Methyl 5-[N-(2-methoxy­carbonyl-1-methyl­vinyl)carbamo­yl]-2,6-dimethyl-4-(3-nitro­phen­yl)-1,4-dihydro­pyridine-3-carboxyl­ate monohydrate

The title compound, C₂₁H₂₅N₃O₇, is a nefidipine analog. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into chains running parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.138
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3     ..  H3A     ..       1.92 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O3     ..  O3      ..       2.89 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.60 Deg.
              O3'  -N2   -O3      1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Methyl 5-[N-(2-methoxycarbonyl-1-methylvinyl)carbamoyl]-2,6-dimethyl- 4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate monohydrate

Crystal data

C21H25N3O8	F(000) = 472
Mr = 447.44	Dx = 1.374 Mg m^−3
Triclinic, P1	Melting point = 393–394 K
a = 7.872 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.800 (7) Å	Cell parameters from 1645 reflections
c = 12.277 (7) Å	θ = 2.4–24.9°
α = 90.238 (10)°	µ = 0.11 mm^−1
β = 91.757 (10)°	T = 294 K
γ = 108.391 (9)°	Block, yellow
V = 1081.5 (10) Å^3	0.26 × 0.24 × 0.14 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3802 independent reflections
Radiation source: fine-focus sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.973, Tmax = 0.985	k = −12→14
5562 measured reflections	l = −10→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.1639P] where P = (Fo^2 + 2Fc^2)/3
3802 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.31 e Å^−3
24 restraints	Δρmin = −0.18 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)
O1	0.4034 (3)	0.61631 (16)	0.19917 (17)	0.0737 (7)
O2	0.4786 (2)	0.47152 (15)	0.27893 (15)	0.0549 (5)
O3	0.0264 (11)	0.386 (2)	0.5206 (11)	0.086 (4)	0.54 (4)
O3'	0.0129 (17)	0.328 (3)	0.5348 (7)	0.075 (4)	0.46 (4)
O4	−0.2608 (3)	0.3208 (2)	0.51173 (18)	0.0890 (8)
O5	0.2751 (3)	0.02830 (16)	0.00440 (15)	0.0609 (6)
O6	0.2558 (3)	0.12534 (18)	0.39596 (15)	0.0668 (6)
O7	0.2622 (3)	−0.01355 (19)	0.51579 (16)	0.0743 (7)
N1	0.1746 (3)	0.35367 (18)	−0.04983 (16)	0.0429 (5)
H1	0.1162	0.3662	−0.1064	0.051*
N2	−0.1184 (4)	0.3253 (3)	0.4746 (2)	0.0704 (8)
N3	0.2709 (3)	0.06223 (16)	0.18549 (16)	0.0389 (5)
H3	0.2535	0.1114	0.2325	0.047*
C1	0.2459 (3)	0.4468 (2)	0.0234 (2)	0.0394 (6)
C2	0.2947 (3)	0.42000 (19)	0.12334 (19)	0.0343 (6)
C3	0.2372 (3)	0.29055 (19)	0.15830 (19)	0.0350 (6)
H3A	0.3251	0.2810	0.2128	0.042*
C4	0.2334 (3)	0.2093 (2)	0.06219 (19)	0.0348 (6)
C5	0.1917 (3)	0.2421 (2)	−0.03753 (19)	0.0379 (6)
C6	0.1624 (4)	0.1714 (2)	−0.14141 (19)	0.0496 (7)
H6A	0.2753	0.1824	−0.1744	0.074*
H6B	0.0856	0.1979	−0.1902	0.074*
H6C	0.1073	0.0883	−0.1264	0.074*
C7	0.2631 (4)	0.5666 (2)	−0.0213 (2)	0.0523 (7)
H7A	0.1773	0.5976	0.0114	0.078*
H7B	0.2412	0.5600	−0.0988	0.078*
H7C	0.3818	0.6197	−0.0054	0.078*
C8	0.3947 (3)	0.5129 (2)	0.2008 (2)	0.0436 (6)
C9	0.5820 (4)	0.5571 (3)	0.3586 (2)	0.0711 (9)
H9A	0.6740	0.6177	0.3230	0.107*
H9B	0.6359	0.5176	0.4110	0.107*
H9C	0.5053	0.5931	0.3949	0.107*
C10	0.0570 (3)	0.2633 (2)	0.21184 (18)	0.0345 (6)
C11	0.0495 (3)	0.3015 (2)	0.31808 (19)	0.0422 (6)
H11	0.1543	0.3378	0.3588	0.051*
C12	−0.1139 (4)	0.2851 (2)	0.3622 (2)	0.0452 (7)
C13	−0.2718 (4)	0.2328 (2)	0.3062 (2)	0.0531 (7)
H13	−0.3810	0.2249	0.3374	0.064*
C14	−0.2642 (4)	0.1922 (3)	0.2025 (2)	0.0561 (8)
H14	−0.3698	0.1546	0.1629	0.067*
C15	−0.1019 (3)	0.2066 (2)	0.1561 (2)	0.0444 (6)
H15	−0.0995	0.1776	0.0858	0.053*
C16	0.2620 (3)	0.0934 (2)	0.0778 (2)	0.0389 (6)
C17	0.3039 (3)	−0.0373 (2)	0.2281 (2)	0.0435 (6)
C18	0.3446 (4)	−0.1246 (2)	0.1537 (2)	0.0602 (8)
H18A	0.3689	−0.1865	0.1958	0.090*
H18B	0.4476	−0.0844	0.1125	0.090*
H18C	0.2438	−0.1591	0.1048	0.090*
C19	0.3017 (4)	−0.0529 (2)	0.3364 (2)	0.0506 (7)
H19	0.3216	−0.1217	0.3625	0.061*
C20	0.2711 (4)	0.0283 (3)	0.4147 (2)	0.0526 (7)
C21	0.2315 (5)	0.0615 (3)	0.6003 (3)	0.0904 (12)
H21A	0.3363	0.1297	0.6117	0.136*
H21B	0.2060	0.0173	0.6666	0.136*
H21C	0.1315	0.0875	0.5792	0.136*
O8	0.0179 (3)	0.5996 (2)	0.24107 (16)	0.0800 (7)
H8A	0.0030	0.6040	0.3093	0.096*
H8B	0.1216	0.5990	0.2233	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1013 (18)	0.0355 (11)	0.0854 (16)	0.0258 (11)	−0.0224 (13)	−0.0067 (10)
O2	0.0618 (13)	0.0431 (10)	0.0572 (12)	0.0147 (9)	−0.0175 (10)	−0.0044 (9)
O3	0.078 (4)	0.115 (8)	0.058 (4)	0.019 (4)	0.007 (3)	−0.027 (5)
O3'	0.072 (5)	0.105 (9)	0.042 (4)	0.020 (5)	−0.002 (3)	−0.013 (4)
O4	0.0853 (18)	0.126 (2)	0.0698 (15)	0.0499 (16)	0.0341 (13)	0.0016 (14)
O5	0.0943 (16)	0.0509 (11)	0.0496 (12)	0.0401 (11)	0.0051 (10)	−0.0058 (10)
O6	0.1025 (17)	0.0585 (13)	0.0538 (12)	0.0460 (12)	0.0016 (11)	0.0041 (10)
O7	0.1121 (19)	0.0774 (15)	0.0472 (13)	0.0487 (14)	0.0105 (12)	0.0161 (11)
N1	0.0521 (14)	0.0442 (13)	0.0367 (12)	0.0215 (11)	−0.0030 (10)	0.0062 (10)
N2	0.070 (2)	0.097 (2)	0.0482 (16)	0.0298 (18)	0.0150 (15)	−0.0046 (15)
N3	0.0463 (13)	0.0311 (11)	0.0433 (12)	0.0178 (9)	0.0033 (10)	0.0035 (9)
C1	0.0382 (14)	0.0375 (14)	0.0467 (16)	0.0171 (11)	0.0109 (12)	0.0059 (12)
C2	0.0306 (13)	0.0311 (13)	0.0435 (15)	0.0124 (10)	0.0049 (11)	0.0051 (11)
C3	0.0361 (14)	0.0332 (13)	0.0370 (14)	0.0128 (11)	0.0003 (11)	0.0024 (11)
C4	0.0349 (13)	0.0322 (13)	0.0372 (14)	0.0103 (11)	0.0038 (11)	0.0011 (11)
C5	0.0370 (14)	0.0385 (14)	0.0396 (15)	0.0136 (11)	0.0050 (11)	0.0013 (11)
C6	0.0554 (18)	0.0551 (17)	0.0404 (15)	0.0207 (14)	−0.0005 (13)	−0.0022 (13)
C7	0.0637 (19)	0.0428 (15)	0.0572 (18)	0.0256 (14)	0.0099 (14)	0.0140 (13)
C8	0.0423 (15)	0.0362 (15)	0.0537 (17)	0.0138 (12)	0.0094 (13)	0.0041 (13)
C9	0.077 (2)	0.065 (2)	0.061 (2)	0.0095 (17)	−0.0159 (17)	−0.0105 (17)
C10	0.0394 (14)	0.0293 (12)	0.0357 (14)	0.0119 (11)	0.0014 (11)	0.0053 (10)
C11	0.0413 (15)	0.0464 (15)	0.0384 (15)	0.0134 (12)	−0.0001 (12)	0.0003 (12)
C12	0.0476 (17)	0.0503 (16)	0.0398 (15)	0.0179 (13)	0.0083 (13)	0.0060 (13)
C13	0.0423 (17)	0.0632 (19)	0.0569 (19)	0.0197 (14)	0.0147 (14)	0.0149 (15)
C14	0.0380 (16)	0.0657 (19)	0.0570 (19)	0.0055 (14)	0.0025 (14)	0.0027 (15)
C15	0.0438 (16)	0.0468 (15)	0.0399 (15)	0.0103 (12)	0.0017 (12)	0.0021 (12)
C16	0.0393 (15)	0.0337 (14)	0.0444 (16)	0.0124 (11)	0.0037 (11)	−0.0009 (12)
C17	0.0413 (15)	0.0316 (13)	0.0583 (18)	0.0123 (11)	0.0030 (13)	0.0074 (12)
C18	0.077 (2)	0.0428 (16)	0.072 (2)	0.0328 (15)	0.0106 (16)	0.0062 (14)
C19	0.0617 (19)	0.0411 (15)	0.0552 (18)	0.0248 (14)	0.0039 (14)	0.0129 (13)
C20	0.0576 (18)	0.0539 (18)	0.0515 (18)	0.0251 (15)	0.0012 (14)	0.0110 (14)
C21	0.132 (4)	0.105 (3)	0.051 (2)	0.061 (3)	0.007 (2)	0.001 (2)
O8	0.0903 (17)	0.1188 (19)	0.0482 (12)	0.0579 (15)	−0.0017 (11)	0.0045 (12)

Geometric parameters (Å, º)

O1—C8	1.201 (3)	C6—H6C	0.9600
O2—C8	1.327 (3)	C7—H7A	0.9600
O2—C9	1.436 (3)	C7—H7B	0.9600
O3—N2	1.254 (7)	C7—H7C	0.9600
O3'—N2	1.242 (7)	C9—H9A	0.9600
O4—N2	1.209 (3)	C9—H9B	0.9600
O5—C16	1.210 (3)	C9—H9C	0.9600
O6—C20	1.211 (3)	C10—C15	1.377 (3)
O7—C20	1.333 (3)	C10—C11	1.387 (3)
O7—C21	1.436 (4)	C11—C12	1.368 (3)
N1—C5	1.373 (3)	C11—H11	0.9300
N1—C1	1.379 (3)	C12—C13	1.364 (4)
N1—H1	0.8600	C13—C14	1.368 (4)
N2—C12	1.463 (4)	C13—H13	0.9300
N3—C16	1.379 (3)	C14—C15	1.376 (4)
N3—C17	1.382 (3)	C14—H14	0.9300
N3—H3	0.8600	C15—H15	0.9300
C1—C2	1.343 (3)	C17—C19	1.342 (4)
C1—C7	1.487 (3)	C17—C18	1.489 (4)
C2—C8	1.458 (3)	C18—H18A	0.9600
C2—C3	1.518 (3)	C18—H18B	0.9600
C3—C4	1.511 (3)	C18—H18C	0.9600
C3—C10	1.523 (3)	C19—C20	1.433 (4)
C3—H3A	0.9800	C19—H19	0.9300
C4—C5	1.348 (3)	C21—H21A	0.9600
C4—C16	1.466 (3)	C21—H21B	0.9600
C5—C6	1.493 (3)	C21—H21C	0.9600
C6—H6A	0.9600	O8—H8A	0.8530
C6—H6B	0.9600	O8—H8B	0.8537
C8—O2—C9	116.5 (2)	O2—C9—H9B	109.5
C20—O7—C21	116.6 (2)	H9A—C9—H9B	109.5
C5—N1—C1	123.7 (2)	O2—C9—H9C	109.5
C5—N1—H1	118.2	H9A—C9—H9C	109.5
C1—N1—H1	118.2	H9B—C9—H9C	109.5
O4—N2—O3'	121.4 (6)	C15—C10—C11	118.1 (2)
O4—N2—O3	121.1 (6)	C15—C10—C3	122.0 (2)
O3'—N2—O3	31.6 (5)	C11—C10—C3	119.8 (2)
O4—N2—C12	119.0 (3)	C12—C11—C10	119.3 (2)
O3'—N2—C12	116.2 (6)	C12—C11—H11	120.4
O3—N2—C12	118.1 (5)	C10—C11—H11	120.4
C16—N3—C17	128.8 (2)	C13—C12—C11	122.9 (3)
C16—N3—H3	115.6	C13—C12—N2	118.8 (3)
C17—N3—H3	115.6	C11—C12—N2	118.2 (2)
C2—C1—N1	117.6 (2)	C12—C13—C14	117.8 (3)
C2—C1—C7	128.2 (2)	C12—C13—H13	121.1
N1—C1—C7	114.2 (2)	C14—C13—H13	121.1
C1—C2—C8	121.5 (2)	C13—C14—C15	120.7 (3)
C1—C2—C3	119.2 (2)	C13—C14—H14	119.7
C8—C2—C3	119.2 (2)	C15—C14—H14	119.7
C4—C3—C2	110.4 (2)	C14—C15—C10	121.2 (3)
C4—C3—C10	113.21 (19)	C14—C15—H15	119.4
C2—C3—C10	108.12 (18)	C10—C15—H15	119.4
C4—C3—H3A	108.3	O5—C16—N3	121.5 (2)
C2—C3—H3A	108.3	O5—C16—C4	124.3 (2)
C10—C3—H3A	108.3	N3—C16—C4	114.1 (2)
C5—C4—C16	120.6 (2)	C19—C17—N3	119.5 (2)
C5—C4—C3	118.5 (2)	C19—C17—C18	120.9 (2)
C16—C4—C3	120.8 (2)	N3—C17—C18	119.6 (2)
C4—C5—N1	118.8 (2)	C17—C18—H18A	109.5
C4—C5—C6	127.7 (2)	C17—C18—H18B	109.5
N1—C5—C6	113.4 (2)	H18A—C18—H18B	109.5
C5—C6—H6A	109.5	C17—C18—H18C	109.5
C5—C6—H6B	109.5	H18A—C18—H18C	109.5
H6A—C6—H6B	109.5	H18B—C18—H18C	109.5
C5—C6—H6C	109.5	C17—C19—C20	125.0 (2)
H6A—C6—H6C	109.5	C17—C19—H19	117.5
H6B—C6—H6C	109.5	C20—C19—H19	117.5
C1—C7—H7A	109.5	O6—C20—O7	121.3 (3)
C1—C7—H7B	109.5	O6—C20—C19	126.2 (3)
H7A—C7—H7B	109.5	O7—C20—C19	112.4 (2)
C1—C7—H7C	109.5	O7—C21—H21A	109.5
H7A—C7—H7C	109.5	O7—C21—H21B	109.5
H7B—C7—H7C	109.5	H21A—C21—H21B	109.5
O1—C8—O2	121.0 (2)	O7—C21—H21C	109.5
O1—C8—C2	126.4 (2)	H21A—C21—H21C	109.5
O2—C8—C2	112.6 (2)	H21B—C21—H21C	109.5
O2—C9—H9A	109.5	H8A—O8—H8B	115.6
C5—N1—C1—C2	−17.1 (3)	C15—C10—C11—C12	−2.0 (3)
C5—N1—C1—C7	161.3 (2)	C3—C10—C11—C12	174.7 (2)
N1—C1—C2—C8	171.0 (2)	C10—C11—C12—C13	−0.2 (4)
C7—C1—C2—C8	−7.2 (4)	C10—C11—C12—N2	179.6 (2)
N1—C1—C2—C3	−11.9 (3)	O4—N2—C12—C13	−6.4 (4)
C7—C1—C2—C3	170.0 (2)	O3'—N2—C12—C13	153.0 (15)
C1—C2—C3—C4	34.4 (3)	O3—N2—C12—C13	−171.4 (16)
C8—C2—C3—C4	−148.4 (2)	O4—N2—C12—C11	173.8 (3)
C1—C2—C3—C10	−89.9 (3)	O3'—N2—C12—C11	−26.8 (15)
C8—C2—C3—C10	87.3 (2)	O3—N2—C12—C11	8.8 (16)
C2—C3—C4—C5	−31.8 (3)	C11—C12—C13—C14	2.0 (4)
C10—C3—C4—C5	89.6 (3)	N2—C12—C13—C14	−177.8 (2)
C2—C3—C4—C16	152.4 (2)	C12—C13—C14—C15	−1.4 (4)
C10—C3—C4—C16	−86.2 (3)	C13—C14—C15—C10	−0.8 (4)
C16—C4—C5—N1	−176.8 (2)	C11—C10—C15—C14	2.6 (4)
C3—C4—C5—N1	7.4 (3)	C3—C10—C15—C14	−174.1 (2)
C16—C4—C5—C6	2.3 (4)	C17—N3—C16—O5	3.8 (4)
C3—C4—C5—C6	−173.5 (2)	C17—N3—C16—C4	−177.0 (2)
C1—N1—C5—C4	19.5 (3)	C5—C4—C16—O5	10.5 (4)
C1—N1—C5—C6	−159.7 (2)	C3—C4—C16—O5	−173.8 (2)
C9—O2—C8—O1	−1.4 (4)	C5—C4—C16—N3	−168.7 (2)
C9—O2—C8—C2	179.4 (2)	C3—C4—C16—N3	7.0 (3)
C1—C2—C8—O1	20.8 (4)	C16—N3—C17—C19	−178.1 (2)
C3—C2—C8—O1	−156.3 (3)	C16—N3—C17—C18	3.1 (4)
C1—C2—C8—O2	−160.0 (2)	N3—C17—C19—C20	−1.5 (4)
C3—C2—C8—O2	22.8 (3)	C18—C17—C19—C20	177.4 (3)
C4—C3—C10—C15	−23.9 (3)	C21—O7—C20—O6	0.7 (4)
C2—C3—C10—C15	98.7 (2)	C21—O7—C20—C19	−179.9 (3)
C4—C3—C10—C11	159.5 (2)	C17—C19—C20—O6	−5.6 (5)
C2—C3—C10—C11	−77.9 (3)	C17—C19—C20—O7	175.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O3′^i	0.85	2.09	2.916 (10)	162
O8—H8A···O3^i	0.85	2.11	2.967 (12)	178

Symmetry code: (i) −x, −y+1, −z+1.