The antifungal agent methyl 2-benzyl-6-diethyl­amino-4-phenyl-2H-1,3,5-thia­diazine-2-carboxyl­ate

The title compound, C₂₂H₂₅N₃O₂S, a new thio­urea derivative of phenyl­alanine, has been synthesized and its antifungal activity investigated against the fungus Penicillium digitatum and the yeast Saccharomyces cerevisiae.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.108
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............       0.00 Deg.

Author Response: X-ray diffraction data were collected on a four circle Seifert XRD 3003 SC but we do not have an area-detector, for this reason we have not eliminated the level A alerts which appear in the checkCIF.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.00

Author Response: we do not have an area-detector

PLAT037_ALERT_1_A _diffrn_reflns_theta_full .......... Not Given .          ?

Author Response: we do not have an area-detector

PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max  Not Given .          ?

Author Response: we do not have an area-detecto

PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given .          ?

Author Response: we do not have an area-detector

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5607
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      59.83 Deg.
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....         C8
PLAT391_ALERT_3_B Deviating Methyl C9      H-C-H Bond Angle ......     120.00 Deg.

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5607
            Proportion of unique data used    0.9997
            Ratio reflections to parameters   8.7514
WEIGH01_ALERT_1_C  Extra text has been found in the
            _refine_ls_weighting_scheme field. This should be in the
            _refine_ls_weighting_details field.
            Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.047P)^2^+3.392P]
            Weighting scheme identified as calc
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.75
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
GOODF01_ALERT_1_G  _refine_ls_goodness_of_fit_obs is an old dataname which has
            been superseded by _refine_ls_goodness_of_fit_ref
REFLE01_ALERT_1_G  _reflns_observed_criterion is an old dataname which has been
            superseded by _reflns_threshold_expression
REFLG01_ALERT_1_G  _reflns_number_observed is an old dataname which has been
            superseded by _reflns_number_gt
RFACG01_ALERT_3_G  _refine_ls_R_factor_obs is an old dataname which has been
            superseded by _refine_ls_R_factor_gt
RFACR01_ALERT_3_G  _refine_ls_wR_factor_obs is an old dataname which has been
            superseded by _refine_ls_wR_factor_ref
SHFSU01_ALERT_2_G  _refine_ls_shift/esd_max is an old dataname which has been
            superseded by _refine_ls_shift/su_max

   5 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   7 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
  11 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CRYSOM (Martinez-Ripoll & Cano, 1996); cell refinement: CRYSOM; data reduction: XRAY80 (Stewart et al., 1990); program(s) used to solve structure: SHELXTL (Siemens, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-benzyl-6-diethylamino-4-phenyl-2H-1,3,5-thiadiazine-2-carboxylate

Crystal data

C22H25N3O2S	F(000) = 1680
Mr = 395.51	Dx = 1.257 Mg m^−3
Monoclinic, C2/c	Melting point: 91(1) K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54180 Å
a = 25.671 (5) Å	Cell parameters from 25 reflections
b = 9.252 (2) Å	θ = 8–20°
c = 18.329 (4) Å	µ = 1.55 mm^−1
β = 106.27 (3)°	T = 293 K
V = 4179.1 (15) Å^3	Prismatic, pale yellow
Z = 8	0.08 × 0.06 × 0.05 mm

Data collection

SEIFERT XRD 3000 S diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 59.8°, θmin = 3.6°
Graphite monochromator	h = −27→28
2θ–ω scans	k = −10→10
5943 measured reflections	l = −19→0
3099 independent reflections	2 standard reflections every 100 reflections
2529 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	All H-atom parameters refined
wR(F^2) = 0.118	Calculated w = 1/[σ^2(Fo^2) + (0.047P)^2 + 3.392P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.002
3098 reflections	Δρmax = 0.35 e Å^−3
354 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (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 on F² for all reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors r are based on F, with F set to zero for negative F². The observed criterion of F²> σ(F²) is used only for calculating _R_factor_obs 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
S1	0.15786 (3)	0.39028 (9)	0.21029 (4)	0.0603 (3)
O1	0.0644 (2)	0.1533 (3)	0.2133 (2)	0.160 (2)
O2	0.09634 (12)	0.2166 (2)	0.32974 (14)	0.0989 (8)
N1	0.18925 (8)	0.4519 (2)	0.36024 (12)	0.0541 (6)
N2	0.25103 (9)	0.3361 (3)	0.31289 (13)	0.0609 (6)
N3	0.09537 (8)	0.4953 (2)	0.29814 (11)	0.0501 (5)
C1	0.2878 (2)	0.1990 (5)	0.4312 (3)	0.0978 (13)
C2	0.28970 (13)	0.3369 (4)	0.3888 (2)	0.0751 (10)
C3	0.26909 (15)	0.2710 (4)	0.2519 (2)	0.0711 (9)
C4	0.2978 (2)	0.3754 (6)	0.2145 (3)	0.0938 (12)
C5	0.20159 (10)	0.3920 (3)	0.30284 (15)	0.0525 (6)
C6	0.13943 (10)	0.5138 (3)	0.35113 (14)	0.0466 (6)
C7	0.09389 (10)	0.3966 (3)	0.23784 (14)	0.0532 (6)
C8	0.08323 (13)	0.2419 (3)	0.2586 (2)	0.0658 (8)
C9	0.0883 (3)	0.0700 (5)	0.3531 (3)	0.116 (2)
C10	0.04929 (12)	0.4380 (3)	0.1666 (2)	0.0583 (7)
C11	0.05632 (10)	0.5779 (3)	0.1292 (2)	0.0546 (7)
C12	0.06181 (12)	0.5777 (4)	0.0564 (2)	0.0683 (8)
C13	0.06429 (14)	0.7031 (4)	0.0176 (2)	0.0817 (10)
C14	0.06201 (14)	0.8311 (4)	0.0518 (2)	0.0833 (10)
C15	0.05759 (14)	0.8367 (4)	0.1242 (3)	0.0821 (11)
C16	0.05452 (12)	0.7095 (3)	0.1636 (2)	0.0682 (8)
C17	0.13755 (10)	0.6153 (3)	0.41339 (13)	0.0462 (6)
C18	0.18263 (12)	0.6422 (3)	0.4728 (2)	0.0633 (8)
C19	0.18026 (14)	0.7367 (4)	0.5302 (2)	0.0726 (9)
C20	0.13257 (13)	0.8025 (3)	0.5291 (2)	0.0644 (8)
C21	0.08780 (13)	0.7767 (3)	0.4705 (2)	0.0624 (7)
C22	0.08992 (11)	0.6839 (3)	0.4127 (2)	0.0554 (7)
H1A	0.3120 (18)	0.203 (5)	0.478 (3)	0.125 (15)*
H1B	0.2484 (17)	0.186 (4)	0.433 (2)	0.112 (13)*
H1C	0.3007 (16)	0.108 (4)	0.404 (2)	0.116 (13)*
H2A	0.2818 (13)	0.420 (4)	0.4158 (18)	0.089 (11)*
H2B	0.3242 (16)	0.352 (4)	0.3795 (19)	0.102 (12)*
H3A	0.2372 (13)	0.227 (4)	0.2134 (17)	0.081 (10)*
H3B	0.2944 (13)	0.195 (4)	0.2765 (17)	0.082 (10)*
H4A	0.3267 (16)	0.424 (4)	0.250 (2)	0.110 (14)*
H4B	0.2709 (19)	0.452 (5)	0.188 (3)	0.144 (18)*
H4C	0.3102 (16)	0.329 (4)	0.174 (2)	0.117 (13)*
H9A	0.100 (2)	0.003 (7)	0.319 (4)	0.21 (3)*
H9B	0.113 (2)	0.060 (6)	0.404 (3)	0.16 (2)*
H9C	0.046 (2)	0.065 (6)	0.345 (3)	0.17 (2)*
H10A	0.0154 (12)	0.439 (3)	0.1822 (16)	0.074 (9)*
H10B	0.0462 (10)	0.365 (3)	0.1320 (15)	0.057 (8)*
H12	0.0624 (12)	0.488 (4)	0.0324 (17)	0.083 (10)*
H13	0.0670 (14)	0.698 (4)	−0.040 (2)	0.109 (12)*
H14	0.0613 (16)	0.921 (5)	0.023 (2)	0.118 (14)*
H15	0.0548 (14)	0.917 (4)	0.153 (2)	0.097 (12)*
H16	0.0493 (11)	0.711 (3)	0.2141 (17)	0.071 (9)*
H18	0.2169 (12)	0.595 (3)	0.4744 (15)	0.071 (9)*
H19	0.2133 (13)	0.752 (4)	0.5693 (18)	0.086 (10)*
H20	0.1323 (11)	0.864 (3)	0.5709 (16)	0.072 (9)*
H21	0.0544 (13)	0.823 (3)	0.4693 (16)	0.076 (9)*
H22	0.0562 (12)	0.668 (3)	0.3717 (16)	0.074 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0571 (4)	0.0749 (5)	0.0516 (4)	0.0054 (4)	0.0199 (3)	−0.0017 (4)
O1	0.312 (5)	0.060 (2)	0.091 (2)	−0.049 (2)	0.030 (2)	−0.0144 (15)
O2	0.166 (2)	0.0621 (15)	0.077 (2)	−0.0269 (15)	0.048 (2)	0.0049 (12)
N1	0.0504 (12)	0.0565 (13)	0.0552 (13)	0.0061 (10)	0.0145 (10)	−0.0033 (11)
N2	0.0519 (13)	0.0657 (15)	0.0671 (15)	0.0105 (11)	0.0202 (11)	−0.0058 (12)
N3	0.0492 (12)	0.0488 (12)	0.0537 (12)	−0.0024 (10)	0.0166 (10)	−0.0057 (10)
C1	0.102 (3)	0.113 (4)	0.074 (3)	0.024 (3)	0.019 (2)	0.014 (2)
C2	0.052 (2)	0.090 (3)	0.079 (2)	0.014 (2)	0.011 (2)	−0.016 (2)
C3	0.070 (2)	0.073 (2)	0.077 (2)	0.016 (2)	0.032 (2)	−0.007 (2)
C4	0.086 (3)	0.111 (3)	0.100 (3)	0.001 (3)	0.051 (3)	−0.002 (3)
C5	0.0524 (15)	0.0479 (15)	0.060 (2)	0.0000 (12)	0.0194 (12)	0.0004 (13)
C6	0.0468 (14)	0.0442 (14)	0.0494 (14)	−0.0007 (11)	0.0147 (12)	0.0036 (11)
C7	0.0548 (15)	0.0486 (15)	0.058 (2)	−0.0041 (12)	0.0184 (12)	−0.0070 (13)
C8	0.085 (2)	0.051 (2)	0.065 (2)	−0.007 (2)	0.026 (2)	−0.008 (2)
C9	0.197 (6)	0.062 (2)	0.110 (4)	−0.016 (3)	0.076 (4)	0.015 (2)
C10	0.057 (2)	0.057 (2)	0.058 (2)	−0.0086 (14)	0.0107 (14)	−0.0108 (14)
C11	0.0433 (13)	0.055 (2)	0.059 (2)	−0.0032 (12)	0.0034 (11)	−0.0067 (13)
C12	0.068 (2)	0.067 (2)	0.067 (2)	0.000 (2)	0.0145 (15)	−0.007 (2)
C13	0.082 (2)	0.082 (3)	0.079 (2)	−0.009 (2)	0.019 (2)	0.012 (2)
C14	0.070 (2)	0.074 (2)	0.094 (3)	−0.011 (2)	0.004 (2)	0.016 (2)
C15	0.071 (2)	0.055 (2)	0.104 (3)	−0.001 (2)	−0.001 (2)	−0.013 (2)
C16	0.062 (2)	0.065 (2)	0.071 (2)	0.0008 (15)	0.0076 (15)	−0.013 (2)
C17	0.0497 (14)	0.0435 (13)	0.0476 (14)	−0.0019 (11)	0.0170 (11)	0.0019 (11)
C18	0.059 (2)	0.074 (2)	0.053 (2)	0.010 (2)	0.0096 (14)	−0.0057 (14)
C19	0.070 (2)	0.085 (2)	0.055 (2)	0.006 (2)	0.004 (2)	−0.011 (2)
C20	0.082 (2)	0.058 (2)	0.056 (2)	0.002 (2)	0.022 (2)	−0.0067 (14)
C21	0.065 (2)	0.055 (2)	0.072 (2)	0.0058 (15)	0.028 (2)	−0.0065 (15)
C22	0.055 (2)	0.051 (2)	0.061 (2)	−0.0002 (13)	0.0180 (14)	−0.0054 (13)

Geometric parameters (Å, º)

S1—C5	1.752 (3)	C9—H9B	0.98 (5)
S1—C7	1.849 (3)	C9—H9C	1.07 (5)
O1—C8	1.171 (4)	C10—C11	1.500 (4)
O2—C8	1.274 (3)	C10—H10A	0.99 (3)
O2—C9	1.454 (4)	C10—H10B	0.91 (3)
N1—C5	1.304 (3)	C11—C16	1.377 (4)
N1—C6	1.369 (3)	C11—C12	1.379 (4)
N2—C5	1.335 (3)	C12—C13	1.372 (5)
N2—C3	1.455 (4)	C12—H12	0.94 (3)
N2—C2	1.466 (4)	C13—C14	1.349 (5)
N3—C6	1.279 (3)	C13—H13	1.07 (4)
N3—C7	1.426 (3)	C14—C15	1.364 (5)
C1—C2	1.502 (6)	C14—H14	0.98 (4)
C1—H1A	0.91 (4)	C15—C16	1.396 (5)
C1—H1B	1.03 (4)	C15—H15	0.92 (4)
C1—H1C	1.08 (4)	C16—H16	0.97 (3)
C2—H2A	0.96 (3)	C17—C18	1.372 (4)
C2—H2B	0.96 (4)	C17—C22	1.375 (4)
C3—C4	1.494 (5)	C18—C19	1.382 (4)
C3—H3A	1.00 (3)	C18—H18	0.98 (3)
C3—H3B	0.98 (3)	C19—C20	1.363 (4)
C4—H4A	0.96 (4)	C19—H19	0.96 (3)
C4—H4B	1.02 (5)	C20—C21	1.356 (4)
C4—H4C	0.98 (4)	C20—H20	0.96 (3)
C6—C17	1.489 (3)	C21—C22	1.377 (4)
C7—C10	1.525 (4)	C21—H21	0.95 (3)
C7—C8	1.525 (4)	C22—H22	0.98 (3)
C9—H9A	0.99 (7)
C5—S1—C7	96.46 (12)	O2—C9—H9B	105 (3)
C8—O2—C9	117.0 (3)	H9A—C9—H9B	109 (5)
C5—N1—C6	120.6 (2)	O2—C9—H9C	103 (3)
C5—N2—C3	123.3 (3)	H9A—C9—H9C	112 (5)
C5—N2—C2	119.6 (2)	H9B—C9—H9C	119 (4)
C3—N2—C2	117.1 (2)	C11—C10—C7	116.8 (2)
C6—N3—C7	120.0 (2)	C11—C10—H10A	110.9 (17)
C2—C1—H1A	110 (3)	C7—C10—H10A	105.3 (16)
C2—C1—H1B	107 (2)	C11—C10—H10B	108.4 (17)
H1A—C1—H1B	113 (3)	C7—C10—H10B	108.0 (17)
C2—C1—H1C	112 (2)	H10A—C10—H10B	107 (2)
H1A—C1—H1C	105 (3)	C16—C11—C12	118.0 (3)
H1B—C1—H1C	111 (3)	C16—C11—C10	122.0 (3)
N2—C2—C1	112.0 (3)	C12—C11—C10	119.9 (3)
N2—C2—H2A	108.0 (19)	C13—C12—C11	122.1 (3)
C1—C2—H2A	111.5 (19)	C13—C12—H12	119.5 (19)
N2—C2—H2B	104 (2)	C11—C12—H12	118 (2)
C1—C2—H2B	113 (2)	C14—C13—C12	119.2 (4)
H2A—C2—H2B	108 (3)	C14—C13—H13	121 (2)
N2—C3—C4	112.9 (3)	C12—C13—H13	120 (2)
N2—C3—H3A	109.6 (17)	C13—C14—C15	120.7 (4)
C4—C3—H3A	110.4 (18)	C13—C14—H14	119 (2)
N2—C3—H3B	104.8 (18)	C15—C14—H14	120 (2)
C4—C3—H3B	109.2 (18)	C14—C15—C16	120.3 (4)
H3A—C3—H3B	110 (3)	C14—C15—H15	129 (2)
C3—C4—H4A	112 (2)	C16—C15—H15	111 (2)
C3—C4—H4B	109 (3)	C11—C16—C15	119.6 (3)
H4A—C4—H4B	107 (4)	C11—C16—H16	118.7 (18)
C3—C4—H4C	112 (2)	C15—C16—H16	121.6 (18)
H4A—C4—H4C	112 (3)	C18—C17—C22	118.3 (2)
H4B—C4—H4C	105 (3)	C18—C17—C6	121.5 (2)
N1—C5—N2	119.3 (2)	C22—C17—C6	120.2 (2)
N1—C5—S1	123.4 (2)	C17—C18—C19	120.8 (3)
N2—C5—S1	117.2 (2)	C17—C18—H18	119.6 (16)
N3—C6—N1	129.3 (2)	C19—C18—H18	119.6 (17)
N3—C6—C17	117.1 (2)	C20—C19—C18	120.1 (3)
N1—C6—C17	113.6 (2)	C20—C19—H19	123.6 (19)
N3—C7—C10	110.7 (2)	C18—C19—H19	116.3 (19)
N3—C7—C8	112.0 (2)	C21—C20—C19	119.5 (3)
C10—C7—C8	107.8 (2)	C21—C20—H20	123.0 (17)
N3—C7—S1	113.5 (2)	C19—C20—H20	117.5 (17)
C10—C7—S1	106.6 (2)	C20—C21—C22	120.8 (3)
C8—C7—S1	105.9 (2)	C20—C21—H21	119.7 (18)
O1—C8—O2	122.4 (3)	C22—C21—H21	119.5 (18)
O1—C8—C7	123.2 (3)	C17—C22—C21	120.5 (3)
O2—C8—C7	114.4 (3)	C17—C22—H22	121.8 (17)
O2—C9—H9A	108 (4)	C21—C22—H22	117.7 (17)
C5—S1—C7—C8	−80.8 (2)	S1—C7—C8—O2	100.5 (2)
C5—S1—C7—C10	164.6 (2)	S1—C7—C8—O1	−79.7 (3)
C5—S1—C7—N3	42.5 (2)	N3—C7—C8—O2	−23.6 (3)
C7—S1—C5—N1	−28.3 (3)	N3—C7—C8—O1	156.0 (3)
C7—S1—C5—N2	155.7 (2)	N3—C7—C10—C11	66.1 (3)
C9—O2—C8—O1	1.6 (4)	S1—C7—C10—C11	−57.7 (3)
C9—O2—C8—C7	−178.5 (2)	C10—C7—C8—O2	−145.7 (2)
C6—N1—C5—S1	2.2 (4)	C10—C7—C8—O1	34.1 (3)
C5—N1—C6—C17	−161.9 (2)	C8—C7—C10—C11	−171.1 (2)
C5—N1—C6—N3	18.9 (4)	C7—C10—C11—C12	116.6 (3)
C6—N1—C5—N2	178.0 (2)	C7—C10—C11—C16	−67.2 (3)
C3—N2—C5—S1	−2.0 (4)	C10—C11—C16—C15	−175.6 (2)
C2—N2—C5—S1	178.9 (2)	C10—C11—C12—C13	175.1 (2)
C3—N2—C5—N1	−178.1 (2)	C12—C11—C16—C15	0.7 (4)
C2—N2—C5—N1	2.7 (4)	C16—C11—C12—C13	−1.4 (4)
C2—N2—C3—C4	−87.5 (3)	C11—C12—C13—C14	0.8 (4)
C5—N2—C2—C1	93.4 (3)	C12—C13—C14—C15	0.3 (4)
C3—N2—C2—C1	−85.7 (3)	C13—C14—C15—C16	−0.9 (4)
C5—N2—C3—C4	93.3 (3)	C14—C15—C16—C11	0.4 (4)
C6—N3—C7—S1	−34.8 (3)	C6—C17—C22—C21	179.3 (2)
C7—N3—C6—N1	0.8 (4)	C6—C17—C18—C19	−179.9 (2)
C6—N3—C7—C8	85.0 (3)	C18—C17—C22—C21	−0.2 (4)
C6—N3—C7—C10	−154.6 (2)	C22—C17—C18—C19	−0.4 (4)
C7—N3—C6—C17	−178.2 (2)	C17—C18—C19—C20	1.1 (4)
N3—C6—C17—C18	179.9 (2)	C18—C19—C20—C21	−1.2 (4)
N1—C6—C17—C18	0.6 (4)	C19—C20—C21—C22	0.5 (4)
N3—C6—C17—C22	0.3 (4)	C20—C21—C22—C17	0.1 (4)
N1—C6—C17—C22	−178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N1	0.97 (4)	2.33 (3)	2.702 (4)	102 (2)
C3—H3A···S1	1.01 (3)	2.52 (4)	2.955 (4)	106 (2)
C10—H10B···O1	0.92 (3)	2.43 (3)	2.763 (4)	102 (2)
C15—H15···O1^i	0.93 (4)	2.43 (4)	3.334 (5)	165 (3)
C16—H16···N3	0.97 (3)	2.60 (3)	3.108 (4)	113 (2)
C18—H18···N1	0.98 (3)	2.41 (3)	2.754 (4)	100 (2)

Symmetry code: (i) x, y+1, z.