A second monoclinic polymorph of methyl 4-hydroxy-benzoate.

A second monoclinic polymorph of methyl 4-hydroxy-benzoate, C(8)H(8)O(3), is reported. The unit-cell dimensions are different from those of the previously reported monoclinic form [Vujovic & Nassimbeni (2006 ▶). Cryst. Growth Des.6, 1595-1597]. The asymmetric unit contains three crystallographically independent mol-ecules, as observed in the previous form. The crystal structure is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions, which link the mol-ecules into a three-dimensional network.

Related literature

For the other monoclinic polymorph of methyl 4-hydroxy­benzoate, see: Lin (1983 ▶); Vujovic & Nassimbeni (2006 ▶).

Experimental

Crystal data

C8H8O3

M = 152.14

Monoclinic,

a = 12.9708 (4) Å

b = 17.2485 (7) Å

c = 10.8428 (3) Å

β = 119.260 (1)°

V = 2116.32 (12) Å3

Z = 12

Mo Kα radiation

μ = 0.11 mm−1

T = 100.0 (1) K

0.29 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.969, T max = 0.979

25224 measured reflections

3278 independent reflections

2705 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.05

3278 reflections

301 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017327/ci2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017327/ci2607Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8O3	F000 = 960
Mr = 152.14	Dx = 1.433 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6163 reflections
a = 12.9708 (4) Å	θ = 2.3–28.8º
b = 17.2485 (7) Å	µ = 0.11 mm−1
c = 10.8428 (3) Å	T = 100.0 (1) K
β = 119.260 (1)º	Block, purple
V = 2116.32 (12) Å3	0.29 × 0.27 × 0.19 mm
Z = 12

Bruker SMART APEXII CCD area-detector diffractometer	3278 independent reflections
Radiation source: fine-focus sealed tube	2705 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 100.0(1) K	θmax = 30.6º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −18→18
Tmin = 0.969, Tmax = 0.979	k = −24→24
25224 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2705P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3278 reflections	Δρmax = 0.40 e Å−3
301 parameters	Δρmin = −0.24 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
O1A	0.29177 (16)	0.36449 (10)	0.60077 (19)	0.0230 (4)
H1A	0.2494	0.3725	0.5160	0.034*
O2A	0.66456 (16)	0.08828 (9)	0.82151 (18)	0.0209 (4)
O3A	0.57101 (15)	0.06897 (9)	0.58740 (18)	0.0181 (3)
C1A	0.3604 (2)	0.30138 (13)	0.6194 (3)	0.0171 (5)
C2A	0.4381 (2)	0.27923 (15)	0.7586 (3)	0.0202 (5)
H2A	0.4414	0.3072	0.8337	0.024*
C3A	0.5102 (2)	0.21526 (14)	0.7836 (2)	0.0182 (5)
H3A	0.5621	0.2005	0.8762	0.022*
C4A	0.5061 (2)	0.17242 (14)	0.6716 (3)	0.0161 (5)
C5A	0.4260 (2)	0.19429 (13)	0.5327 (3)	0.0167 (5)
H5A	0.4209	0.1657	0.4572	0.020*
C6A	0.3542 (2)	0.25858 (14)	0.5077 (3)	0.0181 (5)
H6A	0.3014	0.2731	0.4152	0.022*
C7A	0.58804 (19)	0.10701 (13)	0.7037 (2)	0.0151 (5)
C8A	0.6476 (2)	0.00343 (13)	0.6093 (3)	0.0198 (5)
H8A1	0.7280	0.0209	0.6512	0.030*
H8A2	0.6256	−0.0209	0.5202	0.030*
H8A3	0.6401	−0.0332	0.6712	0.030*
O1B	1.02411 (15)	0.30607 (10)	0.65189 (19)	0.0217 (4)
H1B	1.0678	0.2996	0.7369	0.033*
O2B	0.65142 (15)	0.58228 (9)	0.42254 (18)	0.0213 (4)
O3B	0.74271 (14)	0.60350 (9)	0.65507 (17)	0.0192 (3)
C1B	0.95497 (19)	0.36928 (13)	0.6311 (2)	0.0170 (5)
C2B	0.8748 (2)	0.38876 (14)	0.4925 (2)	0.0174 (5)
H2B	0.8700	0.3591	0.4182	0.021*
C3B	0.8020 (2)	0.45249 (13)	0.4652 (2)	0.0168 (4)
H3B	0.7476	0.4650	0.3723	0.020*
C4B	0.8090 (2)	0.49832 (13)	0.5752 (2)	0.0149 (4)
C5B	0.89218 (19)	0.47907 (13)	0.7148 (2)	0.0166 (4)
H5B	0.8988	0.5096	0.7890	0.020*
C6B	0.9648 (2)	0.41474 (13)	0.7432 (3)	0.0166 (4)
H6B	1.0195	0.4020	0.8359	0.020*
C7B	0.72729 (19)	0.56418 (13)	0.5416 (2)	0.0161 (4)
C8B	0.6628 (3)	0.66766 (15)	0.6307 (3)	0.0198 (4)
H8B1	0.6704	0.7050	0.5699	0.030*
H8B2	0.6820	0.6916	0.7192	0.030*
H8B3	0.5830	0.6488	0.5866	0.030*
O1C	0.53025 (16)	0.53612 (10)	0.14682 (19)	0.0225 (4)
H1C	0.5731	0.5436	0.2317	0.034*
O2C	0.25159 (14)	0.24040 (9)	0.16008 (17)	0.0198 (3)
O3C	0.15783 (15)	0.25965 (9)	−0.07388 (18)	0.0219 (4)
C1C	0.4608 (2)	0.47356 (13)	0.1275 (3)	0.0176 (5)
C2C	0.4694 (2)	0.42967 (13)	0.2407 (3)	0.0178 (5)
H2C	0.5232	0.4436	0.3332	0.021*
C3C	0.3977 (2)	0.36557 (14)	0.2147 (3)	0.0176 (5)
H3C	0.4035	0.3362	0.2898	0.021*
C4C	0.3163 (2)	0.34464 (13)	0.0758 (2)	0.0164 (5)
C5C	0.3096 (2)	0.38827 (14)	−0.0364 (3)	0.0182 (5)
H5C	0.2566	0.3741	−0.1290	0.022*
C6C	0.3811 (2)	0.45228 (14)	−0.0109 (3)	0.0194 (5)
H6C	0.3761	0.4812	−0.0861	0.023*
C7C	0.2344 (2)	0.27824 (13)	0.0442 (2)	0.0173 (5)
C8C	0.1753 (2)	0.17432 (14)	0.1380 (3)	0.0206 (5)
H8C1	0.0942	0.1907	0.0882	0.031*
H8C2	0.1926	0.1528	0.2278	0.031*
H8C3	0.1885	0.1357	0.0835	0.031*

	U11	U22	U33	U12	U13	U23
O1A	0.0207 (9)	0.0252 (9)	0.0182 (10)	0.0078 (7)	0.0058 (8)	0.0009 (7)
O2A	0.0188 (9)	0.0202 (8)	0.0173 (9)	0.0021 (7)	0.0039 (7)	0.0009 (7)
O3A	0.0153 (8)	0.0200 (8)	0.0158 (8)	0.0043 (6)	0.0052 (7)	−0.0001 (7)
C1A	0.0133 (11)	0.0180 (11)	0.0177 (12)	0.0011 (9)	0.0058 (10)	0.0022 (9)
C2A	0.0203 (13)	0.0217 (11)	0.0146 (12)	0.0002 (10)	0.0054 (10)	−0.0029 (10)
C3A	0.0169 (12)	0.0206 (11)	0.0121 (11)	−0.0006 (9)	0.0033 (10)	0.0001 (9)
C4A	0.0123 (11)	0.0175 (11)	0.0165 (12)	−0.0020 (8)	0.0054 (9)	0.0009 (9)
C5A	0.0153 (12)	0.0176 (11)	0.0160 (12)	−0.0012 (9)	0.0068 (10)	−0.0019 (9)
C6A	0.0127 (11)	0.0226 (12)	0.0144 (12)	0.0001 (9)	0.0029 (10)	0.0007 (9)
C7A	0.0114 (11)	0.0176 (11)	0.0143 (12)	−0.0025 (8)	0.0047 (10)	−0.0002 (9)
C8A	0.0187 (12)	0.0170 (11)	0.0226 (13)	0.0026 (9)	0.0093 (10)	−0.0004 (10)
O1B	0.0213 (9)	0.0215 (9)	0.0171 (8)	0.0063 (7)	0.0053 (7)	0.0000 (7)
O2B	0.0197 (8)	0.0221 (8)	0.0141 (8)	0.0019 (7)	0.0020 (7)	0.0001 (7)
O3B	0.0194 (8)	0.0201 (8)	0.0147 (8)	0.0044 (6)	0.0056 (7)	0.0007 (7)
C1B	0.0141 (10)	0.0188 (11)	0.0177 (12)	−0.0030 (8)	0.0076 (9)	−0.0010 (9)
C2B	0.0173 (11)	0.0212 (11)	0.0136 (11)	−0.0008 (9)	0.0074 (9)	−0.0030 (9)
C3B	0.0133 (10)	0.0212 (11)	0.0139 (10)	−0.0015 (8)	0.0052 (9)	0.0003 (9)
C4B	0.0135 (10)	0.0143 (10)	0.0150 (11)	−0.0005 (8)	0.0055 (9)	0.0000 (8)
C5B	0.0150 (11)	0.0195 (11)	0.0133 (11)	0.0003 (8)	0.0053 (9)	−0.0003 (9)
C6B	0.0162 (11)	0.0190 (11)	0.0125 (10)	−0.0001 (9)	0.0054 (9)	0.0010 (9)
C7B	0.0150 (10)	0.0167 (10)	0.0154 (11)	−0.0017 (8)	0.0065 (9)	0.0001 (8)
C8B	0.0188 (10)	0.0197 (10)	0.0180 (10)	0.0059 (8)	0.0068 (8)	0.0016 (8)
O1C	0.0226 (9)	0.0218 (8)	0.0195 (9)	−0.0068 (7)	0.0075 (7)	−0.0003 (7)
O2C	0.0203 (8)	0.0195 (8)	0.0170 (8)	−0.0045 (6)	0.0070 (7)	0.0012 (7)
O3C	0.0200 (8)	0.0206 (8)	0.0166 (8)	−0.0012 (7)	0.0024 (7)	−0.0006 (7)
C1C	0.0135 (11)	0.0167 (11)	0.0213 (13)	0.0002 (8)	0.0076 (10)	0.0019 (9)
C2C	0.0168 (11)	0.0197 (11)	0.0149 (11)	0.0004 (8)	0.0061 (10)	−0.0015 (9)
C3C	0.0158 (11)	0.0211 (11)	0.0144 (12)	0.0001 (9)	0.0062 (9)	0.0011 (9)
C4C	0.0157 (11)	0.0148 (10)	0.0179 (12)	0.0010 (9)	0.0077 (9)	0.0010 (9)
C5C	0.0186 (11)	0.0199 (10)	0.0145 (11)	0.0013 (9)	0.0068 (9)	0.0001 (9)
C6C	0.0166 (12)	0.0213 (12)	0.0186 (12)	0.0009 (9)	0.0074 (10)	0.0046 (10)
C7C	0.0169 (11)	0.0155 (10)	0.0187 (12)	0.0026 (8)	0.0081 (10)	0.0008 (9)
C8C	0.0179 (13)	0.0199 (11)	0.0222 (13)	−0.0019 (9)	0.0084 (11)	0.0009 (10)

O1A—C1A	1.357 (3)	C3B—H3B	0.93
O1A—H1A	0.82	C4B—C5B	1.403 (3)
O2A—C7A	1.218 (3)	C4B—C7B	1.472 (3)
O3A—C7A	1.340 (3)	C5B—C6B	1.389 (3)
O3A—C8A	1.446 (3)	C5B—H5B	0.93
C1A—C6A	1.387 (3)	C6B—H6B	0.93
C1A—C2A	1.397 (4)	C8B—H8B1	0.96
C2A—C3A	1.384 (3)	C8B—H8B2	0.96
C2A—H2A	0.93	C8B—H8B3	0.96
C3A—C4A	1.400 (3)	O1C—C1C	1.354 (3)
C3A—H3A	0.93	O1C—H1C	0.82
C4A—C5A	1.401 (4)	O2C—C7C	1.334 (3)
C4A—C7A	1.471 (3)	O2C—C8C	1.451 (3)
C5A—C6A	1.387 (3)	O3C—C7C	1.219 (3)
C5A—H5A	0.93	C1C—C6C	1.393 (3)
C6A—H6A	0.93	C1C—C2C	1.399 (3)
C8A—H8A1	0.96	C2C—C3C	1.383 (3)
C8A—H8A2	0.96	C2C—H2C	0.93
C8A—H8A3	0.96	C3C—C4C	1.400 (3)
O1B—C1B	1.359 (3)	C3C—H3C	0.93
O1B—H1B	0.82	C4C—C5C	1.398 (3)
O2B—C7B	1.221 (3)	C4C—C7C	1.484 (3)
O3B—C7B	1.331 (3)	C5C—C6C	1.380 (3)
O3B—C8B	1.449 (3)	C5C—H5C	0.93
C1B—C2B	1.388 (3)	C6C—H6C	0.93
C1B—C6B	1.399 (3)	C8C—H8C1	0.96
C2B—C3B	1.384 (3)	C8C—H8C2	0.96
C2B—H2B	0.93	C8C—H8C3	0.96
C3B—C4B	1.396 (3)
C1A—O1A—H1A	109.5	C6B—C5B—H5B	119.7
C7A—O3A—C8A	116.4 (2)	C4B—C5B—H5B	119.7
O1A—C1A—C6A	122.9 (2)	C5B—C6B—C1B	119.4 (2)
O1A—C1A—C2A	117.1 (2)	C5B—C6B—H6B	120.3
C6A—C1A—C2A	120.1 (2)	C1B—C6B—H6B	120.3
C3A—C2A—C1A	119.4 (2)	O2B—C7B—O3B	121.7 (2)
C3A—C2A—H2A	120.3	O2B—C7B—C4B	124.7 (2)
C1A—C2A—H2A	120.3	O3B—C7B—C4B	113.54 (19)
C2A—C3A—C4A	121.0 (2)	O3B—C8B—H8B1	109.5
C2A—C3A—H3A	119.5	O3B—C8B—H8B2	109.5
C4A—C3A—H3A	119.5	H8B1—C8B—H8B2	109.5
C3A—C4A—C5A	119.0 (2)	O3B—C8B—H8B3	109.5
C3A—C4A—C7A	118.9 (2)	H8B1—C8B—H8B3	109.5
C5A—C4A—C7A	122.1 (2)	H8B2—C8B—H8B3	109.5
C6A—C5A—C4A	120.0 (2)	C1C—O1C—H1C	109.5
C6A—C5A—H5A	120.0	C7C—O2C—C8C	116.3 (2)
C4A—C5A—H5A	120.0	O1C—C1C—C6C	117.6 (2)
C5A—C6A—C1A	120.5 (2)	O1C—C1C—C2C	122.3 (2)
C5A—C6A—H6A	119.7	C6C—C1C—C2C	120.1 (2)
C1A—C6A—H6A	119.7	C3C—C2C—C1C	119.8 (2)
O2A—C7A—O3A	122.2 (2)	C3C—C2C—H2C	120.1
O2A—C7A—C4A	125.2 (2)	C1C—C2C—H2C	120.1
O3A—C7A—C4A	112.7 (2)	C2C—C3C—C4C	120.3 (2)
O3A—C8A—H8A1	109.5	C2C—C3C—H3C	119.8
O3A—C8A—H8A2	109.5	C4C—C3C—H3C	119.8
H8A1—C8A—H8A2	109.5	C5C—C4C—C3C	119.4 (2)
O3A—C8A—H8A3	109.5	C5C—C4C—C7C	118.8 (2)
H8A1—C8A—H8A3	109.5	C3C—C4C—C7C	121.8 (2)
H8A2—C8A—H8A3	109.5	C6C—C5C—C4C	120.4 (2)
C1B—O1B—H1B	109.5	C6C—C5C—H5C	119.8
C7B—O3B—C8B	116.7 (2)	C4C—C5C—H5C	119.8
O1B—C1B—C2B	117.3 (2)	C5C—C6C—C1C	119.9 (2)
O1B—C1B—C6B	122.2 (2)	C5C—C6C—H6C	120.0
C2B—C1B—C6B	120.5 (2)	C1C—C6C—H6C	120.0
C3B—C2B—C1B	119.7 (2)	O3C—C7C—O2C	122.4 (2)
C3B—C2B—H2B	120.1	O3C—C7C—C4C	124.7 (2)
C1B—C2B—H2B	120.1	O2C—C7C—C4C	112.8 (2)
C2B—C3B—C4B	121.0 (2)	O2C—C8C—H8C1	109.5
C2B—C3B—H3B	119.5	O2C—C8C—H8C2	109.5
C4B—C3B—H3B	119.5	H8C1—C8C—H8C2	109.5
C3B—C4B—C5B	118.8 (2)	O2C—C8C—H8C3	109.5
C3B—C4B—C7B	119.1 (2)	H8C1—C8C—H8C3	109.5
C5B—C4B—C7B	122.05 (19)	H8C2—C8C—H8C3	109.5
C6B—C5B—C4B	120.6 (2)
O1A—C1A—C2A—C3A	180.0 (2)	O1B—C1B—C6B—C5B	179.4 (2)
C6A—C1A—C2A—C3A	1.2 (4)	C2B—C1B—C6B—C5B	1.0 (3)
C1A—C2A—C3A—C4A	−0.1 (4)	C8B—O3B—C7B—O2B	1.6 (3)
C2A—C3A—C4A—C5A	−1.2 (4)	C8B—O3B—C7B—C4B	−178.0 (2)
C2A—C3A—C4A—C7A	177.3 (2)	C3B—C4B—C7B—O2B	0.5 (3)
C3A—C4A—C5A—C6A	1.5 (3)	C5B—C4B—C7B—O2B	−178.1 (2)
C7A—C4A—C5A—C6A	−177.0 (2)	C3B—C4B—C7B—O3B	−179.9 (2)
C4A—C5A—C6A—C1A	−0.4 (3)	C5B—C4B—C7B—O3B	1.5 (3)
O1A—C1A—C6A—C5A	−179.7 (2)	O1C—C1C—C2C—C3C	−178.9 (2)
C2A—C1A—C6A—C5A	−1.0 (3)	C6C—C1C—C2C—C3C	−0.7 (3)
C8A—O3A—C7A—O2A	0.8 (3)	C1C—C2C—C3C—C4C	−0.3 (3)
C8A—O3A—C7A—C4A	−179.72 (19)	C2C—C3C—C4C—C5C	1.1 (3)
C3A—C4A—C7A—O2A	−3.4 (4)	C2C—C3C—C4C—C7C	−177.4 (2)
C5A—C4A—C7A—O2A	175.1 (2)	C3C—C4C—C5C—C6C	−1.1 (3)
C3A—C4A—C7A—O3A	177.1 (2)	C7C—C4C—C5C—C6C	177.5 (2)
C5A—C4A—C7A—O3A	−4.3 (3)	C4C—C5C—C6C—C1C	0.2 (3)
O1B—C1B—C2B—C3B	179.9 (2)	O1C—C1C—C6C—C5C	179.0 (2)
C6B—C1B—C2B—C3B	−1.6 (3)	C2C—C1C—C6C—C5C	0.7 (3)
C1B—C2B—C3B—C4B	0.8 (4)	C8C—O2C—C7C—O3C	1.2 (3)
C2B—C3B—C4B—C5B	0.5 (3)	C8C—O2C—C7C—C4C	−179.69 (18)
C2B—C3B—C4B—C7B	−178.1 (2)	C5C—C4C—C7C—O3C	−2.4 (3)
C3B—C4B—C5B—C6B	−1.2 (3)	C3C—C4C—C7C—O3C	176.2 (2)
C7B—C4B—C5B—C6B	177.5 (2)	C5C—C4C—C7C—O2C	178.6 (2)
C4B—C5B—C6B—C1B	0.4 (3)	C3C—C4C—C7C—O2C	−2.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Ai	0.82	1.96	2.770 (2)	168
O1B—H1B···O3Cii	0.82	1.93	2.729 (2)	167
O1C—H1C···O2B	0.82	1.92	2.729 (2)	167
C6A—H6A···O2C	0.93	2.58	3.343 (3)	140
C8C—H8C1···Cg1i	0.96	2.76	3.539 (3)	139
C8C—H8C3···Cg2	0.96	2.70	3.442 (3)	134
C8A—H8A1···Cg3iii	0.96	2.68	3.515 (3)	145
C8B—H8B3···Cg3iv	0.96	2.78	3.655 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2Ai	0.82	1.96	2.770 (2)	168
O1B—H1B⋯O3Cii	0.82	1.93	2.729 (2)	167
O1C—H1C⋯O2B	0.82	1.92	2.729 (2)	167
C6A—H6A⋯O2C	0.93	2.58	3.343 (3)	140
C8C—H8C1⋯Cg1i	0.96	2.76	3.539 (3)	139
C8C—H8C3⋯Cg2	0.96	2.70	3.442 (3)	134
C8A—H8A1⋯Cg3iii	0.96	2.68	3.515 (3)	145
C8B—H8B3⋯Cg3iv	0.96	2.78	3.655 (4)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C1B–C6B and C1C–C6C rings, respectively.