2-Norbornene-exo-cis-5,6-di­carboxyl­ic acid

The crystal structure of the title compound, C₉H₁₀O₄, contains three independent mol­ecules in the asymmetric unit, with different orientations of carboxyl groups, all linked into an infinite chain through hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.102
• Data-to-parameter ratio = 12.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C9 H10 O4
          Atom count from the _atom_site data:  C9 H9.946666 O4

CELLZ_01
         From the CIF: _cell_formula_units_Z    6
         From the CIF: _chemical_formula_sum  C9 H10 O4
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         54.00     54.00    0.00
         H         60.00     59.68    0.32
         O         24.00     24.00    0.00
          Difference between formula and atom_site contents detected.
          ALERT: check formula stoichiometry or atom site occupancies.

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

bicyclo[2.2.1]hept-2-ene-exo-cis-5,6-dicarboxylic acid

Crystal data

C9H10O4	F(000) = 576
Mr = 182.17	Dx = 1.382 Mg m^−3
Triclinic, P1	Melting point: 150–151° C K
a = 11.282 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.482 (2) Å	Cell parameters from 429 reflections
c = 11.702 (2) Å	θ = 12.1–20.6°
α = 114.22 (1)°	µ = 0.11 mm^−1
β = 97.44 (1)°	T = 150 K
γ = 101.93 (1)°	Bulk, colorless
V = 1313.0 (4) Å^3	0.4 × 0.3 × 0.2 mm
Z = 6

Data collection

Siemens SMART 1K CCD area-detector diffractometer	4833 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.6°, θmin = 1.9°
Detector resolution: 8 pixels mm^-1	h = −14→12
ω scans	k = −14→14
9582 measured reflections	l = −10→15
5970 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	All H-atom parameters refined
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + 1.1369P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
5970 reflections	Δρmax = 0.32 e Å^−3
493 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0205 (9)

Special details

Experimental. The data collection nominally covered more than a hemisphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (15 sec exposure) covering 0.3° in ω. Crystal to detector distance 4.4 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 178 duplicate reflections.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. The C5, C8, O1B and O2B atoms were restrained to coplanarity.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.20726 (17)	0.75940 (18)	0.88599 (17)	0.0214 (4)
H1	0.2424 (19)	0.732 (2)	0.946 (2)	0.025 (5)*
C2	0.11123 (17)	0.83415 (18)	0.92526 (17)	0.0248 (4)
H2	0.059 (2)	0.823 (2)	0.984 (2)	0.031 (6)*
C3	0.10188 (18)	0.89875 (19)	0.85439 (19)	0.0278 (4)
H3	0.043 (2)	0.946 (2)	0.849 (2)	0.036 (6)*
C4	0.19060 (18)	0.86850 (18)	0.76626 (18)	0.0245 (4)
H4	0.2138 (19)	0.928 (2)	0.728 (2)	0.030 (6)*
C5	0.12747 (17)	0.72023 (18)	0.66513 (17)	0.0228 (4)
H5	0.0390 (19)	0.7046 (19)	0.6293 (19)	0.023 (5)*
C6	0.13858 (17)	0.64215 (17)	0.74764 (17)	0.0213 (4)
H6	0.0592 (18)	0.5960 (18)	0.7480 (17)	0.016 (5)*
C7	0.29615 (17)	0.85395 (18)	0.85173 (17)	0.0222 (4)
H71	0.3427 (19)	0.941 (2)	0.930 (2)	0.029 (5)*
H72	0.3552 (19)	0.813 (2)	0.8036 (19)	0.024 (5)*
C8	0.18248 (18)	0.67455 (19)	0.54889 (17)	0.0267 (4)
C9	0.21083 (18)	0.54171 (18)	0.70558 (17)	0.0253 (4)
O1A	0.11724 (17)	0.5541 (2)	0.45869 (16)	0.0425 (5)	0.92
H01A	0.147 (3)	0.530 (3)	0.383 (4)	0.085 (12)*	0.92
O2A	0.2760 (2)	0.7416 (2)	0.5381 (2)	0.0230 (4)	0.92
O3A	0.1684 (3)	0.4366 (3)	0.7256 (3)	0.0348 (5)	0.92
H03A	0.222 (3)	0.378 (3)	0.697 (3)	0.066 (9)*	0.92
O4A	0.30355 (16)	0.55607 (15)	0.66312 (19)	0.0343 (4)	0.92
O1B	0.090 (2)	0.604 (2)	0.447 (2)	0.033 (5)*	0.08
O2B	0.289 (3)	0.713 (3)	0.534 (3)	0.029 (9)*	0.08
O3B	0.253 (2)	0.529 (2)	0.605 (2)	0.042 (6)*	0.08
O4B	0.205 (3)	0.465 (3)	0.747 (3)	0.034 (9)*	0.08
C11	0.26122 (18)	−0.07162 (19)	0.26903 (18)	0.0258 (4)
H11	0.182 (2)	−0.143 (2)	0.223 (2)	0.029 (5)*
C12	0.38093 (19)	−0.10864 (19)	0.24788 (19)	0.0280 (4)
H12	0.388 (2)	−0.200 (2)	0.218 (2)	0.042 (6)*
C13	0.47143 (19)	0.00376 (19)	0.29011 (19)	0.0270 (4)
H13	0.558 (2)	0.015 (2)	0.299 (2)	0.027 (5)*
C14	0.41403 (17)	0.11859 (18)	0.33831 (18)	0.0233 (4)
H14	0.4619 (19)	0.204 (2)	0.3474 (19)	0.025 (5)*
C15	0.38077 (17)	0.12735 (17)	0.46640 (17)	0.0209 (4)
H15	0.452 (2)	0.133 (2)	0.526 (2)	0.029 (5)*
C16	0.27821 (16)	−0.00877 (18)	0.41998 (17)	0.0212 (4)
H16	0.3105 (18)	−0.063 (2)	0.4546 (19)	0.022 (5)*
C17	0.28400 (19)	0.0528 (2)	0.24607 (18)	0.0271 (4)
H171	0.2256 (19)	0.107 (2)	0.2752 (19)	0.025 (5)*
H172	0.287 (2)	0.031 (2)	0.157 (2)	0.031 (6)*
C18	0.34145 (18)	0.24947 (18)	0.54236 (18)	0.0253 (4)
C19	0.15569 (17)	−0.00005 (19)	0.45546 (18)	0.0243 (4)
O11	0.35842 (15)	0.34077 (14)	0.50097 (15)	0.0345 (3)
H011	0.341 (3)	0.415 (3)	0.557 (3)	0.068 (9)*
O12	0.30148 (15)	0.26339 (14)	0.63797 (13)	0.0358 (4)
O13	0.12244 (16)	−0.05902 (18)	0.52244 (17)	0.0422 (4)
H013	0.052 (5)	−0.063 (4)	0.530 (4)	0.049 (13)*	0.60
O14	0.09035 (15)	0.05729 (17)	0.41505 (16)	0.0384 (4)
H014	0.025 (6)	0.052 (5)	0.434 (5)	0.025 (14)*	0.40
C21	0.38484 (19)	0.3337 (2)	0.1277 (2)	0.0295 (4)
H21	0.421 (2)	0.345 (2)	0.212 (2)	0.034 (6)*
C22	0.4626 (2)	0.2950 (2)	0.0294 (2)	0.0357 (5)
H22	0.551 (2)	0.308 (2)	0.049 (2)	0.044 (7)*
C23	0.3889 (2)	0.2539 (2)	−0.0855 (2)	0.0329 (5)
H23	0.410 (2)	0.229 (2)	−0.167 (2)	0.036 (6)*
C24	0.25993 (18)	0.26365 (19)	−0.06683 (19)	0.0262 (4)
H24	0.190 (2)	0.213 (2)	−0.143 (2)	0.035 (6)*
C25	0.27388 (17)	0.41583 (18)	−0.00166 (17)	0.0212 (4)
H25	0.3137 (18)	0.4605 (19)	−0.0467 (18)	0.019 (5)*
C26	0.36091 (17)	0.46715 (18)	0.13559 (17)	0.0225 (4)
H26	0.4370 (19)	0.530 (2)	0.1473 (19)	0.024 (5)*
C27	0.2575 (2)	0.2336 (2)	0.0491 (2)	0.0302 (4)
H271	0.261 (2)	0.141 (2)	0.027 (2)	0.043 (7)*
H272	0.187 (2)	0.254 (2)	0.091 (2)	0.026 (5)*
C28	0.15086 (16)	0.44824 (17)	−0.00077 (17)	0.0209 (4)
C29	0.30380 (17)	0.52761 (18)	0.24700 (17)	0.0234 (4)
O21	0.16514 (13)	0.57781 (13)	0.05335 (14)	0.0279 (3)
H021	0.088 (3)	0.593 (3)	0.050 (3)	0.064 (9)*
O22	0.04919 (12)	0.36414 (12)	−0.04842 (13)	0.0255 (3)
O23	0.37683 (13)	0.63862 (13)	0.34188 (14)	0.0313 (3)
H023	0.339 (3)	0.671 (3)	0.410 (3)	0.073 (10)*
O24	0.19938 (13)	0.47429 (15)	0.25020 (13)	0.0387 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0229 (9)	0.0215 (9)	0.0171 (8)	0.0048 (7)	0.0037 (7)	0.0074 (7)
C2	0.0241 (9)	0.0237 (9)	0.0205 (9)	0.0049 (7)	0.0085 (7)	0.0041 (7)
C3	0.0258 (10)	0.0238 (9)	0.0293 (10)	0.0103 (8)	0.0053 (8)	0.0064 (8)
C4	0.0282 (10)	0.0222 (9)	0.0234 (9)	0.0069 (7)	0.0063 (7)	0.0107 (8)
C5	0.0193 (9)	0.0261 (9)	0.0180 (8)	0.0029 (7)	0.0006 (7)	0.0081 (7)
C6	0.0196 (9)	0.0200 (9)	0.0212 (9)	0.0036 (7)	0.0061 (7)	0.0069 (7)
C7	0.0208 (9)	0.0201 (9)	0.0201 (9)	0.0036 (7)	0.0045 (7)	0.0049 (7)
C8	0.0251 (9)	0.0295 (10)	0.0176 (9)	0.0013 (8)	0.0000 (7)	0.0077 (8)
C9	0.0307 (10)	0.0179 (8)	0.0215 (9)	0.0045 (7)	0.0049 (8)	0.0051 (7)
O1A	0.0365 (10)	0.0422 (11)	0.0199 (8)	−0.0135 (9)	0.0091 (7)	−0.0022 (8)
O2A	0.0238 (10)	0.0198 (10)	0.0255 (9)	0.0067 (8)	0.0069 (6)	0.0097 (8)
O3A	0.0503 (17)	0.0273 (12)	0.0394 (13)	0.0169 (12)	0.0240 (13)	0.0204 (11)
O4A	0.0327 (9)	0.0227 (8)	0.0484 (11)	0.0109 (7)	0.0189 (9)	0.0128 (8)
C11	0.0245 (9)	0.0231 (9)	0.0234 (9)	0.0027 (8)	0.0060 (8)	0.0061 (8)
C12	0.0324 (10)	0.0227 (9)	0.0300 (10)	0.0105 (8)	0.0145 (8)	0.0096 (8)
C13	0.0266 (10)	0.0268 (10)	0.0310 (10)	0.0102 (8)	0.0141 (8)	0.0127 (8)
C14	0.0262 (9)	0.0202 (9)	0.0253 (9)	0.0073 (7)	0.0105 (7)	0.0104 (7)
C15	0.0206 (9)	0.0209 (9)	0.0216 (9)	0.0082 (7)	0.0050 (7)	0.0087 (7)
C16	0.0212 (9)	0.0220 (9)	0.0245 (9)	0.0092 (7)	0.0078 (7)	0.0124 (7)
C17	0.0317 (10)	0.0309 (10)	0.0197 (9)	0.0110 (8)	0.0072 (8)	0.0111 (8)
C18	0.0281 (10)	0.0237 (9)	0.0228 (9)	0.0087 (8)	0.0048 (7)	0.0090 (8)
C19	0.0243 (9)	0.0282 (9)	0.0255 (9)	0.0100 (8)	0.0086 (7)	0.0150 (8)
O11	0.0507 (9)	0.0265 (7)	0.0403 (8)	0.0215 (7)	0.0233 (7)	0.0196 (7)
O12	0.0581 (10)	0.0318 (8)	0.0290 (7)	0.0243 (7)	0.0221 (7)	0.0158 (6)
O13	0.0349 (9)	0.0681 (12)	0.0598 (11)	0.0284 (8)	0.0283 (8)	0.0515 (10)
O14	0.0307 (8)	0.0572 (10)	0.0554 (10)	0.0270 (8)	0.0229 (8)	0.0416 (9)
C21	0.0318 (10)	0.0312 (10)	0.0284 (10)	0.0129 (8)	0.0018 (8)	0.0158 (8)
C22	0.0296 (11)	0.0368 (12)	0.0445 (13)	0.0199 (9)	0.0085 (9)	0.0173 (10)
C23	0.0343 (11)	0.0326 (11)	0.0358 (11)	0.0201 (9)	0.0145 (9)	0.0124 (9)
C24	0.0262 (10)	0.0242 (9)	0.0270 (10)	0.0123 (8)	0.0056 (8)	0.0083 (8)
C25	0.0223 (9)	0.0236 (9)	0.0217 (9)	0.0092 (7)	0.0074 (7)	0.0123 (7)
C26	0.0195 (9)	0.0217 (9)	0.0249 (9)	0.0041 (7)	0.0052 (7)	0.0102 (7)
C27	0.0341 (11)	0.0214 (9)	0.0367 (11)	0.0094 (8)	0.0072 (9)	0.0144 (8)
C28	0.0240 (9)	0.0217 (9)	0.0210 (9)	0.0082 (7)	0.0073 (7)	0.0119 (7)
C29	0.0240 (9)	0.0223 (9)	0.0225 (9)	0.0036 (7)	0.0029 (7)	0.0109 (7)
O21	0.0231 (7)	0.0200 (6)	0.0402 (8)	0.0082 (5)	0.0081 (6)	0.0121 (6)
O22	0.0215 (6)	0.0214 (6)	0.0321 (7)	0.0073 (5)	0.0060 (5)	0.0104 (6)
O23	0.0270 (7)	0.0245 (7)	0.0276 (7)	−0.0015 (6)	0.0063 (6)	0.0021 (6)
O24	0.0287 (8)	0.0415 (9)	0.0242 (7)	−0.0078 (6)	0.0104 (6)	0.0014 (6)

Geometric parameters (Å, º)

C1—C2	1.520 (3)	C14—H14	0.97 (2)
C1—C7	1.535 (2)	C15—C18	1.513 (2)
C1—C6	1.578 (2)	C15—C16	1.571 (2)
C1—H1	0.95 (2)	C15—H15	0.97 (2)
C2—C3	1.328 (3)	C16—C19	1.505 (2)
C2—H2	0.99 (2)	C16—H16	0.97 (2)
C3—C4	1.518 (3)	C17—H171	0.99 (2)
C3—H3	0.95 (2)	C17—H172	0.97 (2)
C4—C7	1.535 (3)	C18—O12	1.222 (2)
C4—C5	1.560 (3)	C18—O11	1.314 (2)
C4—H4	0.97 (2)	C19—O14	1.252 (2)
C5—C8	1.509 (3)	C19—O13	1.273 (2)
C5—C6	1.574 (3)	O11—H011	0.92 (3)
C5—H5	0.98 (2)	O13—H013	0.81 (5)
C6—C9	1.504 (3)	O14—H014	0.80 (7)
C6—H6	0.943 (19)	C21—C22	1.514 (3)
C7—H71	1.01 (2)	C21—C27	1.529 (3)
C7—H72	1.00 (2)	C21—C26	1.578 (3)
C8—O2A	1.225 (3)	C21—H21	0.97 (2)
C8—O2B	1.25 (4)	C22—C23	1.322 (3)
C8—O1B	1.31 (2)	C22—H22	0.96 (2)
C8—O1A	1.323 (2)	C23—C24	1.518 (3)
C9—O4B	1.16 (4)	C23—H23	0.96 (2)
C9—O4A	1.224 (2)	C24—C27	1.533 (3)
C9—O3B	1.29 (2)	C24—C25	1.556 (3)
C9—O3A	1.327 (3)	C24—H24	0.98 (2)
O1A—H01A	0.94 (4)	C25—C28	1.510 (2)
O3A—H03A	0.98 (3)	C25—C26	1.571 (2)
O1B—H01A	1.24 (4)	C25—H25	0.965 (19)
O4B—H03A	1.00 (5)	C26—C29	1.502 (3)
C11—C12	1.518 (3)	C26—H26	0.95 (2)
C11—C17	1.536 (3)	C27—H271	0.99 (2)
C11—C16	1.577 (3)	C27—H272	1.01 (2)
C11—H11	0.98 (2)	C28—O22	1.222 (2)
C12—C13	1.324 (3)	C28—O21	1.320 (2)
C12—H12	0.98 (2)	C29—O24	1.223 (2)
C13—C14	1.521 (3)	C29—O23	1.305 (2)
C13—H13	0.95 (2)	O21—H021	0.93 (3)
C14—C17	1.533 (3)	O23—H023	0.93 (3)
C14—C15	1.560 (2)
C2—C1—C7	101.20 (15)	C15—C14—H14	112.8 (12)
C2—C1—C6	104.02 (14)	C18—C15—C14	114.74 (15)
C7—C1—C6	101.12 (14)	C18—C15—C16	114.46 (15)
C2—C1—H1	115.6 (12)	C14—C15—C16	102.90 (14)
C7—C1—H1	117.9 (12)	C18—C15—H15	103.6 (13)
C6—C1—H1	114.8 (12)	C14—C15—H15	111.4 (12)
C3—C2—C1	107.20 (16)	C16—C15—H15	109.9 (13)
C3—C2—H2	128.5 (13)	C19—C16—C15	116.31 (15)
C1—C2—H2	123.8 (13)	C19—C16—C11	111.07 (15)
C2—C3—C4	107.91 (17)	C15—C16—C11	101.72 (14)
C2—C3—H3	127.2 (14)	C19—C16—H16	107.5 (12)
C4—C3—H3	124.4 (14)	C15—C16—H16	109.4 (12)
C3—C4—C7	100.88 (15)	C11—C16—H16	110.8 (12)
C3—C4—C5	103.92 (15)	C14—C17—C11	93.87 (15)
C7—C4—C5	101.10 (14)	C14—C17—H171	111.9 (12)
C3—C4—H4	117.7 (13)	C11—C17—H171	114.0 (12)
C7—C4—H4	117.3 (13)	C14—C17—H172	112.4 (13)
C5—C4—H4	113.6 (13)	C11—C17—H172	112.1 (13)
C8—C5—C4	114.25 (15)	H171—C17—H172	111.6 (17)
C8—C5—C6	114.49 (15)	O12—C18—O11	122.97 (17)
C4—C5—C6	103.03 (14)	O12—C18—C15	121.93 (17)
C8—C5—H5	104.6 (12)	O11—C18—C15	115.03 (16)
C4—C5—H5	111.6 (12)	O14—C19—O13	123.67 (17)
C6—C5—H5	109.0 (12)	O14—C19—C16	120.44 (17)
C9—C6—C5	115.61 (15)	O13—C19—C16	115.81 (16)
C9—C6—C1	110.82 (15)	C18—O11—H011	109.2 (18)
C5—C6—C1	101.64 (14)	C19—O13—H013	113 (3)
C9—C6—H6	106.7 (11)	C19—O14—H014	113 (4)
C5—C6—H6	111.2 (11)	C22—C21—C27	100.83 (17)
C1—C6—H6	110.8 (11)	C22—C21—C26	105.46 (16)
C1—C7—C4	93.93 (14)	C27—C21—C26	101.00 (15)
C1—C7—H71	112.1 (12)	C22—C21—H21	115.9 (13)
C4—C7—H71	112.4 (12)	C27—C21—H21	120.8 (13)
C1—C7—H72	113.7 (12)	C26—C21—H21	110.9 (13)
C4—C7—H72	113.2 (12)	C23—C22—C21	107.35 (18)
H71—C7—H72	110.7 (16)	C23—C22—H22	126.9 (15)
O2B—C8—O1B	118.8 (19)	C21—C22—H22	125.4 (14)
O2A—C8—O1A	123.5 (2)	C22—C23—C24	107.84 (19)
O2A—C8—C5	124.13 (19)	C22—C23—H23	128.9 (14)
O2B—C8—C5	131.6 (16)	C24—C23—H23	123.0 (14)
O1B—C8—C5	107.7 (10)	C23—C24—C27	100.37 (16)
O1A—C8—C5	112.32 (16)	C23—C24—C25	104.78 (16)
O4B—C9—O4A	112.4 (17)	C27—C24—C25	100.66 (15)
O4B—C9—O3B	124 (2)	C23—C24—H24	116.9 (13)
O4A—C9—O3B	33.8 (10)	C27—C24—H24	118.5 (13)
O4B—C9—O3A	18.9 (15)	C25—C24—H24	113.4 (13)
O4A—C9—O3A	122.1 (2)	C28—C25—C24	113.64 (15)
O3B—C9—O3A	121.0 (11)	C28—C25—C26	114.78 (14)
O4B—C9—C6	119.2 (18)	C24—C25—C26	103.48 (14)
O4A—C9—C6	124.61 (17)	C28—C25—H25	103.6 (11)
O3B—C9—C6	115.5 (11)	C24—C25—H25	112.3 (11)
O3A—C9—C6	113.21 (18)	C26—C25—H25	109.2 (11)
C8—O1A—H01A	112 (2)	C29—C26—C25	115.17 (15)
C9—O3A—H03A	107.7 (19)	C29—C26—C21	109.94 (15)
C8—O1B—H01A	96 (2)	C25—C26—C21	101.15 (14)
C9—O4B—H03A	120 (4)	C29—C26—H26	108.7 (12)
C12—C11—C17	100.29 (15)	C25—C26—H26	110.8 (12)
C12—C11—C16	104.30 (15)	C21—C26—H26	110.9 (12)
C17—C11—C16	101.84 (14)	C21—C27—C24	93.94 (16)
C12—C11—H11	117.2 (12)	C21—C27—H271	110.6 (14)
C17—C11—H11	118.8 (12)	C24—C27—H271	111.4 (14)
C16—C11—H11	112.2 (12)	C21—C27—H272	113.8 (12)
C13—C12—C11	107.40 (17)	C24—C27—H272	114.3 (12)
C13—C12—H12	128.4 (14)	H271—C27—H272	111.6 (18)
C11—C12—H12	123.7 (14)	O22—C28—O21	123.60 (16)
C12—C13—C14	107.77 (17)	O22—C28—C25	123.89 (16)
C12—C13—H13	128.1 (13)	O21—C28—C25	112.47 (15)
C14—C13—H13	123.8 (13)	O24—C29—O23	123.02 (17)
C13—C14—C17	100.35 (15)	O24—C29—C26	122.57 (16)
C13—C14—C15	106.04 (15)	O23—C29—C26	114.36 (16)
C17—C14—C15	100.35 (14)	C28—O21—H021	109.5 (17)
C13—C14—H14	117.0 (12)	C29—O23—H023	111.8 (19)
C17—C14—H14	118.2 (12)
O2A—C8—C5—C6	−111.7 (2)	C15—C16—C19—O14	61.7 (2)
C8—C5—C6—C9	4.7 (2)	O22—C28—C25—C26	−120.13 (19)
C5—C6—C9—O4A	36.4 (3)	C28—C25—C26—C29	6.3 (2)
O12—C18—C15—C16	54.3 (2)	C25—C26—C29—O24	47.2 (3)
C18—C15—C16—C19	0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H01A···O24	0.94 (4)	1.66 (4)	2.599 (2)	175 (3)
O3A—H03A···O12	0.98 (3)	1.71 (3)	2.688 (3)	174 (3)
O11—H011···O4A	0.92 (3)	1.76 (3)	2.680 (2)	179 (3)
O13—H013···O14^i	0.81 (5)	1.81 (5)	2.600 (2)	167 (5)
O14—H014···O13^i	0.80 (7)	1.80 (7)	2.600 (2)	173 (6)
O21—H021···O22^ii	0.93 (3)	1.71 (3)	2.6374 (19)	175 (3)
O23—H023···O2A	0.93 (3)	1.72 (3)	2.640 (3)	176 (3)
O23—H023···O2B	0.93 (3)	1.56 (4)	2.48 (3)	169 (3)

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