2-[5-(2,3-Di­meth­oxy­naphthalen-1-yl)-4,5-di­hydro-1H-pyrazol-3-yl]-3-meth­oxy­phenol

In the title compound, C₂₂H₂₂N₂O₄, the central pyrazoline ring exhibits a nearly planar structure (r.m.s. deviation = 0.025 Å) despite having two sp³ carbon atoms. The pyrazoline ring subtends dihedral angles of 4.61 (1) and 87.31 (1)° with the pendant benzene ring and naphthalene ring system, respectively. The dihedral angle between the planes of the benzene ring and the naphthalene ring system is 89.76 (2)°. An intra­molecular O—H...N hydrogen bond forms an S(6) ring motif. In the crystal, inversion dimers formed by pairwise weak N—H...N hydrogen bonds generate R²₂(4) loops and the dimers are linked by pairwise C—H...O hydrogen bonds [which generate R²₂(8) loops] into [100] chains.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.184
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19      --C20      .        5.5 s.u.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00443 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N2       --H2A      .     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.524 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..N2       .       2.68 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2012); cell refinement: SMART (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

2-[5-(2,3-Dimethoxynaphthalen-1-yl)-4,5-dihydro-1H-pyrazol-3-yl]-3-methoxyphenol

Crystal data

C22H22N2O4	F(000) = 800
Mr = 378.42	Dx = 1.337 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2685 reflections
a = 9.6536 (9) Å	θ = 2.3–25.9°
b = 9.0435 (9) Å	µ = 0.09 mm^−1
c = 21.599 (2) Å	T = 200 K
β = 94.473 (2)°	Block, colorless
V = 1879.9 (3) Å^3	0.26 × 0.21 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	1933 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
phi and ω scans	h = −11→11
11235 measured reflections	k = −11→10
3687 independent reflections	l = −21→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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.093P)^2] where P = (Fo^2 + 2Fc^2)/3
3687 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.28 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.

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 > 2sigma(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
O1	0.8751 (3)	1.3353 (3)	0.02640 (12)	0.0694 (7)
H1	0.8035	1.2849	0.0310	0.104*
C1	0.9888 (3)	1.2574 (4)	0.04692 (14)	0.0506 (8)
C2	0.9795 (3)	1.1101 (3)	0.06640 (12)	0.0398 (7)
C3	1.1048 (3)	1.0390 (4)	0.08642 (13)	0.0501 (8)
C4	1.2308 (3)	1.1127 (5)	0.08911 (15)	0.0671 (11)
H4	1.3138	1.0633	0.1038	0.080*
C5	1.2350 (4)	1.2572 (6)	0.07051 (17)	0.0747 (13)
H5	1.3216	1.3076	0.0726	0.090*
C6	1.1167 (4)	1.3309 (4)	0.04891 (17)	0.0701 (11)
H6	1.1215	1.4306	0.0354	0.084*
O2	1.0935 (2)	0.8949 (3)	0.10310 (11)	0.0653 (7)
C7	1.2171 (3)	0.8106 (5)	0.11670 (17)	0.0791 (13)
H7A	1.2748	0.8154	0.0814	0.119*
H7B	1.1924	0.7074	0.1243	0.119*
H7C	1.2689	0.8511	0.1537	0.119*
C8	0.8433 (3)	1.0377 (3)	0.06725 (11)	0.0335 (6)
C9	0.8141 (3)	0.8850 (3)	0.09064 (13)	0.0373 (7)
H9A	0.8446	0.8750	0.1353	0.045*
H9B	0.8610	0.8086	0.0669	0.045*
C10	0.6550 (3)	0.8726 (3)	0.07970 (12)	0.0345 (7)
H10	0.6331	0.8009	0.0451	0.041*
N1	0.7304 (2)	1.1080 (3)	0.04944 (10)	0.0396 (6)
N2	0.6126 (2)	1.0220 (3)	0.05752 (11)	0.0441 (6)
H2A	0.5262	1.0522	0.0505	0.053*
C11	0.5866 (2)	0.8181 (3)	0.13617 (11)	0.0320 (6)
C12	0.5293 (3)	0.6788 (3)	0.13404 (12)	0.0364 (7)
C13	0.4716 (3)	0.6134 (3)	0.18643 (13)	0.0405 (7)
C14	0.4723 (3)	0.6915 (3)	0.23996 (13)	0.0442 (8)
H14	0.4354	0.6478	0.2751	0.053*
C15	0.5264 (3)	0.8358 (3)	0.24460 (12)	0.0401 (7)
C16	0.5249 (3)	0.9182 (4)	0.30062 (14)	0.0544 (9)
H16	0.4853	0.8758	0.3354	0.065*
C17	0.5787 (3)	1.0556 (4)	0.30515 (15)	0.0596 (9)
H17	0.5734	1.1103	0.3424	0.072*
C18	0.6427 (3)	1.1186 (4)	0.25521 (15)	0.0561 (9)
H18	0.6841	1.2137	0.2595	0.067*
C19	0.6453 (3)	1.0430 (3)	0.20025 (14)	0.0473 (8)
H19	0.6875	1.0876	0.1666	0.057*
C20	0.5872 (3)	0.9015 (3)	0.19266 (12)	0.0361 (7)
O3	0.51575 (19)	0.5996 (2)	0.07876 (9)	0.0458 (6)
C21	0.6160 (4)	0.4843 (4)	0.07440 (16)	0.0641 (10)
H21A	0.7097	0.5268	0.0779	0.096*
H21B	0.5998	0.4341	0.0343	0.096*
H21C	0.6073	0.4129	0.1080	0.096*
O4	0.4194 (2)	0.4742 (2)	0.17676 (10)	0.0552 (6)
C22	0.3611 (4)	0.4043 (4)	0.22780 (17)	0.0702 (11)
H22A	0.4324	0.3948	0.2624	0.105*
H22B	0.3269	0.3059	0.2152	0.105*
H22C	0.2839	0.4641	0.2409	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0720 (17)	0.0475 (15)	0.0932 (19)	−0.0040 (13)	0.0345 (15)	0.0078 (13)
C1	0.053 (2)	0.054 (2)	0.0474 (19)	−0.0117 (17)	0.0242 (15)	−0.0107 (16)
C2	0.0361 (16)	0.055 (2)	0.0295 (15)	−0.0084 (15)	0.0084 (12)	−0.0068 (14)
C3	0.0368 (18)	0.079 (3)	0.0350 (17)	−0.0054 (17)	0.0065 (13)	−0.0057 (16)
C4	0.0354 (19)	0.121 (4)	0.045 (2)	−0.014 (2)	0.0082 (15)	−0.011 (2)
C5	0.054 (2)	0.120 (4)	0.053 (2)	−0.042 (3)	0.0256 (18)	−0.036 (2)
C6	0.079 (3)	0.072 (3)	0.064 (2)	−0.034 (2)	0.037 (2)	−0.024 (2)
O2	0.0289 (12)	0.096 (2)	0.0708 (16)	0.0136 (12)	0.0008 (10)	0.0202 (14)
C7	0.0374 (19)	0.132 (4)	0.067 (2)	0.027 (2)	−0.0023 (17)	0.014 (2)
C8	0.0325 (15)	0.0428 (17)	0.0259 (14)	−0.0002 (13)	0.0057 (11)	−0.0012 (12)
C9	0.0307 (15)	0.0443 (17)	0.0373 (16)	0.0040 (13)	0.0057 (12)	0.0031 (13)
C10	0.0331 (15)	0.0417 (17)	0.0288 (15)	−0.0007 (13)	0.0035 (11)	−0.0003 (13)
N1	0.0344 (13)	0.0459 (15)	0.0393 (14)	0.0032 (12)	0.0074 (10)	0.0079 (11)
N2	0.0241 (12)	0.0538 (16)	0.0536 (16)	0.0054 (11)	−0.0020 (10)	0.0145 (12)
C11	0.0213 (13)	0.0447 (17)	0.0297 (15)	0.0025 (12)	0.0001 (11)	−0.0004 (12)
C12	0.0302 (15)	0.0444 (18)	0.0349 (16)	0.0035 (13)	0.0050 (12)	−0.0011 (13)
C13	0.0355 (16)	0.0420 (18)	0.0438 (18)	0.0007 (14)	0.0028 (13)	0.0044 (14)
C14	0.0360 (16)	0.059 (2)	0.0376 (18)	0.0008 (15)	0.0018 (13)	0.0097 (15)
C15	0.0308 (15)	0.061 (2)	0.0281 (15)	0.0051 (14)	−0.0006 (12)	−0.0056 (14)
C16	0.0481 (19)	0.077 (3)	0.0387 (18)	−0.0045 (18)	0.0085 (14)	−0.0060 (17)
C17	0.063 (2)	0.074 (3)	0.043 (2)	−0.004 (2)	0.0132 (17)	−0.0211 (18)
C18	0.0483 (19)	0.059 (2)	0.060 (2)	−0.0057 (16)	0.0004 (16)	−0.0177 (18)
C19	0.0406 (17)	0.059 (2)	0.0434 (18)	−0.0050 (16)	0.0088 (14)	−0.0124 (16)
C20	0.0263 (14)	0.0462 (18)	0.0360 (16)	−0.0035 (13)	0.0034 (12)	−0.0051 (13)
O3	0.0458 (12)	0.0512 (13)	0.0400 (12)	−0.0005 (10)	0.0016 (9)	−0.0119 (10)
C21	0.065 (2)	0.064 (2)	0.063 (2)	0.0168 (19)	0.0026 (18)	−0.0185 (18)
O4	0.0632 (14)	0.0494 (14)	0.0546 (14)	−0.0158 (12)	0.0142 (11)	0.0026 (11)
C22	0.073 (2)	0.062 (2)	0.077 (3)	−0.016 (2)	0.016 (2)	0.016 (2)

Geometric parameters (Å, º)

O1—C1	1.350 (4)	C11—C12	1.376 (4)
O1—H1	0.8400	C11—C20	1.434 (4)
C1—C6	1.400 (5)	C12—O3	1.390 (3)
C1—C2	1.402 (4)	C12—C13	1.428 (4)
C2—C3	1.407 (4)	C13—C14	1.354 (4)
C2—C8	1.470 (4)	C13—O4	1.365 (3)
C3—O2	1.358 (4)	C14—C15	1.406 (4)
C3—C4	1.385 (4)	C14—H14	0.9500
C4—C5	1.369 (5)	C15—C16	1.422 (4)
C4—H4	0.9500	C15—C20	1.435 (4)
C5—C6	1.372 (5)	C16—C17	1.347 (4)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.405 (5)
O2—C7	1.427 (4)	C17—H17	0.9500
C7—H7A	0.9800	C18—C19	1.372 (4)
C7—H7B	0.9800	C18—H18	0.9500
C7—H7C	0.9800	C19—C20	1.402 (4)
C8—N1	1.295 (3)	C19—H19	0.9500
C8—C9	1.505 (4)	O3—C21	1.431 (3)
C9—C10	1.539 (4)	C21—H21A	0.9800
C9—H9A	0.9900	C21—H21B	0.9800
C9—H9B	0.9900	C21—H21C	0.9800
C10—N2	1.481 (3)	O4—C22	1.424 (4)
C10—C11	1.514 (4)	C22—H22A	0.9800
C10—H10	1.0000	C22—H22B	0.9800
N1—N2	1.400 (3)	C22—H22C	0.9800
N2—H2A	0.8800
C1—O1—H1	109.5	C12—C11—C20	119.0 (2)
O1—C1—C6	117.1 (3)	C12—C11—C10	118.1 (2)
O1—C1—C2	121.7 (3)	C20—C11—C10	122.8 (2)
C6—C1—C2	121.2 (3)	C11—C12—O3	120.7 (2)
C1—C2—C3	116.9 (3)	C11—C12—C13	122.3 (3)
C1—C2—C8	120.3 (3)	O3—C12—C13	116.8 (2)
C3—C2—C8	122.7 (3)	C14—C13—O4	126.1 (3)
O2—C3—C4	122.6 (3)	C14—C13—C12	118.9 (3)
O2—C3—C2	115.8 (3)	O4—C13—C12	115.0 (3)
C4—C3—C2	121.6 (4)	C13—C14—C15	121.5 (3)
C5—C4—C3	119.6 (4)	C13—C14—H14	119.3
C5—C4—H4	120.2	C15—C14—H14	119.3
C3—C4—H4	120.2	C14—C15—C16	121.2 (3)
C4—C5—C6	121.4 (3)	C14—C15—C20	120.1 (3)
C4—C5—H5	119.3	C16—C15—C20	118.7 (3)
C6—C5—H5	119.3	C17—C16—C15	121.0 (3)
C5—C6—C1	119.3 (4)	C17—C16—H16	119.5
C5—C6—H6	120.4	C15—C16—H16	119.5
C1—C6—H6	120.4	C16—C17—C18	120.6 (3)
C3—O2—C7	119.0 (3)	C16—C17—H17	119.7
O2—C7—H7A	109.5	C18—C17—H17	119.7
O2—C7—H7B	109.5	C19—C18—C17	120.1 (3)
H7A—C7—H7B	109.5	C19—C18—H18	120.0
O2—C7—H7C	109.5	C17—C18—H18	120.0
H7A—C7—H7C	109.5	C18—C19—C20	121.4 (3)
H7B—C7—H7C	109.5	C18—C19—H19	119.3
N1—C8—C2	120.7 (3)	C20—C19—H19	119.3
N1—C8—C9	112.0 (2)	C19—C20—C11	123.7 (3)
C2—C8—C9	127.2 (2)	C19—C20—C15	118.1 (3)
C8—C9—C10	103.1 (2)	C11—C20—C15	118.2 (3)
C8—C9—H9A	111.1	C12—O3—C21	114.4 (2)
C10—C9—H9A	111.1	O3—C21—H21A	109.5
C8—C9—H9B	111.1	O3—C21—H21B	109.5
C10—C9—H9B	111.1	H21A—C21—H21B	109.5
H9A—C9—H9B	109.1	O3—C21—H21C	109.5
N2—C10—C11	115.5 (2)	H21A—C21—H21C	109.5
N2—C10—C9	103.3 (2)	H21B—C21—H21C	109.5
C11—C10—C9	113.1 (2)	C13—O4—C22	117.0 (3)
N2—C10—H10	108.2	O4—C22—H22A	109.5
C11—C10—H10	108.2	O4—C22—H22B	109.5
C9—C10—H10	108.2	H22A—C22—H22B	109.5
C8—N1—N2	111.3 (2)	O4—C22—H22C	109.5
N1—N2—C10	109.9 (2)	H22A—C22—H22C	109.5
N1—N2—H2A	125.0	H22B—C22—H22C	109.5
C10—N2—H2A	125.0
O1—C1—C2—C3	179.5 (3)	C9—C10—C11—C20	65.6 (3)
C6—C1—C2—C3	−1.6 (4)	C20—C11—C12—O3	174.4 (2)
O1—C1—C2—C8	−2.4 (4)	C10—C11—C12—O3	−9.6 (4)
C6—C1—C2—C8	176.5 (3)	C20—C11—C12—C13	−0.7 (4)
C1—C2—C3—O2	−177.9 (2)	C10—C11—C12—C13	175.3 (2)
C8—C2—C3—O2	4.1 (4)	C11—C12—C13—C14	0.5 (4)
C1—C2—C3—C4	2.5 (4)	O3—C12—C13—C14	−174.8 (2)
C8—C2—C3—C4	−175.6 (3)	C11—C12—C13—O4	−179.7 (2)
O2—C3—C4—C5	178.8 (3)	O3—C12—C13—O4	5.0 (3)
C2—C3—C4—C5	−1.6 (5)	O4—C13—C14—C15	−178.7 (3)
C3—C4—C5—C6	−0.3 (5)	C12—C13—C14—C15	1.0 (4)
C4—C5—C6—C1	1.2 (5)	C13—C14—C15—C16	179.0 (3)
O1—C1—C6—C5	178.8 (3)	C13—C14—C15—C20	−2.3 (4)
C2—C1—C6—C5	−0.2 (5)	C14—C15—C16—C17	179.0 (3)
C4—C3—O2—C7	−7.9 (4)	C20—C15—C16—C17	0.3 (4)
C2—C3—O2—C7	172.5 (3)	C15—C16—C17—C18	−2.5 (5)
C1—C2—C8—N1	0.8 (4)	C16—C17—C18—C19	2.9 (5)
C3—C2—C8—N1	178.8 (3)	C17—C18—C19—C20	−1.1 (5)
C1—C2—C8—C9	−175.6 (3)	C18—C19—C20—C11	179.7 (3)
C3—C2—C8—C9	2.4 (4)	C18—C19—C20—C15	−1.1 (4)
N1—C8—C9—C10	3.2 (3)	C12—C11—C20—C19	178.7 (2)
C2—C8—C9—C10	179.8 (2)	C10—C11—C20—C19	2.8 (4)
C8—C9—C10—N2	−5.2 (3)	C12—C11—C20—C15	−0.5 (4)
C8—C9—C10—C11	−130.8 (2)	C10—C11—C20—C15	−176.4 (2)
C2—C8—N1—N2	−176.4 (2)	C14—C15—C20—C19	−177.3 (2)
C9—C8—N1—N2	0.5 (3)	C16—C15—C20—C19	1.5 (4)
C8—N1—N2—C10	−4.2 (3)	C14—C15—C20—C11	2.0 (4)
C11—C10—N2—N1	129.9 (2)	C16—C15—C20—C11	−179.2 (2)
C9—C10—N2—N1	5.8 (3)	C11—C12—O3—C21	103.7 (3)
N2—C10—C11—C12	130.9 (3)	C13—C12—O3—C21	−80.9 (3)
C9—C10—C11—C12	−110.3 (3)	C14—C13—O4—C22	−0.4 (4)
N2—C10—C11—C20	−53.2 (3)	C12—C13—O4—C22	179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.81	2.556 (3)	148
N2—H2A···N2^i	0.88	2.68	3.196 (5)	118
C6—H6···O1^ii	0.95	2.50	3.433 (5)	166

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