290	0.473378	0.026*
C12	0.64511 (7)	0.1896 (5)	0.49680 (9)	0.0213 (4)
H12	0.643093	0.114554	0.452561	0.026*
C13	0.68800 (6)	0.1176 (5)	0.55022 (9)	0.0199 (4)
C14	0.72687 (7)	−0.0821 (5)	0.53619 (10)	0.0230 (4)
H14	0.722444	−0.163999	0.491820	0.028*
C15	0.88208 (8)	0.8160 (5)	0.68439 (9)	0.0265 (4)
H15A	0.902174	0.905029	0.726989	0.040*
H15B	0.860603	0.642822	0.693463	0.040*
H15C	0.862872	0.997972	0.658394	0.040*
C16	0.91438 (7)	0.6628 (5)	0.64413 (9)	0.0214 (4)
C17	0.96492 (7)	0.6431 (5)	0.66858 (9)	0.0256 (4)
H17	0.979856	0.730010	0.711994	0.031*
C18	0.99471 (7)	0.4977 (5)	0.63077 (10)	0.0270 (4)
H18	1.028583	0.491116	0.649516	0.032*
C19	0.97440 (7)	0.3645 (5)	0.56619 (9)	0.0232 (4)
H19	0.994149	0.267196	0.541288	0.028*
C20	0.92328 (6)	0.3795 (5)	0.53906 (9)	0.0187 (3)
C21	0.89409 (6)	0.5292 (5)	0.57814 (8)	0.0179 (3)
C22	0.80092 (6)	0.2763 (5)	0.42718 (9)	0.0183 (3)
C23	0.84263 (6)	0.3534 (4)	0.47993 (8)	0.0176 (3)
C24	0.89000 (6)	0.2655 (5)	0.47573 (8)	0.0180 (3)
C25	0.89635 (7)	0.0985 (5)	0.41705 (9)	0.0218 (4)
H25	0.927599	0.043979	0.413640	0.026*
C26	0.85547 (7)	0.0181 (5)	0.36514 (9)	0.0232 (4)
H26	0.859196	−0.093655	0.326343	0.028*
C27	0.80755 (7)	0.1021 (5)	0.36941 (9)	0.0206 (4)
C28	0.76490 (7)	−0.0010 (5)	0.31623 (9)	0.0254 (4)
H28	0.769894	−0.116522	0.278565	0.030*
N1	0.64768 (5)	0.5391 (4)	0.69071 (8)	0.0191 (3)
N2	0.84527 (5)	0.5107 (4)	0.54173 (7)	0.0187 (3)
O1	0.73268 (5)	0.1687 (4)	0.67024 (6)	0.0238 (3)
O2	0.76604 (5)	−0.1520 (4)	0.57967 (7)	0.0276 (3)
O3	0.75629 (5)	0.3697 (4)	0.43310 (7)	0.0230 (3)
O4	0.72203 (5)	0.0536 (4)	0.31724 (7)	0.0298 (3)
H1	0.6700 (9)	0.527 (7)	0.7295 (13)	0.033 (6)*
H1D	0.7530 (11)	0.035 (9)	0.6508 (16)	0.065 (9)*
H2	0.8187 (8)	0.600 (6)	0.5531 (12)	0.031 (6)*
H3A	0.7344 (11)	0.288 (9)	0.3952 (16)	0.063 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0445 (12)	0.0266 (10)	0.0261 (10)	0.0013 (9)	0.0192 (9)	−0.0015 (8)
C2	0.0284 (9)	0.0157 (9)	0.0283 (9)	−0.0017 (7)	0.0160 (8)	0.0015 (7)
C3	0.0298 (10)	0.0167 (9)	0.0411 (11)	0.0003 (7)	0.0213 (9)	0.0011 (8)
C4	0.0212 (9)	0.0196 (9)	0.0443 (12)	0.0017 (7)	0.0120 (8)	0.0058 (8)
C5	0.0203 (8)	0.0193 (9)	0.0310 (10)	−0.0008 (7)	0.0053 (7)	0.0067 (7)
C6	0.0191 (8)	0.0169 (8)	0.0218 (8)	−0.0018 (6)	0.0068 (6)	0.0048 (7)
C7	0.0208 (8)	0.0157 (8)	0.0219 (8)	0.0002 (6)	0.0096 (7)	0.0042 (7)
C8	0.0188 (8)	0.0193 (9)	0.0182 (8)	−0.0015 (7)	0.0059 (6)	0.0015 (6)
C9	0.0181 (7)	0.0172 (8)	0.0170 (8)	−0.0028 (6)	0.0066 (6)	0.0026 (6)
C10	0.0182 (7)	0.0172 (8)	0.0173 (8)	−0.0025 (6)	0.0061 (6)	0.0034 (6)
C11	0.0227 (8)	0.0226 (9)	0.0177 (8)	−0.0034 (7)	0.0041 (6)	0.0027 (7)
C12	0.0268 (9)	0.0218 (9)	0.0158 (8)	−0.0064 (7)	0.0067 (7)	−0.0003 (7)
C13	0.0215 (8)	0.0203 (9)	0.0199 (8)	−0.0039 (7)	0.0089 (6)	−0.0004 (7)
C14	0.0276 (9)	0.0214 (9)	0.0238 (9)	−0.0023 (7)	0.0133 (7)	0.0004 (7)
C15	0.0382 (10)	0.0237 (10)	0.0179 (8)	−0.0029 (8)	0.0083 (7)	−0.0025 (7)
C16	0.0300 (9)	0.0177 (9)	0.0160 (8)	−0.0027 (7)	0.0053 (7)	0.0030 (7)
C17	0.0330 (10)	0.0216 (9)	0.0181 (8)	−0.0055 (8)	−0.0001 (7)	0.0028 (7)
C18	0.0244 (9)	0.0262 (10)	0.0265 (9)	−0.0019 (7)	0.0005 (7)	0.0064 (8)
C19	0.0226 (8)	0.0237 (10)	0.0232 (9)	0.0031 (7)	0.0062 (7)	0.0061 (7)
C20	0.0209 (8)	0.0171 (8)	0.0188 (8)	0.0008 (7)	0.0064 (6)	0.0039 (6)
C21	0.0206 (8)	0.0165 (8)	0.0166 (8)	−0.0004 (6)	0.0052 (6)	0.0034 (6)
C22	0.0214 (8)	0.0180 (8)	0.0166 (8)	0.0002 (7)	0.0068 (6)	0.0031 (6)
C23	0.0222 (8)	0.0174 (8)	0.0143 (8)	0.0004 (7)	0.0070 (6)	0.0016 (6)
C24	0.0206 (8)	0.0171 (8)	0.0171 (8)	0.0028 (6)	0.0064 (6)	0.0040 (6)
C25	0.0245 (9)	0.0225 (9)	0.0203 (8)	0.0045 (7)	0.0092 (7)	0.0024 (7)
C26	0.0325 (10)	0.0220 (9)	0.0165 (8)	0.0030 (8)	0.0093 (7)	−0.0003 (7)
C27	0.0270 (9)	0.0202 (9)	0.0143 (8)	0.0001 (7)	0.0051 (6)	0.0012 (7)
C28	0.0346 (10)	0.0233 (10)	0.0162 (8)	−0.0013 (8)	0.0035 (7)	0.0003 (7)
N1	0.0197 (7)	0.0218 (8)	0.0165 (7)	0.0019 (6)	0.0060 (6)	0.0013 (6)
N2	0.0204 (7)	0.0216 (8)	0.0149 (7)	0.0002 (6)	0.0062 (5)	−0.0005 (6)
O1	0.0187 (6)	0.0312 (8)	0.0203 (6)	0.0047 (5)	0.0034 (5)	−0.0006 (5)
O2	0.0247 (7)	0.0301 (8)	0.0308 (7)	0.0022 (6)	0.0123 (6)	−0.0014 (6)
O3	0.0186 (6)	0.0318 (8)	0.0187 (6)	−0.0013 (5)	0.0051 (5)	−0.0013 (5)
O4	0.0278 (7)	0.0397 (9)	0.0193 (6)	−0.0043 (6)	0.0019 (5)	−0.0011 (6)

Geometric parameters (Å, º)

C1—C2	1.500 (3)	C15—H15B	0.9600
C1—H1A	0.9600	C15—H15C	0.9600
C1—H1B	0.9600	C16—C17	1.382 (3)
C1—H1C	0.9600	C16—C21	1.404 (2)
C2—C3	1.387 (3)	C17—C18	1.404 (3)
C2—C7	1.404 (2)	C17—H17	0.9300
C3—C4	1.405 (3)	C18—C19	1.380 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.376 (3)	C19—C20	1.401 (2)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.402 (2)	C20—C21	1.417 (2)
C5—H5	0.9300	C20—C24	1.440 (2)
C6—C7	1.411 (2)	C21—N2	1.379 (2)
C6—C10	1.438 (2)	C22—O3	1.350 (2)
C7—N1	1.378 (2)	C22—C23	1.392 (2)
C8—O1	1.354 (2)	C22—C27	1.410 (2)
C8—C9	1.393 (2)	C23—N2	1.379 (2)
C8—C13	1.409 (2)	C23—C24	1.408 (2)
C9—N1	1.378 (2)	C24—C25	1.410 (2)
C9—C10	1.410 (2)	C25—C26	1.371 (3)
C10—C11	1.409 (2)	C25—H25	0.9300
C11—C12	1.374 (3)	C26—C27	1.420 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.417 (2)	C27—C28	1.439 (2)
C12—H12	0.9300	C28—O4	1.237 (2)
C13—C14	1.438 (3)	C28—H28	0.9300
C14—O2	1.244 (2)	N1—H1	0.87 (2)
C14—H14	0.9300	N2—H2	0.91 (2)
C15—C16	1.505 (3)	O1—H1D	0.94 (3)
C15—H15A	0.9600	O3—H3A	0.90 (3)
C2—C1—H1A	109.5	H15A—C15—H15C	109.5
C2—C1—H1B	109.5	H15B—C15—H15C	109.5
H1A—C1—H1B	109.5	C17—C16—C21	115.81 (17)
C2—C1—H1C	109.5	C17—C16—C15	123.33 (17)
H1A—C1—H1C	109.5	C21—C16—C15	120.86 (16)
H1B—C1—H1C	109.5	C16—C17—C18	122.89 (17)
C3—C2—C7	115.79 (17)	C16—C17—H17	118.6
C3—C2—C1	122.54 (17)	C18—C17—H17	118.6
C7—C2—C1	121.68 (17)	C19—C18—C17	120.89 (18)
C2—C3—C4	122.71 (18)	C19—C18—H18	119.6
C2—C3—H3	118.6	C17—C18—H18	119.6
C4—C3—H3	118.6	C18—C19—C20	118.34 (18)
C5—C4—C3	120.74 (17)	C18—C19—H19	120.8
C5—C4—H4	119.6	C20—C19—H19	120.8
C3—C4—H4	119.6	C19—C20—C21	119.64 (16)
C4—C5—C6	118.62 (18)	C19—C20—C24	133.72 (17)
C4—C5—H5	120.7	C21—C20—C24	106.64 (15)
C6—C5—H5	120.7	N2—C21—C16	128.23 (16)
C5—C6—C7	119.64 (17)	N2—C21—C20	109.32 (15)
C5—C6—C10	133.48 (17)	C16—C21—C20	122.43 (16)
C7—C6—C10	106.86 (15)	O3—C22—C23	119.39 (15)
N1—C7—C2	128.29 (17)	O3—C22—C27	122.90 (16)
N1—C7—C6	109.21 (15)	C23—C22—C27	117.71 (16)
C2—C7—C6	122.50 (16)	N2—C23—C22	128.21 (16)
O1—C8—C9	119.60 (15)	N2—C23—C24	110.28 (15)
O1—C8—C13	122.58 (16)	C22—C23—C24	121.50 (16)
C9—C8—C13	117.81 (16)	C23—C24—C25	120.38 (16)
N1—C9—C8	128.95 (16)	C23—C24—C20	105.83 (15)
N1—C9—C10	109.92 (15)	C25—C24—C20	133.78 (16)
C8—C9—C10	121.13 (16)	C26—C25—C24	118.57 (16)
C11—C10—C9	120.79 (16)	C26—C25—H25	120.7
C11—C10—C6	133.37 (16)	C24—C25—H25	120.7
C9—C10—C6	105.84 (15)	C25—C26—C27	121.34 (17)
C12—C11—C10	118.20 (16)	C25—C26—H26	119.3
C12—C11—H11	120.9	C27—C26—H26	119.3
C10—C11—H11	120.9	C22—C27—C26	120.48 (16)
C11—C12—C13	121.50 (16)	C22—C27—C28	118.85 (17)
C11—C12—H12	119.3	C26—C27—C28	120.62 (17)
C13—C12—H12	119.3	O4—C28—C27	124.41 (18)
C8—C13—C12	120.56 (16)	O4—C28—H28	117.8
C8—C13—C14	119.52 (16)	C27—C28—H28	117.8
C12—C13—C14	119.89 (16)	C9—N1—C7	108.16 (14)
O2—C14—C13	124.09 (17)	C9—N1—H1	124.4 (16)
O2—C14—H14	118.0	C7—N1—H1	127.5 (16)
C13—C14—H14	118.0	C23—N2—C21	107.92 (15)
C16—C15—H15A	109.5	C23—N2—H2	123.7 (15)
C16—C15—H15B	109.5	C21—N2—H2	128.2 (15)
H15A—C15—H15B	109.5	C8—O1—H1D	104.5 (18)
C16—C15—H15C	109.5	C22—O3—H3A	105.7 (19)
C7—C2—C3—C4	0.8 (3)	C18—C19—C20—C21	0.0 (3)
C1—C2—C3—C4	−179.15 (19)	C18—C19—C20—C24	−178.91 (19)
C2—C3—C4—C5	−0.9 (3)	C17—C16—C21—N2	179.02 (18)
C3—C4—C5—C6	0.2 (3)	C15—C16—C21—N2	−0.9 (3)
C4—C5—C6—C7	0.5 (3)	C17—C16—C21—C20	0.7 (3)
C4—C5—C6—C10	178.98 (19)	C15—C16—C21—C20	−179.26 (17)
C3—C2—C7—N1	−179.66 (18)	C19—C20—C21—N2	−179.13 (16)
C1—C2—C7—N1	0.3 (3)	C24—C20—C21—N2	0.0 (2)
C3—C2—C7—C6	0.0 (3)	C19—C20—C21—C16	−0.5 (3)
C1—C2—C7—C6	179.92 (17)	C24—C20—C21—C16	178.64 (16)
C5—C6—C7—N1	179.06 (16)	O3—C22—C23—N2	2.3 (3)
C10—C6—C7—N1	0.2 (2)	C27—C22—C23—N2	−177.78 (17)
C5—C6—C7—C2	−0.6 (3)	O3—C22—C23—C24	−179.11 (16)
C10—C6—C7—C2	−179.45 (16)	C27—C22—C23—C24	0.8 (3)
O1—C8—C9—N1	−0.6 (3)	N2—C23—C24—C25	179.47 (16)
C13—C8—C9—N1	178.76 (17)	C22—C23—C24—C25	0.6 (3)
O1—C8—C9—C10	−179.52 (16)	N2—C23—C24—C20	−0.3 (2)
C13—C8—C9—C10	−0.2 (3)	C22—C23—C24—C20	−179.20 (16)
N1—C9—C10—C11	179.77 (16)	C19—C20—C24—C23	179.2 (2)
C8—C9—C10—C11	−1.1 (3)	C21—C20—C24—C23	0.18 (19)
N1—C9—C10—C6	−0.63 (19)	C19—C20—C24—C25	−0.6 (4)
C8—C9—C10—C6	178.49 (16)	C21—C20—C24—C25	−179.59 (19)
C5—C6—C10—C11	1.2 (4)	C23—C24—C25—C26	−1.3 (3)
C7—C6—C10—C11	179.77 (19)	C20—C24—C25—C26	178.46 (19)
C5—C6—C10—C9	−178.36 (19)	C24—C25—C26—C27	0.5 (3)
C7—C6—C10—C9	0.24 (19)	O3—C22—C27—C26	178.33 (17)
C9—C10—C11—C12	1.6 (3)	C23—C22—C27—C26	−1.6 (3)
C6—C10—C11—C12	−177.90 (19)	O3—C22—C27—C28	−4.1 (3)
C10—C11—C12—C13	−0.8 (3)	C23—C22—C27—C28	175.89 (16)
O1—C8—C13—C12	−179.70 (16)	C25—C26—C27—C22	1.0 (3)
C9—C8—C13—C12	1.0 (3)	C25—C26—C27—C28	−176.49 (18)
O1—C8—C13—C14	2.4 (3)	C22—C27—C28—O4	0.3 (3)
C9—C8—C13—C14	−176.92 (16)	C26—C27—C28—O4	177.80 (19)
C11—C12—C13—C8	−0.5 (3)	C8—C9—N1—C7	−178.24 (18)
C11—C12—C13—C14	177.38 (17)	C10—C9—N1—C7	0.8 (2)
C8—C13—C14—O2	−3.4 (3)	C2—C7—N1—C9	179.03 (18)
C12—C13—C14—O2	178.69 (18)	C6—C7—N1—C9	−0.6 (2)
C21—C16—C17—C18	−0.4 (3)	C22—C23—N2—C21	179.13 (17)
C15—C16—C17—C18	179.59 (18)	C24—C23—N2—C21	0.4 (2)
C16—C17—C18—C19	−0.1 (3)	C16—C21—N2—C23	−178.75 (18)
C17—C18—C19—C20	0.3 (3)	C20—C21—N2—C23	−0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3^i	0.93	2.50	3.254 (2)	138
N1—H1···O4^ii	0.87 (2)	2.00 (2)	2.862 (2)	174 (2)
O1—H1D···O2	0.94 (3)	1.74 (3)	2.602 (2)	151 (3)
N2—H2···O2^iii	0.91 (2)	1.97 (2)	2.879 (2)	173 (2)
O3—H3A···O4	0.90 (3)	1.78 (3)	2.595 (2)	150 (3)

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