Two different three-dimensional hydrogen-bonded framework structures in two hydrated adducts meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–terephthalic acid–water (1/1/4) and (1/1/6)

Co-crystallization of meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C₁₆H₃₆N₄, with terephthalic acid (1,4-benzenedicarboxylic acid), C₈H₆O₄, from ethanol yields the tetrahydrate (C₁₆H₃₆N₄).(C₈H₆O₄).(H₂O)₄ (1), meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane–terephthalic acid–water (1/1/4), while similar co-crystallization from methanol yields the hexahydrate (C₁₆H₃₆N₄).(C₈H₆O₄).(H₂O)₆ (2), meso-5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetraazacyclotetradecane–terephthalic acid–water (1/­1/6). Both compounds are salts, [C₁₆H₃₈N₄]²⁺.[C₈H₄O₄]²⁻.4H₂O (1) and [C₁₆H₃₈N₄]²⁺.[C₈H₄O₄]²⁻.6H₂O (2): in (2) both ionic components lie across centres of inversion and in both salts there are two protons held within the N₄ cavity of the cation. In the structure of (1), the cations and anions are linked into chains by means of paired N—H...O hydrogen bonds, and the water molecules are linked into continuous chains by means of O—H...O hydrogen bonds, in which each of the H atoms is independently disordered over two equally populated sites. The water chains link the ionic chains into a continuous three-dimensional framework by means of further O—H...O hydrogen bonds. In (2) the cations and anions are linked by single N—H...O hydrogen bonds, again into chains: at the same time the anions and the water molecules are linked by multiple O—H...O hydrogen bonds into continuous two-dimensional nets, which are linked by the cations, by means of N—H...O hydrogen bonds into a three-dimensional framework, entirely different from that in (1).

Computing details

For both compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b) for (1); SOLVER in NRCVAX96 (Gabe et al., 1989) for (2). Program(s) used to refine structure: NRCVAX96 (Gabe et al., 1989)and SHELXL97 (Sheldrick, 1997a) for (1); NRCVAX96 and SHELXL97 (Sheldrick, 1997b) for (2). For both compounds, molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

(1) Meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra- azacyclotetradecane–terephthalic acid–water (1/1/4).

Crystal data

C16H38N4·C8H4O4·4H2O	F(000) = 1144
Mr = 522.68	Dx = 1.234 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.3213 (4) Å	Cell parameters from 6427 reflections
b = 14.0499 (4) Å	θ = 4.1–27.5°
c = 16.0491 (6) Å	µ = 0.09 mm^−1
β = 110.549 (2)°	T = 100 K
V = 2812.67 (16) Å^3	Block, colourless
Z = 4	0.35 × 0.30 × 0.10 mm

Data collection

Kappa-CCD diffractometer	6427 independent reflections
Radiation source: fine-focus sealed X-ray tube	4031 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 4.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→17
Tmin = 0.969, Tmax = 0.991	k = 0→18
32836 measured reflections	l = −20→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0512P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max = 0.002
6427 reflections	Δρmax = 0.23 e Å^−3
371 parameters	Δρmin = −0.20 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (7)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.55614 (9)	0.41092 (8)	0.28573 (8)	0.0175 (3)
C2	0.54253 (11)	0.37934 (10)	0.36943 (10)	0.0199 (3)
C3	0.57108 (11)	0.27535 (10)	0.38679 (10)	0.0202 (3)
N4	0.49519 (9)	0.21587 (8)	0.31778 (8)	0.0179 (3)
C5	0.52038 (11)	0.11208 (10)	0.32400 (10)	0.0198 (3)
C51	0.53580 (13)	0.07242 (11)	0.41651 (10)	0.0279 (4)
C52	0.62127 (11)	0.09660 (10)	0.30045 (11)	0.0244 (4)
C6	0.42294 (11)	0.05990 (10)	0.25729 (10)	0.0218 (3)
C7	0.39833 (11)	0.07637 (10)	0.15823 (10)	0.0207 (3)
C71	0.30228 (12)	0.01707 (10)	0.10253 (11)	0.0273 (4)
N8	0.37573 (9)	0.18045 (8)	0.13754 (8)	0.0183 (3)
C9	0.38448 (12)	0.21265 (10)	0.05212 (10)	0.0212 (3)
C10	0.35345 (12)	0.31622 (10)	0.03572 (10)	0.0230 (3)
N11	0.42840 (9)	0.37652 (8)	0.10425 (8)	0.0203 (3)
C12	0.39486 (11)	0.47798 (10)	0.10703 (10)	0.0216 (3)
C121	0.35486 (13)	0.52561 (11)	0.01525 (11)	0.0290 (4)
C122	0.30590 (12)	0.48136 (11)	0.14643 (11)	0.0282 (4)
C13	0.49530 (11)	0.53232 (10)	0.16589 (10)	0.0217 (3)
C14	0.53339 (11)	0.51514 (9)	0.26577 (10)	0.0200 (3)
C141	0.63364 (12)	0.57322 (10)	0.31442 (10)	0.0231 (3)
O21	1.26221 (8)	0.25406 (8)	0.28097 (7)	0.0306 (3)
O22	1.17553 (8)	0.21642 (7)	0.13845 (7)	0.0256 (3)
O23	0.68658 (8)	0.34160 (7)	0.17262 (7)	0.0266 (3)
O24	0.76698 (8)	0.37946 (7)	0.31595 (7)	0.0244 (2)
C21	1.07375 (11)	0.27914 (9)	0.22109 (10)	0.0180 (3)
C22	0.98667 (11)	0.30231 (9)	0.14531 (10)	0.0188 (3)
C23	0.88937 (11)	0.32757 (9)	0.15198 (10)	0.0186 (3)
C24	0.87689 (11)	0.33057 (9)	0.23473 (10)	0.0182 (3)
C25	0.96450 (11)	0.30995 (9)	0.31087 (10)	0.0198 (3)
C26	1.06222 (11)	0.28429 (10)	0.30423 (10)	0.0195 (3)
C27	1.17891 (11)	0.24799 (10)	0.21385 (10)	0.0208 (3)
C28	0.76858 (11)	0.35204 (10)	0.24072 (10)	0.0200 (3)
O3	0.99709 (10)	0.08941 (8)	0.04474 (8)	0.0324 (3)
O4	0.82252 (11)	0.20923 (10)	−0.03716 (9)	0.0408 (3)
O5	0.65694 (10)	0.20483 (9)	0.03737 (9)	0.0370 (3)
O6	0.59445 (10)	0.02185 (9)	0.06940 (9)	0.0359 (3)
H1A	0.6254	0.3984	0.2894	0.021*
H1B	0.5110	0.3759	0.2392	0.021*
H2A	0.4673	0.3894	0.3649	0.024*
H2B	0.5891	0.4179	0.4198	0.024*
H3A	0.6447	0.2645	0.3872	0.024*
H3B	0.5693	0.2573	0.4459	0.024*
H4A	0.4279	0.2239	0.3206	0.021*
H51A	0.5969	0.1041	0.4608	0.042*
H51B	0.5494	0.0038	0.4174	0.042*
H51C	0.4709	0.0840	0.4305	0.042*
H52A	0.6132	0.1297	0.2447	0.037*
H52B	0.6312	0.0284	0.2933	0.037*
H52C	0.6838	0.1219	0.3483	0.037*
H6A	0.4337	−0.0093	0.2686	0.026*
H6B	0.3586	0.0781	0.2709	0.026*
H7	0.4623	0.0576	0.1431	0.025*
H71A	0.2393	0.0348	0.1172	0.041*
H71B	0.3180	−0.0506	0.1154	0.041*
H71C	0.2879	0.0289	0.0392	0.041*
H8A	0.3076	0.1935	0.1364	0.022*
H8B	0.4227	0.2155	0.1830	0.022*
H9A	0.3368	0.1736	0.0027	0.025*
H9B	0.4590	0.2039	0.0541	0.025*
H10A	0.3537	0.3352	−0.0236	0.028*
H10B	0.2800	0.3253	0.0362	0.028*
H11A	0.4932	0.3762	0.0957	0.024*
H12A	0.4109	0.5222	−0.0111	0.044*
H12B	0.3376	0.5924	0.0216	0.044*
H12C	0.2905	0.4926	−0.0234	0.044*
H12D	0.2400	0.4544	0.1038	0.042*
H12E	0.2930	0.5476	0.1591	0.042*
H12F	0.3276	0.4443	0.2017	0.042*
H13A	0.5550	0.5162	0.1452	0.026*
H13B	0.4811	0.6013	0.1554	0.026*
H14	0.4752	0.5349	0.2880	0.024*
H14A	0.6592	0.5574	0.3779	0.035*
H14B	0.6165	0.6412	0.3067	0.035*
H14C	0.6896	0.5584	0.2899	0.035*
H22	0.9941	0.3008	0.0886	0.023*
H23	0.8305	0.3430	0.0998	0.022*
H25	0.9575	0.3134	0.3677	0.024*
H26	1.1215	0.2702	0.3565	0.023*
H31	1.0527 (12)	0.1232 (13)	0.0723 (13)	0.061 (4)*
H32	0.949 (3)	0.127 (3)	0.014 (3)	0.076 (6)*	0.50
H33	0.999 (4)	0.042 (2)	0.013 (3)	0.076 (6)*	0.50
H41	0.7984 (16)	0.2144 (15)	−0.0937 (8)	0.061 (4)*
H42	0.778 (3)	0.197 (3)	−0.012 (3)	0.076 (6)*	0.50
H43	0.864 (3)	0.166 (2)	−0.009 (3)	0.076 (6)*	0.50
H51	0.6722 (16)	0.2457 (13)	0.0791 (11)	0.061 (4)*
H52	0.7144 (19)	0.197 (3)	0.027 (3)	0.076 (6)*	0.50
H53	0.641 (4)	0.1498 (14)	0.050 (3)	0.076 (6)*	0.50
H61	0.6315 (15)	−0.0212 (12)	0.1038 (13)	0.061 (4)*
H62	0.539 (2)	0.005 (4)	0.028 (2)	0.076 (6)*	0.50
H63	0.621 (3)	0.0731 (17)	0.059 (3)	0.076 (6)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0172 (6)	0.0168 (6)	0.0192 (7)	0.0012 (5)	0.0072 (5)	−0.0020 (5)
C2	0.0213 (8)	0.0208 (7)	0.0184 (8)	0.0004 (6)	0.0081 (6)	−0.0014 (6)
C3	0.0203 (8)	0.0203 (7)	0.0184 (8)	0.0007 (6)	0.0048 (6)	0.0012 (6)
N4	0.0145 (6)	0.0181 (6)	0.0216 (7)	0.0011 (5)	0.0070 (5)	−0.0012 (5)
C5	0.0213 (8)	0.0175 (7)	0.0197 (8)	0.0024 (6)	0.0063 (7)	0.0018 (6)
C51	0.0349 (9)	0.0203 (8)	0.0265 (9)	−0.0015 (7)	0.0083 (8)	0.0019 (7)
C52	0.0209 (8)	0.0229 (8)	0.0270 (9)	0.0035 (6)	0.0056 (7)	−0.0024 (6)
C6	0.0224 (8)	0.0169 (7)	0.0253 (9)	−0.0009 (6)	0.0075 (7)	0.0007 (6)
C7	0.0195 (7)	0.0167 (7)	0.0256 (9)	0.0019 (6)	0.0076 (7)	−0.0021 (6)
C71	0.0255 (8)	0.0220 (8)	0.0304 (9)	−0.0019 (6)	0.0050 (7)	−0.0022 (7)
N8	0.0159 (6)	0.0184 (6)	0.0203 (7)	0.0002 (5)	0.0060 (5)	−0.0021 (5)
C9	0.0218 (8)	0.0235 (8)	0.0192 (8)	0.0004 (6)	0.0084 (6)	−0.0015 (6)
C10	0.0244 (8)	0.0244 (8)	0.0181 (8)	0.0003 (6)	0.0049 (7)	0.0000 (6)
N11	0.0191 (6)	0.0198 (6)	0.0219 (7)	0.0011 (5)	0.0072 (5)	−0.0002 (5)
C12	0.0223 (8)	0.0186 (7)	0.0224 (9)	0.0033 (6)	0.0059 (7)	0.0012 (6)
C121	0.0350 (9)	0.0235 (8)	0.0248 (9)	0.0044 (7)	0.0058 (7)	0.0029 (7)
C122	0.0209 (8)	0.0330 (9)	0.0283 (9)	0.0028 (7)	0.0056 (7)	−0.0039 (7)
C13	0.0234 (8)	0.0184 (7)	0.0240 (9)	0.0024 (6)	0.0092 (7)	0.0027 (6)
C14	0.0206 (8)	0.0157 (7)	0.0238 (9)	0.0026 (6)	0.0080 (7)	−0.0004 (6)
C141	0.0239 (8)	0.0177 (7)	0.0267 (9)	−0.0008 (6)	0.0077 (7)	−0.0001 (6)
O21	0.0164 (6)	0.0473 (7)	0.0272 (7)	0.0033 (5)	0.0066 (5)	−0.0064 (5)
O22	0.0202 (5)	0.0334 (6)	0.0245 (6)	0.0034 (4)	0.0096 (5)	−0.0058 (5)
O23	0.0175 (5)	0.0331 (6)	0.0286 (7)	0.0026 (4)	0.0072 (5)	−0.0035 (5)
O24	0.0205 (6)	0.0264 (6)	0.0290 (6)	0.0012 (4)	0.0122 (5)	−0.0051 (5)
C21	0.0169 (7)	0.0150 (7)	0.0230 (8)	−0.0016 (6)	0.0081 (6)	−0.0018 (6)
C22	0.0209 (7)	0.0156 (7)	0.0222 (8)	−0.0010 (6)	0.0104 (6)	−0.0010 (6)
C23	0.0178 (7)	0.0157 (7)	0.0212 (8)	0.0004 (6)	0.0053 (6)	−0.0001 (6)
C24	0.0165 (7)	0.0133 (7)	0.0258 (9)	−0.0011 (5)	0.0088 (6)	−0.0018 (6)
C25	0.0215 (8)	0.0187 (7)	0.0212 (8)	−0.0011 (6)	0.0099 (7)	−0.0019 (6)
C26	0.0169 (7)	0.0183 (7)	0.0222 (8)	0.0005 (6)	0.0056 (6)	−0.0011 (6)
C27	0.0183 (8)	0.0202 (7)	0.0256 (9)	0.0009 (6)	0.0097 (7)	−0.0009 (6)
C28	0.0184 (7)	0.0166 (7)	0.0279 (9)	0.0011 (6)	0.0119 (7)	−0.0002 (6)
O3	0.0397 (7)	0.0322 (7)	0.0278 (7)	−0.0073 (6)	0.0148 (6)	−0.0022 (5)
O4	0.0449 (8)	0.0489 (8)	0.0232 (7)	−0.0094 (6)	0.0052 (6)	0.0003 (6)
O5	0.0327 (7)	0.0341 (7)	0.0371 (8)	0.0016 (6)	0.0036 (6)	−0.0092 (6)
O6	0.0336 (7)	0.0378 (8)	0.0340 (8)	0.0074 (6)	0.0091 (6)	0.0079 (6)

Geometric parameters (Å, º)

N1—C2	1.485 (2)	C12—C121	1.533 (2)
N1—C14	1.507 (2)	C12—C13	1.542 (2)
C2—C3	1.511 (2)	C13—C14	1.521 (2)
C3—N4	1.470 (2)	C14—C141	1.525 (2)
N4—C5	1.492 (2)	O21—C27	1.249 (2)
C5—C51	1.531 (2)	O22—C27	1.275 (2)
C5—C52	1.534 (2)	O23—C28	1.254 (2)
C5—C6	1.547 (2)	O24—C28	1.275 (2)
C6—C7	1.524 (2)	C21—C22	1.393 (2)
C7—N8	1.506 (2)	C21—C26	1.398 (2)
C7—C71	1.526 (2)	C21—C27	1.511 (2)
N8—C9	1.487 (2)	C22—C23	1.384 (2)
C9—C10	1.510 (2)	C23—C24	1.396 (2)
C10—N11	1.467 (2)	C24—C25	1.392 (2)
N11—C12	1.499 (2)	C24—C28	1.510 (2)
C12—C122	1.527 (2)	C25—C26	1.391 (2)
C2—N1—C14	113.78 (10)	C122—C12—C13	111.31 (12)
N1—C2—C3	110.67 (11)	C121—C12—C13	107.86 (12)
N4—C3—C2	110.42 (11)	C14—C13—C12	117.62 (12)
C3—N4—C5	115.23 (11)	N1—C14—C13	110.24 (11)
N4—C5—C51	111.79 (12)	N1—C14—C141	109.66 (11)
N4—C5—C52	108.55 (11)	C13—C14—C141	111.27 (12)
C51—C5—C52	110.88 (12)	C22—C21—C26	118.98 (13)
N4—C5—C6	107.61 (11)	C22—C21—C27	120.74 (13)
C51—C5—C6	107.05 (11)	C26—C21—C27	120.28 (13)
C52—C5—C6	110.92 (12)	C23—C22—C21	120.53 (14)
C7—C6—C5	118.10 (12)	C22—C23—C24	120.60 (14)
N8—C7—C6	109.30 (11)	C25—C24—C23	119.07 (13)
N8—C7—C71	109.84 (11)	C25—C24—C28	120.73 (13)
C6—C7—C71	110.94 (12)	C23—C24—C28	120.15 (13)
C9—N8—C7	115.12 (11)	C26—C25—C24	120.37 (14)
N8—C9—C10	110.41 (11)	C25—C26—C21	120.42 (13)
N11—C10—C9	110.67 (12)	O21—C27—O22	124.56 (13)
C10—N11—C12	116.09 (11)	O21—C27—C21	118.75 (13)
N11—C12—C122	108.94 (11)	O22—C27—C21	116.69 (13)
N11—C12—C121	113.15 (12)	O23—C28—O24	124.19 (13)
C122—C12—C121	109.01 (12)	O23—C28—C24	118.75 (13)
N11—C12—C13	106.58 (11)	O24—C28—C24	117.06 (13)
N1—C2—C3—N4	−65.42 (15)	C13—C14—N1—C2	−152.22 (11)
C2—C3—N4—C5	175.44 (11)	C14—N1—C2—C3	−177.67 (11)
C3—N4—C5—C51	53.07 (16)	C2—N1—C14—C141	84.95 (14)
C3—N4—C5—C52	−69.55 (15)	C12—C13—C14—C141	179.54 (12)
C3—N4—C5—C6	170.33 (11)	C26—C21—C22—C23	−1.7 (2)
N4—C5—C6—C7	67.49 (15)	C27—C21—C22—C23	177.71 (12)
C51—C5—C6—C7	−172.19 (12)	C21—C22—C23—C24	0.2 (2)
C52—C5—C6—C7	−51.10 (16)	C22—C23—C24—C25	1.49 (19)
C5—C6—C7—N8	−60.57 (16)	C22—C23—C24—C28	−176.07 (12)
C5—C6—C7—C71	178.15 (12)	C23—C24—C25—C26	−1.7 (2)
C6—C7—N8—C9	161.45 (11)	C28—C24—C25—C26	175.86 (12)
C71—C7—N8—C9	−76.61 (15)	C24—C25—C26—C21	0.2 (2)
C7—N8—C9—C10	176.44 (11)	C22—C21—C26—C25	1.5 (2)
N8—C9—C10—N11	63.91 (15)	C27—C21—C26—C25	−177.91 (12)
C9—C10—N11—C12	−167.97 (12)	C22—C21—C27—O21	159.70 (13)
C10—N11—C12—C122	73.79 (16)	C26—C21—C27—O21	−20.9 (2)
C10—N11—C12—C121	−47.62 (17)	C22—C21—C27—O22	−20.7 (2)
C10—N11—C12—C13	−166.01 (12)	C26—C21—C27—O22	158.69 (13)
N11—C12—C13—C14	−73.27 (15)	C25—C24—C28—O23	−158.41 (13)
C122—C12—C13—C14	45.40 (17)	C23—C24—C28—O23	19.11 (19)
C121—C12—C13—C14	164.94 (12)	C25—C24—C28—O24	21.24 (19)
C12—C13—C14—N1	57.65 (16)	C23—C24—C28—O24	−161.24 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N11	0.92	2.06	2.852 (2)	144
N1—H1A···O24	0.92	1.80	2.714 (2)	170
N4—H4A···O21^i	0.92	2.11	2.997 (2)	160
N8—H8A···O22^i	0.92	1.80	2.720 (2)	178
N8—H8B···N4	0.92	2.04	2.814 (2)	141
N11—H11A···O23	0.92	2.48	3.260 (2)	142
O3—H31···O22	0.86	2.07	2.930 (2)	174
O3—H32···O4	0.84	1.97	2.797 (2)	167
O3—H33···O3^ii	0.84	2.07	2.908 (2)	169
O4—H41···O21^iii	0.85	1.95	2.790 (2)	169
O4—H42···O5	0.84	2.03	2.855 (2)	164
O4—H43···O3	0.84	1.99	2.797 (2)	160
O5—H51···O23	0.85	1.98	2.821 (2)	172
O5—H52···O4	0.85	2.05	2.855 (2)	159
O5—H53···O6	0.85	1.96	2.805 (2)	175
O6—H61···O24^iv	0.85	2.05	2.900 (2)	175
O6—H62···O6^v	0.84	1.95	2.781 (2)	175
O6—H63···O5	0.84	1.97	2.805 (2)	168

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

(2) meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra- azacyclotetradecane–terephthalic acid–water (1/1/6)

Crystal data

C16H38N4·C8H4O4·6H2O	F(000) = 612
Mr = 558.71	Dx = 1.209 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1772 (3) Å	Cell parameters from 3512 reflections
b = 12.3974 (4) Å	θ = 4.1–27.5°
c = 16.8804 (5) Å	µ = 0.09 mm^−1
β = 116.231 (2)°	T = 100 K
V = 1535.04 (9) Å^3	Block, colourless
Z = 2	0.40 × 0.32 × 0.24 mm

Data collection

Kappa-CCD diffractometer	3512 independent reflections
Radiation source: fine-focus sealed X-ray tube	2756 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 4.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→10
Tmin = 0.964, Tmax = 0.978	k = −16→0
16757 measured reflections	l = −21→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 0.1606P] where P = (Fo^2 + 2Fc^2)/3
3512 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.24 e Å^−3
6 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.43906 (13)	0.34031 (7)	0.45781 (6)	0.0186 (2)
C2	0.34495 (16)	0.37368 (9)	0.36312 (7)	0.0229 (3)
C3	0.46504 (17)	0.44708 (9)	0.33952 (8)	0.0218 (3)
N4	0.48453 (13)	0.55262 (7)	0.38237 (6)	0.0181 (2)
C5	0.62579 (15)	0.62579 (9)	0.37848 (7)	0.0202 (2)
C51	0.59812 (18)	0.64618 (11)	0.28345 (8)	0.0277 (3)
C52	0.81481 (16)	0.57641 (10)	0.43225 (8)	0.0258 (3)
C6	0.60556 (16)	0.73514 (9)	0.41699 (8)	0.0217 (2)
C7	0.66696 (16)	0.74052 (9)	0.51631 (8)	0.0219 (3)
C71	0.64470 (19)	0.85370 (10)	0.54544 (9)	0.0306 (3)
O11	0.86632 (13)	0.20922 (7)	0.61269 (6)	0.0290 (2)
O12	0.75750 (11)	0.25689 (6)	0.47077 (5)	0.0236 (2)
C11	0.92580 (15)	0.09386 (9)	0.51667 (7)	0.0176 (2)
C12	1.06615 (15)	0.03939 (9)	0.58550 (7)	0.0191 (2)
C13	1.14005 (15)	−0.05361 (9)	0.56921 (7)	0.0186 (2)
C14	0.84476 (16)	0.19463 (9)	0.53520 (8)	0.0203 (2)
O3	0.90241 (12)	0.36486 (7)	0.73534 (6)	0.0254 (2)
O4	1.13898 (14)	0.53980 (7)	0.77455 (6)	0.0309 (2)
O5	0.87974 (13)	0.19899 (7)	0.84420 (6)	0.0282 (2)
H1A	0.5480	0.3116	0.4686	0.022*
H1B	0.4596	0.3993	0.4920	0.022*
H2A	0.2327	0.4110	0.3522	0.027*
H2B	0.3138	0.3101	0.3258	0.027*
H3A	0.5842	0.4144	0.3585	0.026*
H3B	0.4116	0.4565	0.2760	0.026*
H4A	0.3762	0.5866	0.3572	0.022*
H51A	0.5972	0.5785	0.2556	0.042*
H51B	0.6958	0.6902	0.2847	0.042*
H51C	0.4841	0.6825	0.2508	0.042*
H52A	0.8253	0.5528	0.4885	0.039*
H52B	0.9067	0.6296	0.4411	0.039*
H52C	0.8309	0.5160	0.4008	0.039*
H6A	0.6740	0.7886	0.4020	0.026*
H6B	0.4782	0.7560	0.3875	0.026*
H7	0.7964	0.7211	0.5464	0.026*
H71A	0.5205	0.8766	0.5126	0.046*
H71B	0.7238	0.9025	0.5347	0.046*
H71C	0.6758	0.8532	0.6073	0.046*
H12	1.1105	0.0657	0.6428	0.023*
H13	1.2337	−0.0893	0.6155	0.022*
H3C	0.901 (2)	0.3263 (14)	0.6913 (9)	0.054 (2)*
H3D	0.984 (2)	0.4159 (12)	0.7468 (12)	0.054 (2)*
H4C	1.140 (3)	0.5793 (13)	0.7317 (9)	0.054 (2)*
H4D	1.136 (2)	0.5849 (13)	0.8140 (10)	0.054 (2)*
H5C	0.837 (2)	0.2163 (15)	0.8821 (10)	0.054 (2)*
H5D	0.889 (3)	0.2556 (11)	0.8152 (11)	0.054 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0192 (5)	0.0160 (4)	0.0206 (5)	0.0002 (4)	0.0087 (4)	−0.0018 (4)
C2	0.0244 (6)	0.0204 (6)	0.0189 (6)	−0.0010 (5)	0.0050 (5)	−0.0027 (4)
C3	0.0276 (6)	0.0195 (6)	0.0181 (6)	0.0013 (5)	0.0099 (5)	−0.0009 (4)
N4	0.0174 (5)	0.0169 (5)	0.0197 (5)	0.0011 (4)	0.0078 (4)	−0.0009 (4)
C5	0.0190 (5)	0.0226 (6)	0.0200 (6)	−0.0004 (4)	0.0096 (5)	0.0016 (4)
C51	0.0301 (6)	0.0325 (7)	0.0224 (6)	−0.0001 (5)	0.0132 (5)	0.0039 (5)
C52	0.0201 (6)	0.0308 (6)	0.0255 (6)	0.0025 (5)	0.0091 (5)	−0.0003 (5)
C6	0.0221 (6)	0.0191 (5)	0.0250 (6)	−0.0013 (4)	0.0115 (5)	0.0019 (4)
C7	0.0207 (6)	0.0203 (6)	0.0262 (6)	−0.0037 (5)	0.0117 (5)	−0.0019 (4)
C71	0.0377 (7)	0.0203 (6)	0.0394 (8)	−0.0091 (5)	0.0222 (6)	−0.0067 (5)
O11	0.0462 (5)	0.0216 (4)	0.0258 (5)	0.0051 (4)	0.0219 (4)	−0.0003 (3)
O12	0.0268 (4)	0.0204 (4)	0.0284 (5)	0.0058 (3)	0.0166 (4)	0.0056 (3)
C11	0.0197 (5)	0.0155 (5)	0.0207 (6)	−0.0017 (4)	0.0117 (5)	0.0009 (4)
C12	0.0213 (5)	0.0194 (5)	0.0170 (5)	−0.0020 (4)	0.0088 (5)	−0.0005 (4)
C13	0.0182 (5)	0.0181 (5)	0.0183 (5)	0.0010 (4)	0.0069 (4)	0.0033 (4)
C14	0.0221 (5)	0.0174 (5)	0.0253 (6)	−0.0002 (5)	0.0140 (5)	0.0013 (4)
O3	0.0298 (5)	0.0239 (4)	0.0246 (5)	−0.0012 (4)	0.0140 (4)	−0.0032 (3)
O4	0.0484 (6)	0.0222 (5)	0.0290 (5)	−0.0024 (4)	0.0234 (5)	−0.0007 (4)
O5	0.0405 (5)	0.0237 (4)	0.0274 (5)	0.0004 (4)	0.0214 (4)	−0.0014 (4)

Geometric parameters (Å, º)

N1—C2	1.494 (2)	C7—N1^i	1.5104 (14)
N1—C7^i	1.510 (2)	C7—C71	1.5241 (16)
C2—C3	1.5155 (16)	O11—C14	1.254 (2)
C3—N4	1.469 (2)	O12—C14	1.266 (2)
N4—C5	1.493 (2)	C11—C12	1.3945 (16)
C5—C52	1.5321 (16)	C11—C13^ii	1.3965 (16)
C5—C51	1.5385 (16)	C11—C14	1.5103 (15)
C5—C6	1.5437 (16)	C12—C13	1.3846 (16)
C6—C7	1.5243 (16)	C13—C11^ii	1.3965 (16)
C2—N1—C7^i	113.8 (1)	N1^i—C7—C71	110.60 (9)
N1—C2—C3	111.12 (9)	N1^i—C7—C6	109.70 (9)
N4—C3—C2	110.32 (9)	C71—C7—C6	111.52 (10)
C3—N4—C5	115.9 (1)	C12—C11—C13^ii	119.32 (10)
N4—C5—C52	109.19 (9)	C12—C11—C14	120.19 (10)
N4—C5—C51	112.69 (9)	C13^ii—C11—C14	120.49 (10)
C52—C5—C51	109.17 (10)	C13—C12—C11	120.56 (10)
N4—C5—C6	106.62 (9)	C12—C13—C11^ii	120.12 (10)
C52—C5—C6	111.66 (10)	O11—C14—O12	125.1 (2)
C51—C5—C6	107.51 (9)	O11—C14—C11	117.60 (10)
C7—C6—C5	117.20 (10)	O12—C14—C11	117.31 (10)
C7^i—N1—C2—C3	−175.1 (1)	C5—C6—C7—N1^i	−58.9 (2)
N1—C2—C3—N4	−70.1 (2)	C5—C6—C7—C71	178.25 (10)
C2—C3—N4—C5	169.2 (1)	C13^ii—C11—C12—C13	0.08 (18)
C3—N4—C5—C52	−65.94 (12)	C14—C11—C12—C13	179.39 (10)
C3—N4—C5—C51	55.55 (13)	C11—C12—C13—C11^ii	−0.07 (18)
C3—N4—C5—C6	173.3 (1)	C12—C11—C14—O11	−20.59 (16)
N4—C5—C6—C7	71.7 (2)	C13^ii—C11—C14—O11	158.72 (11)
C52—C5—C6—C7	−47.49 (13)	C12—C11—C14—O12	160.6 (1)
C51—C5—C6—C7	−167.21 (10)	C13^ii—C11—C14—O12	−20.1 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O12	0.90	1.83	2.719 (2)	170
N1—H1B···N4^i	0.90	2.05	2.818 (2)	142
O3—H3C···O11	0.88 (2)	1.90 (2)	2.749 (2)	161
O3—H3D···O4	0.88 (2)	1.91 (2)	2.784 (2)	172
N4—H4A···O3^i	0.90	2.20	3.074 (2)	163
O4—H4C···O5^iii	0.88 (2)	1.92 (2)	2.769 (2)	163
O4—H4D···O11^iii	0.88 (2)	1.98 (2)	2.848 (2)	169
O5—H5C···O12^iv	0.88 (2)	1.91 (2)	2.784 (2)	175
O5—H5D···O3	0.88 (2)	1.95 (2)	2.818 (2)	171
C7—H7···O5^iii	0.98	2.49	3.440 (2)	165

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