2,5-Di­methyl­anilinium 4-hy­droxy­benzoate–2,5-di­methyl­aniline–4-hy­droxy­benzoic acid (1/1/1)

The asymmetric unit of the title compound, C₈H₁₂N⁺·C₇H₅O₃⁻·C₈H₁₁N·C₇H₆O₃, contains a 2,5-di­methyl­anilinium cation, 4-hy­droxy­benzoate anion and neutral 2,5-di­methyl­aniline and 4-hy­droxy­benzoic acid mol­ecules. The components are connected by N—H...O, O—H...O and N—H...N hydrogen bonds, which generate R₂²(8), R₄⁴(20) and R₄⁴(24) loops, as part of a three-dimensional network. The crystal structure also features weak C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.145
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2A    ...     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     10.309 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.061 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         67 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         13 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          8 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          8 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        274 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           3 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
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/4 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015) and PLATON (Spek, 2009).

2,5-Dimethylanilinium 4-hydroxybenzoate–2,5-dimethylaniline–4-hydroxybenzoic acid (1/1/1)

Crystal data

C8H12N^+·C7H5O3^−·C8H11N·C7H6O3	Z = 2
Mr = 518.59	F(000) = 552
Triclinic, P1	Dx = 1.304 Mg m^−3
a = 9.6854 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9169 (6) Å	Cell parameters from 6719 reflections
c = 13.1450 (7) Å	θ = 2.3–29.4°
α = 79.029 (4)°	µ = 0.09 mm^−1
β = 75.615 (3)°	T = 295 K
γ = 85.345 (4)°	Block, colourless
V = 1320.86 (13) Å^3	0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4026 reflections with I > 2σ(I)
ω and φ scan	Rint = 0.070
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 29.5°, θmin = 2.2°
Tmin = 0.688, Tmax = 0.746	h = −13→13
35698 measured reflections	k = −15→15
7024 independent reflections	l = −18→18

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.3498P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
7024 reflections	Δρmax = 0.26 e Å^−3
376 parameters	Δρmin = −0.30 e Å^−3
8 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	0.86255 (19)	0.17699 (16)	0.55783 (14)	0.0292 (4)
C2	0.72606 (19)	0.22707 (16)	0.59077 (14)	0.0277 (4)
C3	0.6211 (2)	0.16170 (17)	0.66719 (14)	0.0323 (4)
H3	0.529843	0.197520	0.685334	0.039*
C4	0.6513 (2)	0.04190 (18)	0.71738 (15)	0.0377 (5)
C5	0.7887 (2)	−0.00660 (18)	0.68915 (16)	0.0406 (5)
H5	0.812282	−0.085084	0.723802	0.049*
C6	0.8915 (2)	0.05903 (17)	0.61069 (15)	0.0358 (4)
H6	0.982781	0.023265	0.592701	0.043*
C7	0.9738 (2)	0.24619 (19)	0.46942 (16)	0.0400 (5)
H7A	1.060098	0.195534	0.457843	0.060*
H7B	0.992273	0.322696	0.488735	0.060*
H7C	0.940066	0.264569	0.405190	0.060*
C8	0.5368 (3)	−0.0305 (2)	0.8010 (2)	0.0635 (7)
H8A	0.503145	−0.092472	0.771013	0.095*
H8B	0.459104	0.025493	0.825236	0.095*
H8C	0.575279	−0.070556	0.860116	0.095*
C9	0.7449 (2)	0.49451 (19)	0.82967 (18)	0.0437 (5)
C10	0.6808 (2)	0.4508 (2)	0.93580 (18)	0.0498 (6)
H10	0.632124	0.507313	0.978034	0.060*
C11	0.6869 (2)	0.3264 (2)	0.98062 (17)	0.0492 (6)
H11	0.643147	0.300354	1.052185	0.059*
C12	0.7577 (2)	0.24010 (19)	0.91973 (16)	0.0405 (5)
C13	0.8226 (2)	0.28259 (18)	0.81374 (15)	0.0360 (4)
H13	0.869464	0.225492	0.771407	0.043*
C14	0.8192 (2)	0.40806 (18)	0.76934 (15)	0.0355 (5)
C15	0.7351 (3)	0.6308 (2)	0.7828 (2)	0.0734 (8)
H15A	0.672759	0.674199	0.834325	0.110*
H15B	0.698040	0.640291	0.720302	0.110*
H15C	0.828262	0.664817	0.763670	0.110*
C16	0.7672 (3)	0.1037 (2)	0.9659 (2)	0.0704 (8)
H16A	0.854196	0.085435	0.989195	0.106*
H16B	0.765939	0.055034	0.912536	0.106*
H16C	0.687379	0.083353	1.025583	0.106*
C17	0.29119 (19)	0.44302 (15)	0.80120 (13)	0.0267 (4)
C18	0.1466 (2)	0.45138 (17)	0.84845 (15)	0.0332 (4)
H18	0.089970	0.513913	0.818656	0.040*
C19	0.0851 (2)	0.36894 (17)	0.93867 (15)	0.0356 (5)
H19	−0.012149	0.375521	0.968950	0.043*
C20	0.1690 (2)	0.27650 (17)	0.98379 (15)	0.0365 (5)
C21	0.3135 (2)	0.26666 (17)	0.93802 (15)	0.0398 (5)
H21	0.369889	0.204221	0.968234	0.048*
C22	0.3739 (2)	0.34920 (16)	0.84780 (14)	0.0324 (4)
H22	0.471145	0.342192	0.817592	0.039*
C23	0.3543 (2)	0.53064 (16)	0.70188 (14)	0.0293 (4)
C24	0.73147 (18)	0.84066 (16)	0.39196 (14)	0.0283 (4)
C25	0.82153 (19)	0.85457 (17)	0.29055 (15)	0.0321 (4)
H25	0.858731	0.784245	0.261371	0.039*
C26	0.8563 (2)	0.97198 (17)	0.23265 (15)	0.0348 (4)
H26	0.916804	0.980486	0.164794	0.042*
C27	0.80129 (19)	1.07684 (16)	0.27555 (14)	0.0303 (4)
C28	0.70977 (19)	1.06454 (16)	0.37624 (15)	0.0321 (4)
H28	0.671854	1.135002	0.404962	0.039*
C29	0.67551 (19)	0.94683 (17)	0.43341 (15)	0.0326 (4)
H29	0.613906	0.938508	0.500819	0.039*
C30	0.6966 (2)	0.71342 (17)	0.45436 (15)	0.0319 (4)
N1	0.69424 (19)	0.35629 (15)	0.54491 (14)	0.0348 (4)
N2	0.8895 (2)	0.44564 (19)	0.66002 (15)	0.0488 (5)
O1	0.28132 (14)	0.62590 (11)	0.67266 (10)	0.0380 (3)
O2	0.47869 (14)	0.50631 (11)	0.64920 (10)	0.0391 (3)
O3	0.11541 (18)	0.19274 (14)	1.07406 (13)	0.0578 (5)
O4	0.57699 (16)	0.71376 (13)	0.52863 (13)	0.0515 (4)
O5	0.77000 (15)	0.62033 (12)	0.43902 (12)	0.0455 (4)
O6	0.83921 (16)	1.19187 (12)	0.21635 (11)	0.0446 (4)
H1A	0.755 (2)	0.4040 (18)	0.5552 (18)	0.057 (7)*
H1B	0.6106 (14)	0.379 (2)	0.5801 (16)	0.052 (7)*
H1C	0.698 (3)	0.363 (2)	0.4768 (9)	0.063 (8)*
H2A	0.898 (3)	0.5244 (10)	0.643 (2)	0.080 (9)*
H2B	0.9714 (16)	0.409 (2)	0.644 (2)	0.077 (10)*
H3A	0.0300 (14)	0.206 (3)	1.099 (3)	0.116*
H4A	0.555 (3)	0.6430 (15)	0.564 (2)	0.116*
H6A	0.798 (3)	1.248 (2)	0.248 (2)	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (10)	0.0291 (9)	0.0274 (9)	−0.0006 (8)	−0.0047 (7)	−0.0066 (7)
C2	0.0305 (10)	0.0246 (9)	0.0270 (9)	0.0016 (7)	−0.0079 (7)	−0.0017 (7)
C3	0.0280 (10)	0.0344 (10)	0.0321 (10)	0.0014 (8)	−0.0061 (8)	−0.0024 (8)
C4	0.0402 (12)	0.0352 (10)	0.0346 (11)	−0.0067 (9)	−0.0087 (9)	0.0033 (8)
C5	0.0507 (13)	0.0272 (10)	0.0431 (12)	0.0037 (9)	−0.0168 (10)	0.0016 (8)
C6	0.0351 (11)	0.0340 (10)	0.0386 (11)	0.0106 (8)	−0.0108 (9)	−0.0094 (8)
C7	0.0324 (11)	0.0423 (11)	0.0404 (11)	−0.0010 (9)	−0.0002 (9)	−0.0066 (9)
C8	0.0565 (16)	0.0587 (15)	0.0611 (16)	−0.0163 (12)	−0.0068 (12)	0.0209 (12)
C9	0.0435 (13)	0.0386 (11)	0.0511 (13)	0.0002 (9)	−0.0115 (10)	−0.0137 (10)
C10	0.0416 (13)	0.0555 (14)	0.0532 (14)	0.0027 (11)	−0.0014 (10)	−0.0263 (12)
C11	0.0422 (13)	0.0647 (15)	0.0369 (12)	−0.0092 (11)	0.0037 (9)	−0.0137 (11)
C12	0.0399 (12)	0.0432 (11)	0.0370 (11)	−0.0069 (9)	−0.0063 (9)	−0.0054 (9)
C13	0.0364 (11)	0.0356 (10)	0.0353 (11)	−0.0017 (9)	−0.0044 (8)	−0.0099 (8)
C14	0.0334 (11)	0.0396 (11)	0.0343 (10)	−0.0070 (9)	−0.0060 (8)	−0.0089 (9)
C15	0.099 (2)	0.0411 (14)	0.078 (2)	0.0072 (14)	−0.0171 (17)	−0.0165 (13)
C16	0.096 (2)	0.0541 (15)	0.0500 (15)	−0.0076 (14)	−0.0086 (14)	0.0071 (12)
C17	0.0291 (10)	0.0227 (8)	0.0254 (9)	−0.0010 (7)	−0.0025 (7)	−0.0021 (7)
C18	0.0308 (10)	0.0305 (9)	0.0348 (10)	0.0013 (8)	−0.0058 (8)	−0.0007 (8)
C19	0.0267 (10)	0.0370 (10)	0.0372 (11)	−0.0046 (8)	0.0034 (8)	−0.0053 (8)
C20	0.0438 (12)	0.0292 (10)	0.0300 (10)	−0.0079 (9)	0.0010 (8)	0.0011 (8)
C21	0.0426 (12)	0.0315 (10)	0.0363 (11)	0.0069 (9)	−0.0038 (9)	0.0055 (8)
C22	0.0284 (10)	0.0324 (10)	0.0312 (10)	0.0037 (8)	−0.0015 (8)	−0.0025 (8)
C23	0.0328 (10)	0.0235 (9)	0.0287 (9)	−0.0025 (8)	−0.0032 (8)	−0.0021 (7)
C24	0.0236 (9)	0.0265 (9)	0.0325 (10)	−0.0014 (7)	−0.0054 (7)	−0.0009 (7)
C25	0.0303 (10)	0.0279 (9)	0.0356 (10)	0.0022 (8)	−0.0031 (8)	−0.0073 (8)
C26	0.0350 (11)	0.0338 (10)	0.0288 (10)	0.0009 (8)	0.0025 (8)	−0.0030 (8)
C27	0.0266 (10)	0.0280 (9)	0.0314 (10)	−0.0020 (7)	−0.0036 (7)	0.0027 (7)
C28	0.0320 (10)	0.0257 (9)	0.0356 (10)	0.0019 (8)	−0.0025 (8)	−0.0064 (8)
C29	0.0284 (10)	0.0326 (10)	0.0311 (10)	0.0001 (8)	0.0004 (8)	−0.0018 (8)
C30	0.0288 (10)	0.0296 (10)	0.0363 (10)	−0.0041 (8)	−0.0084 (8)	−0.0011 (8)
N1	0.0363 (10)	0.0284 (9)	0.0343 (10)	0.0036 (8)	−0.0029 (8)	−0.0013 (7)
N2	0.0612 (14)	0.0395 (11)	0.0398 (11)	−0.0093 (10)	−0.0009 (9)	−0.0037 (9)
O1	0.0447 (8)	0.0263 (7)	0.0345 (7)	0.0083 (6)	−0.0022 (6)	0.0023 (5)
O2	0.0354 (8)	0.0313 (7)	0.0373 (8)	0.0019 (6)	0.0073 (6)	0.0044 (6)
O3	0.0618 (11)	0.0443 (9)	0.0462 (9)	−0.0062 (8)	0.0100 (8)	0.0156 (7)
O4	0.0413 (9)	0.0330 (8)	0.0599 (10)	−0.0007 (7)	0.0115 (7)	0.0101 (7)
O5	0.0466 (9)	0.0274 (7)	0.0550 (9)	0.0009 (6)	−0.0031 (7)	−0.0017 (6)
O6	0.0520 (9)	0.0282 (7)	0.0404 (8)	−0.0031 (7)	0.0064 (7)	0.0036 (6)

Geometric parameters (Å, º)

C1—C6	1.385 (2)	C17—C18	1.387 (2)
C1—C2	1.386 (3)	C17—C22	1.392 (2)
C1—C7	1.503 (2)	C17—C23	1.489 (2)
C2—C3	1.375 (2)	C18—C19	1.379 (2)
C2—N1	1.465 (2)	C18—H18	0.9300
C3—C4	1.392 (3)	C19—C20	1.381 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.380 (3)	C20—O3	1.368 (2)
C4—C8	1.506 (3)	C20—C21	1.384 (3)
C5—C6	1.376 (3)	C21—C22	1.376 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—H7A	0.9600	C23—O1	1.262 (2)
C7—H7B	0.9600	C23—O2	1.267 (2)
C7—H7C	0.9600	C24—C29	1.388 (2)
C8—H8A	0.9600	C24—C25	1.388 (2)
C8—H8B	0.9600	C24—C30	1.490 (2)
C8—H8C	0.9600	C25—C26	1.381 (2)
C9—C10	1.387 (3)	C25—H25	0.9300
C9—C14	1.389 (3)	C26—C27	1.382 (3)
C9—C15	1.503 (3)	C26—H26	0.9300
C10—C11	1.376 (3)	C27—O6	1.371 (2)
C10—H10	0.9300	C27—C28	1.387 (2)
C11—C12	1.381 (3)	C28—C29	1.380 (2)
C11—H11	0.9300	C28—H28	0.9300
C12—C13	1.385 (3)	C29—H29	0.9300
C12—C16	1.502 (3)	C30—O5	1.212 (2)
C13—C14	1.384 (3)	C30—O4	1.317 (2)
C13—H13	0.9300	N1—H1A	0.869 (9)
C14—N2	1.425 (3)	N1—H1B	0.871 (9)
C15—H15A	0.9600	N1—H1C	0.876 (10)
C15—H15B	0.9600	N2—H2A	0.852 (10)
C15—H15C	0.9600	N2—H2B	0.856 (10)
C16—H16A	0.9600	O3—H3A	0.824 (10)
C16—H16B	0.9600	O4—H4A	0.834 (10)
C16—H16C	0.9600	O6—H6A	0.830 (10)
C6—C1—C2	116.45 (16)	C12—C16—H16C	109.5
C6—C1—C7	121.39 (17)	H16A—C16—H16C	109.5
C2—C1—C7	122.15 (16)	H16B—C16—H16C	109.5
C3—C2—C1	122.61 (16)	C18—C17—C22	118.19 (16)
C3—C2—N1	118.80 (17)	C18—C17—C23	120.40 (16)
C1—C2—N1	118.55 (16)	C22—C17—C23	121.39 (16)
C2—C3—C4	119.97 (18)	C19—C18—C17	121.40 (17)
C2—C3—H3	120.0	C19—C18—H18	119.3
C4—C3—H3	120.0	C17—C18—H18	119.3
C5—C4—C3	117.97 (17)	C18—C19—C20	119.55 (17)
C5—C4—C8	121.70 (19)	C18—C19—H19	120.2
C3—C4—C8	120.3 (2)	C20—C19—H19	120.2
C6—C5—C4	121.20 (17)	O3—C20—C19	122.63 (18)
C6—C5—H5	119.4	O3—C20—C21	117.39 (18)
C4—C5—H5	119.4	C19—C20—C21	119.98 (16)
C5—C6—C1	121.67 (18)	C22—C21—C20	120.05 (18)
C5—C6—H6	119.2	C22—C21—H21	120.0
C1—C6—H6	119.2	C20—C21—H21	120.0
C1—C7—H7A	109.5	C21—C22—C17	120.83 (17)
C1—C7—H7B	109.5	C21—C22—H22	119.6
H7A—C7—H7B	109.5	C17—C22—H22	119.6
C1—C7—H7C	109.5	O1—C23—O2	122.37 (16)
H7A—C7—H7C	109.5	O1—C23—C17	118.75 (16)
H7B—C7—H7C	109.5	O2—C23—C17	118.87 (16)
C4—C8—H8A	109.5	C29—C24—C25	118.81 (16)
C4—C8—H8B	109.5	C29—C24—C30	121.15 (16)
H8A—C8—H8B	109.5	C25—C24—C30	120.04 (16)
C4—C8—H8C	109.5	C26—C25—C24	120.55 (17)
H8A—C8—H8C	109.5	C26—C25—H25	119.7
H8B—C8—H8C	109.5	C24—C25—H25	119.7
C10—C9—C14	117.50 (19)	C25—C26—C27	119.99 (17)
C10—C9—C15	120.9 (2)	C25—C26—H26	120.0
C14—C9—C15	121.6 (2)	C27—C26—H26	120.0
C11—C10—C9	122.1 (2)	O6—C27—C26	118.45 (16)
C11—C10—H10	118.9	O6—C27—C28	121.39 (16)
C9—C10—H10	118.9	C26—C27—C28	120.16 (16)
C10—C11—C12	120.2 (2)	C29—C28—C27	119.41 (17)
C10—C11—H11	119.9	C29—C28—H28	120.3
C12—C11—H11	119.9	C27—C28—H28	120.3
C11—C12—C13	118.20 (19)	C28—C29—C24	121.08 (17)
C11—C12—C16	121.8 (2)	C28—C29—H29	119.5
C13—C12—C16	120.0 (2)	C24—C29—H29	119.5
C14—C13—C12	121.52 (19)	O5—C30—O4	123.77 (16)
C14—C13—H13	119.2	O5—C30—C24	124.02 (17)
C12—C13—H13	119.2	O4—C30—C24	112.21 (16)
C13—C14—C9	120.33 (18)	C2—N1—H1A	108.4 (16)
C13—C14—N2	118.65 (18)	C2—N1—H1B	108.7 (15)
C9—C14—N2	120.99 (19)	H1A—N1—H1B	106 (2)
C9—C15—H15A	109.5	C2—N1—H1C	110.5 (16)
C9—C15—H15B	109.5	H1A—N1—H1C	111 (2)
H15A—C15—H15B	109.5	H1B—N1—H1C	111 (2)
C9—C15—H15C	109.5	C14—N2—H2A	112.1 (19)
H15A—C15—H15C	109.5	C14—N2—H2B	112.1 (19)
H15B—C15—H15C	109.5	H2A—N2—H2B	109 (3)
C12—C16—H16A	109.5	C20—O3—H3A	113 (2)
C12—C16—H16B	109.5	C30—O4—H4A	113 (2)
H16A—C16—H16B	109.5	C27—O6—H6A	111 (2)
C6—C1—C2—C3	−3.8 (3)	C23—C17—C18—C19	178.08 (17)
C7—C1—C2—C3	176.07 (18)	C17—C18—C19—C20	0.5 (3)
C6—C1—C2—N1	173.96 (17)	C18—C19—C20—O3	179.08 (19)
C7—C1—C2—N1	−6.1 (3)	C18—C19—C20—C21	−0.4 (3)
C1—C2—C3—C4	2.3 (3)	O3—C20—C21—C22	−179.26 (18)
N1—C2—C3—C4	−175.54 (18)	C19—C20—C21—C22	0.3 (3)
C2—C3—C4—C5	1.1 (3)	C20—C21—C22—C17	−0.2 (3)
C2—C3—C4—C8	−179.88 (19)	C18—C17—C22—C21	0.3 (3)
C3—C4—C5—C6	−2.7 (3)	C23—C17—C22—C21	−178.23 (17)
C8—C4—C5—C6	178.3 (2)	C18—C17—C23—O1	13.0 (3)
C4—C5—C6—C1	1.0 (3)	C22—C17—C23—O1	−168.48 (17)
C2—C1—C6—C5	2.2 (3)	C18—C17—C23—O2	−166.33 (17)
C7—C1—C6—C5	−177.70 (18)	C22—C17—C23—O2	12.2 (3)
C14—C9—C10—C11	−1.3 (3)	C29—C24—C25—C26	0.9 (3)
C15—C9—C10—C11	179.4 (2)	C30—C24—C25—C26	−179.00 (17)
C9—C10—C11—C12	−0.4 (4)	C24—C25—C26—C27	−0.1 (3)
C10—C11—C12—C13	0.6 (3)	C25—C26—C27—O6	179.34 (17)
C10—C11—C12—C16	179.7 (2)	C25—C26—C27—C28	−0.7 (3)
C11—C12—C13—C14	0.9 (3)	O6—C27—C28—C29	−179.42 (17)
C16—C12—C13—C14	−178.2 (2)	C26—C27—C28—C29	0.7 (3)
C12—C13—C14—C9	−2.6 (3)	C27—C28—C29—C24	0.2 (3)
C12—C13—C14—N2	179.36 (19)	C25—C24—C29—C28	−1.0 (3)
C10—C9—C14—C13	2.7 (3)	C30—C24—C29—C28	178.92 (17)
C15—C9—C14—C13	−177.9 (2)	C29—C24—C30—O5	−157.41 (19)
C10—C9—C14—N2	−179.3 (2)	C25—C24—C30—O5	22.5 (3)
C15—C9—C14—N2	0.1 (3)	C29—C24—C30—O4	22.3 (2)
C22—C17—C18—C19	−0.5 (3)	C25—C24—C30—O4	−157.83 (18)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C9–C14 and C24–C29 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.87 (1)	2.55 (2)	3.015 (2)	114 (2)
N1—H1A···N2	0.87 (1)	2.24 (2)	3.016 (3)	149 (2)
N1—H1B···O2	0.87 (1)	2.00 (1)	2.792 (2)	151 (2)
O4—H4A···O2	0.83 (1)	1.78 (1)	2.6041 (17)	169 (3)
N1—H1C···O1^i	0.88 (1)	1.91 (1)	2.781 (2)	176 (2)
N2—H2B···O5^ii	0.86 (1)	2.49 (1)	3.306 (3)	159 (2)
O3—H3A···O6^iii	0.82 (1)	2.09 (2)	2.858 (2)	156 (3)
O6—H6A···O1^iv	0.83 (1)	1.88 (1)	2.7075 (19)	175 (3)
C13—H13···Cg1	0.93	2.80	3.437 (2)	127
C6—H6···Cg3^ii	0.93	2.87	3.554 (2)	132
C19—H19···Cg2^v	0.93	2.87	3.532 (2)	129

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