Tetrakis­[(4-cyano­phenoxy)­methyl]­methane

The title compound, C₃₃H₂₄N₄O₄, is a symmetric mol­ecule with four chemically identical substituents bonded to a central C atom. In the crystal structure, there are C—H...N, C—H...O, C—H...C, C—H...π(C[triple bond]N) and edge-to-face aromatic interactions. The four chemically identical substituents have different conformations.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.062
• wR factor = 0.145
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.83 Sigma

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O4
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C31
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C27
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C30
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C9     -   C12    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C16    -   C19    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C23    -   C26    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C30    -   C33    ...       1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H32    ..  N2      ..       2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  N1      ..       2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28    ..  O1      ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  N2      ..       2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  N2      ..       2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  N3      ..       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  N3      ..       2.77 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3     ..  N3      ..       3.79 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXTL (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C33H24N4O4	F(000) = 1128
Mr = 540.56	Dx = 1.238 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2069 (17) Å	Cell parameters from 2967 reflections
b = 12.703 (2) Å	θ = 2.5–22.2°
c = 20.750 (3) Å	µ = 0.08 mm^−1
β = 101.003 (2)°	T = 293 K
V = 2899.7 (8) Å^3	Parallelepiped, colourless
Z = 4	0.60 × 0.50 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5683 independent reflections
Radiation source: fine-focus sealed tube	3685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SABABS; Sheldrick, 1997a)	h = −13→13
Tmin = 0.952, Tmax = 0.976	k = −14→15
13056 measured reflections	l = −15→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.3945P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5683 reflections	Δρmax = 0.16 e Å^−3
371 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0011 (6)

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
N1	0.4130 (2)	0.3972 (2)	0.21734 (14)	0.0981 (9)
N2	0.3690 (2)	1.4301 (2)	0.02001 (12)	0.0840 (7)
N3	1.5697 (2)	0.8890 (2)	0.04384 (12)	0.0899 (8)
N4	1.0622 (3)	1.2920 (3)	0.59841 (16)	0.1324 (12)
O1	0.79809 (14)	0.78618 (13)	0.18395 (7)	0.0610 (4)
O2	0.80940 (14)	1.10969 (13)	0.17182 (9)	0.0716 (5)
O3	1.07757 (15)	0.87828 (14)	0.18272 (9)	0.0716 (5)
O4	0.90275 (15)	1.01077 (15)	0.32340 (9)	0.0771 (6)
C1	0.90065 (19)	0.94781 (18)	0.21588 (11)	0.0535 (6)
C2	0.8690 (2)	0.83932 (18)	0.23879 (12)	0.0565 (6)
H2A	0.9426	0.7999	0.2553	0.068*
H2B	0.8231	0.8459	0.2738	0.068*
C3	0.7813 (2)	1.00549 (19)	0.19072 (12)	0.0621 (7)
H3A	0.7348	0.9684	0.1534	0.074*
H3B	0.7333	1.0087	0.2249	0.074*
C4	0.9734 (2)	0.9424 (2)	0.16099 (12)	0.0620 (6)
H4A	0.9240	0.9124	0.1218	0.074*
H4B	0.9982	1.0126	0.1506	0.074*
C5	0.9749 (2)	1.0063 (2)	0.27423 (11)	0.0608 (7)
H5A	1.0503	0.9693	0.2905	0.073*
H5B	0.9941	1.0768	0.2614	0.073*
C6	0.72602 (18)	0.70444 (17)	0.19523 (11)	0.0477 (5)
C7	0.6477 (2)	0.66758 (19)	0.14035 (11)	0.0553 (6)
H7	0.6488	0.6971	0.0995	0.066*
C8	0.5685 (2)	0.58779 (19)	0.14596 (13)	0.0602 (6)
H8	0.5155	0.5634	0.1089	0.072*
C9	0.56725 (19)	0.54330 (19)	0.20661 (12)	0.0551 (6)
C10	0.6481 (2)	0.57877 (18)	0.26084 (12)	0.0588 (6)
H10	0.6484	0.5481	0.3016	0.071*
C11	0.72813 (19)	0.65876 (18)	0.25555 (11)	0.0525 (6)
H11	0.7830	0.6817	0.2923	0.063*
C12	0.4818 (2)	0.4612 (2)	0.21275 (13)	0.0694 (7)
C13	0.7147 (2)	1.1710 (2)	0.14337 (12)	0.0610 (6)
C14	0.5944 (2)	1.1447 (2)	0.13769 (13)	0.0695 (7)
H14	0.5729	1.0813	0.1547	0.083*
C15	0.5056 (2)	1.2124 (2)	0.10670 (13)	0.0740 (8)
H15	0.4242	1.1943	0.1033	0.089*
C16	0.5353 (2)	1.3058 (2)	0.08090 (12)	0.0614 (6)
C17	0.6561 (3)	1.3337 (2)	0.08850 (15)	0.0823 (9)
H17	0.6775	1.3977	0.0721	0.099*
C18	0.7452 (2)	1.2673 (2)	0.12022 (15)	0.0833 (9)
H18	0.8264	1.2873	0.1261	0.100*
C19	0.4421 (3)	1.3746 (2)	0.04689 (13)	0.0675 (7)
C20	1.1692 (2)	0.8795 (2)	0.14816 (13)	0.0623 (7)
C21	1.1685 (2)	0.9361 (2)	0.09165 (13)	0.0709 (7)
H21	1.0998	0.9740	0.0726	0.085*
C22	1.2710 (2)	0.9363 (2)	0.06322 (13)	0.0754 (8)
H22	1.2708	0.9748	0.0251	0.090*
C23	1.3728 (2)	0.8802 (2)	0.09079 (13)	0.0667 (7)
C24	1.3714 (2)	0.8215 (2)	0.14676 (14)	0.0749 (8)
H24	1.4393	0.7821	0.1653	0.090*
C25	1.2702 (2)	0.8210 (2)	0.17512 (14)	0.0747 (8)
H25	1.2698	0.7810	0.2126	0.090*
C26	1.4814 (3)	0.8848 (2)	0.06359 (13)	0.0737 (8)
C27	0.9426 (2)	1.06740 (19)	0.37853 (12)	0.0592 (6)
C28	1.0519 (2)	1.1176 (2)	0.39282 (14)	0.0726 (8)
H28	1.1058	1.1133	0.3639	0.087*
C29	1.0825 (2)	1.1743 (2)	0.44966 (14)	0.0788 (8)
H29	1.1576	1.2078	0.4592	0.095*
C30	1.0049 (3)	1.1824 (2)	0.49252 (13)	0.0715 (7)
C31	0.8950 (3)	1.1300 (3)	0.47787 (15)	0.1010 (11)
H31	0.8413	1.1337	0.5069	0.121*
C32	0.8642 (3)	1.0732 (3)	0.42182 (15)	0.0914 (10)
H32	0.7901	1.0381	0.4127	0.110*
C33	1.0367 (3)	1.2433 (3)	0.55169 (17)	0.0967 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0839 (17)	0.0927 (19)	0.129 (2)	−0.0343 (15)	0.0492 (16)	−0.0232 (16)
N2	0.0760 (16)	0.0890 (19)	0.0812 (17)	0.0057 (14)	0.0006 (13)	0.0005 (14)
N3	0.0764 (16)	0.116 (2)	0.0834 (18)	0.0108 (15)	0.0309 (14)	0.0067 (15)
N4	0.131 (3)	0.166 (3)	0.096 (2)	−0.026 (2)	0.0123 (19)	−0.053 (2)
O1	0.0707 (10)	0.0596 (11)	0.0555 (10)	−0.0155 (8)	0.0192 (8)	−0.0062 (8)
O2	0.0550 (10)	0.0572 (11)	0.1064 (15)	0.0003 (8)	0.0251 (10)	0.0144 (10)
O3	0.0702 (11)	0.0732 (12)	0.0798 (13)	0.0139 (9)	0.0356 (10)	0.0118 (9)
O4	0.0687 (11)	0.0942 (14)	0.0773 (12)	−0.0395 (10)	0.0365 (10)	−0.0279 (11)
C1	0.0473 (13)	0.0551 (14)	0.0603 (15)	−0.0061 (11)	0.0160 (11)	−0.0008 (11)
C2	0.0512 (13)	0.0572 (15)	0.0611 (16)	−0.0057 (11)	0.0108 (11)	−0.0010 (12)
C3	0.0563 (14)	0.0547 (15)	0.0769 (17)	−0.0087 (12)	0.0168 (12)	0.0069 (13)
C4	0.0579 (14)	0.0644 (16)	0.0664 (17)	0.0000 (13)	0.0185 (12)	0.0019 (13)
C5	0.0538 (14)	0.0657 (16)	0.0678 (17)	−0.0105 (12)	0.0234 (12)	−0.0030 (13)
C6	0.0425 (12)	0.0472 (13)	0.0563 (15)	0.0025 (10)	0.0163 (11)	−0.0035 (11)
C7	0.0607 (14)	0.0572 (15)	0.0485 (14)	0.0020 (12)	0.0116 (11)	−0.0037 (11)
C8	0.0516 (14)	0.0666 (16)	0.0607 (17)	−0.0045 (12)	0.0067 (12)	−0.0154 (13)
C9	0.0475 (13)	0.0567 (15)	0.0654 (17)	−0.0028 (11)	0.0218 (12)	−0.0108 (13)
C10	0.0650 (15)	0.0573 (15)	0.0575 (16)	−0.0033 (12)	0.0204 (13)	0.0013 (12)
C11	0.0519 (13)	0.0547 (14)	0.0495 (15)	−0.0029 (11)	0.0062 (11)	−0.0038 (11)
C12	0.0592 (15)	0.0733 (18)	0.0820 (19)	−0.0111 (14)	0.0296 (14)	−0.0188 (15)
C13	0.0586 (15)	0.0564 (15)	0.0729 (17)	0.0006 (13)	0.0246 (13)	0.0021 (13)
C14	0.0611 (16)	0.0638 (17)	0.085 (2)	−0.0056 (13)	0.0179 (14)	0.0132 (14)
C15	0.0554 (16)	0.077 (2)	0.089 (2)	−0.0041 (14)	0.0100 (14)	0.0058 (16)
C16	0.0635 (16)	0.0635 (17)	0.0581 (16)	0.0054 (13)	0.0138 (12)	−0.0048 (13)
C17	0.0751 (19)	0.0711 (19)	0.109 (2)	0.0077 (16)	0.0377 (17)	0.0214 (17)
C18	0.0593 (16)	0.0697 (19)	0.127 (3)	0.0032 (15)	0.0320 (16)	0.0213 (18)
C19	0.0708 (18)	0.0694 (18)	0.0617 (17)	0.0012 (15)	0.0110 (14)	−0.0095 (14)
C20	0.0658 (16)	0.0602 (16)	0.0659 (17)	0.0028 (13)	0.0251 (13)	−0.0031 (13)
C21	0.0631 (16)	0.092 (2)	0.0600 (17)	0.0131 (14)	0.0180 (13)	0.0068 (15)
C22	0.0791 (19)	0.096 (2)	0.0566 (17)	0.0080 (16)	0.0255 (14)	0.0041 (15)
C23	0.0696 (17)	0.0758 (18)	0.0599 (17)	0.0084 (14)	0.0251 (14)	−0.0065 (14)
C24	0.0731 (17)	0.082 (2)	0.0751 (19)	0.0233 (15)	0.0275 (15)	0.0006 (15)
C25	0.0864 (19)	0.0682 (18)	0.0776 (19)	0.0211 (15)	0.0363 (16)	0.0118 (14)
C26	0.0759 (19)	0.087 (2)	0.0623 (18)	0.0072 (16)	0.0234 (15)	−0.0059 (14)
C27	0.0573 (14)	0.0616 (16)	0.0613 (16)	−0.0136 (12)	0.0180 (12)	−0.0055 (12)
C28	0.0568 (15)	0.091 (2)	0.0736 (19)	−0.0217 (14)	0.0226 (13)	−0.0140 (15)
C29	0.0592 (16)	0.097 (2)	0.080 (2)	−0.0229 (15)	0.0117 (15)	−0.0134 (17)
C30	0.0724 (17)	0.080 (2)	0.0616 (17)	−0.0084 (15)	0.0118 (14)	−0.0099 (14)
C31	0.093 (2)	0.136 (3)	0.085 (2)	−0.040 (2)	0.0442 (18)	−0.037 (2)
C32	0.0716 (18)	0.124 (3)	0.089 (2)	−0.0450 (18)	0.0413 (17)	−0.036 (2)
C33	0.088 (2)	0.119 (3)	0.081 (2)	−0.018 (2)	0.0133 (18)	−0.021 (2)

Geometric parameters (Å, º)

N1—C12	1.137 (3)	C11—H11	0.9300
N2—C19	1.143 (3)	C13—C14	1.371 (3)
N3—C26	1.142 (3)	C13—C18	1.380 (3)
N4—C33	1.139 (4)	C14—C15	1.378 (3)
O1—C6	1.363 (2)	C14—H14	0.9300
O1—C2	1.427 (3)	C15—C16	1.369 (3)
O2—C13	1.358 (3)	C15—H15	0.9300
O2—C3	1.432 (3)	C16—C17	1.380 (3)
O3—C20	1.360 (3)	C16—C19	1.439 (4)
O3—C4	1.425 (3)	C17—C18	1.376 (4)
O4—C27	1.353 (3)	C17—H17	0.9300
O4—C5	1.419 (2)	C18—H18	0.9300
C1—C2	1.522 (3)	C20—C21	1.374 (3)
C1—C4	1.523 (3)	C20—C25	1.381 (3)
C1—C5	1.525 (3)	C21—C22	1.388 (3)
C1—C3	1.527 (3)	C21—H21	0.9300
C2—H2A	0.9700	C22—C23	1.374 (3)
C2—H2B	0.9700	C22—H22	0.9300
C3—H3A	0.9700	C23—C24	1.383 (4)
C3—H3B	0.9700	C23—C26	1.437 (4)
C4—H4A	0.9700	C24—C25	1.373 (3)
C4—H4B	0.9700	C24—H24	0.9300
C5—H5A	0.9700	C25—H25	0.9300
C5—H5B	0.9700	C27—C28	1.363 (3)
C6—C11	1.376 (3)	C27—C32	1.372 (3)
C6—C7	1.380 (3)	C28—C29	1.368 (4)
C7—C8	1.367 (3)	C28—H28	0.9300
C7—H7	0.9300	C29—C30	1.361 (4)
C8—C9	1.382 (3)	C29—H29	0.9300
C8—H8	0.9300	C30—C31	1.383 (4)
C9—C10	1.379 (3)	C30—C33	1.438 (4)
C9—C12	1.438 (3)	C31—C32	1.356 (4)
C10—C11	1.374 (3)	C31—H31	0.9300
C10—H10	0.9300	C32—H32	0.9300
C6—O1—C2	118.77 (17)	C14—C13—C18	119.4 (2)
C13—O2—C3	117.07 (18)	C13—C14—C15	119.9 (2)
C20—O3—C4	118.80 (19)	C13—C14—H14	120.0
C27—O4—C5	119.22 (18)	C15—C14—H14	120.0
C2—C1—C4	112.5 (2)	C16—C15—C14	121.0 (2)
C2—C1—C5	108.51 (19)	C16—C15—H15	119.5
C4—C1—C5	109.08 (18)	C14—C15—H15	119.5
C2—C1—C3	107.47 (18)	C15—C16—C17	119.0 (2)
C4—C1—C3	108.93 (19)	C15—C16—C19	120.7 (2)
C5—C1—C3	110.3 (2)	C17—C16—C19	120.3 (2)
O1—C2—C1	107.87 (19)	C18—C17—C16	120.3 (3)
O1—C2—H2A	110.1	C18—C17—H17	119.9
C1—C2—H2A	110.1	C16—C17—H17	119.9
O1—C2—H2B	110.1	C17—C18—C13	120.3 (3)
C1—C2—H2B	110.1	C17—C18—H18	119.9
H2A—C2—H2B	108.4	C13—C18—H18	119.9
O2—C3—C1	108.26 (18)	N2—C19—C16	179.2 (3)
O2—C3—H3A	110.0	O3—C20—C21	125.1 (2)
C1—C3—H3A	110.0	O3—C20—C25	115.0 (2)
O2—C3—H3B	110.0	C21—C20—C25	119.9 (2)
C1—C3—H3B	110.0	C20—C21—C22	119.6 (2)
H3A—C3—H3B	108.4	C20—C21—H21	120.2
O3—C4—C1	108.18 (19)	C22—C21—H21	120.2
O3—C4—H4A	110.1	C23—C22—C21	120.7 (3)
C1—C4—H4A	110.1	C23—C22—H22	119.6
O3—C4—H4B	110.1	C21—C22—H22	119.6
C1—C4—H4B	110.1	C22—C23—C24	119.2 (2)
H4A—C4—H4B	108.4	C22—C23—C26	120.9 (3)
O4—C5—C1	106.92 (18)	C24—C23—C26	119.9 (3)
O4—C5—H5A	110.3	C25—C24—C23	120.3 (3)
C1—C5—H5A	110.3	C25—C24—H24	119.8
O4—C5—H5B	110.3	C23—C24—H24	119.8
C1—C5—H5B	110.3	C24—C25—C20	120.3 (3)
H5A—C5—H5B	108.6	C24—C25—H25	119.9
O1—C6—C11	124.7 (2)	C20—C25—H25	119.9
O1—C6—C7	114.9 (2)	N3—C26—C23	177.9 (3)
C11—C6—C7	120.4 (2)	O4—C27—C28	124.8 (2)
C8—C7—C6	120.1 (2)	O4—C27—C32	115.6 (2)
C8—C7—H7	119.9	C28—C27—C32	119.6 (2)
C6—C7—H7	119.9	C27—C28—C29	120.0 (2)
C7—C8—C9	120.0 (2)	C27—C28—H28	120.0
C7—C8—H8	120.0	C29—C28—H28	120.0
C9—C8—H8	120.0	C30—C29—C28	121.1 (3)
C10—C9—C8	119.4 (2)	C30—C29—H29	119.4
C10—C9—C12	120.6 (2)	C28—C29—H29	119.4
C8—C9—C12	120.0 (2)	C29—C30—C31	118.3 (3)
C11—C10—C9	120.9 (2)	C29—C30—C33	120.9 (3)
C11—C10—H10	119.5	C31—C30—C33	120.8 (3)
C9—C10—H10	119.5	C32—C31—C30	121.0 (3)
C10—C11—C6	119.1 (2)	C32—C31—H31	119.5
C10—C11—H11	120.4	C30—C31—H31	119.5
C6—C11—H11	120.4	C31—C32—C27	120.0 (3)
N1—C12—C9	179.1 (3)	C31—C32—H32	120.0
O2—C13—C14	124.9 (2)	C27—C32—H32	120.0
O2—C13—C18	115.7 (2)	N4—C33—C30	179.7 (5)
C1—C2—O1—C6	−158.68 (18)	C1—C4—O3—C20	−166.3 (2)
C1—C3—O2—C13	175.16 (19)	C1—C5—O4—C27	−173.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···N2^i	0.93	2.82	3.577 (4)	139
C2—H2B···N1^ii	0.97	2.77	3.529 (3)	136
C11—H11···N4^iii	0.93	2.60	3.518 (4)	169
C28—H28···O1^iv	0.93	2.72	3.312 (3)	123
C28—H28···C6^iv	0.93	2.70	3.533 (4)	150
C8—H8···N2^v	0.93	2.79	3.689 (3)	162
C7—H7···N2^vi	0.93	2.93	3.523 (3)	123
C3—H3A···N3^vii	0.97	2.83	3.788 (4)	170
C7—H7···N3^vii	0.93	2.77	3.467 (4)	133
C3—H3B···N1^ii	0.97	2.62	3.444 (3)	143

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