4′-[2-Butyl-4-chloro-5-(hydroxy­imino­methyl)-1H-imidazol-3-yl­methyl]­bi­phenyl-2-carbo­nitrile

The title compound, C₂₂H₂₁ClN₄O, is used as an intermediate for the synthesis of biologically active compounds. Geometric parameters are in the usual ranges. The packing is stabilized by O—H...N hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.105
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.77 Ratio

Author Response: The terminal two atoms of the butyl group are disordered.

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8

Alert level C
PLAT213_ALERT_2_C Atom C8'     has ADP max/min Ratio .............       3.90 prolat
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       3.07 Ratio

Author Response: The terminal two atoms of the butyl group are disordered.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C22    -   C27    ...       1.45 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         57
            C23 -C22 -C27 -N27   -12.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         58
            C21 -C22 -C27 -N27   166.00  6.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.20 Deg.
              C8   -C7   -C8'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       9.30 Deg.
              H7A  -C7   -H7C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.40 Deg.
              H7B  -C7   -H7D     1.555   1.555   1.555

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

4'-[2-Butyl-4-chloro-5-(hydroxyiminomethyl)-1H-imidazol-3-ylmethyl]biphenyl- 2-carbonitrile

Crystal data

C22H21ClN4O	Z = 2
Mr = 392.88	F(000) = 412
Triclinic, P1	Dx = 1.267 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6974 (6) Å	Cell parameters from 29921 reflections
b = 7.8682 (6) Å	θ = 3.6–25.7°
c = 19.1907 (16) Å	µ = 0.21 mm^−1
α = 79.823 (6)°	T = 173 K
β = 84.248 (7)°	Block, colourless
γ = 64.220 (6)°	0.36 × 0.33 × 0.32 mm
V = 1029.77 (14) Å^3

Data collection

Stoe IPDS-II two-circle diffractometer	3815 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −9→9
Tmin = 0.927, Tmax = 0.941	k = −9→9
16926 measured reflections	l = −23→23

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.7181P] where P = (Fo^2 + 2Fc^2)/3
3815 reflections	(Δ/σ)max = 0.002
276 parameters	Δρmax = 0.49 e Å^−3
1 restraint	Δρmin = −0.53 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	Occ. (<1)
N1	0.4484 (2)	0.21590 (19)	0.88959 (8)	0.0187 (3)
C2	0.3068 (2)	0.1550 (2)	0.91707 (9)	0.0176 (3)
C3	0.4029 (2)	−0.0407 (2)	0.92618 (9)	0.0186 (3)
N4	0.5928 (2)	−0.1023 (2)	0.90548 (8)	0.0213 (3)
C5	0.6168 (2)	0.0567 (2)	0.88369 (10)	0.0225 (4)
C1	0.4263 (2)	0.4152 (2)	0.87535 (9)	0.0212 (4)
H1A	0.5312	0.4234	0.8985	0.025*
H1B	0.3020	0.4984	0.8965	0.025*
C2'	0.1039 (2)	0.2674 (2)	0.93240 (10)	0.0212 (4)
H2'	0.0346	0.2029	0.9597	0.025*
N2	0.0112 (2)	0.4467 (2)	0.91202 (8)	0.0221 (3)
O2	−0.18413 (17)	0.50671 (18)	0.93454 (8)	0.0303 (3)
H2	−0.235 (4)	0.637 (4)	0.9221 (15)	0.060 (8)*
Cl3	0.30731 (6)	−0.20032 (6)	0.96048 (3)	0.02670 (14)
C6	0.8031 (3)	0.0582 (3)	0.85378 (14)	0.0422 (6)
H6A	0.9105	−0.0442	0.8819	0.051*
H6B	0.8031	0.1816	0.8583	0.051*
C7	0.8385 (4)	0.0292 (5)	0.77597 (18)	0.0824 (12)
H7A	0.7398	0.1452	0.7494	0.099*	0.567 (11)
H7B	0.8037	−0.0764	0.7730	0.099*	0.567 (11)
H7C	0.7370	0.1307	0.7452	0.099*	0.433 (11)
H7D	0.8511	−0.0977	0.7694	0.099*	0.433 (11)
C8	1.0228 (7)	−0.0158 (6)	0.7346 (3)	0.0379 (14)	0.567 (11)
H8A	1.0074	−0.0301	0.6857	0.045*	0.567 (11)
H8B	1.1260	−0.1358	0.7571	0.045*	0.567 (11)
C9	1.0714 (8)	0.1524 (9)	0.7345 (4)	0.0609 (18)	0.567 (11)
H9A	1.1921	0.1315	0.7075	0.091*	0.567 (11)
H9B	1.0864	0.1640	0.7833	0.091*	0.567 (11)
H9C	0.9669	0.2699	0.7127	0.091*	0.567 (11)
C8'	1.0422 (9)	0.0536 (17)	0.7655 (5)	0.085 (5)	0.433 (11)
H8'1	1.0289	0.1594	0.7900	0.101*	0.433 (11)
H8'2	1.1465	−0.0647	0.7883	0.101*	0.433 (11)
C9'	1.0966 (12)	0.0909 (16)	0.6941 (6)	0.083 (4)	0.433 (11)
H9'1	1.2217	0.0968	0.6918	0.125*	0.433 (11)
H9'2	0.9991	0.2131	0.6719	0.125*	0.433 (11)
H9'3	1.1068	−0.0113	0.6689	0.125*	0.433 (11)
C11	0.4316 (2)	0.4875 (2)	0.79682 (9)	0.0204 (4)
C12	0.3272 (3)	0.4554 (3)	0.74906 (10)	0.0260 (4)
H12	0.2524	0.3866	0.7660	0.031*
C13	0.3315 (3)	0.5225 (3)	0.67727 (10)	0.0258 (4)
H13	0.2596	0.4988	0.6458	0.031*
C14	0.4403 (2)	0.6250 (2)	0.65051 (10)	0.0228 (4)
C15	0.5421 (3)	0.6598 (3)	0.69876 (10)	0.0260 (4)
H15	0.6146	0.7312	0.6821	0.031*
C16	0.5385 (3)	0.5910 (3)	0.77086 (10)	0.0240 (4)
H16	0.6096	0.6150	0.8026	0.029*
C21	0.4378 (3)	0.6997 (3)	0.57330 (10)	0.0252 (4)
C22	0.6018 (3)	0.7013 (3)	0.53370 (10)	0.0282 (4)
C23	0.5924 (3)	0.7757 (3)	0.46124 (11)	0.0358 (5)
H23	0.7043	0.7775	0.4359	0.043*
C24	0.4191 (3)	0.8466 (3)	0.42675 (11)	0.0389 (5)
H24	0.4117	0.8973	0.3778	0.047*
C25	0.2568 (3)	0.8428 (3)	0.46439 (12)	0.0411 (5)
H25	0.1385	0.8896	0.4408	0.049*
C26	0.2654 (3)	0.7714 (3)	0.53625 (11)	0.0338 (5)
H26	0.1522	0.7709	0.5609	0.041*
C27	0.7898 (3)	0.6196 (3)	0.56520 (11)	0.0370 (5)
N27	0.9418 (3)	0.5551 (4)	0.58767 (11)	0.0574 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0155 (7)	0.0125 (7)	0.0252 (8)	−0.0038 (5)	−0.0007 (5)	−0.0012 (5)
C2	0.0156 (8)	0.0139 (8)	0.0205 (8)	−0.0039 (6)	−0.0013 (6)	−0.0019 (6)
C3	0.0163 (8)	0.0128 (8)	0.0241 (9)	−0.0040 (6)	−0.0003 (6)	−0.0025 (6)
N4	0.0148 (7)	0.0152 (7)	0.0280 (8)	−0.0012 (6)	−0.0004 (6)	−0.0028 (6)
C5	0.0151 (8)	0.0178 (8)	0.0299 (10)	−0.0033 (7)	−0.0004 (7)	−0.0019 (7)
C1	0.0217 (8)	0.0128 (8)	0.0284 (9)	−0.0067 (7)	−0.0020 (7)	−0.0021 (6)
C2'	0.0165 (8)	0.0143 (8)	0.0298 (9)	−0.0042 (7)	0.0021 (7)	−0.0033 (7)
N2	0.0136 (7)	0.0164 (7)	0.0304 (8)	−0.0012 (6)	0.0005 (6)	−0.0035 (6)
O2	0.0131 (6)	0.0150 (6)	0.0534 (9)	0.0006 (5)	0.0047 (6)	−0.0029 (6)
Cl3	0.0224 (2)	0.0128 (2)	0.0421 (3)	−0.00644 (16)	0.00277 (18)	−0.00211 (17)
C6	0.0163 (9)	0.0272 (11)	0.0725 (16)	−0.0052 (8)	0.0069 (10)	0.0033 (10)
C7	0.0497 (17)	0.072 (2)	0.079 (2)	0.0002 (15)	0.0410 (16)	0.0086 (17)
C8	0.037 (2)	0.038 (2)	0.037 (3)	−0.0124 (18)	0.0109 (19)	−0.0185 (18)
C9	0.072 (4)	0.072 (4)	0.060 (4)	−0.048 (3)	0.043 (3)	−0.039 (3)
C8'	0.033 (3)	0.120 (9)	0.052 (6)	−0.011 (4)	0.022 (3)	0.032 (6)
C9'	0.061 (5)	0.084 (7)	0.073 (7)	−0.021 (4)	0.013 (4)	0.027 (5)
C11	0.0161 (8)	0.0128 (8)	0.0286 (9)	−0.0028 (6)	−0.0020 (7)	−0.0021 (6)
C12	0.0232 (9)	0.0244 (9)	0.0340 (10)	−0.0140 (8)	−0.0038 (7)	−0.0006 (7)
C13	0.0220 (9)	0.0268 (9)	0.0308 (10)	−0.0114 (8)	−0.0064 (7)	−0.0032 (7)
C14	0.0181 (8)	0.0191 (8)	0.0269 (9)	−0.0041 (7)	−0.0024 (7)	−0.0020 (7)
C15	0.0263 (9)	0.0249 (9)	0.0310 (10)	−0.0159 (8)	−0.0014 (7)	−0.0012 (7)
C16	0.0232 (9)	0.0228 (9)	0.0286 (10)	−0.0119 (7)	−0.0039 (7)	−0.0027 (7)
C21	0.0241 (9)	0.0199 (9)	0.0292 (10)	−0.0068 (7)	−0.0034 (7)	−0.0027 (7)
C22	0.0277 (10)	0.0274 (10)	0.0291 (10)	−0.0115 (8)	−0.0027 (8)	−0.0028 (8)
C23	0.0398 (12)	0.0347 (11)	0.0300 (11)	−0.0149 (9)	0.0032 (9)	−0.0028 (8)
C24	0.0489 (13)	0.0311 (11)	0.0270 (11)	−0.0090 (10)	−0.0071 (9)	0.0016 (8)
C25	0.0363 (11)	0.0373 (12)	0.0375 (12)	−0.0043 (9)	−0.0148 (9)	0.0014 (9)
C26	0.0265 (10)	0.0331 (11)	0.0352 (11)	−0.0072 (8)	−0.0066 (8)	−0.0001 (8)
C27	0.0302 (11)	0.0534 (13)	0.0301 (11)	−0.0221 (10)	0.0030 (8)	−0.0031 (9)
N27	0.0315 (11)	0.0985 (19)	0.0424 (12)	−0.0305 (11)	−0.0025 (9)	−0.0025 (11)

Geometric parameters (Å, º)

N1—C5	1.367 (2)	C9—H9C	0.9800
N1—C2	1.395 (2)	C8'—C9'	1.410 (14)
N1—C1	1.479 (2)	C8'—H8'1	0.9900
C2—C3	1.374 (2)	C8'—H8'2	0.9900
C2—C2'	1.451 (2)	C9'—H9'1	0.9800
C3—N4	1.365 (2)	C9'—H9'2	0.9800
C3—Cl3	1.7228 (17)	C9'—H9'3	0.9800
N4—C5	1.332 (2)	C11—C16	1.395 (2)
C5—C6	1.494 (2)	C11—C12	1.398 (3)
C1—C11	1.517 (2)	C12—C13	1.388 (3)
C1—H1A	0.9900	C12—H12	0.9500
C1—H1B	0.9900	C13—C14	1.404 (3)
C2'—N2	1.280 (2)	C13—H13	0.9500
C2'—H2'	0.9500	C14—C15	1.403 (3)
N2—O2	1.4121 (18)	C14—C21	1.493 (3)
O2—H2	0.92 (3)	C15—C16	1.396 (3)
C6—C7	1.530 (4)	C15—H15	0.9500
C6—H6A	0.9900	C16—H16	0.9500
C6—H6B	0.9900	C21—C26	1.408 (3)
C7—C8	1.484 (5)	C21—C22	1.411 (3)
C7—C8'	1.649 (7)	C22—C23	1.406 (3)
C7—H7A	0.9900	C22—C27	1.450 (3)
C7—H7B	0.9900	C23—C24	1.388 (3)
C7—H7C	0.9900	C23—H23	0.9500
C7—H7D	0.9900	C24—C25	1.389 (3)
C8—C9	1.524 (8)	C24—H24	0.9500
C8—H8A	0.9900	C25—C26	1.391 (3)
C8—H8B	0.9900	C25—H25	0.9500
C9—H9A	0.9800	C26—H26	0.9500
C9—H9B	0.9800	C27—N27	1.149 (3)
C5—N1—C2	107.55 (14)	H8A—C8—H8B	108.8
C5—N1—C1	125.74 (14)	C8—C9—H9A	109.5
C2—N1—C1	126.50 (14)	C8—C9—H9B	109.5
C3—C2—N1	103.89 (14)	H9A—C9—H9B	109.5
C3—C2—C2'	126.79 (16)	C8—C9—H9C	109.5
N1—C2—C2'	129.32 (15)	H9A—C9—H9C	109.5
N4—C3—C2	112.34 (15)	H9B—C9—H9C	109.5
N4—C3—Cl3	121.08 (12)	C9'—C8'—C7	113.9 (9)
C2—C3—Cl3	126.57 (13)	C9'—C8'—H8'1	108.8
C5—N4—C3	104.82 (14)	C7—C8'—H8'1	108.8
N4—C5—N1	111.39 (15)	C9'—C8'—H8'2	108.8
N4—C5—C6	123.61 (16)	C7—C8'—H8'2	108.8
N1—C5—C6	124.95 (16)	H8'1—C8'—H8'2	107.7
N1—C1—C11	112.59 (14)	C8'—C9'—H9'1	109.5
N1—C1—H1A	109.1	C8'—C9'—H9'2	109.5
C11—C1—H1A	109.1	H9'1—C9'—H9'2	109.5
N1—C1—H1B	109.1	C8'—C9'—H9'3	109.5
C11—C1—H1B	109.1	H9'1—C9'—H9'3	109.5
H1A—C1—H1B	107.8	H9'2—C9'—H9'3	109.5
N2—C2'—C2	125.07 (16)	C16—C11—C12	118.49 (16)
N2—C2'—H2'	117.5	C16—C11—C1	120.44 (15)
C2—C2'—H2'	117.5	C12—C11—C1	121.06 (15)
C2'—N2—O2	109.53 (14)	C13—C12—C11	120.98 (16)
N2—O2—H2	103.2 (18)	C13—C12—H12	119.5
C5—C6—C7	113.0 (2)	C11—C12—H12	119.5
C5—C6—H6A	109.0	C12—C13—C14	120.97 (17)
C7—C6—H6A	109.0	C12—C13—H13	119.5
C5—C6—H6B	109.0	C14—C13—H13	119.5
C7—C6—H6B	109.0	C15—C14—C13	117.89 (17)
H6A—C6—H6B	107.8	C15—C14—C21	122.36 (16)
C8—C7—C6	126.8 (3)	C13—C14—C21	119.69 (16)
C8—C7—C8'	34.2 (4)	C16—C15—C14	120.95 (16)
C6—C7—C8'	96.1 (5)	C16—C15—H15	119.5
C8—C7—H7A	106.8	C14—C15—H15	119.5
C6—C7—H7A	105.7	C11—C16—C15	120.70 (16)
C8'—C7—H7A	106.7	C11—C16—H16	119.7
C8—C7—H7B	104.9	C15—C16—H16	119.7
C6—C7—H7B	104.9	C26—C21—C22	116.70 (18)
C8'—C7—H7B	134.0	C26—C21—C14	119.76 (17)
H7A—C7—H7B	106.2	C22—C21—C14	123.54 (16)
C8—C7—H7C	106.0	C23—C22—C21	121.67 (18)
C6—C7—H7C	112.2	C23—C22—C27	116.80 (18)
C8'—C7—H7C	111.5	C21—C22—C27	121.48 (17)
H7A—C7—H7C	9.3	C24—C23—C22	119.9 (2)
H7B—C7—H7C	97.7	C24—C23—H23	120.1
C8—C7—H7D	86.8	C22—C23—H23	120.1
C6—C7—H7D	111.8	C23—C24—C25	119.43 (19)
C8'—C7—H7D	114.5	C23—C24—H24	120.3
H7A—C7—H7D	119.2	C25—C24—H24	120.3
H7B—C7—H7D	19.4	C24—C25—C26	120.8 (2)
H7C—C7—H7D	110.0	C24—C25—H25	119.6
C7—C8—C9	105.5 (4)	C26—C25—H25	119.6
C7—C8—H8A	110.6	C25—C26—C21	121.6 (2)
C9—C8—H8A	110.6	C25—C26—H26	119.2
C7—C8—H8B	110.6	C21—C26—H26	119.2
C9—C8—H8B	110.6	N27—C27—C22	177.4 (2)
C5—N1—C2—C3	0.30 (18)	N1—C1—C11—C16	−135.97 (16)
C1—N1—C2—C3	−174.68 (16)	N1—C1—C11—C12	45.2 (2)
C5—N1—C2—C2'	−179.10 (17)	C16—C11—C12—C13	0.8 (3)
C1—N1—C2—C2'	5.9 (3)	C1—C11—C12—C13	179.66 (16)
N1—C2—C3—N4	−0.54 (19)	C11—C12—C13—C14	−0.1 (3)
C2'—C2—C3—N4	178.88 (16)	C12—C13—C14—C15	−1.0 (3)
N1—C2—C3—Cl3	178.57 (13)	C12—C13—C14—C21	−178.42 (17)
C2'—C2—C3—Cl3	−2.0 (3)	C13—C14—C15—C16	1.4 (3)
C2—C3—N4—C5	0.6 (2)	C21—C14—C15—C16	178.75 (17)
Cl3—C3—N4—C5	−178.60 (13)	C12—C11—C16—C15	−0.4 (3)
C3—N4—C5—N1	−0.4 (2)	C1—C11—C16—C15	−179.26 (16)
C3—N4—C5—C6	−177.88 (19)	C14—C15—C16—C11	−0.7 (3)
C2—N1—C5—N4	0.0 (2)	C15—C14—C21—C26	−139.81 (19)
C1—N1—C5—N4	175.07 (15)	C13—C14—C21—C26	37.5 (3)
C2—N1—C5—C6	177.52 (19)	C15—C14—C21—C22	40.9 (3)
C1—N1—C5—C6	−7.4 (3)	C13—C14—C21—C22	−141.71 (19)
C5—N1—C1—C11	75.1 (2)	C26—C21—C22—C23	1.7 (3)
C2—N1—C1—C11	−110.84 (18)	C14—C21—C22—C23	−179.02 (18)
C3—C2—C2'—N2	−166.97 (18)	C26—C21—C22—C27	−175.87 (19)
N1—C2—C2'—N2	12.3 (3)	C14—C21—C22—C27	3.4 (3)
C2—C2'—N2—O2	178.05 (16)	C21—C22—C23—C24	−1.2 (3)
N4—C5—C6—C7	79.9 (3)	C27—C22—C23—C24	176.5 (2)
N1—C5—C6—C7	−97.3 (3)	C22—C23—C24—C25	−0.1 (3)
C5—C6—C7—C8	−166.6 (3)	C23—C24—C25—C26	0.9 (3)
C5—C6—C7—C8'	176.8 (4)	C24—C25—C26—C21	−0.3 (3)
C6—C7—C8—C9	−61.5 (6)	C22—C21—C26—C25	−0.9 (3)
C8'—C7—C8—C9	−31.3 (6)	C14—C21—C26—C25	179.78 (19)
C8—C7—C8'—C9'	41.3 (8)	C23—C22—C27—N27	−12 (6)
C6—C7—C8'—C9'	−162.6 (10)	C21—C22—C27—N27	166 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N4^i	0.92 (3)	1.88 (3)	2.7776 (19)	163 (3)

Symmetry code: (i) x−1, y+1, z.