Crystal structure, Hirshfeld surface analysis, inter­action energy and DFT studies of 4-[(4-allyl-2-meth­oxy­phen­oxy)meth­yl]-1-(4-meth­oxy­phen­yl)-1H-1,2,3-triazole

In the crystal structure, C—H_Mthphn...O_Mthphn (Mthphn = meth­oxy­phen­yl) hydrogen bonds form corrugated layers parallel to (100) that are connected along the a axis by C—H...π(ring) and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.132
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.48 Report
PLAT411_ALERT_2_C Short Inter H...H Contact  H14      ..H14      .       2.11 Ang.
                                               1-x,-1-y,1-z  =      3_646 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         28 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

4-[(4-Allyl-2-methoxyphenoxy)methyl]-1-(4-methoxyphenyl)-1H-1,2,3-triazole

Crystal data

C20H21N3O3	F(000) = 744
Mr = 351.40	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.212 (3) Å	Cell parameters from 9905 reflections
b = 5.9584 (12) Å	θ = 2.2–29.3°
c = 19.450 (4) Å	µ = 0.09 mm^−1
β = 110.537 (3)°	T = 150 K
V = 1759.5 (6) Å^3	Block, colourless
Z = 4	0.38 × 0.33 × 0.32 mm

Data collection

Bruker SMART APEX CCD diffractometer	4788 independent reflections
Radiation source: fine-focus sealed tube	3978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.3°, θmin = 2.2°
φ and ω scans	h = −22→21
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −8→8
Tmin = 0.88, Tmax = 0.97	l = −26→26
32548 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: difference Fourier map
wR(F^2) = 0.132	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0858P)^2 + 0.1761P] where P = (Fo^2 + 2Fc^2)/3
4788 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 10 sec/frame.

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	0.22952 (5)	−0.13314 (13)	0.17036 (4)	0.02658 (18)
O2	0.13208 (6)	0.21761 (14)	0.12923 (5)	0.0343 (2)
O3	0.45455 (5)	0.16414 (14)	0.66870 (4)	0.03039 (19)
N1	0.35850 (6)	−0.22912 (14)	0.39234 (4)	0.02175 (18)
N2	0.36971 (7)	−0.45263 (15)	0.38817 (5)	0.0295 (2)
N3	0.34449 (6)	−0.50475 (15)	0.31817 (5)	0.0293 (2)
C1	0.19702 (6)	−0.09553 (18)	0.09610 (5)	0.0237 (2)
C2	0.14239 (7)	0.09424 (18)	0.07352 (6)	0.0253 (2)
C3	0.10348 (7)	0.14141 (19)	−0.00049 (6)	0.0298 (2)
H3	0.0643 (10)	0.270 (3)	−0.0155 (8)	0.039 (4)*
C4	0.11724 (7)	0.0034 (2)	−0.05366 (6)	0.0314 (2)
C5	0.17275 (8)	−0.1789 (2)	−0.03076 (6)	0.0331 (3)
H5	0.1821 (11)	−0.278 (3)	−0.0671 (9)	0.043 (4)*
C6	0.21292 (7)	−0.2286 (2)	0.04393 (6)	0.0290 (2)
H6	0.2500 (9)	−0.359 (2)	0.0595 (8)	0.031 (3)*
C7	0.07032 (8)	0.0524 (3)	−0.13467 (7)	0.0394 (3)
H7A	0.0142 (12)	0.144 (3)	−0.1426 (10)	0.051 (5)*
H7B	0.0508 (15)	−0.099 (4)	−0.1622 (13)	0.086 (7)*
C8	0.12580 (9)	0.1689 (3)	−0.17069 (7)	0.0451 (3)
H8	0.1781 (14)	0.088 (3)	−0.1728 (11)	0.066 (5)*
C9	0.10758 (12)	0.3641 (4)	−0.20373 (8)	0.0597 (5)
H9	0.0469 (18)	0.449 (4)	−0.2068 (14)	0.099 (8)*
H9B	0.1442 (14)	0.434 (4)	−0.2293 (12)	0.071 (6)*
C10	0.28746 (7)	−0.31981 (18)	0.19593 (6)	0.0249 (2)
H10A	0.2564 (9)	−0.465 (2)	0.1772 (8)	0.028 (3)*
H10B	0.3377 (9)	−0.304 (2)	0.1801 (7)	0.026 (3)*
C11	0.31793 (6)	−0.31470 (17)	0.27769 (6)	0.0230 (2)
C12	0.32669 (7)	−0.13692 (17)	0.32445 (6)	0.0232 (2)
H12	0.3179 (9)	0.025 (2)	0.3173 (8)	0.031 (3)*
C13	0.38036 (6)	−0.12328 (16)	0.46256 (5)	0.0210 (2)
C14	0.44278 (7)	−0.22392 (18)	0.52340 (6)	0.0246 (2)
H14	0.4712 (9)	−0.363 (2)	0.5174 (8)	0.029 (3)*
C15	0.46548 (7)	−0.12254 (18)	0.59111 (6)	0.0249 (2)
H15	0.5101 (11)	−0.194 (3)	0.6325 (9)	0.040 (4)*
C16	0.42651 (6)	0.08019 (17)	0.59909 (5)	0.0226 (2)
C17	0.36412 (7)	0.17993 (17)	0.53822 (6)	0.0240 (2)
H17	0.3362 (10)	0.328 (3)	0.5429 (8)	0.039 (4)*
C18	0.34120 (7)	0.07693 (17)	0.46974 (5)	0.0232 (2)
H18	0.2975 (8)	0.148 (2)	0.4265 (7)	0.025 (3)*
C19	0.41329 (10)	0.3629 (2)	0.68101 (7)	0.0373 (3)
H19A	0.3554 (13)	0.341 (3)	0.6731 (10)	0.050 (5)*
H19B	0.4447 (11)	0.399 (3)	0.7326 (10)	0.047 (4)*
H19C	0.4223 (12)	0.480 (3)	0.6507 (10)	0.056 (5)*
C20	0.07124 (9)	0.3989 (2)	0.10918 (8)	0.0374 (3)
H20A	0.0124 (13)	0.347 (3)	0.0825 (11)	0.060 (5)*
H20B	0.0740 (10)	0.471 (3)	0.1585 (10)	0.047 (4)*
H20C	0.0901 (10)	0.514 (3)	0.0820 (9)	0.046 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0318 (4)	0.0271 (4)	0.0177 (4)	0.0090 (3)	0.0046 (3)	0.0019 (3)
O2	0.0408 (5)	0.0298 (4)	0.0294 (4)	0.0122 (3)	0.0088 (3)	0.0000 (3)
O3	0.0365 (4)	0.0303 (4)	0.0194 (4)	0.0041 (3)	0.0036 (3)	−0.0023 (3)
N1	0.0260 (4)	0.0191 (4)	0.0178 (4)	0.0022 (3)	0.0048 (3)	0.0024 (3)
N2	0.0424 (5)	0.0192 (4)	0.0227 (4)	0.0025 (4)	0.0063 (4)	0.0018 (3)
N3	0.0394 (5)	0.0216 (4)	0.0222 (4)	0.0017 (4)	0.0051 (4)	0.0006 (3)
C1	0.0232 (4)	0.0261 (5)	0.0187 (5)	0.0007 (4)	0.0035 (3)	0.0012 (4)
C2	0.0241 (5)	0.0244 (5)	0.0251 (5)	0.0012 (4)	0.0057 (4)	0.0009 (4)
C3	0.0269 (5)	0.0297 (5)	0.0272 (5)	0.0027 (4)	0.0025 (4)	0.0060 (4)
C4	0.0275 (5)	0.0396 (6)	0.0217 (5)	−0.0023 (4)	0.0018 (4)	0.0041 (4)
C5	0.0338 (6)	0.0409 (6)	0.0209 (5)	0.0036 (5)	0.0051 (4)	−0.0023 (5)
C6	0.0289 (5)	0.0317 (5)	0.0229 (5)	0.0057 (4)	0.0045 (4)	−0.0008 (4)
C7	0.0349 (6)	0.0502 (8)	0.0241 (6)	−0.0033 (5)	−0.0010 (4)	0.0065 (5)
C8	0.0337 (6)	0.0741 (10)	0.0234 (6)	0.0000 (6)	0.0047 (5)	0.0015 (6)
C9	0.0578 (9)	0.0807 (12)	0.0296 (7)	−0.0256 (9)	0.0014 (6)	0.0125 (7)
C10	0.0273 (5)	0.0240 (5)	0.0199 (5)	0.0057 (4)	0.0040 (4)	0.0003 (4)
C11	0.0238 (4)	0.0222 (5)	0.0207 (5)	0.0020 (3)	0.0051 (4)	0.0015 (4)
C12	0.0267 (5)	0.0221 (5)	0.0189 (5)	0.0035 (4)	0.0055 (4)	0.0036 (4)
C13	0.0240 (4)	0.0206 (4)	0.0170 (4)	−0.0005 (3)	0.0055 (3)	0.0017 (3)
C14	0.0270 (5)	0.0238 (5)	0.0217 (5)	0.0059 (4)	0.0070 (4)	0.0035 (4)
C15	0.0258 (5)	0.0264 (5)	0.0196 (5)	0.0043 (4)	0.0044 (4)	0.0042 (4)
C16	0.0247 (4)	0.0234 (5)	0.0185 (4)	−0.0017 (3)	0.0061 (3)	0.0005 (4)
C17	0.0287 (5)	0.0194 (4)	0.0225 (5)	0.0020 (4)	0.0074 (4)	0.0016 (4)
C18	0.0263 (5)	0.0206 (4)	0.0197 (5)	0.0024 (3)	0.0045 (4)	0.0042 (4)
C19	0.0553 (8)	0.0269 (6)	0.0247 (6)	0.0042 (5)	0.0079 (5)	−0.0040 (4)
C20	0.0363 (6)	0.0290 (6)	0.0471 (7)	0.0098 (5)	0.0148 (5)	0.0040 (5)

Geometric parameters (Å, º)

O1—C1	1.3712 (12)	C8—H8	0.99 (2)
O1—C10	1.4279 (12)	C9—H9	1.09 (3)
O2—C2	1.3673 (13)	C9—H9B	0.99 (2)
O2—C20	1.4220 (14)	C10—C11	1.4908 (14)
O3—C16	1.3631 (12)	C10—H10A	1.002 (14)
O3—C19	1.4213 (15)	C10—H10B	0.971 (14)
N1—N2	1.3504 (13)	C11—C12	1.3708 (15)
N1—C12	1.3541 (13)	C12—H12	0.978 (15)
N1—C13	1.4315 (13)	C13—C18	1.3812 (14)
N2—N3	1.3142 (13)	C13—C14	1.3942 (14)
N3—C11	1.3600 (13)	C14—C15	1.3764 (15)
C1—C6	1.3814 (15)	C14—H14	0.975 (14)
C1—C2	1.4082 (14)	C15—C16	1.3969 (15)
C2—C3	1.3827 (15)	C15—H15	0.970 (17)
C3—C4	1.3991 (17)	C16—C17	1.3921 (14)
C3—H3	0.974 (16)	C17—C18	1.3935 (14)
C4—C5	1.3808 (17)	C17—H17	1.010 (16)
C4—C7	1.5185 (16)	C18—H18	0.984 (13)
C5—C6	1.3995 (16)	C19—H19A	0.905 (19)
C5—H5	0.972 (17)	C19—H19B	0.977 (18)
C6—H6	0.964 (15)	C19—H19C	0.956 (19)
C7—C8	1.491 (2)	C20—H20A	0.96 (2)
C7—H7A	1.025 (18)	C20—H20B	1.037 (18)
C7—H7B	1.04 (2)	C20—H20C	0.979 (17)
C8—C9	1.312 (2)
O1···O2	2.5723 (13)	C18···H12	2.871 (15)
O1···H12	2.870 (14)	C19···H17	2.543 (15)
O2···H10A^i	2.681 (14)	C19···O1^vi	3.3285 (19)
O3···H19B^ii	2.579 (18)	C20···H3	2.508 (15)
N2···C18^iii	3.3320 (15)	C20···H10A^i	2.938 (15)
N2···H14	2.532 (15)	H3···H7A	2.43 (2)
N2···H18^iii	2.864 (13)	H3···H20A	2.38 (3)
N2···H14^iv	2.812 (15)	H3···H20C	2.31 (2)
N3···H12^iii	2.834 (12)	H5···H7B	2.52 (3)
N3···H15^iv	2.848 (18)	H6···H10A	2.34 (2)
C12···C15^v	3.5436 (18)	H6···H10B	2.30 (2)
C13···C15^v	3.3633 (17)	H6···C17^ix	2.791 (14)
C13···C14^v	3.4679 (17)	H6···C18^ix	2.955 (15)
C14···C14^v	3.5463 (18)	H7A···H9	2.37 (3)
C14···C18^v	3.5668 (18)	H7B···H9^x	2.50 (4)
C19···C1^vi	3.589 (2)	H8···N3^ix	2.808 (1)
C19···C10^vi	3.4746 (19)	H9···H20B^xi	2.50 (3)
C1···H20C^iii	2.856 (18)	H9B···O2^xii	2.837 (5)
C3···H20C	2.792 (17)	H10B···C16^ix	2.976 (14)
C3···H20A	2.82 (2)	H10B···C19^xii	2.897 (13)
C4···H20A^vii	2.88 (2)	H12···H18	2.377 (19)
C5···H20A^vii	2.98 (2)	H14···H14^iv	2.107 (19)
C6···H20C^iii	2.811 (17)	H15···H19C^iii	2.51 (3)
C6···H10A	2.814 (4)	H15···H19B^ii	2.53 (2)
C6···H10B	2.748 (13)	H17···H19A	2.44 (2)
C9···H7B^viii	2.96 (2)	H17···H19C	2.26 (2)
C10···H6	2.517 (15)	H18···C8^vi	2.970 (13)
C12···H18	2.776 (13)	H19A···O1^vi	2.67 (2)
C15···H19C^iii	2.830 (18)	H19A···C1^vi	2.91 (2)
C17···H19C	2.725 (18)	H19C···H10B^vi	2.55 (2)
C17···H19A	2.843 (19)
C1—O1—C10	117.19 (8)	C11—C10—H10A	110.0 (8)
C2—O2—C20	117.19 (10)	O1—C10—H10B	109.5 (8)
C16—O3—C19	117.42 (9)	C11—C10—H10B	109.6 (8)
N2—N1—C12	110.77 (8)	H10A—C10—H10B	109.9 (11)
N2—N1—C13	119.89 (8)	N3—C11—C12	108.73 (9)
C12—N1—C13	129.33 (9)	N3—C11—C10	121.31 (9)
N3—N2—N1	107.21 (8)	C12—C11—C10	129.94 (9)
N2—N3—C11	108.86 (9)	N1—C12—C11	104.42 (9)
O1—C1—C6	125.33 (9)	N1—C12—H12	121.7 (8)
O1—C1—C2	115.27 (9)	C11—C12—H12	133.8 (8)
C6—C1—C2	119.40 (10)	C18—C13—C14	120.55 (9)
O2—C2—C3	125.30 (10)	C18—C13—N1	120.54 (8)
O2—C2—C1	115.02 (9)	C14—C13—N1	118.91 (9)
C3—C2—C1	119.68 (10)	C15—C14—C13	119.62 (10)
C2—C3—C4	121.15 (10)	C15—C14—H14	120.6 (8)
C2—C3—H3	118.9 (9)	C13—C14—H14	119.7 (8)
C4—C3—H3	119.9 (9)	C14—C15—C16	120.42 (9)
C5—C4—C3	118.60 (10)	C14—C15—H15	118.3 (9)
C5—C4—C7	121.24 (11)	C16—C15—H15	121.3 (9)
C3—C4—C7	120.15 (11)	O3—C16—C17	125.29 (9)
C4—C5—C6	120.98 (11)	O3—C16—C15	114.93 (9)
C4—C5—H5	119.5 (10)	C17—C16—C15	119.78 (9)
C6—C5—H5	119.5 (10)	C16—C17—C18	119.70 (9)
C1—C6—C5	120.15 (10)	C16—C17—H17	120.7 (9)
C1—C6—H6	119.3 (9)	C18—C17—H17	119.6 (9)
C5—C6—H6	120.5 (9)	C13—C18—C17	119.94 (9)
C8—C7—C4	114.32 (10)	C13—C18—H18	120.2 (8)
C8—C7—H7A	109.4 (10)	C17—C18—H18	119.8 (8)
C4—C7—H7A	110.7 (10)	O3—C19—H19A	111.9 (11)
C8—C7—H7B	106.6 (13)	O3—C19—H19B	104.5 (10)
C4—C7—H7B	108.6 (13)	H19A—C19—H19B	110.0 (15)
H7A—C7—H7B	106.9 (16)	O3—C19—H19C	108.7 (11)
C9—C8—C7	125.01 (16)	H19A—C19—H19C	111.8 (15)
C9—C8—H8	117.5 (12)	H19B—C19—H19C	109.6 (15)
C7—C8—H8	117.4 (12)	O2—C20—H20A	111.5 (11)
C8—C9—H9	118.7 (14)	O2—C20—H20B	105.0 (9)
C8—C9—H9B	123.1 (13)	H20A—C20—H20B	110.1 (14)
H9—C9—H9B	118.0 (18)	O2—C20—H20C	111.3 (9)
O1—C10—C11	106.67 (8)	H20A—C20—H20C	111.8 (15)
O1—C10—H10A	111.1 (8)	H20B—C20—H20C	106.8 (14)
C12—N1—N2—N3	−0.64 (12)	N2—N3—C11—C12	−0.22 (12)
C13—N1—N2—N3	179.75 (8)	N2—N3—C11—C10	178.55 (9)
N1—N2—N3—C11	0.52 (12)	O1—C10—C11—N3	154.23 (9)
C10—O1—C1—C6	2.77 (15)	O1—C10—C11—C12	−27.29 (15)
C10—O1—C1—C2	−178.10 (9)	N2—N1—C12—C11	0.49 (11)
C20—O2—C2—C3	5.04 (16)	C13—N1—C12—C11	−179.94 (9)
C20—O2—C2—C1	−174.39 (10)	N3—C11—C12—N1	−0.16 (11)
O1—C1—C2—O2	2.06 (14)	C10—C11—C12—N1	−178.80 (10)
C6—C1—C2—O2	−178.75 (10)	N2—N1—C13—C18	−155.77 (10)
O1—C1—C2—C3	−177.40 (9)	C12—N1—C13—C18	24.69 (15)
C6—C1—C2—C3	1.79 (16)	N2—N1—C13—C14	25.16 (14)
O2—C2—C3—C4	−179.27 (10)	C12—N1—C13—C14	−154.37 (10)
C1—C2—C3—C4	0.13 (16)	C18—C13—C14—C15	−0.03 (15)
C2—C3—C4—C5	−1.79 (17)	N1—C13—C14—C15	179.04 (9)
C2—C3—C4—C7	177.07 (10)	C13—C14—C15—C16	−0.10 (16)
C3—C4—C5—C6	1.55 (18)	C19—O3—C16—C17	3.73 (16)
C7—C4—C5—C6	−177.30 (11)	C19—O3—C16—C15	−176.25 (10)
O1—C1—C6—C5	177.07 (10)	C14—C15—C16—O3	−179.83 (9)
C2—C1—C6—C5	−2.03 (17)	C14—C15—C16—C17	0.19 (15)
C4—C5—C6—C1	0.35 (18)	O3—C16—C17—C18	179.87 (9)
C5—C4—C7—C8	−80.52 (17)	C15—C16—C17—C18	−0.16 (15)
C3—C4—C7—C8	100.66 (15)	C14—C13—C18—C17	0.06 (15)
C4—C7—C8—C9	−121.28 (16)	N1—C13—C18—C17	−178.99 (9)
C1—O1—C10—C11	176.23 (8)	C16—C17—C18—C13	0.03 (15)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y−1, z; (iv) −x+1, −y−1, −z+1; (v) −x+1, −y, −z+1; (vi) x, −y+1/2, z+1/2; (vii) −x, −y, −z; (viii) −x, y+1/2, −z−1/2; (ix) x, −y−1/2, z−1/2; (x) −x, y−1/2, −z−1/2; (xi) −x, −y+1, −z; (xii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the benzene ring C (C13–C18).

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg3^xiii	0.964 (15)	2.825 (15)	3.5168 (15)	129.4 (11)
C19—H19B···O3^xiv	0.977 (18)	2.578 (18)	3.4587 (16)	150.0 (14)

Symmetry codes: (xiii) x, −y−3/2, z−3/2; (xiv) −x+1, y+1/2, −z+3/2.