Dimethyl 4-[3-(4-meth-oxy-phen-yl)-1-phenyl-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxyl-ate dihydrate.

In the title compound, C(27)H(27)N(3)O(5)·2H(2)O, the dihydro-pyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, mol-ecules are linked via N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C-H⋯π inter-actions.

Related literature

For details and applications of pyrazoles, see: Buhler & Kiowski (1987 ▶); Isloor et al. (2000 ▶, 2009 ▶); Isloor (2011 ▶); Vijesh et al. (2011 ▶); Vo et al. (1995 ▶). For the preparation of the compound, see: Trivedi et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Fun et al. (2011 ▶, 2012 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H27N3O5·2H2O

M = 509.55

Monoclinic,

a = 14.1279 (9) Å

b = 11.6313 (7) Å

c = 15.3780 (9) Å

β = 93.358 (1)°

V = 2522.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.34 × 0.17 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.987

28375 measured reflections

7347 independent reflections

5683 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.131

S = 1.04

7347 reflections

359 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.24 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027936/sj5244sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027936/sj5244Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027936/sj5244Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H27N3O5·2H2O	F(000) = 1080
Mr = 509.55	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7658 reflections
a = 14.1279 (9) Å	θ = 2.3–30.0°
b = 11.6313 (7) Å	µ = 0.10 mm−1
c = 15.3780 (9) Å	T = 100 K
β = 93.358 (1)°	Block, yellow
V = 2522.7 (3) Å3	0.34 × 0.17 × 0.14 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	7347 independent reflections
Radiation source: fine-focus sealed tube	5683 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.968, Tmax = 0.987	k = −16→13
28375 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.6924P] where P = (Fo2 + 2Fc2)/3
7347 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	−0.00103 (7)	0.62548 (9)	0.37770 (6)	0.0226 (2)
O1W	0.41969 (8)	0.86761 (10)	−0.00494 (6)	0.0234 (2)
O2	0.03130 (6)	0.66323 (8)	0.23892 (6)	0.01912 (19)
O2W	0.38758 (7)	0.38977 (8)	0.53450 (6)	0.0195 (2)
O3	0.28443 (7)	0.24426 (8)	0.14770 (6)	0.0219 (2)
O4	0.18314 (7)	0.37519 (8)	0.08778 (6)	0.0200 (2)
O5	0.08804 (7)	0.56032 (9)	−0.20791 (6)	0.0225 (2)
N1	0.25743 (8)	0.42928 (9)	0.38442 (6)	0.0156 (2)
N2	0.34896 (7)	0.74941 (9)	0.22034 (6)	0.01294 (19)
N3	0.32317 (7)	0.74721 (9)	0.13320 (6)	0.0136 (2)
C1	0.13336 (8)	0.53784 (10)	0.31548 (7)	0.0133 (2)
C2	0.17983 (8)	0.50147 (11)	0.39019 (7)	0.0144 (2)
C3	0.27622 (8)	0.36991 (10)	0.30988 (7)	0.0141 (2)
C4	0.23111 (8)	0.40222 (10)	0.23297 (7)	0.0129 (2)
C5	0.17563 (8)	0.51489 (10)	0.22856 (7)	0.0120 (2)
H5A	0.1231	0.5084	0.1824	0.014*
C6	0.23963 (8)	0.61354 (10)	0.20620 (7)	0.0123 (2)
C7	0.25677 (8)	0.66432 (10)	0.12467 (7)	0.0125 (2)
C8	0.29982 (8)	0.67097 (10)	0.26530 (7)	0.0132 (2)
H8A	0.3058	0.6580	0.3264	0.016*
C9	0.21375 (9)	0.63618 (10)	0.03755 (7)	0.0141 (2)
C10	0.11507 (9)	0.62914 (11)	0.02224 (8)	0.0162 (2)
H10A	0.0751	0.6420	0.0688	0.019*
C11	0.07515 (9)	0.60366 (12)	−0.05989 (8)	0.0182 (2)
H11A	0.0082	0.5994	−0.0694	0.022*
C12	0.13333 (9)	0.58421 (11)	−0.12869 (7)	0.0172 (2)
C13	0.23124 (9)	0.58855 (12)	−0.11424 (8)	0.0186 (3)
H13A	0.2712	0.5736	−0.1606	0.022*
C14	0.27062 (9)	0.61488 (11)	−0.03141 (8)	0.0167 (2)
H14A	0.3376	0.6183	−0.0219	0.020*
C15	0.41077 (8)	0.83539 (10)	0.25672 (7)	0.0134 (2)
C16	0.42022 (9)	0.93974 (11)	0.21407 (8)	0.0175 (2)
H16A	0.3877	0.9529	0.1591	0.021*
C17	0.47758 (10)	1.02438 (12)	0.25260 (9)	0.0223 (3)
H17A	0.4849	1.0955	0.2234	0.027*
C18	0.52447 (10)	1.00658 (12)	0.33343 (9)	0.0226 (3)
H18A	0.5631	1.0654	0.3596	0.027*
C19	0.51448 (9)	0.90238 (12)	0.37554 (8)	0.0190 (3)
H19A	0.5464	0.8899	0.4308	0.023*
C20	0.45806 (9)	0.81588 (11)	0.33746 (7)	0.0155 (2)
H20A	0.4518	0.7442	0.3662	0.019*
C21	0.23800 (9)	0.33188 (11)	0.15483 (7)	0.0150 (2)
C22	0.17954 (12)	0.30966 (13)	0.00848 (9)	0.0288 (3)
H22A	0.1412	0.3508	−0.0367	0.043*
H22B	0.1510	0.2344	0.0186	0.043*
H22C	0.2439	0.2991	−0.0106	0.043*
C23	0.04876 (9)	0.61105 (11)	0.31701 (8)	0.0158 (2)
C24	−0.05368 (10)	0.73192 (13)	0.23212 (9)	0.0244 (3)
H24A	−0.0586	0.7705	0.1754	0.037*
H24B	−0.0512	0.7897	0.2786	0.037*
H24C	−0.1091	0.6823	0.2378	0.037*
C25	0.34522 (9)	0.27246 (12)	0.32367 (8)	0.0195 (3)
H25A	0.3937	0.2775	0.2807	0.029*
H25B	0.3114	0.1992	0.3167	0.029*
H25C	0.3756	0.2772	0.3825	0.029*
C26	0.15698 (10)	0.53149 (12)	0.48159 (8)	0.0204 (3)
H26A	0.1351	0.6114	0.4835	0.031*
H26B	0.2139	0.5224	0.5205	0.031*
H26C	0.1070	0.4803	0.5004	0.031*
C27	0.14331 (11)	0.56823 (14)	−0.28286 (8)	0.0267 (3)
H27A	0.1017	0.5606	−0.3358	0.040*
H27B	0.1907	0.5066	−0.2810	0.040*
H27C	0.1754	0.6429	−0.2830	0.040*
H1N1	0.2957 (13)	0.4137 (15)	0.4321 (12)	0.027 (4)*
H2W1	0.3944 (16)	0.828 (2)	0.0380 (14)	0.047 (6)*
H2W2	0.4530 (18)	0.3690 (19)	0.5247 (14)	0.052 (6)*
H1W1	0.4089 (18)	0.939 (2)	0.0070 (16)	0.063 (7)*
H1W2	0.3581 (17)	0.345 (2)	0.5726 (15)	0.053 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0199 (5)	0.0257 (5)	0.0230 (4)	0.0020 (4)	0.0086 (4)	−0.0036 (4)
O1W	0.0300 (5)	0.0186 (5)	0.0229 (5)	−0.0027 (4)	0.0110 (4)	−0.0019 (4)
O2	0.0167 (4)	0.0197 (5)	0.0212 (4)	0.0060 (4)	0.0028 (3)	0.0014 (3)
O2W	0.0218 (5)	0.0177 (5)	0.0190 (4)	−0.0011 (4)	0.0007 (3)	0.0042 (3)
O3	0.0258 (5)	0.0186 (5)	0.0216 (4)	0.0060 (4)	0.0035 (4)	−0.0049 (3)
O4	0.0297 (5)	0.0170 (5)	0.0133 (4)	0.0042 (4)	0.0004 (3)	−0.0036 (3)
O5	0.0245 (5)	0.0303 (5)	0.0126 (4)	−0.0096 (4)	−0.0004 (3)	−0.0005 (3)
N1	0.0166 (5)	0.0170 (5)	0.0132 (4)	0.0014 (4)	0.0010 (4)	0.0005 (4)
N2	0.0147 (5)	0.0121 (5)	0.0119 (4)	−0.0009 (4)	0.0005 (3)	0.0001 (3)
N3	0.0153 (5)	0.0141 (5)	0.0115 (4)	−0.0002 (4)	0.0010 (3)	0.0005 (3)
C1	0.0135 (5)	0.0126 (5)	0.0142 (5)	−0.0020 (4)	0.0048 (4)	−0.0015 (4)
C2	0.0155 (5)	0.0134 (6)	0.0146 (5)	−0.0026 (4)	0.0044 (4)	−0.0006 (4)
C3	0.0140 (5)	0.0124 (6)	0.0162 (5)	−0.0012 (4)	0.0033 (4)	0.0000 (4)
C4	0.0130 (5)	0.0114 (5)	0.0147 (5)	−0.0010 (4)	0.0035 (4)	−0.0011 (4)
C5	0.0123 (5)	0.0117 (5)	0.0123 (5)	−0.0005 (4)	0.0022 (4)	−0.0001 (4)
C6	0.0131 (5)	0.0114 (5)	0.0126 (5)	0.0008 (4)	0.0023 (4)	0.0000 (4)
C7	0.0128 (5)	0.0113 (5)	0.0134 (5)	0.0008 (4)	0.0022 (4)	0.0001 (4)
C8	0.0150 (5)	0.0119 (5)	0.0130 (5)	−0.0005 (4)	0.0025 (4)	0.0004 (4)
C9	0.0165 (5)	0.0129 (6)	0.0130 (5)	−0.0013 (4)	0.0009 (4)	0.0016 (4)
C10	0.0154 (6)	0.0186 (6)	0.0148 (5)	0.0006 (5)	0.0027 (4)	0.0015 (4)
C11	0.0164 (6)	0.0206 (6)	0.0175 (5)	−0.0022 (5)	0.0000 (4)	0.0016 (4)
C12	0.0208 (6)	0.0173 (6)	0.0133 (5)	−0.0050 (5)	0.0002 (4)	0.0010 (4)
C13	0.0196 (6)	0.0229 (7)	0.0138 (5)	−0.0044 (5)	0.0044 (4)	−0.0016 (4)
C14	0.0150 (5)	0.0196 (6)	0.0155 (5)	−0.0034 (5)	0.0026 (4)	0.0003 (4)
C15	0.0126 (5)	0.0124 (6)	0.0153 (5)	−0.0008 (4)	0.0030 (4)	−0.0016 (4)
C16	0.0205 (6)	0.0156 (6)	0.0166 (5)	−0.0027 (5)	0.0027 (4)	0.0014 (4)
C17	0.0265 (7)	0.0173 (6)	0.0235 (6)	−0.0076 (5)	0.0037 (5)	0.0009 (5)
C18	0.0218 (6)	0.0218 (7)	0.0243 (6)	−0.0091 (5)	0.0023 (5)	−0.0043 (5)
C19	0.0155 (6)	0.0227 (7)	0.0187 (5)	−0.0025 (5)	0.0005 (4)	−0.0021 (5)
C20	0.0147 (5)	0.0151 (6)	0.0168 (5)	−0.0001 (4)	0.0020 (4)	−0.0001 (4)
C21	0.0152 (5)	0.0141 (6)	0.0161 (5)	−0.0024 (4)	0.0042 (4)	−0.0006 (4)
C22	0.0461 (9)	0.0240 (7)	0.0158 (6)	0.0082 (6)	−0.0015 (5)	−0.0069 (5)
C23	0.0149 (5)	0.0143 (6)	0.0183 (5)	−0.0019 (4)	0.0033 (4)	−0.0018 (4)
C24	0.0187 (6)	0.0235 (7)	0.0307 (7)	0.0075 (5)	−0.0007 (5)	−0.0011 (5)
C25	0.0203 (6)	0.0180 (6)	0.0203 (6)	0.0050 (5)	0.0023 (4)	0.0015 (4)
C26	0.0243 (6)	0.0227 (7)	0.0146 (5)	0.0020 (5)	0.0048 (4)	−0.0013 (4)
C27	0.0315 (7)	0.0350 (8)	0.0139 (5)	−0.0139 (6)	0.0034 (5)	−0.0020 (5)

O1—C23	1.2129 (15)	C10—C11	1.3848 (16)
O1W—H2W1	0.89 (2)	C10—H10A	0.9500
O1W—H1W1	0.87 (3)	C11—C12	1.3957 (18)
O2—C23	1.3553 (15)	C11—H11A	0.9500
O2—C24	1.4408 (15)	C12—C13	1.3890 (18)
O2W—H2W2	0.98 (2)	C13—C14	1.3939 (16)
O2W—H1W2	0.90 (3)	C13—H13A	0.9500
O3—C21	1.2204 (16)	C14—H14A	0.9500
O4—C21	1.3507 (14)	C15—C16	1.3897 (17)
O4—C22	1.4364 (15)	C15—C20	1.3936 (15)
O5—C12	1.3709 (14)	C16—C17	1.3859 (18)
O5—C27	1.4324 (16)	C16—H16A	0.9500
N1—C3	1.3773 (15)	C17—C18	1.3894 (18)
N1—C2	1.3879 (16)	C17—H17A	0.9500
N1—H1N1	0.904 (18)	C18—C19	1.3853 (19)
N2—C8	1.3596 (15)	C18—H18A	0.9500
N2—N3	1.3683 (13)	C19—C20	1.3915 (17)
N2—C15	1.4207 (15)	C19—H19A	0.9500
N3—C7	1.3463 (15)	C20—H20A	0.9500
C1—C2	1.3570 (15)	C22—H22A	0.9800
C1—C23	1.4688 (17)	C22—H22B	0.9800
C1—C5	1.5192 (15)	C22—H22C	0.9800
C2—C26	1.5015 (16)	C24—H24A	0.9800
C3—C4	1.3630 (15)	C24—H24B	0.9800
C3—C25	1.5018 (17)	C24—H24C	0.9800
C4—C21	1.4616 (16)	C25—H25A	0.9800
C4—C5	1.5266 (16)	C25—H25B	0.9800
C5—C6	1.5129 (16)	C25—H25C	0.9800
C5—H5A	1.0000	C26—H26A	0.9800
C6—C8	1.3801 (15)	C26—H26B	0.9800
C6—C7	1.4194 (15)	C26—H26C	0.9800
C7—C9	1.4751 (15)	C27—H27A	0.9800
C8—H8A	0.9500	C27—H27B	0.9800
C9—C14	1.3897 (17)	C27—H27C	0.9800
C9—C10	1.4026 (17)
H2W1—O1W—H1W1	105 (2)	C13—C14—H14A	119.4
C23—O2—C24	114.85 (10)	C16—C15—C20	120.56 (11)
H2W2—O2W—H1W2	116 (2)	C16—C15—N2	120.19 (10)
C21—O4—C22	116.13 (10)	C20—C15—N2	119.19 (11)
C12—O5—C27	117.00 (10)	C17—C16—C15	119.25 (11)
C3—N1—C2	123.24 (10)	C17—C16—H16A	120.4
C3—N1—H1N1	116.1 (11)	C15—C16—H16A	120.4
C2—N1—H1N1	120.4 (11)	C16—C17—C18	120.85 (12)
C8—N2—N3	111.77 (9)	C16—C17—H17A	119.6
C8—N2—C15	126.34 (10)	C18—C17—H17A	119.6
N3—N2—C15	121.40 (10)	C19—C18—C17	119.50 (12)
C7—N3—N2	104.64 (9)	C19—C18—H18A	120.3
C2—C1—C23	121.39 (11)	C17—C18—H18A	120.3
C2—C1—C5	119.64 (10)	C18—C19—C20	120.49 (11)
C23—C1—C5	118.56 (10)	C18—C19—H19A	119.8
C1—C2—N1	118.63 (10)	C20—C19—H19A	119.8
C1—C2—C26	126.88 (11)	C19—C20—C15	119.35 (12)
N1—C2—C26	114.48 (10)	C19—C20—H20A	120.3
C4—C3—N1	118.73 (11)	C15—C20—H20A	120.3
C4—C3—C25	126.67 (11)	O3—C21—O4	122.02 (11)
N1—C3—C25	114.59 (10)	O3—C21—C4	127.11 (11)
C3—C4—C21	120.58 (11)	O4—C21—C4	110.86 (10)
C3—C4—C5	119.21 (10)	O4—C22—H22A	109.5
C21—C4—C5	120.18 (10)	O4—C22—H22B	109.5
C6—C5—C1	109.73 (9)	H22A—C22—H22B	109.5
C6—C5—C4	110.43 (9)	O4—C22—H22C	109.5
C1—C5—C4	109.81 (9)	H22A—C22—H22C	109.5
C6—C5—H5A	108.9	H22B—C22—H22C	109.5
C1—C5—H5A	108.9	O1—C23—O2	122.43 (11)
C4—C5—H5A	108.9	O1—C23—C1	127.00 (11)
C8—C6—C7	104.47 (10)	O2—C23—C1	110.58 (10)
C8—C6—C5	124.81 (10)	O2—C24—H24A	109.5
C7—C6—C5	130.65 (10)	O2—C24—H24B	109.5
N3—C7—C6	111.46 (10)	H24A—C24—H24B	109.5
N3—C7—C9	119.67 (10)	O2—C24—H24C	109.5
C6—C7—C9	128.86 (11)	H24A—C24—H24C	109.5
N2—C8—C6	107.65 (10)	H24B—C24—H24C	109.5
N2—C8—H8A	126.2	C3—C25—H25A	109.5
C6—C8—H8A	126.2	C3—C25—H25B	109.5
C14—C9—C10	118.35 (10)	H25A—C25—H25B	109.5
C14—C9—C7	120.45 (11)	C3—C25—H25C	109.5
C10—C9—C7	121.20 (11)	H25A—C25—H25C	109.5
C11—C10—C9	120.89 (11)	H25B—C25—H25C	109.5
C11—C10—H10A	119.6	C2—C26—H26A	109.5
C9—C10—H10A	119.6	C2—C26—H26B	109.5
C10—C11—C12	119.97 (11)	H26A—C26—H26B	109.5
C10—C11—H11A	120.0	C2—C26—H26C	109.5
C12—C11—H11A	120.0	H26A—C26—H26C	109.5
O5—C12—C13	123.92 (11)	H26B—C26—H26C	109.5
O5—C12—C11	116.20 (11)	O5—C27—H27A	109.5
C13—C12—C11	119.87 (11)	O5—C27—H27B	109.5
C12—C13—C14	119.64 (11)	H27A—C27—H27B	109.5
C12—C13—H13A	120.2	O5—C27—H27C	109.5
C14—C13—H13A	120.2	H27A—C27—H27C	109.5
C9—C14—C13	121.26 (11)	H27B—C27—H27C	109.5
C9—C14—H14A	119.4
C8—N2—N3—C7	−0.45 (13)	N3—C7—C9—C10	−130.42 (13)
C15—N2—N3—C7	−172.90 (10)	C6—C7—C9—C10	50.89 (18)
C23—C1—C2—N1	177.85 (11)	C14—C9—C10—C11	−1.15 (19)
C5—C1—C2—N1	−9.57 (17)	C7—C9—C10—C11	179.43 (12)
C23—C1—C2—C26	−2.5 (2)	C9—C10—C11—C12	0.2 (2)
C5—C1—C2—C26	170.03 (12)	C27—O5—C12—C13	−15.73 (19)
C3—N1—C2—C1	−16.56 (18)	C27—O5—C12—C11	164.95 (12)
C3—N1—C2—C26	163.79 (11)	C10—C11—C12—O5	−179.56 (12)
C2—N1—C3—C4	15.78 (18)	C10—C11—C12—C13	1.1 (2)
C2—N1—C3—C25	−163.19 (11)	O5—C12—C13—C14	179.27 (12)
N1—C3—C4—C21	−171.01 (11)	C11—C12—C13—C14	−1.4 (2)
C25—C3—C4—C21	7.82 (19)	C10—C9—C14—C13	0.80 (19)
N1—C3—C4—C5	10.87 (17)	C7—C9—C14—C13	−179.78 (12)
C25—C3—C4—C5	−170.29 (11)	C12—C13—C14—C9	0.5 (2)
C2—C1—C5—C6	−89.71 (13)	C8—N2—C15—C16	−148.56 (12)
C23—C1—C5—C6	83.08 (12)	N3—N2—C15—C16	22.74 (17)
C2—C1—C5—C4	31.85 (15)	C8—N2—C15—C20	28.37 (18)
C23—C1—C5—C4	−155.36 (10)	N3—N2—C15—C20	−160.34 (11)
C3—C4—C5—C6	88.64 (13)	C20—C15—C16—C17	0.22 (19)
C21—C4—C5—C6	−89.49 (12)	N2—C15—C16—C17	177.11 (12)
C3—C4—C5—C1	−32.51 (14)	C15—C16—C17—C18	−0.8 (2)
C21—C4—C5—C1	149.37 (11)	C16—C17—C18—C19	0.7 (2)
C1—C5—C6—C8	39.26 (15)	C17—C18—C19—C20	0.0 (2)
C4—C5—C6—C8	−81.93 (14)	C18—C19—C20—C15	−0.63 (19)
C1—C5—C6—C7	−144.34 (12)	C16—C15—C20—C19	0.50 (18)
C4—C5—C6—C7	94.47 (14)	N2—C15—C20—C19	−176.42 (11)
N2—N3—C7—C6	0.19 (13)	C22—O4—C21—O3	2.43 (18)
N2—N3—C7—C9	−178.72 (10)	C22—O4—C21—C4	−176.47 (12)
C8—C6—C7—N3	0.11 (14)	C3—C4—C21—O3	−3.0 (2)
C5—C6—C7—N3	−176.84 (11)	C5—C4—C21—O3	175.14 (12)
C8—C6—C7—C9	178.90 (12)	C3—C4—C21—O4	175.88 (11)
C5—C6—C7—C9	1.9 (2)	C5—C4—C21—O4	−6.03 (15)
N3—N2—C8—C6	0.53 (14)	C24—O2—C23—O1	−3.27 (17)
C15—N2—C8—C6	172.54 (11)	C24—O2—C23—C1	176.54 (10)
C7—C6—C8—N2	−0.38 (13)	C2—C1—C23—O1	−18.1 (2)
C5—C6—C8—N2	176.81 (11)	C5—C1—C23—O1	169.29 (12)
N3—C7—C9—C14	50.18 (17)	C2—C1—C23—O2	162.14 (11)
C6—C7—C9—C14	−128.52 (14)	C5—C1—C23—O2	−10.52 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2W	0.904 (18)	2.001 (18)	2.9020 (14)	175.2 (15)
O1W—H2W1···N3	0.90 (2)	2.05 (2)	2.9449 (14)	174 (2)
O2W—H2W2···O1Wi	0.98 (3)	1.84 (3)	2.7986 (15)	166 (2)
O2W—H1W2···O3ii	0.90 (3)	1.91 (3)	2.8074 (14)	174 (2)
O1W—H1W1···O2Wiii	0.87 (3)	2.06 (3)	2.9274 (15)	178 (2)
C20—H20A···O1Wiv	0.95	2.44	3.2980 (16)	151
C13—H13A···Cg2v	0.95	2.90	3.6957 (14)	142
C18—H18A···Cg1vi	0.95	2.63	3.3682 (15)	135
C25—H25A···Cg2i	0.98	2.87	3.7231 (14)	146
C27—H27C···Cg1v	0.98	2.62	3.5720 (17)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the pyrazole (N2/N3/C6–C8) and benzene (C15–C20) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2W	0.904 (18)	2.001 (18)	2.9020 (14)	175.2 (15)
O1W—H2W1⋯N3	0.90 (2)	2.05 (2)	2.9449 (14)	174 (2)
O2W—H2W2⋯O1W i	0.98 (3)	1.84 (3)	2.7986 (15)	166 (2)
O2W—H1W2⋯O3ii	0.90 (3)	1.91 (3)	2.8074 (14)	174 (2)
O1W—H1W1⋯O2W iii	0.87 (3)	2.06 (3)	2.9274 (15)	178 (2)
C20—H20A⋯O1W iv	0.95	2.44	3.2980 (16)	151
C13—H13A⋯Cg2v	0.95	2.90	3.6957 (14)	142
C18—H18A⋯Cg1vi	0.95	2.63	3.3682 (15)	135
C25—H25A⋯Cg2i	0.98	2.87	3.7231 (14)	146
C27—H27C⋯Cg1v	0.98	2.62	3.5720 (17)	164

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .