Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213027267/gw5021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052519213027267/gw5021Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213027267/gw5021sup3.pdf |
CCDC reference: 964654
Crystal data, data collection and structure refinement details are summarized in Table 1.
Data collection: MarCCD (Paulmann & Morgenroth, 2006); cell refinement: EVAL 15 (Schreurs, 2010); data reduction: EVAL 15 (Schreurs, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).
C11H12NO4P | Z = 4 |
Mr = 253.19 | F(000) = 528 |
Orthorhombic, P212121 | Dx = 1.413 Mg m−3 |
Hall symbol: P 2ac 2ab | Synchrotron radiation, λ = 0.60000 Å |
a = 9.2532 (10) Å | µ = 0.23 mm−1 |
b = 10.1555 (16) Å | T = 100 K |
c = 12.6610 (12) Å | Block, colourless |
V = 1189.8 (3) Å3 | 0.45 × 0.3 × 0.18 mm |
Huber diffractometer | Rint = 0.035 |
Radiation source: synchrotron | θmax = 48.6°, θmin = 2.2° |
ϕ scan | h = −23→21 |
98994 measured reflections | k = −17→25 |
17584 independent reflections | l = −29→29 |
16534 reflections with I > 2σ(I) |
Refinement on F | 534 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.015 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.017 | (Δ/σ)max < 0.001 |
S = 1.37 | Δρmax = 0.13 e Å−3 |
14864 reflections | Δρmin = −0.30 e Å−3 |
C11H12NO4P | V = 1189.8 (3) Å3 |
Mr = 253.19 | Z = 4 |
Orthorhombic, P212121 | Synchrotron radiation, λ = 0.60000 Å |
a = 9.2532 (10) Å | µ = 0.23 mm−1 |
b = 10.1555 (16) Å | T = 100 K |
c = 12.6610 (12) Å | 0.45 × 0.3 × 0.18 mm |
Huber diffractometer | 16534 reflections with I > 2σ(I) |
98994 measured reflections | Rint = 0.035 |
17584 independent reflections |
R[F2 > 2σ(F2)] = 0.015 | 534 parameters |
wR(F2) = 0.017 | 0 restraints |
S = 1.37 | Δρmax = 0.13 e Å−3 |
14864 reflections | Δρmin = −0.30 e Å−3 |
x | y | z | Uiso*/Ueq | ||
P(2) | 0.661925 (5) | 0.482849 (4) | 0.074523 (4) | 0.014 | |
O(1) | 0.79064 (2) | 0.589242 (19) | 0.07178 (2) | 0.018 | |
O(4) | 0.94685 (3) | 0.24666 (3) | 0.20485 (2) | 0.021 | |
O(21) | 0.53019 (3) | 0.55035 (3) | 0.11139 (2) | 0.021 | |
O(22) | 0.65057 (3) | 0.43039 (2) | −0.042492 (16) | 0.019 | |
N(1) | 0.68818 (3) | 0.17020 (2) | 0.264657 (19) | 0.020 | |
C(3) | 0.73085 (2) | 0.350744 (18) | 0.147879 (15) | 0.015 | |
C(4) | 0.88637 (2) | 0.334200 (19) | 0.151694 (15) | 0.015 | |
C(5) | 1.12308 (2) | 0.38966 (2) | 0.066650 (18) | 0.018 | |
C(6) | 1.21239 (3) | 0.47156 (3) | 0.00743 (2) | 0.022 | |
C(7) | 1.16036 (3) | 0.59292 (3) | −0.02899 (2) | 0.023 | |
C(8) | 1.01866 (3) | 0.63147 (2) | −0.00725 (2) | 0.021 | |
C(9) | 0.93004 (2) | 0.546727 (18) | 0.050172 (16) | 0.016 | |
C(10) | 0.97952 (2) | 0.425563 (18) | 0.088410 (14) | 0.015 | |
C(23) | 0.60537 (4) | 0.51966 (3) | −0.12529 (2) | 0.025 | |
C(31) | 0.63736 (2) | 0.26343 (2) | 0.201981 (16) | 0.017 | |
C(311) | 0.47572 (3) | 0.26942 (3) | 0.19046 (2) | 0.025 | |
H(1) | 0.796474 | 0.16279 | 0.271845 | 0.035 | |
H(2) | 0.614406 | 0.117774 | 0.305578 | 0.040 | |
H(5) | 1.161608 | 0.295929 | 0.096151 | 0.036 | |
H(6) | 1.322238 | 0.441658 | −0.009789 | 0.043 | |
H(7) | 1.22733 | 0.659594 | −0.074373 | 0.044 | |
H(8) | 0.973804 | 0.723838 | −0.034655 | 0.038 | |
H(23A) | 0.586691 | 0.460366 | −0.192751 | 0.046 | |
H(23B) | 0.691586 | 0.586417 | −0.137821 | 0.043 | |
H(23C) | 0.509378 | 0.567889 | −0.10134 | 0.045 | |
H(31A) | 0.422351 | 0.191569 | 0.23015 | 0.046 | |
H(31B) | 0.451524 | 0.260552 | 0.10902 | 0.041 | |
H(31C) | 0.432393 | 0.362726 | 0.210244 | 0.042 |
U11 | U22 | U33 | U12 | U13 | U23 | |
P(2) | 0.017529 (15) | 0.011967 (15) | 0.012494 (15) | 0.001408 (12) | 0.000818 (12) | −0.000247 (11) |
O(1) | 0.02055 (6) | 0.01086 (5) | 0.02307 (7) | 0.00051 (5) | −0.00017 (6) | −0.00030 (5) |
O(4) | 0.02124 (7) | 0.01938 (7) | 0.02338 (9) | 0.00517 (6) | 0.00429 (7) | 0.00844 (7) |
O(21) | 0.02100 (7) | 0.02011 (7) | 0.02270 (8) | 0.00577 (6) | 0.00369 (7) | −0.00002 (7) |
O(22) | 0.02992 (9) | 0.01515 (6) | 0.01176 (5) | −0.00107 (6) | −0.00087 (6) | 0.00053 (4) |
N(1) | 0.02209 (7) | 0.01893 (7) | 0.01913 (7) | 0.00005 (6) | 0.00286 (6) | 0.00668 (6) |
C(3) | 0.01831 (6) | 0.01347 (5) | 0.01276 (5) | 0.00047 (5) | 0.00122 (5) | 0.00145 (4) |
C(4) | 0.01857 (6) | 0.01286 (5) | 0.01443 (6) | 0.00179 (5) | 0.00243 (5) | 0.00152 (4) |
C(5) | 0.01772 (6) | 0.01542 (6) | 0.02166 (7) | −0.00023 (5) | 0.00226 (5) | 0.00093 (5) |
C(6) | 0.01860 (7) | 0.01981 (8) | 0.02660 (9) | −0.00359 (6) | 0.00263 (6) | 0.00174 (7) |
C(7) | 0.02188 (7) | 0.01935 (7) | 0.02827 (10) | −0.00631 (7) | 0.00154 (7) | 0.00454 (7) |
C(8) | 0.02301 (8) | 0.01417 (6) | 0.02590 (9) | −0.00413 (6) | −0.00030 (6) | 0.00427 (6) |
C(9) | 0.01930 (6) | 0.01118 (5) | 0.01810 (6) | −0.00129 (5) | −0.00008 (5) | 0.00044 (4) |
C(10) | 0.01797 (6) | 0.01196 (5) | 0.01555 (6) | −0.00007 (4) | 0.00149 (4) | 0.00017 (4) |
C(23) | 0.03553 (11) | 0.02295 (9) | 0.01653 (7) | −0.00569 (9) | −0.00431 (8) | 0.00664 (7) |
C(31) | 0.01919 (6) | 0.01649 (6) | 0.01408 (6) | −0.00068 (5) | 0.00135 (5) | 0.00236 (5) |
C(311) | 0.01989 (7) | 0.02841 (11) | 0.02535 (10) | −0.00272 (8) | −0.00058 (7) | 0.00854 (8) |
H(1) | 0.028540 | 0.038772 | 0.038718 | 0.002235 | 0.001399 | 0.013738 |
H(2) | 0.035769 | 0.043627 | 0.039504 | −0.004827 | 0.007242 | 0.019888 |
H(5) | 0.033045 | 0.028072 | 0.048354 | 0.007933 | 0.005758 | 0.010379 |
H(6) | 0.026194 | 0.045977 | 0.057409 | 0.002887 | 0.012001 | 0.008524 |
H(7) | 0.037782 | 0.038773 | 0.054565 | −0.011459 | 0.009585 | 0.015414 |
H(8) | 0.041533 | 0.022123 | 0.050895 | −0.000455 | 0.000643 | 0.011577 |
H(23A) | 0.064812 | 0.048447 | 0.025551 | −0.006588 | −0.010956 | −0.000789 |
H(23B) | 0.040322 | 0.042842 | 0.044646 | −0.013230 | −0.005697 | 0.017506 |
H(23C) | 0.039060 | 0.052588 | 0.042363 | 0.011650 | 0.002289 | 0.013691 |
H(31A) | 0.037072 | 0.047705 | 0.051792 | −0.009061 | 0.006355 | 0.022578 |
H(31B) | 0.037087 | 0.058937 | 0.025816 | −0.003626 | −0.001535 | 0.001158 |
H(31C) | 0.035110 | 0.038214 | 0.052426 | 0.006607 | 0.003491 | −0.004192 |
P(2)—O(1) | 1.6085 (2) | C(6)—C(7) | 1.4012 (4) |
P(2)—O(21) | 1.4743 (2) | C(6)—H(6) | 1.0830 |
P(2)—O(22) | 1.5779 (2) | C(7)—C(8) | 1.3959 (4) |
P(2)—C(3) | 1.7519 (2) | C(7)—H(7) | 1.0829 |
O(1)—C(9) | 1.3874 (3) | C(8)—C(9) | 1.3934 (3) |
O(4)—C(4) | 1.2476 (3) | C(8)—H(8) | 1.0828 |
N(1)—C(31) | 1.3218 (3) | C(9)—C(10) | 1.3993 (3) |
N(1)—H(1) | 1.0090 | C(23)—H(23A) | 1.0593 |
N(1)—H(2) | 1.0089 | C(23)—H(23B) | 1.0589 |
C(3)—C(4) | 1.4497 (3) | C(23)—H(23C) | 1.0586 |
C(3)—C(31) | 1.4155 (3) | C(31)—C(311) | 1.5040 (3) |
C(4)—C(10) | 1.4986 (3) | C(311)—H(31A) | 1.0589 |
C(5)—C(6) | 1.3918 (3) | C(311)—H(31B) | 1.0590 |
C(5)—C(10) | 1.4048 (3) | C(311)—H(31C) | 1.0590 |
C(5)—H(5) | 1.0829 | ||
O(1)—P(2)—O(21) | 107.861 (14) | C(6)—C(7)—H(7) | 121.87 |
O(1)—P(2)—O(22) | 104.823 (13) | C(8)—C(7)—H(7) | 117.83 |
O(1)—P(2)—C(3) | 104.851 (11) | C(7)—C(8)—C(9) | 118.85 (2) |
O(21)—P(2)—O(22) | 113.525 (16) | C(7)—C(8)—H(8) | 122.67 |
O(21)—P(2)—C(3) | 119.290 (13) | C(9)—C(8)—H(8) | 118.47 |
O(22)—P(2)—C(3) | 105.276 (10) | O(1)—C(9)—C(8) | 117.24 (2) |
P(2)—O(1)—C(9) | 118.922 (15) | O(1)—C(9)—C(10) | 120.639 (19) |
C(31)—N(1)—H(1) | 117.44 | C(8)—C(9)—C(10) | 122.08 (2) |
C(31)—N(1)—H(2) | 116.46 | C(4)—C(10)—C(5) | 119.209 (18) |
H(1)—N(1)—H(2) | 125.89 | C(4)—C(10)—C(9) | 122.768 (18) |
P(2)—C(3)—C(4) | 117.891 (14) | C(5)—C(10)—C(9) | 118.022 (19) |
P(2)—C(3)—C(31) | 120.916 (16) | H(23A)—C(23)—H(23B) | 111.47 |
C(4)—C(3)—C(31) | 121.193 (17) | H(23A)—C(23)—H(23C) | 110.92 |
O(4)—C(4)—C(3) | 123.08 (2) | H(23B)—C(23)—H(23C) | 112.27 |
O(4)—C(4)—C(10) | 118.14 (2) | N(1)—C(31)—C(3) | 121.45 (2) |
C(3)—C(4)—C(10) | 118.775 (17) | N(1)—C(31)—C(311) | 116.16 (2) |
C(6)—C(5)—C(10) | 120.80 (2) | C(3)—C(31)—C(311) | 122.38 (2) |
C(6)—C(5)—H(5) | 121.04 | C(31)—C(311)—H(31A) | 112.81 |
C(10)—C(5)—H(5) | 118.15 | C(31)—C(311)—H(31B) | 107.53 |
C(5)—C(6)—C(7) | 119.93 (2) | C(31)—C(311)—H(31C) | 112.94 |
C(5)—C(6)—H(6) | 119.88 | H(31A)—C(311)—H(31B) | 107.45 |
C(7)—C(6)—H(6) | 120.19 | H(31A)—C(311)—H(31C) | 112.29 |
C(6)—C(7)—C(8) | 120.30 (2) | H(31B)—C(311)—H(31C) | 103.08 |
Experimental details
Crystal data | |
Chemical formula | C11H12NO4P |
Mr | 253.19 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 9.2532 (10), 10.1555 (16), 12.6610 (12) |
V (Å3) | 1189.8 (3) |
Z | 4 |
Radiation type | Synchrotron, λ = 0.60000 Å |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.45 × 0.3 × 0.18 |
Data collection | |
Diffractometer | Huber diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 98994, 17584, 16534 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 1.250 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.015, 0.017, 1.37 |
No. of reflections | 14864 |
No. of parameters | 534 |
Δρmax, Δρmin (e Å−3) | 0.13, −0.30 |
Computer programs: MarCCD (Paulmann & Morgenroth, 2006), EVAL 15 (Schreurs, 2010), SHELXS97 (Sheldrick, 2008), Volkov et al., (2006).
P(2)—O(1) | 1.6085 (2) | C(6)—C(7) | 1.4012 (4) |
P(2)—O(21) | 1.4743 (2) | C(6)—H(6) | 1.0830 |
P(2)—O(22) | 1.5779 (2) | C(7)—C(8) | 1.3959 (4) |
P(2)—C(3) | 1.7519 (2) | C(7)—H(7) | 1.0829 |
O(1)—C(9) | 1.3874 (3) | C(8)—C(9) | 1.3934 (3) |
O(4)—C(4) | 1.2476 (3) | C(8)—H(8) | 1.0828 |
N(1)—C(31) | 1.3218 (3) | C(9)—C(10) | 1.3993 (3) |
N(1)—H(1) | 1.0090 | C(23)—H(23A) | 1.0593 |
N(1)—H(2) | 1.0089 | C(23)—H(23B) | 1.0589 |
C(3)—C(4) | 1.4497 (3) | C(23)—H(23C) | 1.0586 |
C(3)—C(31) | 1.4155 (3) | C(31)—C(311) | 1.5040 (3) |
C(4)—C(10) | 1.4986 (3) | C(311)—H(31A) | 1.0589 |
C(5)—C(6) | 1.3918 (3) | C(311)—H(31B) | 1.0590 |
C(5)—C(10) | 1.4048 (3) | C(311)—H(31C) | 1.0590 |
C(5)—H(5) | 1.0829 | ||
O(1)—P(2)—O(21) | 107.861 (14) | C(6)—C(7)—H(7) | 121.87 |
O(1)—P(2)—O(22) | 104.823 (13) | C(8)—C(7)—H(7) | 117.83 |
O(1)—P(2)—C(3) | 104.851 (11) | C(7)—C(8)—C(9) | 118.85 (2) |
O(21)—P(2)—O(22) | 113.525 (16) | C(7)—C(8)—H(8) | 122.67 |
O(21)—P(2)—C(3) | 119.290 (13) | C(9)—C(8)—H(8) | 118.47 |
O(22)—P(2)—C(3) | 105.276 (10) | O(1)—C(9)—C(8) | 117.24 (2) |
P(2)—O(1)—C(9) | 118.922 (15) | O(1)—C(9)—C(10) | 120.639 (19) |
C(31)—N(1)—H(1) | 117.44 | C(8)—C(9)—C(10) | 122.08 (2) |
C(31)—N(1)—H(2) | 116.46 | C(4)—C(10)—C(5) | 119.209 (18) |
H(1)—N(1)—H(2) | 125.89 | C(4)—C(10)—C(9) | 122.768 (18) |
P(2)—C(3)—C(4) | 117.891 (14) | C(5)—C(10)—C(9) | 118.022 (19) |
P(2)—C(3)—C(31) | 120.916 (16) | H(23A)—C(23)—H(23B) | 111.47 |
C(4)—C(3)—C(31) | 121.193 (17) | H(23A)—C(23)—H(23C) | 110.92 |
O(4)—C(4)—C(3) | 123.08 (2) | H(23B)—C(23)—H(23C) | 112.27 |
O(4)—C(4)—C(10) | 118.14 (2) | N(1)—C(31)—C(3) | 121.45 (2) |
C(3)—C(4)—C(10) | 118.775 (17) | N(1)—C(31)—C(311) | 116.16 (2) |
C(6)—C(5)—C(10) | 120.80 (2) | C(3)—C(31)—C(311) | 122.38 (2) |
C(6)—C(5)—H(5) | 121.04 | C(31)—C(311)—H(31A) | 112.81 |
C(10)—C(5)—H(5) | 118.15 | C(31)—C(311)—H(31B) | 107.53 |
C(5)—C(6)—C(7) | 119.93 (2) | C(31)—C(311)—H(31C) | 112.94 |
C(5)—C(6)—H(6) | 119.88 | H(31A)—C(311)—H(31B) | 107.45 |
C(7)—C(6)—H(6) | 120.19 | H(31A)—C(311)—H(31C) | 112.29 |
C(6)—C(7)—C(8) | 120.30 (2) | H(31B)—C(311)—H(31C) | 103.08 |