Dimethyl 3,3′-[(4-nitro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate) ethanol hemisolvate

There are two main molecules in asymmetric unit of the title compound, C₂₇H₂₁N₃O₆·0.5C₂H₅OH. In both, the indole ring systems are approximately perpendicular to each other, at dihedral angles of 69.3 (5) and 82.8(4)°. In the crystal, mol­ecules are linked by N—H...O and O—H...O hydrogen bonds into a three-dimensional supra­molecular architecture. The solvent ethanol mol­ecule acts as a donor, forming an O—H...O hydrogen bond, reinforcing the structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.104
• wR factor = 0.213
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as psi-scan
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.160
PLAT020_ALERT_3_C The Value of Rint is Greater Than 0.12 .........      0.160 Report
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        43% Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N6       --C51      .        6.2 s.u.
PLAT234_ALERT_4_C Large Hirshfeld Difference N1       --C5       .       0.17 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N2       --C14      .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C5       --C6       .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference O8       --N4       .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C48      --C49      .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C49      --C50      .       0.16 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C31 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C32 Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of        C55 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O13      0.174 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C2       -C7              1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C29      -C34             1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00813 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C55      - C56      .       1.43 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.701 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT344_ALERT_2_G Unusual sp3       Angle Range in Solvent/Ion for        C55 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O8       ..C52              3.01 Ang.
                                            1-x,1/2+y,1/2-z  =      2_655 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C2 H6 O
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         20 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  23 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   1 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: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Dimethyl 3,3'-[(4-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) ethanol hemisolvate

Crystal data

2C27H21N3O6·C2H6O	F(000) = 2120
Mr = 1013.00	Dx = 1.326 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.248 (4) Å	Cell parameters from 25 reflections
b = 10.304 (2) Å	θ = 9–12°
c = 27.541 (6) Å	µ = 0.10 mm^−1
β = 101.41 (3)°	T = 293 K
V = 5076.1 (18) Å^3	Block, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	9324 independent reflections
Radiation source: fine-focus sealed tube	4039 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.160
ω scans	θmax = 25.4°, θmin = 1.1°
Absorption correction: ψ scan (North et al., 1968)	h = 0→22
Tmin = 0.97, Tmax = 0.98	k = 0→12
9324 measured reflections	l = −33→32

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)] = 0.104	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.213	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 2.P] where P = (Fo^2 + 2Fc^2)/3
9324 reflections	(Δ/σ)max < 0.001
676 parameters	Δρmax = 0.36 e Å^−3
2 restraints	Δρmin = −0.28 e Å^−3

Special details

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
N2	0.9831 (3)	0.9393 (4)	0.14010 (17)	0.0539 (13)
H2A	1.0127	1.0046	0.1411	0.065*
C1	0.9320 (3)	0.5961 (5)	0.11280 (19)	0.0408 (14)
H1A	0.9837	0.5646	0.1190	0.049*
N1	0.7905 (4)	0.3205 (6)	0.2503 (2)	0.0752 (17)
O1	0.8245 (4)	0.3088 (7)	0.2916 (2)	0.147 (3)
C2	0.8937 (3)	0.5178 (5)	0.1471 (2)	0.0406 (13)
O2	0.7277 (3)	0.2809 (5)	0.23639 (18)	0.0842 (15)
O3	1.1030 (2)	0.8945 (4)	0.10153 (16)	0.0692 (13)
N3	0.8863 (2)	0.4737 (4)	−0.01617 (16)	0.0488 (12)
H3A	0.8903	0.4179	−0.0387	0.059*
C3	0.9289 (3)	0.5036 (6)	0.1954 (2)	0.0576 (16)
H3B	0.9762	0.5396	0.2055	0.069*
N4	0.6521 (4)	0.5750 (8)	0.2207 (3)	0.092 (2)
O4	1.0854 (2)	0.6789 (4)	0.09867 (14)	0.0573 (11)
C4	0.8975 (4)	0.4384 (6)	0.2296 (2)	0.0641 (18)
H4A	0.9227	0.4296	0.2623	0.077*
O5	0.9967 (2)	0.3403 (4)	0.09448 (16)	0.0741 (14)
C5	0.8273 (4)	0.3867 (6)	0.2139 (2)	0.0556 (17)
N5	0.5897 (2)	0.5494 (4)	0.49143 (17)	0.0487 (12)
H5A	0.5850	0.6178	0.5085	0.058*
O6	0.9745 (2)	0.2731 (3)	0.01570 (14)	0.0635 (12)
C6	0.7899 (3)	0.3955 (5)	0.1665 (2)	0.0551 (17)
H6A	0.7425	0.3595	0.1567	0.066*
N6	0.5217 (3)	−0.0105 (4)	0.39919 (18)	0.0523 (13)
H6B	0.5035	−0.0759	0.4122	0.063*
O7	0.7097 (4)	0.6377 (6)	0.2306 (2)	0.124 (2)
C7	0.8245 (3)	0.4602 (6)	0.1328 (2)	0.0568 (16)
H7A	0.8004	0.4647	0.0998	0.068*
O8	0.6225 (3)	0.5476 (8)	0.1784 (2)	0.158 (3)
C8	0.9376 (3)	0.7386 (5)	0.12664 (18)	0.0400 (13)
C9	0.8841 (3)	0.8163 (5)	0.14583 (18)	0.0410 (14)
O9	0.4550 (2)	0.5844 (4)	0.37946 (17)	0.0687 (13)
O10	0.4921 (2)	0.7300 (4)	0.43938 (17)	0.0739 (13)
C10	0.8120 (3)	0.7974 (6)	0.1546 (2)	0.0534 (16)
H10A	0.7893	0.7165	0.1491	0.064*
C11	0.7748 (3)	0.8978 (6)	0.1714 (2)	0.0627 (18)
H11A	0.7269	0.8847	0.1773	0.075*
O11	0.4208 (2)	0.0506 (4)	0.45411 (17)	0.0748 (14)
C12	0.8081 (4)	1.0198 (6)	0.1798 (2)	0.071 (2)
H12A	0.7821	1.0868	0.1915	0.085*
O12	0.4222 (2)	0.2619 (4)	0.43498 (14)	0.0587 (11)
C13	0.8771 (4)	1.0426 (6)	0.1712 (2)	0.0601 (18)
H13A	0.8990	1.1240	0.1771	0.072*
O13	1.0623 (4)	0.1713 (5)	0.1666 (2)	0.146 (3)
H13B	1.0436	0.2240	0.1454	0.219*
C14	0.9146 (3)	0.9412 (5)	0.1535 (2)	0.0476 (15)
C15	0.9967 (3)	0.8174 (5)	0.12499 (19)	0.0434 (14)
C16	1.0642 (3)	0.7862 (6)	0.1073 (2)	0.0462 (15)
C17	1.1726 (3)	0.8759 (7)	0.0856 (3)	0.096 (3)
H17A	1.1956	0.9586	0.0827	0.144*
H17B	1.2053	0.8236	0.1094	0.144*
H17C	1.1635	0.8331	0.0540	0.144*
C18	0.9023 (3)	0.5722 (5)	0.05790 (18)	0.0379 (13)
C19	0.8530 (3)	0.6490 (5)	0.02260 (19)	0.0415 (14)
C20	0.8157 (3)	0.7670 (5)	0.0226 (2)	0.0546 (16)
H20A	0.8200	0.8140	0.0519	0.066*
C21	0.7729 (3)	0.8144 (6)	−0.0200 (2)	0.0617 (18)
H21A	0.7488	0.8937	−0.0194	0.074*
C22	0.7647 (3)	0.7462 (6)	−0.0643 (2)	0.0653 (18)
H22A	0.7348	0.7804	−0.0927	0.078*
C23	0.8000 (3)	0.6288 (6)	−0.0669 (2)	0.0634 (18)
H23A	0.7940	0.5819	−0.0963	0.076*
C24	0.8455 (3)	0.5837 (5)	−0.0231 (2)	0.0448 (14)
C25	0.9202 (3)	0.4655 (5)	0.0326 (2)	0.0436 (14)
C26	0.9679 (3)	0.3557 (5)	0.0517 (2)	0.0478 (15)
C27	1.0198 (4)	0.1602 (5)	0.0313 (2)	0.076 (2)
H27A	1.0215	0.1064	0.0031	0.115*
H27B	1.0696	0.1870	0.0462	0.115*
H27C	0.9985	0.1121	0.0550	0.115*
C28	0.5378 (3)	0.3441 (5)	0.3791 (2)	0.0435 (14)
H28A	0.4841	0.3632	0.3725	0.052*
C29	0.5678 (3)	0.4072 (5)	0.3375 (2)	0.0425 (14)
C30	0.5284 (3)	0.4046 (6)	0.2900 (2)	0.0698 (19)
H30A	0.4821	0.3636	0.2835	0.084*
C31	0.5543 (4)	0.4603 (8)	0.2512 (2)	0.081 (2)
H31A	0.5262	0.4576	0.2191	0.097*
C32	0.6227 (4)	0.5199 (6)	0.2613 (2)	0.0579 (17)
C33	0.6644 (3)	0.5235 (5)	0.3077 (2)	0.0572 (17)
H33A	0.7113	0.5624	0.3138	0.069*
C34	0.6364 (3)	0.4690 (5)	0.3455 (2)	0.0550 (16)
H34A	0.6644	0.4736	0.3776	0.066*
C35	0.5697 (3)	0.4046 (5)	0.4289 (2)	0.0424 (14)
C36	0.6299 (3)	0.3608 (5)	0.4667 (2)	0.0402 (13)
C37	0.6785 (3)	0.2536 (6)	0.4714 (2)	0.0560 (16)
H37A	0.6731	0.1910	0.4467	0.067*
C38	0.7334 (3)	0.2426 (6)	0.5125 (2)	0.0635 (17)
H38A	0.7663	0.1730	0.5148	0.076*
C39	0.7419 (3)	0.3308 (6)	0.5509 (2)	0.0626 (18)
H39A	0.7792	0.3182	0.5789	0.075*
C40	0.6954 (3)	0.4379 (6)	0.5482 (2)	0.0607 (17)
H40A	0.7010	0.4982	0.5738	0.073*
C41	0.6397 (3)	0.4520 (5)	0.5056 (2)	0.0483 (15)
C42	0.5479 (3)	0.5207 (5)	0.4455 (2)	0.0465 (14)
C43	0.4962 (3)	0.6238 (6)	0.4224 (2)	0.0506 (15)
C44	0.4048 (4)	0.6789 (6)	0.3526 (3)	0.089 (2)
H44A	0.3779	0.6409	0.3224	0.134*
H44B	0.3701	0.7067	0.3725	0.134*
H44C	0.4329	0.7522	0.3449	0.134*
C45	0.5442 (3)	0.1959 (5)	0.3796 (2)	0.0434 (14)
C46	0.5886 (3)	0.1132 (5)	0.3559 (2)	0.0469 (15)
C47	0.6385 (3)	0.1274 (6)	0.3240 (2)	0.0561 (17)
H47A	0.6513	0.2098	0.3147	0.067*
C48	0.6686 (4)	0.0199 (7)	0.3062 (3)	0.073 (2)
H48A	0.7019	0.0302	0.2849	0.088*
C49	0.6505 (4)	−0.1041 (6)	0.3196 (2)	0.0636 (19)
H49A	0.6721	−0.1752	0.3071	0.076*
C50	0.6018 (3)	−0.1247 (6)	0.3504 (2)	0.0596 (17)
H50A	0.5888	−0.2081	0.3584	0.072*
C51	0.5727 (3)	−0.0167 (5)	0.3692 (2)	0.0455 (15)
C52	0.5040 (3)	0.1183 (5)	0.4053 (2)	0.0475 (15)
C53	0.4451 (3)	0.1516 (6)	0.4333 (2)	0.0460 (15)
C54	0.3624 (4)	0.0783 (6)	0.4808 (3)	0.084 (2)
H54A	0.3478	−0.0005	0.4949	0.126*
H54B	0.3804	0.1393	0.5068	0.126*
H54C	0.3202	0.1144	0.4586	0.126*
C55	1.1147 (7)	0.2243 (9)	0.1965 (4)	0.226 (8)
H55A	1.1595	0.1774	0.1930	0.271*
H55B	1.1060	0.2029	0.2292	0.271*
C56	1.1354 (5)	0.3581 (9)	0.1991 (4)	0.151 (4)
H56A	1.1776	0.3708	0.2256	0.227*
H56B	1.1484	0.3838	0.1683	0.227*
H56C	1.0942	0.4096	0.2049	0.227*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.070 (4)	0.031 (3)	0.059 (3)	−0.009 (3)	0.007 (3)	−0.009 (2)
C1	0.042 (3)	0.035 (3)	0.045 (3)	0.004 (3)	0.007 (3)	−0.010 (3)
N1	0.098 (5)	0.071 (4)	0.058 (4)	−0.008 (4)	0.018 (4)	−0.002 (3)
O1	0.152 (6)	0.222 (8)	0.063 (4)	−0.065 (5)	0.013 (4)	0.040 (5)
C2	0.048 (4)	0.030 (3)	0.041 (3)	0.000 (3)	0.004 (3)	−0.004 (3)
O2	0.097 (4)	0.074 (3)	0.091 (4)	−0.020 (3)	0.041 (3)	−0.009 (3)
O3	0.056 (3)	0.062 (3)	0.093 (4)	−0.017 (2)	0.024 (3)	0.003 (3)
N3	0.071 (3)	0.037 (3)	0.036 (3)	0.001 (3)	0.005 (2)	−0.002 (2)
C3	0.054 (4)	0.068 (4)	0.047 (4)	−0.012 (3)	0.001 (3)	0.007 (3)
N4	0.079 (5)	0.134 (6)	0.064 (4)	0.005 (4)	0.016 (4)	0.029 (5)
O4	0.063 (3)	0.051 (3)	0.062 (3)	−0.002 (2)	0.023 (2)	−0.011 (2)
C4	0.081 (5)	0.073 (4)	0.033 (4)	−0.014 (4)	−0.001 (3)	0.010 (3)
O5	0.107 (4)	0.050 (3)	0.054 (3)	0.028 (3)	−0.011 (3)	−0.005 (2)
C5	0.070 (5)	0.046 (4)	0.059 (5)	−0.006 (3)	0.033 (4)	−0.002 (3)
N5	0.061 (3)	0.028 (3)	0.057 (3)	−0.006 (2)	0.014 (3)	−0.011 (2)
O6	0.093 (3)	0.033 (2)	0.060 (3)	0.013 (2)	0.004 (2)	−0.008 (2)
C6	0.062 (4)	0.053 (4)	0.047 (4)	−0.018 (3)	0.005 (3)	−0.012 (3)
N6	0.062 (3)	0.021 (2)	0.072 (4)	0.001 (2)	0.009 (3)	0.000 (2)
O7	0.154 (6)	0.131 (5)	0.099 (5)	−0.043 (5)	0.055 (4)	0.009 (4)
C7	0.059 (4)	0.064 (4)	0.046 (4)	−0.008 (3)	0.005 (3)	−0.002 (3)
O8	0.111 (5)	0.280 (9)	0.076 (4)	−0.012 (5)	0.002 (4)	0.062 (5)
C8	0.047 (4)	0.032 (3)	0.041 (3)	−0.001 (3)	0.008 (3)	−0.001 (3)
C9	0.057 (4)	0.034 (3)	0.032 (3)	−0.001 (3)	0.008 (3)	−0.002 (3)
O9	0.067 (3)	0.043 (2)	0.089 (4)	0.019 (2)	−0.002 (3)	0.009 (2)
O10	0.094 (4)	0.028 (2)	0.100 (4)	0.004 (2)	0.020 (3)	−0.005 (2)
C10	0.056 (4)	0.044 (4)	0.061 (4)	−0.003 (3)	0.014 (3)	−0.011 (3)
C11	0.057 (4)	0.062 (4)	0.070 (5)	0.022 (4)	0.015 (4)	0.008 (4)
O11	0.075 (3)	0.049 (3)	0.109 (4)	−0.011 (2)	0.040 (3)	0.017 (3)
C12	0.079 (5)	0.054 (4)	0.084 (5)	0.019 (4)	0.025 (4)	−0.005 (4)
O12	0.069 (3)	0.040 (2)	0.072 (3)	0.004 (2)	0.025 (2)	−0.005 (2)
C13	0.074 (5)	0.036 (3)	0.071 (5)	0.009 (3)	0.017 (4)	−0.005 (3)
O13	0.187 (6)	0.069 (4)	0.136 (5)	−0.052 (4)	−0.079 (5)	0.024 (4)
C14	0.053 (4)	0.046 (4)	0.045 (4)	0.004 (3)	0.013 (3)	−0.005 (3)
C15	0.051 (4)	0.039 (3)	0.039 (3)	−0.009 (3)	0.006 (3)	−0.004 (3)
C16	0.041 (4)	0.053 (4)	0.042 (3)	−0.012 (3)	0.003 (3)	−0.007 (3)
C17	0.054 (5)	0.104 (6)	0.138 (7)	−0.024 (4)	0.037 (5)	−0.002 (5)
C18	0.039 (3)	0.039 (3)	0.036 (3)	−0.009 (3)	0.006 (3)	0.000 (3)
C19	0.049 (4)	0.038 (3)	0.038 (3)	−0.004 (3)	0.009 (3)	−0.005 (3)
C20	0.063 (4)	0.046 (4)	0.055 (4)	0.006 (3)	0.012 (3)	0.001 (3)
C21	0.071 (5)	0.058 (4)	0.054 (4)	0.019 (3)	0.009 (4)	0.004 (4)
C22	0.081 (5)	0.062 (4)	0.044 (4)	0.020 (4)	−0.010 (3)	0.009 (3)
C23	0.069 (4)	0.062 (4)	0.057 (4)	0.003 (4)	0.005 (3)	0.000 (4)
C24	0.056 (4)	0.038 (3)	0.040 (4)	0.005 (3)	0.009 (3)	0.004 (3)
C25	0.056 (4)	0.029 (3)	0.047 (4)	−0.003 (3)	0.014 (3)	−0.002 (3)
C26	0.053 (4)	0.036 (3)	0.056 (4)	0.001 (3)	0.015 (3)	−0.009 (3)
C27	0.109 (6)	0.042 (4)	0.079 (5)	0.021 (4)	0.021 (4)	0.007 (4)
C28	0.039 (3)	0.033 (3)	0.057 (4)	−0.003 (3)	0.005 (3)	−0.006 (3)
C29	0.039 (3)	0.030 (3)	0.057 (4)	0.004 (3)	0.005 (3)	0.005 (3)
C30	0.053 (4)	0.082 (5)	0.067 (5)	−0.018 (4)	−0.007 (4)	0.007 (4)
C31	0.066 (5)	0.128 (7)	0.043 (4)	−0.006 (5)	−0.002 (4)	0.015 (4)
C32	0.066 (5)	0.057 (4)	0.051 (4)	0.009 (4)	0.013 (4)	0.017 (3)
C33	0.059 (4)	0.047 (4)	0.064 (5)	−0.005 (3)	0.009 (4)	−0.005 (3)
C34	0.058 (4)	0.052 (4)	0.053 (4)	−0.004 (3)	0.005 (3)	−0.004 (3)
C35	0.039 (3)	0.028 (3)	0.061 (4)	−0.002 (3)	0.012 (3)	0.001 (3)
C36	0.044 (3)	0.026 (3)	0.050 (4)	−0.004 (3)	0.007 (3)	0.005 (3)
C37	0.051 (4)	0.055 (4)	0.059 (4)	−0.003 (3)	0.005 (3)	0.002 (3)
C38	0.070 (5)	0.056 (4)	0.059 (4)	0.006 (4)	−0.001 (4)	0.001 (4)
C39	0.065 (4)	0.057 (4)	0.062 (5)	−0.003 (4)	0.002 (3)	0.013 (4)
C40	0.075 (5)	0.055 (4)	0.049 (4)	−0.022 (4)	0.005 (3)	0.001 (3)
C41	0.057 (4)	0.037 (3)	0.052 (4)	−0.009 (3)	0.014 (3)	0.002 (3)
C42	0.040 (3)	0.041 (3)	0.057 (4)	−0.004 (3)	0.006 (3)	0.006 (3)
C43	0.045 (4)	0.042 (4)	0.068 (5)	−0.004 (3)	0.016 (3)	0.006 (3)
C44	0.071 (5)	0.060 (4)	0.129 (7)	0.013 (4)	0.000 (5)	0.013 (5)
C45	0.038 (3)	0.029 (3)	0.058 (4)	−0.009 (3)	−0.002 (3)	−0.002 (3)
C46	0.047 (4)	0.031 (3)	0.061 (4)	0.001 (3)	0.007 (3)	−0.011 (3)
C47	0.056 (4)	0.041 (4)	0.074 (5)	0.006 (3)	0.020 (4)	−0.005 (3)
C48	0.068 (5)	0.073 (5)	0.085 (5)	0.009 (4)	0.031 (4)	−0.009 (4)
C49	0.074 (5)	0.034 (4)	0.080 (5)	0.013 (3)	0.007 (4)	−0.010 (3)
C50	0.057 (4)	0.040 (4)	0.084 (5)	0.002 (3)	0.019 (4)	−0.005 (3)
C51	0.040 (3)	0.034 (3)	0.062 (4)	0.005 (3)	0.011 (3)	−0.013 (3)
C52	0.050 (4)	0.032 (3)	0.058 (4)	−0.006 (3)	0.004 (3)	−0.003 (3)
C53	0.042 (4)	0.045 (4)	0.049 (4)	−0.006 (3)	0.005 (3)	−0.011 (3)
C54	0.084 (5)	0.072 (5)	0.113 (6)	−0.009 (4)	0.060 (5)	0.010 (4)
C55	0.255 (14)	0.116 (9)	0.228 (14)	−0.099 (9)	−0.142 (11)	0.105 (9)
C56	0.115 (8)	0.165 (10)	0.157 (10)	−0.038 (7)	−0.013 (7)	−0.020 (8)

Geometric parameters (Å, º)

N2—C15	1.362 (6)	C19—C24	1.410 (7)
N2—C14	1.371 (6)	C20—C21	1.364 (7)
N2—H2A	0.8600	C20—H20A	0.9300
C1—C8	1.516 (7)	C21—C22	1.391 (8)
C1—C2	1.515 (7)	C21—H21A	0.9300
C1—C18	1.522 (7)	C22—C23	1.380 (8)
C1—H1A	0.9800	C22—H22A	0.9300
N1—O1	1.189 (7)	C23—C24	1.402 (7)
N1—O2	1.205 (6)	C23—H23A	0.9300
N1—C5	1.479 (8)	C25—C26	1.461 (7)
C2—C3	1.366 (7)	C27—H27A	0.9600
C2—C7	1.380 (7)	C27—H27B	0.9600
O3—C16	1.349 (6)	C27—H27C	0.9600
O3—C17	1.436 (6)	C28—C29	1.509 (7)
N3—C24	1.349 (6)	C28—C35	1.517 (7)
N3—C25	1.365 (6)	C28—C45	1.531 (7)
N3—H3A	0.8600	C28—H28A	0.9800
C3—C4	1.372 (7)	C29—C30	1.364 (7)
C3—H3B	0.9300	C29—C34	1.383 (7)
N4—O8	1.217 (8)	C30—C31	1.376 (8)
N4—O7	1.217 (7)	C30—H30A	0.9300
N4—C32	1.449 (8)	C31—C32	1.368 (8)
O4—C16	1.211 (6)	C31—H31A	0.9300
C4—C5	1.375 (7)	C32—C33	1.353 (8)
C4—H4A	0.9300	C33—C34	1.368 (7)
O5—C26	1.202 (6)	C33—H33A	0.9300
C5—C6	1.352 (8)	C34—H34A	0.9300
N5—C41	1.360 (6)	C35—C42	1.367 (7)
N5—C42	1.375 (6)	C35—C36	1.429 (7)
N5—H5A	0.8600	C36—C37	1.406 (7)
O6—C26	1.330 (6)	C36—C41	1.409 (7)
O6—C27	1.442 (6)	C37—C38	1.359 (7)
C6—C7	1.392 (7)	C37—H37A	0.9300
C6—H6A	0.9300	C38—C39	1.381 (8)
N6—C51	1.363 (6)	C38—H38A	0.9300
N6—C52	1.384 (6)	C39—C40	1.385 (8)
N6—H6B	0.8600	C39—H39A	0.9300
C7—H7A	0.9300	C40—C41	1.401 (7)
C8—C15	1.358 (7)	C40—H40A	0.9300
C8—C9	1.440 (7)	C42—C43	1.478 (7)
C9—C10	1.399 (7)	C44—H44A	0.9600
C9—C14	1.402 (7)	C44—H44B	0.9600
O9—C43	1.333 (7)	C44—H44C	0.9600
O9—C44	1.437 (6)	C45—C52	1.372 (7)
O10—C43	1.198 (6)	C45—C46	1.422 (7)
C10—C11	1.367 (7)	C46—C47	1.392 (7)
C10—H10A	0.9300	C46—C51	1.432 (7)
C11—C12	1.395 (8)	C47—C48	1.369 (8)
C11—H11A	0.9300	C47—H47A	0.9300
O11—C53	1.307 (6)	C48—C49	1.388 (8)
O11—C54	1.438 (6)	C48—H48A	0.9300
C12—C13	1.346 (8)	C49—C50	1.361 (8)
C12—H12A	0.9300	C49—H49A	0.9300
O12—C53	1.214 (6)	C50—C51	1.378 (7)
C13—C14	1.390 (7)	C50—H50A	0.9300
C13—H13A	0.9300	C52—C53	1.482 (7)
O13—C55	1.259 (9)	C54—H54A	0.9600
O13—H13B	0.8200	C54—H54B	0.9600
C15—C16	1.447 (7)	C54—H54C	0.9600
C17—H17A	0.9600	C55—C56	1.427 (8)
C17—H17B	0.9600	C55—H55A	0.9700
C17—H17C	0.9600	C55—H55B	0.9700
C18—C25	1.376 (7)	C56—H56A	0.9600
C18—C19	1.426 (7)	C56—H56B	0.9600
C19—C20	1.394 (7)	C56—H56C	0.9600
C15—N2—C14	109.1 (5)	O6—C27—H27B	109.5
C15—N2—H2A	125.5	H27A—C27—H27B	109.5
C14—N2—H2A	125.5	O6—C27—H27C	109.5
C8—C1—C2	112.0 (4)	H27A—C27—H27C	109.5
C8—C1—C18	113.5 (4)	H27B—C27—H27C	109.5
C2—C1—C18	114.6 (4)	C29—C28—C35	112.2 (4)
C8—C1—H1A	105.2	C29—C28—C45	113.6 (5)
C2—C1—H1A	105.2	C35—C28—C45	112.7 (5)
C18—C1—H1A	105.2	C29—C28—H28A	105.9
O1—N1—O2	123.5 (7)	C35—C28—H28A	105.9
O1—N1—C5	118.3 (7)	C45—C28—H28A	105.9
O2—N1—C5	118.2 (6)	C30—C29—C34	116.7 (6)
C3—C2—C7	117.4 (5)	C30—C29—C28	121.2 (5)
C3—C2—C1	118.6 (5)	C34—C29—C28	122.1 (5)
C7—C2—C1	124.0 (5)	C29—C30—C31	122.7 (6)
C16—O3—C17	116.3 (5)	C29—C30—H30A	118.6
C24—N3—C25	108.7 (5)	C31—C30—H30A	118.6
C24—N3—H3A	125.6	C32—C31—C30	117.9 (6)
C25—N3—H3A	125.6	C32—C31—H31A	121.0
C2—C3—C4	122.7 (6)	C30—C31—H31A	121.0
C2—C3—H3B	118.6	C33—C32—C31	121.7 (6)
C4—C3—H3B	118.6	C33—C32—N4	119.5 (7)
O8—N4—O7	122.5 (7)	C31—C32—N4	118.8 (6)
O8—N4—C32	119.0 (7)	C32—C33—C34	118.9 (6)
O7—N4—C32	118.1 (7)	C32—C33—H33A	120.6
C3—C4—C5	117.6 (6)	C34—C33—H33A	120.6
C3—C4—H4A	121.2	C33—C34—C29	122.1 (6)
C5—C4—H4A	121.2	C33—C34—H34A	118.9
C6—C5—C4	122.7 (6)	C29—C34—H34A	118.9
C6—C5—N1	118.3 (6)	C42—C35—C36	105.5 (5)
C4—C5—N1	119.1 (6)	C42—C35—C28	125.2 (5)
C41—N5—C42	108.9 (5)	C36—C35—C28	129.2 (5)
C41—N5—H5A	125.5	C37—C36—C41	118.1 (5)
C42—N5—H5A	125.5	C37—C36—C35	134.0 (5)
C26—O6—C27	115.2 (5)	C41—C36—C35	107.8 (5)
C5—C6—C7	117.8 (6)	C38—C37—C36	119.3 (6)
C5—C6—H6A	121.1	C38—C37—H37A	120.3
C7—C6—H6A	121.1	C36—C37—H37A	120.3
C51—N6—C52	108.8 (5)	C37—C38—C39	122.4 (6)
C51—N6—H6B	125.6	C37—C38—H38A	118.8
C52—N6—H6B	125.6	C39—C38—H38A	118.8
C2—C7—C6	121.7 (6)	C40—C39—C38	120.6 (6)
C2—C7—H7A	119.1	C40—C39—H39A	119.7
C6—C7—H7A	119.1	C38—C39—H39A	119.7
C15—C8—C9	106.3 (5)	C39—C40—C41	117.6 (6)
C15—C8—C1	125.8 (5)	C39—C40—H40A	121.2
C9—C8—C1	127.9 (5)	C41—C40—H40A	121.2
C10—C9—C14	117.4 (5)	N5—C41—C40	130.6 (6)
C10—C9—C8	135.7 (5)	N5—C41—C36	107.3 (5)
C14—C9—C8	106.7 (5)	C40—C41—C36	122.0 (6)
C43—O9—C44	116.1 (5)	C35—C42—N5	110.5 (5)
C11—C10—C9	120.0 (6)	C35—C42—C43	133.6 (6)
C11—C10—H10A	120.0	N5—C42—C43	115.6 (5)
C9—C10—H10A	120.0	O10—C43—O9	123.8 (6)
C10—C11—C12	120.6 (6)	O10—C43—C42	124.9 (6)
C10—C11—H11A	119.7	O9—C43—C42	111.2 (5)
C12—C11—H11A	119.7	O9—C44—H44A	109.5
C53—O11—C54	114.6 (5)	O9—C44—H44B	109.5
C13—C12—C11	121.3 (6)	H44A—C44—H44B	109.5
C13—C12—H12A	119.3	O9—C44—H44C	109.5
C11—C12—H12A	119.3	H44A—C44—H44C	109.5
C12—C13—C14	118.3 (6)	H44B—C44—H44C	109.5
C12—C13—H13A	120.9	C52—C45—C46	107.4 (5)
C14—C13—H13A	120.9	C52—C45—C28	122.6 (5)
C55—O13—H13B	109.5	C46—C45—C28	129.9 (5)
N2—C14—C13	130.1 (6)	C47—C46—C45	137.0 (5)
N2—C14—C9	107.6 (5)	C47—C46—C51	116.8 (5)
C13—C14—C9	122.3 (6)	C45—C46—C51	106.2 (5)
C8—C15—N2	110.3 (5)	C48—C47—C46	120.0 (6)
C8—C15—C16	127.8 (5)	C48—C47—H47A	120.0
N2—C15—C16	121.8 (5)	C46—C47—H47A	120.0
O4—C16—O3	122.5 (5)	C47—C48—C49	121.1 (6)
O4—C16—C15	126.5 (5)	C47—C48—H48A	119.5
O3—C16—C15	111.0 (5)	C49—C48—H48A	119.5
O3—C17—H17A	109.5	C50—C49—C48	121.9 (6)
O3—C17—H17B	109.5	C50—C49—H49A	119.1
H17A—C17—H17B	109.5	C48—C49—H49A	119.1
O3—C17—H17C	109.5	C49—C50—C51	117.2 (6)
H17A—C17—H17C	109.5	C49—C50—H50A	121.4
H17B—C17—H17C	109.5	C51—C50—H50A	121.4
C25—C18—C19	106.1 (5)	N6—C51—C50	128.8 (5)
C25—C18—C1	124.0 (5)	N6—C51—C46	108.0 (5)
C19—C18—C1	129.8 (5)	C50—C51—C46	123.1 (5)
C20—C19—C24	117.1 (5)	C45—C52—N6	109.6 (5)
C20—C19—C18	136.6 (5)	C45—C52—C53	130.5 (5)
C24—C19—C18	106.3 (5)	N6—C52—C53	119.7 (5)
C21—C20—C19	120.6 (6)	O12—C53—O11	125.5 (5)
C21—C20—H20A	119.7	O12—C53—C52	121.8 (5)
C19—C20—H20A	119.7	O11—C53—C52	112.8 (5)
C20—C21—C22	121.2 (6)	O11—C54—H54A	109.5
C20—C21—H21A	119.4	O11—C54—H54B	109.5
C22—C21—H21A	119.4	H54A—C54—H54B	109.5
C23—C22—C21	121.2 (6)	O11—C54—H54C	109.5
C23—C22—H22A	119.4	H54A—C54—H54C	109.5
C21—C22—H22A	119.4	H54B—C54—H54C	109.5
C22—C23—C24	116.7 (6)	O13—C55—C56	127.6 (9)
C22—C23—H23A	121.7	O13—C55—H55A	105.4
C24—C23—H23A	121.7	C56—C55—H55A	105.4
N3—C24—C23	128.0 (5)	O13—C55—H55B	105.4
N3—C24—C19	108.8 (5)	C56—C55—H55B	105.4
C23—C24—C19	123.2 (5)	H55A—C55—H55B	106.0
N3—C25—C18	110.1 (5)	C55—C56—H56A	109.5
N3—C25—C26	121.6 (5)	C55—C56—H56B	109.5
C18—C25—C26	128.3 (5)	H56A—C56—H56B	109.5
O5—C26—O6	124.0 (5)	C55—C56—H56C	109.5
O5—C26—C25	124.7 (5)	H56A—C56—H56C	109.5
O6—C26—C25	111.3 (5)	H56B—C56—H56C	109.5
O6—C27—H27A	109.5
C8—C1—C2—C3	−67.2 (6)	C35—C28—C29—C30	−154.9 (5)
C18—C1—C2—C3	161.6 (5)	C45—C28—C29—C30	75.9 (7)
C8—C1—C2—C7	112.2 (6)	C35—C28—C29—C34	25.8 (7)
C18—C1—C2—C7	−19.0 (7)	C45—C28—C29—C34	−103.4 (6)
C7—C2—C3—C4	−1.8 (9)	C34—C29—C30—C31	−0.2 (10)
C1—C2—C3—C4	177.6 (5)	C28—C29—C30—C31	−179.5 (6)
C2—C3—C4—C5	−0.4 (9)	C29—C30—C31—C32	0.3 (11)
C3—C4—C5—C6	1.4 (9)	C30—C31—C32—C33	0.6 (10)
C3—C4—C5—N1	−177.5 (6)	C30—C31—C32—N4	177.8 (7)
O1—N1—C5—C6	177.4 (7)	O8—N4—C32—C33	164.3 (7)
O2—N1—C5—C6	−2.3 (9)	O7—N4—C32—C33	−9.2 (10)
O1—N1—C5—C4	−3.6 (10)	O8—N4—C32—C31	−12.9 (11)
O2—N1—C5—C4	176.7 (6)	O7—N4—C32—C31	173.5 (7)
C4—C5—C6—C7	−0.2 (9)	C31—C32—C33—C34	−1.7 (10)
N1—C5—C6—C7	178.8 (5)	N4—C32—C33—C34	−178.8 (6)
C3—C2—C7—C6	3.1 (8)	C32—C33—C34—C29	1.8 (9)
C1—C2—C7—C6	−176.3 (5)	C30—C29—C34—C33	−0.9 (8)
C5—C6—C7—C2	−2.2 (9)	C28—C29—C34—C33	178.4 (5)
C2—C1—C8—C15	141.4 (5)	C29—C28—C35—C42	77.0 (7)
C18—C1—C8—C15	−86.9 (6)	C45—C28—C35—C42	−153.3 (5)
C2—C1—C8—C9	−35.8 (7)	C29—C28—C35—C36	−98.6 (6)
C18—C1—C8—C9	95.9 (6)	C45—C28—C35—C36	31.1 (8)
C15—C8—C9—C10	176.7 (6)	C42—C35—C36—C37	−176.1 (6)
C1—C8—C9—C10	−5.7 (10)	C28—C35—C36—C37	0.2 (10)
C15—C8—C9—C14	1.5 (6)	C42—C35—C36—C41	2.2 (6)
C1—C8—C9—C14	179.2 (5)	C28—C35—C36—C41	178.5 (5)
C14—C9—C10—C11	−1.8 (8)	C41—C36—C37—C38	−0.9 (8)
C8—C9—C10—C11	−176.5 (6)	C35—C36—C37—C38	177.3 (6)
C9—C10—C11—C12	0.2 (9)	C36—C37—C38—C39	2.2 (9)
C10—C11—C12—C13	0.6 (10)	C37—C38—C39—C40	−2.1 (10)
C11—C12—C13—C14	0.4 (10)	C38—C39—C40—C41	0.5 (9)
C15—N2—C14—C13	179.8 (6)	C42—N5—C41—C40	178.0 (6)
C15—N2—C14—C9	−0.8 (6)	C42—N5—C41—C36	1.3 (6)
C12—C13—C14—N2	177.2 (6)	C39—C40—C41—N5	−175.5 (6)
C12—C13—C14—C9	−2.1 (9)	C39—C40—C41—C36	0.7 (8)
C10—C9—C14—N2	−176.6 (5)	C37—C36—C41—N5	176.5 (5)
C8—C9—C14—N2	−0.5 (6)	C35—C36—C41—N5	−2.1 (6)
C10—C9—C14—C13	2.8 (8)	C37—C36—C41—C40	−0.6 (8)
C8—C9—C14—C13	179.0 (5)	C35—C36—C41—C40	−179.2 (5)
C9—C8—C15—N2	−2.1 (6)	C36—C35—C42—N5	−1.4 (6)
C1—C8—C15—N2	−179.8 (5)	C28—C35—C42—N5	−177.9 (5)
C9—C8—C15—C16	−178.3 (5)	C36—C35—C42—C43	170.9 (6)
C1—C8—C15—C16	4.0 (9)	C28—C35—C42—C43	−5.5 (9)
C14—N2—C15—C8	1.8 (6)	C41—N5—C42—C35	0.1 (6)
C14—N2—C15—C16	178.3 (5)	C41—N5—C42—C43	−173.8 (4)
C17—O3—C16—O4	−1.4 (8)	C44—O9—C43—O10	1.7 (9)
C17—O3—C16—C15	178.1 (5)	C44—O9—C43—C42	−177.4 (5)
C8—C15—C16—O4	−13.5 (9)	C35—C42—C43—O10	−167.3 (6)
N2—C15—C16—O4	170.7 (6)	N5—C42—C43—O10	4.7 (8)
C8—C15—C16—O3	167.0 (5)	C35—C42—C43—O9	11.8 (9)
N2—C15—C16—O3	−8.8 (7)	N5—C42—C43—O9	−176.2 (5)
C8—C1—C18—C25	151.5 (5)	C29—C28—C45—C52	−162.7 (5)
C2—C1—C18—C25	−78.0 (6)	C35—C28—C45—C52	68.3 (7)
C8—C1—C18—C19	−28.3 (8)	C29—C28—C45—C46	17.1 (8)
C2—C1—C18—C19	102.1 (6)	C35—C28—C45—C46	−111.9 (7)
C25—C18—C19—C20	−178.6 (6)	C52—C45—C46—C47	177.4 (7)
C1—C18—C19—C20	1.3 (10)	C28—C45—C46—C47	−2.4 (11)
C25—C18—C19—C24	−1.4 (6)	C52—C45—C46—C51	−0.4 (6)
C1—C18—C19—C24	178.5 (5)	C28—C45—C46—C51	179.8 (5)
C24—C19—C20—C21	1.3 (8)	C45—C46—C47—C48	−176.4 (7)
C18—C19—C20—C21	178.2 (6)	C51—C46—C47—C48	1.2 (9)
C19—C20—C21—C22	0.6 (9)	C46—C47—C48—C49	−0.1 (10)
C20—C21—C22—C23	−0.5 (10)	C47—C48—C49—C50	0.4 (11)
C21—C22—C23—C24	−1.3 (9)	C48—C49—C50—C51	−1.9 (10)
C25—N3—C24—C23	−178.0 (6)	C52—N6—C51—C50	−174.8 (6)
C25—N3—C24—C19	−0.1 (6)	C52—N6—C51—C46	0.4 (6)
C22—C23—C24—N3	−179.1 (6)	C49—C50—C51—N6	177.6 (6)
C22—C23—C24—C19	3.3 (9)	C49—C50—C51—C46	3.1 (9)
C20—C19—C24—N3	178.7 (5)	C47—C46—C51—N6	−178.3 (5)
C18—C19—C24—N3	1.0 (6)	C45—C46—C51—N6	0.0 (6)
C20—C19—C24—C23	−3.3 (8)	C47—C46—C51—C50	−2.8 (9)
C18—C19—C24—C23	179.0 (5)	C45—C46—C51—C50	175.5 (5)
C24—N3—C25—C18	−0.8 (6)	C46—C45—C52—N6	0.6 (6)
C24—N3—C25—C26	179.4 (5)	C28—C45—C52—N6	−179.6 (5)
C19—C18—C25—N3	1.4 (6)	C46—C45—C52—C53	−174.8 (5)
C1—C18—C25—N3	−178.5 (4)	C28—C45—C52—C53	5.0 (10)
C19—C18—C25—C26	−178.9 (5)	C51—N6—C52—C45	−0.6 (6)
C1—C18—C25—C26	1.2 (9)	C51—N6—C52—C53	175.4 (5)
C27—O6—C26—O5	−0.1 (8)	C54—O11—C53—O12	−0.2 (9)
C27—O6—C26—C25	−179.1 (5)	C54—O11—C53—C52	−178.7 (5)
N3—C25—C26—O5	−176.8 (6)	C45—C52—C53—O12	3.1 (10)
C18—C25—C26—O5	3.5 (10)	N6—C52—C53—O12	−171.9 (5)
N3—C25—C26—O6	2.2 (7)	C45—C52—C53—O11	−178.3 (6)
C18—C25—C26—O6	−177.5 (5)	N6—C52—C53—O11	6.7 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O13^i	0.86	2.00	2.814 (7)	157
N3—H3A···O4^ii	0.86	2.05	2.892 (6)	166
N5—H5A···O12^iii	0.86	2.01	2.848 (6)	163
N6—H6B···O10^iv	0.86	2.16	2.984 (6)	160
O13—H13B···O5	0.82	1.91	2.733 (7)	177

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