N-[2-(Azepan-1-yl)-9-iso­propyl-9H-purin-6-yl]-4-methoxy­benzyl­amine

The title compound, C₂₂H₃₀N₆O, is a potent inhibitor of estrogen sulfotransferase which catalyses the transfer of a sulfuryl group from 3′-phospho­adenosine 5′-phospho­sulfate to estrogen and estrogen-like compounds. The pyrimidine plane forms dihedral angles of 81.53 (4) and 2.99 (4)° with the benzene and imidazole rings, respectively. The crystal structure is stabilized by N—H...N hydrogen bonds connecting two adjacent mol­ecules, thus forming centrosymmetric dimers, the N...N distance being 3.0403 (16) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.097
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Barnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

N-[2-(Azepan-1-yl)-9-isopropyl-9H-purin-6-yl]-4-methoxybenzylamine

Crystal data

C22H30N6O	F(000) = 848
Mr = 394.52	Dx = 1.255 Mg m^−3
Monoclinic, P21/c	Melting point: 441.25 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.8709 (9) Å	Cell parameters from 4123 reflections
b = 16.2732 (10) Å	θ = 2.2–30.4°
c = 10.8433 (7) Å	µ = 0.08 mm^−1
β = 94.656 (6)°	T = 100 K
V = 2087.8 (2) Å^3	Prism, white
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Xcalibur2 (Sapphire2 CCD) diffractometer	3104 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Enhance (Oxford Diffraction) monochromator	θmax = 25.0°, θmin = 3.7°
Detector resolution: 16.3 pixels mm^-1	h = −14→12
ω scans	k = −19→14
9776 measured reflections	l = −12→12
3625 independent reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.4543P] where P = (Fo^2 + 2Fc^2)/3
3625 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.84283 (9)	0.01005 (6)	0.62047 (9)	0.0162 (2)
O1	0.55693 (9)	−0.13747 (6)	1.17467 (9)	0.0295 (3)
N2	1.02010 (9)	0.06800 (7)	0.62260 (10)	0.0182 (3)
C2	0.90990 (11)	0.06890 (8)	0.57636 (11)	0.0163 (3)
N3	0.88022 (9)	0.12703 (6)	0.49126 (9)	0.0172 (3)
C4	0.77039 (11)	0.12114 (7)	0.45322 (11)	0.0157 (3)
C5	0.69129 (11)	0.06737 (8)	0.49357 (11)	0.0155 (3)
N6	0.66760 (9)	−0.05334 (7)	0.61771 (10)	0.0194 (3)
H6A	0.5945	−0.0515	0.5962	0.023*
C6	0.73375 (11)	0.00726 (8)	0.57879 (11)	0.0156 (3)
N7	0.58507 (9)	0.08189 (7)	0.43246 (10)	0.0197 (3)
C8	0.60365 (11)	0.14239 (8)	0.35642 (12)	0.0210 (3)
H8A	0.5461	0.1657	0.3012	0.025*
N9	0.71350 (9)	0.16888 (7)	0.36392 (10)	0.0193 (3)
C9	0.71179 (12)	−0.12157 (8)	0.69359 (12)	0.0202 (3)
H9A	0.7953	−0.1183	0.7019	0.024*
H9B	0.6906	−0.1737	0.6508	0.024*
C10	0.66934 (11)	−0.12321 (8)	0.82133 (12)	0.0185 (3)
C11	0.67705 (12)	−0.05454 (8)	0.89739 (13)	0.0220 (3)
H11A	0.7089	−0.0054	0.8681	0.026*
C12	0.63927 (12)	−0.05590 (9)	1.01559 (13)	0.0232 (3)
H12A	0.6448	−0.0081	1.0661	0.028*
C13	0.59353 (12)	−0.12776 (9)	1.05879 (12)	0.0219 (3)
C14	0.58428 (12)	−0.19680 (8)	0.98389 (12)	0.0220 (3)
H14A	0.5516	−0.2457	1.0130	0.026*
C15	0.62268 (11)	−0.19459 (8)	0.86657 (12)	0.0204 (3)
H15A	0.6171	−0.2424	0.8163	0.024*
C16	0.56443 (13)	−0.06819 (10)	1.25553 (13)	0.0298 (3)
H16A	0.5360	−0.0832	1.3348	0.045*
H16B	0.5190	−0.0230	1.2181	0.045*
H16C	0.6435	−0.0507	1.2692	0.045*
C17	0.76565 (12)	0.22674 (8)	0.28102 (12)	0.0223 (3)
H17A	0.8459	0.2352	0.3141	0.027*
C18	0.76668 (14)	0.19039 (10)	0.15243 (14)	0.0333 (4)
H18A	0.8057	0.1373	0.1573	0.050*
H18B	0.8062	0.2278	0.0998	0.050*
H18C	0.6888	0.1826	0.1170	0.050*
C19	0.70688 (14)	0.30930 (9)	0.28075 (15)	0.0339 (4)
H19A	0.7086	0.3303	0.3656	0.051*
H19B	0.6282	0.3030	0.2470	0.051*
H19C	0.7458	0.3480	0.2295	0.051*
C20	1.05978 (12)	0.01094 (8)	0.72012 (12)	0.0208 (3)
H20A	1.1429	0.0059	0.7203	0.025*
H20B	1.0269	−0.0438	0.7003	0.025*
C21	1.03091 (13)	0.03504 (9)	0.85026 (13)	0.0270 (3)
H21A	0.9587	0.0084	0.8668	0.032*
H21B	1.0902	0.0129	0.9107	0.032*
C22	1.02024 (14)	0.12693 (10)	0.87252 (14)	0.0331 (4)
H22A	1.0204	0.1361	0.9628	0.040*
H22B	0.9458	0.1451	0.8345	0.040*
C23	1.11126 (14)	0.18207 (10)	0.82337 (14)	0.0334 (4)
H23A	1.1176	0.2328	0.8739	0.040*
H23B	1.1848	0.1532	0.8345	0.040*
C24	1.08934 (13)	0.20634 (9)	0.68701 (14)	0.0273 (3)
H24A	1.0135	0.2317	0.6746	0.033*
H24B	1.1454	0.2484	0.6675	0.033*
C25	1.09543 (12)	0.13540 (8)	0.59677 (13)	0.0220 (3)
H25A	1.0755	0.1557	0.5117	0.026*
H25B	1.1740	0.1146	0.6006	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0177 (6)	0.0159 (5)	0.0149 (5)	−0.0002 (4)	0.0019 (4)	−0.0007 (4)
O1	0.0364 (6)	0.0319 (6)	0.0209 (5)	−0.0026 (5)	0.0067 (4)	0.0009 (4)
N2	0.0160 (6)	0.0205 (6)	0.0178 (6)	−0.0018 (5)	−0.0012 (4)	0.0014 (4)
C2	0.0186 (7)	0.0167 (6)	0.0138 (6)	0.0008 (5)	0.0026 (5)	−0.0032 (5)
N3	0.0176 (6)	0.0179 (6)	0.0161 (5)	−0.0017 (5)	0.0005 (4)	−0.0002 (4)
C4	0.0193 (7)	0.0144 (6)	0.0134 (6)	0.0001 (5)	0.0012 (5)	−0.0015 (5)
C5	0.0156 (7)	0.0162 (6)	0.0146 (6)	0.0001 (5)	0.0006 (5)	−0.0018 (5)
N6	0.0169 (6)	0.0191 (6)	0.0222 (6)	−0.0011 (5)	0.0016 (5)	0.0056 (5)
C6	0.0187 (7)	0.0150 (6)	0.0133 (6)	0.0002 (5)	0.0034 (5)	−0.0027 (5)
N7	0.0195 (6)	0.0206 (6)	0.0189 (6)	−0.0012 (5)	0.0010 (4)	0.0028 (5)
C8	0.0174 (7)	0.0230 (7)	0.0222 (7)	−0.0008 (6)	−0.0015 (5)	0.0054 (6)
N9	0.0185 (6)	0.0197 (6)	0.0193 (6)	−0.0024 (5)	−0.0004 (4)	0.0058 (5)
C9	0.0215 (7)	0.0162 (7)	0.0231 (7)	0.0007 (6)	0.0029 (6)	0.0043 (5)
C10	0.0148 (7)	0.0183 (7)	0.0218 (7)	0.0013 (5)	−0.0018 (5)	0.0042 (5)
C11	0.0228 (7)	0.0167 (7)	0.0261 (7)	−0.0014 (6)	−0.0009 (6)	0.0037 (5)
C12	0.0255 (8)	0.0202 (7)	0.0233 (7)	0.0019 (6)	−0.0019 (6)	−0.0015 (6)
C13	0.0181 (7)	0.0275 (7)	0.0198 (7)	0.0026 (6)	−0.0004 (5)	0.0042 (6)
C14	0.0229 (8)	0.0201 (7)	0.0228 (7)	−0.0032 (6)	−0.0003 (6)	0.0071 (6)
C15	0.0215 (7)	0.0170 (7)	0.0221 (7)	0.0002 (6)	−0.0017 (5)	0.0026 (5)
C16	0.0292 (8)	0.0372 (9)	0.0229 (7)	0.0033 (7)	0.0019 (6)	−0.0040 (6)
C17	0.0188 (7)	0.0231 (7)	0.0248 (7)	−0.0049 (6)	0.0012 (6)	0.0094 (6)
C18	0.0391 (9)	0.0338 (9)	0.0278 (8)	−0.0048 (7)	0.0081 (7)	0.0073 (6)
C19	0.0372 (9)	0.0255 (8)	0.0400 (9)	0.0007 (7)	0.0090 (7)	0.0118 (7)
C20	0.0181 (7)	0.0212 (7)	0.0226 (7)	0.0034 (6)	−0.0017 (5)	0.0011 (5)
C21	0.0284 (8)	0.0320 (8)	0.0200 (7)	0.0037 (7)	−0.0008 (6)	0.0021 (6)
C22	0.0370 (9)	0.0365 (9)	0.0260 (8)	0.0069 (7)	0.0041 (7)	−0.0054 (7)
C23	0.0323 (9)	0.0315 (8)	0.0353 (9)	−0.0021 (7)	−0.0028 (7)	−0.0120 (7)
C24	0.0215 (8)	0.0220 (8)	0.0380 (8)	−0.0025 (6)	0.0003 (6)	−0.0008 (6)
C25	0.0162 (7)	0.0249 (7)	0.0247 (7)	−0.0032 (6)	0.0005 (5)	0.0021 (6)

Geometric parameters (Å, º)

N1—C6	1.3372 (17)	C14—H14A	0.95
N1—C2	1.3571 (16)	C15—H15A	0.95
O1—C13	1.3716 (16)	C16—H16A	0.98
O1—C16	1.4266 (18)	C16—H16B	0.98
N2—C2	1.3625 (17)	C16—H16C	0.98
N2—C25	1.4565 (17)	C17—C19	1.514 (2)
N2—C20	1.4566 (17)	C17—C18	1.516 (2)
C2—N3	1.3482 (16)	C17—H17A	1.00
N3—C4	1.3387 (17)	C18—H18A	0.98
C4—N9	1.3751 (16)	C18—H18B	0.98
C4—C5	1.3804 (18)	C18—H18C	0.98
C5—N7	1.3962 (17)	C19—H19A	0.98
C5—C6	1.4104 (18)	C19—H19B	0.98
N6—C6	1.3494 (16)	C19—H19C	0.98
N6—C9	1.4544 (16)	C20—C21	1.5301 (19)
N6—H6A	0.88	C20—H20A	0.99
N7—C8	1.3143 (17)	C20—H20B	0.99
C8—N9	1.3696 (17)	C21—C22	1.522 (2)
C8—H8A	0.95	C21—H21A	0.99
N9—C17	1.4724 (16)	C21—H21B	0.99
C9—C10	1.5121 (18)	C22—C23	1.533 (2)
C9—H9A	0.99	C22—H22A	0.99
C9—H9B	0.99	C22—H22B	0.99
C10—C11	1.3874 (19)	C23—C24	1.532 (2)
C10—C15	1.3931 (18)	C23—H23A	0.99
C11—C12	1.3920 (19)	C23—H23B	0.99
C11—H11A	0.95	C24—C25	1.519 (2)
C12—C13	1.387 (2)	C24—H24A	0.99
C12—H12A	0.95	C24—H24B	0.99
C13—C14	1.385 (2)	C25—H25A	0.99
C14—C15	1.3863 (19)	C25—H25B	0.99
C6—N1—C2	118.99 (11)	H16A—C16—H16C	109.5
C13—O1—C16	117.60 (11)	H16B—C16—H16C	109.5
C2—N2—C25	120.48 (11)	N9—C17—C19	110.62 (11)
C2—N2—C20	121.21 (11)	N9—C17—C18	110.33 (11)
C25—N2—C20	116.89 (10)	C19—C17—C18	112.50 (12)
N3—C2—N1	127.46 (12)	N9—C17—H17A	107.7
N3—C2—N2	116.69 (11)	C19—C17—H17A	107.7
N1—C2—N2	115.85 (11)	C18—C17—H17A	107.7
C4—N3—C2	110.77 (10)	C17—C18—H18A	109.5
N3—C4—N9	125.93 (11)	C17—C18—H18B	109.5
N3—C4—C5	128.19 (12)	H18A—C18—H18B	109.5
N9—C4—C5	105.88 (11)	C17—C18—H18C	109.5
C4—C5—N7	110.71 (11)	H18A—C18—H18C	109.5
C4—C5—C6	115.55 (12)	H18B—C18—H18C	109.5
N7—C5—C6	133.57 (12)	C17—C19—H19A	109.5
C6—N6—C9	122.86 (11)	C17—C19—H19B	109.5
C6—N6—H6A	118.6	H19A—C19—H19B	109.5
C9—N6—H6A	118.6	C17—C19—H19C	109.5
N1—C6—N6	119.43 (11)	H19A—C19—H19C	109.5
N1—C6—C5	118.86 (11)	H19B—C19—H19C	109.5
N6—C6—C5	121.71 (12)	N2—C20—C21	115.01 (11)
C8—N7—C5	103.50 (11)	N2—C20—H20A	108.5
N7—C8—N9	113.95 (12)	C21—C20—H20A	108.5
N7—C8—H8A	123.0	N2—C20—H20B	108.5
N9—C8—H8A	123.0	C21—C20—H20B	108.5
C8—N9—C4	105.95 (10)	H20A—C20—H20B	107.5
C8—N9—C17	127.62 (11)	C22—C21—C20	115.21 (12)
C4—N9—C17	125.76 (11)	C22—C21—H21A	108.5
N6—C9—C10	113.58 (11)	C20—C21—H21A	108.5
N6—C9—H9A	108.9	C22—C21—H21B	108.5
C10—C9—H9A	108.9	C20—C21—H21B	108.5
N6—C9—H9B	108.9	H21A—C21—H21B	107.5
C10—C9—H9B	108.9	C21—C22—C23	116.75 (13)
H9A—C9—H9B	107.7	C21—C22—H22A	108.1
C11—C10—C15	118.11 (12)	C23—C22—H22A	108.1
C11—C10—C9	121.30 (12)	C21—C22—H22B	108.1
C15—C10—C9	120.58 (12)	C23—C22—H22B	108.1
C10—C11—C12	121.60 (13)	H22A—C22—H22B	107.3
C10—C11—H11A	119.2	C24—C23—C22	114.65 (13)
C12—C11—H11A	119.2	C24—C23—H23A	108.6
C13—C12—C11	119.25 (13)	C22—C23—H23A	108.6
C13—C12—H12A	120.4	C24—C23—H23B	108.6
C11—C12—H12A	120.4	C22—C23—H23B	108.6
O1—C13—C14	115.32 (12)	H23A—C23—H23B	107.6
O1—C13—C12	124.64 (13)	C25—C24—C23	114.36 (12)
C14—C13—C12	120.03 (12)	C25—C24—H24A	108.7
C13—C14—C15	120.03 (12)	C23—C24—H24A	108.7
C13—C14—H14A	120.0	C25—C24—H24B	108.7
C15—C14—H14A	120.0	C23—C24—H24B	108.7
C14—C15—C10	120.97 (12)	H24A—C24—H24B	107.6
C14—C15—H15A	119.5	N2—C25—C24	112.73 (11)
C10—C15—H15A	119.5	N2—C25—H25A	109.0
O1—C16—H16A	109.5	C24—C25—H25A	109.0
O1—C16—H16B	109.5	N2—C25—H25B	109.0
H16A—C16—H16B	109.5	C24—C25—H25B	109.0
O1—C16—H16C	109.5	H25A—C25—H25B	107.8
C6—N1—C2—N3	−0.82 (18)	C5—C4—N9—C17	−170.35 (12)
C6—N1—C2—N2	−179.84 (10)	C6—N6—C9—C10	115.22 (13)
C25—N2—C2—N3	10.39 (17)	N6—C9—C10—C11	−51.92 (17)
C20—N2—C2—N3	176.38 (11)	N6—C9—C10—C15	129.03 (13)
C25—N2—C2—N1	−170.47 (11)	C15—C10—C11—C12	−0.2 (2)
C20—N2—C2—N1	−4.49 (17)	C9—C10—C11—C12	−179.28 (12)
N1—C2—N3—C4	0.81 (17)	C10—C11—C12—C13	0.5 (2)
N2—C2—N3—C4	179.82 (10)	C16—O1—C13—C14	−179.91 (12)
C2—N3—C4—N9	−177.50 (11)	C16—O1—C13—C12	1.3 (2)
C2—N3—C4—C5	2.44 (18)	C11—C12—C13—O1	177.78 (13)
N3—C4—C5—N7	178.86 (12)	C11—C12—C13—C14	−0.9 (2)
N9—C4—C5—N7	−1.19 (14)	O1—C13—C14—C15	−177.63 (12)
N3—C4—C5—C6	−5.22 (19)	C12—C13—C14—C15	1.2 (2)
N9—C4—C5—C6	174.73 (11)	C13—C14—C15—C10	−1.0 (2)
C2—N1—C6—N6	176.92 (11)	C11—C10—C15—C14	0.5 (2)
C2—N1—C6—C5	−2.17 (16)	C9—C10—C15—C14	179.55 (12)
C9—N6—C6—N1	−6.66 (18)	C8—N9—C17—C19	59.87 (18)
C9—N6—C6—C5	172.40 (11)	C4—N9—C17—C19	−130.86 (14)
C4—C5—C6—N1	4.75 (17)	C8—N9—C17—C18	−65.27 (17)
N7—C5—C6—N1	179.49 (12)	C4—N9—C17—C18	104.01 (15)
C4—C5—C6—N6	−174.32 (11)	C2—N2—C20—C21	−77.88 (15)
N7—C5—C6—N6	0.4 (2)	C25—N2—C20—C21	88.59 (15)
C4—C5—N7—C8	1.05 (14)	N2—C20—C21—C22	−28.93 (18)
C6—C5—N7—C8	−173.87 (14)	C20—C21—C22—C23	−44.21 (19)
C5—N7—C8—N9	−0.51 (15)	C21—C22—C23—C24	84.52 (17)
N7—C8—N9—C4	−0.20 (15)	C22—C23—C24—C25	−67.17 (17)
N7—C8—N9—C17	170.76 (12)	C2—N2—C25—C24	85.56 (14)
N3—C4—N9—C8	−179.21 (12)	C20—N2—C25—C24	−81.02 (14)
C5—C4—N9—C8	0.83 (13)	C23—C24—C25—N2	55.14 (16)
N3—C4—N9—C17	9.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N7^i	0.88	2.19	3.0403 (16)	164

Symmetry code: (i) −x+1, −y, −z+1.