N′-tert-Butyl-4-chloro-N′-(4-oxo-4H-chromen-3-ylcarbon­yl)benzohydrazide 0.65-hydrate

In the crystal structure of the title compound, C₂₁H₁₉ClN₂O₄·0.65H₂O, the dihedral angle formed by the bicyclic benzopyran system and the chloro­benzene ring is 55.1 (2)°. In the crystal structure, mol­ecules are linked into mol­ecular tapes through weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 94%
• Disorder in solvent or counterion
• R factor = 0.055
• wR factor = 0.182
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O4     ..  O5      ..       2.68 Ang.

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.56 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      65.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        >O5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2A    ..  H21     ..       1.97 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O1     ..  O5      ..       2.87 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O2      ..       3.19 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C21 H20.3 Cl1 N2 O4.65
            Atom count from the _atom_site data:  C21 H19 Cl1 N2 O4.65
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C21 H20.30 Cl N2 O4.65
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         42.00     42.00    0.00
           H         40.60     38.00    2.60
           Cl         2.00      2.00    0.00
           N          4.00      4.00    0.00
           O          9.30      9.30    0.00

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); 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, 2001) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

N'-tert-Butyl-4-chloro-N'-(4-oxo-4H-chromen-3-ylcarbonyl)benzohydrazide 0.65-hydrate

Crystal data

C21H19ClN2O4·0.65H2O	Z = 2
Mr = 409.23	F(000) = 427
Triclinic, P1	Dx = 1.307 Mg m^−3
Hall symbol: -P 1	Melting point: 496 K
a = 6.7913 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7863 (18) Å	Cell parameters from 4083 reflections
c = 13.799 (2) Å	θ = 2.6–27.0°
α = 75.463 (2)°	µ = 0.22 mm^−1
β = 81.619 (3)°	T = 292 K
γ = 77.108 (3)°	Block, colourless
V = 1037.5 (3) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −7→8
7452 measured reflections	k = −14→14
3610 independent reflections	l = −16→16

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.182	w = 1/[σ^2(Fo^2) + (0.1051P)^2 + 0.222P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3610 reflections	Δρmax = 0.39 e Å^−3
267 parameters	Δρmin = −0.30 e Å^−3
18 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (7)

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)
C1	0.3022 (4)	0.4186 (2)	0.90167 (17)	0.0541 (6)
C2	0.3278 (5)	0.2949 (2)	0.9260 (2)	0.0695 (7)
H2	0.2160	0.2580	0.9419	0.083*
C3	0.5198 (5)	0.2287 (3)	0.9263 (2)	0.0799 (8)
H3	0.5393	0.1457	0.9422	0.096*
C4	0.6867 (5)	0.2840 (3)	0.9028 (2)	0.0797 (8)
H4	0.8172	0.2380	0.9023	0.096*
C5	0.6595 (4)	0.4057 (3)	0.8805 (2)	0.0678 (7)
H5	0.7720	0.4419	0.8656	0.081*
C6	0.4636 (3)	0.4769 (2)	0.87981 (16)	0.0533 (6)
C7	0.4304 (3)	0.6075 (2)	0.85799 (17)	0.0537 (6)
C8	0.2179 (3)	0.6661 (2)	0.85518 (16)	0.0520 (6)
C9	0.0744 (3)	0.6006 (2)	0.87746 (18)	0.0552 (6)
H9	−0.0596	0.6415	0.8767	0.066*
C10	0.1455 (4)	0.7992 (2)	0.83934 (19)	0.0587 (6)
C11	0.1696 (7)	1.0043 (3)	0.7302 (3)	0.1031 (12)
C12	−0.0535 (9)	1.0518 (4)	0.7337 (5)	0.150 (2)
H12A	−0.1119	1.0189	0.6903	0.225*
H12B	−0.0781	1.1373	0.7117	0.225*
H12C	−0.1139	1.0299	0.8013	0.225*
C13	0.2631 (10)	1.0407 (5)	0.8090 (5)	0.1527 (19)
H13A	0.4046	1.0045	0.8086	0.229*
H13B	0.1954	1.0143	0.8743	0.229*
H13C	0.2482	1.1260	0.7938	0.229*
C14	0.2605 (10)	1.0495 (4)	0.6230 (4)	0.157 (2)
H14A	0.4051	1.0230	0.6189	0.235*
H14B	0.2284	1.1352	0.6057	0.235*
H14C	0.2050	1.0186	0.5772	0.235*
C15	0.2633 (5)	0.7744 (2)	0.6137 (2)	0.0714 (7)
C16	0.4206 (4)	0.7150 (2)	0.54457 (19)	0.0681 (7)
C17	0.3624 (5)	0.6999 (3)	0.4581 (2)	0.0841 (9)
H17	0.2269	0.7245	0.4453	0.101*
C18	0.5005 (6)	0.6493 (3)	0.3903 (2)	0.0918 (10)
H18	0.4589	0.6396	0.3321	0.110*
C19	0.6987 (6)	0.6134 (3)	0.4092 (2)	0.0804 (9)
C20	0.7603 (5)	0.6254 (3)	0.4949 (2)	0.0888 (10)
H20	0.8959	0.6001	0.5074	0.107*
C21	0.6217 (5)	0.6749 (3)	0.5629 (2)	0.0873 (10)
H21	0.6637	0.6815	0.6221	0.105*
Cl1	0.87490 (19)	0.55222 (11)	0.32298 (7)	0.1278 (5)
N1	0.2112 (3)	0.86863 (18)	0.75180 (17)	0.0681 (6)
N2	0.3377 (3)	0.81071 (18)	0.68316 (16)	0.0652 (6)
H2A	0.4670	0.7978	0.6852	0.078*
O1	0.5713 (3)	0.66166 (17)	0.84479 (16)	0.0731 (6)
O2	0.1054 (2)	0.48071 (15)	0.90095 (13)	0.0587 (5)
O3	0.0276 (3)	0.84079 (18)	0.90247 (16)	0.0851 (7)
O4	0.0824 (4)	0.7890 (3)	0.6067 (2)	0.1101 (9)
O5	0.7140 (6)	0.8534 (4)	0.6990 (4)	0.1089 (12)	0.65

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0529 (13)	0.0670 (14)	0.0452 (12)	−0.0124 (10)	−0.0033 (10)	−0.0177 (10)
C2	0.0762 (17)	0.0666 (15)	0.0709 (17)	−0.0202 (13)	−0.0061 (13)	−0.0203 (13)
C3	0.093 (2)	0.0634 (16)	0.083 (2)	−0.0020 (15)	−0.0218 (16)	−0.0213 (14)
C4	0.0701 (18)	0.0793 (18)	0.092 (2)	0.0077 (14)	−0.0237 (15)	−0.0335 (16)
C5	0.0521 (14)	0.0799 (17)	0.0757 (17)	−0.0061 (12)	−0.0142 (12)	−0.0267 (13)
C6	0.0489 (12)	0.0685 (14)	0.0457 (12)	−0.0108 (10)	−0.0069 (9)	−0.0180 (10)
C7	0.0486 (12)	0.0677 (14)	0.0472 (12)	−0.0158 (10)	−0.0070 (9)	−0.0120 (10)
C8	0.0478 (12)	0.0643 (13)	0.0451 (12)	−0.0123 (10)	−0.0034 (9)	−0.0140 (10)
C9	0.0448 (12)	0.0670 (14)	0.0536 (13)	−0.0094 (10)	−0.0002 (9)	−0.0171 (11)
C10	0.0511 (13)	0.0647 (14)	0.0600 (14)	−0.0093 (10)	−0.0031 (11)	−0.0167 (11)
C11	0.142 (3)	0.0582 (17)	0.103 (3)	−0.0242 (19)	0.020 (2)	−0.0205 (16)
C12	0.164 (4)	0.087 (3)	0.164 (4)	0.037 (3)	−0.020 (4)	−0.016 (3)
C13	0.187 (4)	0.121 (3)	0.180 (4)	−0.055 (3)	−0.020 (3)	−0.065 (3)
C14	0.211 (4)	0.082 (2)	0.154 (4)	−0.031 (3)	0.030 (3)	−0.009 (2)
C15	0.083 (2)	0.0681 (16)	0.0568 (15)	−0.0040 (13)	−0.0142 (13)	−0.0073 (12)
C16	0.0874 (19)	0.0593 (14)	0.0529 (14)	−0.0097 (13)	−0.0116 (13)	−0.0056 (11)
C17	0.088 (2)	0.100 (2)	0.0678 (18)	−0.0180 (17)	−0.0162 (15)	−0.0198 (16)
C18	0.116 (3)	0.109 (2)	0.0572 (17)	−0.020 (2)	−0.0183 (17)	−0.0279 (16)
C19	0.110 (2)	0.0706 (17)	0.0526 (15)	0.0018 (16)	−0.0126 (15)	−0.0134 (13)
C20	0.096 (2)	0.091 (2)	0.0732 (19)	0.0203 (17)	−0.0251 (16)	−0.0309 (16)
C21	0.103 (2)	0.091 (2)	0.0641 (17)	0.0209 (17)	−0.0309 (16)	−0.0316 (15)
Cl1	0.1470 (10)	0.1531 (10)	0.0666 (6)	0.0329 (7)	−0.0135 (5)	−0.0475 (6)
N1	0.0772 (15)	0.0548 (11)	0.0681 (14)	−0.0116 (10)	0.0072 (11)	−0.0156 (10)
N2	0.0698 (13)	0.0632 (12)	0.0594 (12)	−0.0140 (10)	0.0051 (10)	−0.0136 (10)
O1	0.0521 (10)	0.0773 (12)	0.0915 (14)	−0.0227 (9)	−0.0150 (9)	−0.0087 (10)
O2	0.0485 (9)	0.0657 (10)	0.0639 (10)	−0.0177 (7)	0.0027 (7)	−0.0172 (8)
O3	0.0816 (13)	0.0791 (13)	0.0810 (14)	0.0009 (10)	0.0183 (11)	−0.0228 (11)
O4	0.0835 (17)	0.143 (2)	0.1038 (18)	0.0163 (14)	−0.0308 (13)	−0.0493 (16)
O5	0.084 (2)	0.125 (3)	0.130 (3)	−0.036 (2)	−0.006 (2)	−0.040 (3)

Geometric parameters (Å, º)

C1—O2	1.373 (3)	C12—H12B	0.9600
C1—C6	1.378 (3)	C12—H12C	0.9600
C1—C2	1.388 (4)	C13—H13A	0.9600
C2—C3	1.362 (4)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.390 (5)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.364 (4)	C14—H14C	0.9600
C4—H4	0.9300	C15—O4	1.217 (4)
C5—C6	1.406 (3)	C15—N2	1.342 (4)
C5—H5	0.9300	C15—C16	1.499 (4)
C6—C7	1.464 (3)	C16—C17	1.373 (4)
C7—O1	1.233 (3)	C16—C21	1.380 (4)
C7—C8	1.456 (3)	C17—C18	1.373 (5)
C8—C9	1.331 (3)	C17—H17	0.9300
C8—C10	1.505 (3)	C18—C19	1.360 (5)
C9—O2	1.343 (3)	C18—H18	0.9300
C9—H9	0.9300	C19—C20	1.360 (4)
C10—O3	1.215 (3)	C19—Cl1	1.731 (3)
C10—N1	1.355 (3)	C20—C21	1.371 (4)
C11—C12	1.492 (7)	C20—H20	0.9300
C11—N1	1.520 (4)	C21—H21	0.9300
C11—C13	1.526 (7)	N1—N2	1.388 (3)
C11—C14	1.528 (6)	N2—H2A	0.8600
C12—H12A	0.9600
O2—C1—C6	121.4 (2)	H12B—C12—H12C	109.5
O2—C1—C2	116.2 (2)	C11—C13—H13A	109.5
C6—C1—C2	122.5 (2)	C11—C13—H13B	109.5
C3—C2—C1	118.7 (3)	H13A—C13—H13B	109.5
C3—C2—H2	120.6	C11—C13—H13C	109.5
C1—C2—H2	120.6	H13A—C13—H13C	109.5
C2—C3—C4	120.6 (3)	H13B—C13—H13C	109.5
C2—C3—H3	119.7	C11—C14—H14A	109.5
C4—C3—H3	119.7	C11—C14—H14B	109.5
C5—C4—C3	120.1 (3)	H14A—C14—H14B	109.5
C5—C4—H4	119.9	C11—C14—H14C	109.5
C3—C4—H4	119.9	H14A—C14—H14C	109.5
C4—C5—C6	120.8 (3)	H14B—C14—H14C	109.5
C4—C5—H5	119.6	O4—C15—N2	122.9 (3)
C6—C5—H5	119.6	O4—C15—C16	122.4 (3)
C1—C6—C5	117.2 (2)	N2—C15—C16	114.8 (3)
C1—C6—C7	120.9 (2)	C17—C16—C21	118.0 (3)
C5—C6—C7	121.9 (2)	C17—C16—C15	118.5 (3)
O1—C7—C8	123.7 (2)	C21—C16—C15	123.5 (3)
O1—C7—C6	122.3 (2)	C18—C17—C16	121.2 (3)
C8—C7—C6	114.0 (2)	C18—C17—H17	119.4
C9—C8—C7	119.7 (2)	C16—C17—H17	119.4
C9—C8—C10	116.2 (2)	C19—C18—C17	119.4 (3)
C7—C8—C10	123.7 (2)	C19—C18—H18	120.3
C8—C9—O2	125.9 (2)	C17—C18—H18	120.3
C8—C9—H9	117.0	C20—C19—C18	120.7 (3)
O2—C9—H9	117.0	C20—C19—Cl1	119.5 (3)
O3—C10—N1	122.2 (2)	C18—C19—Cl1	119.7 (2)
O3—C10—C8	120.1 (2)	C19—C20—C21	119.7 (3)
N1—C10—C8	117.6 (2)	C19—C20—H20	120.1
C12—C11—N1	110.0 (3)	C21—C20—H20	120.1
C12—C11—C13	110.9 (4)	C20—C21—C16	120.8 (3)
N1—C11—C13	107.9 (4)	C20—C21—H21	119.6
C12—C11—C14	107.4 (4)	C16—C21—H21	119.6
N1—C11—C14	107.7 (3)	C10—N1—N2	117.1 (2)
C13—C11—C14	112.9 (4)	C10—N1—C11	123.4 (2)
C11—C12—H12A	109.5	N2—N1—C11	119.2 (2)
C11—C12—H12B	109.5	C15—N2—N1	121.6 (2)
H12A—C12—H12B	109.5	C15—N2—H2A	119.2
C11—C12—H12C	109.5	N1—N2—H2A	119.2
H12A—C12—H12C	109.5	C9—O2—C1	117.94 (18)
O2—C1—C2—C3	178.9 (2)	N2—C15—C16—C21	14.4 (4)
C6—C1—C2—C3	−1.4 (4)	C21—C16—C17—C18	−1.7 (5)
C1—C2—C3—C4	0.2 (5)	C15—C16—C17—C18	178.1 (3)
C2—C3—C4—C5	0.8 (5)	C16—C17—C18—C19	0.0 (5)
C3—C4—C5—C6	−0.7 (5)	C17—C18—C19—C20	1.1 (5)
O2—C1—C6—C5	−178.8 (2)	C17—C18—C19—Cl1	−178.7 (3)
C2—C1—C6—C5	1.6 (4)	C18—C19—C20—C21	−0.5 (5)
O2—C1—C6—C7	1.9 (3)	Cl1—C19—C20—C21	179.3 (3)
C2—C1—C6—C7	−177.8 (2)	C19—C20—C21—C16	−1.3 (5)
C4—C5—C6—C1	−0.5 (4)	C17—C16—C21—C20	2.3 (5)
C4—C5—C6—C7	178.8 (2)	C15—C16—C21—C20	−177.5 (3)
C1—C6—C7—O1	175.1 (2)	O3—C10—N1—N2	−176.8 (2)
C5—C6—C7—O1	−4.2 (4)	C8—C10—N1—N2	1.0 (3)
C1—C6—C7—C8	−3.9 (3)	O3—C10—N1—C11	9.1 (4)
C5—C6—C7—C8	176.8 (2)	C8—C10—N1—C11	−173.1 (3)
O1—C7—C8—C9	−175.1 (2)	C12—C11—N1—C10	−61.0 (5)
C6—C7—C8—C9	3.9 (3)	C13—C11—N1—C10	60.1 (5)
O1—C7—C8—C10	−2.1 (4)	C14—C11—N1—C10	−177.8 (4)
C6—C7—C8—C10	176.8 (2)	C12—C11—N1—N2	124.9 (4)
C7—C8—C9—O2	−1.8 (4)	C13—C11—N1—N2	−114.0 (4)
C10—C8—C9—O2	−175.3 (2)	C14—C11—N1—N2	8.2 (5)
C9—C8—C10—O3	52.2 (3)	O4—C15—N2—N1	−0.5 (4)
C7—C8—C10—O3	−121.0 (3)	C16—C15—N2—N1	179.1 (2)
C9—C8—C10—N1	−125.6 (2)	C10—N1—N2—C15	88.9 (3)
C7—C8—C10—N1	61.2 (3)	C11—N1—N2—C15	−96.7 (3)
O4—C15—C16—C17	14.3 (4)	C8—C9—O2—C1	−0.5 (3)
N2—C15—C16—C17	−165.3 (3)	C6—C1—O2—C9	0.5 (3)
O4—C15—C16—C21	−165.9 (3)	C2—C1—O2—C9	−179.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O5^i	0.96	2.47	3.259 (8)	140
C9—H9···O1^i	0.93	2.56	3.403 (3)	152
C5—H5···O2^ii	0.93	2.54	3.406 (3)	155
N2—H2A···O1	0.86	2.47	2.898 (3)	112
N2—H2A···O5	0.86	1.98	2.761 (4)	150

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