Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an experimental and theoretical electron density analysis

Experimental electron density analysis by means of high-resolution X-ray diffraction data up to sinθ/λ_max = 1.11 Å⁻¹ at 100 (1) K has been performed to analyze the detailed structure and the strength of intermolecular interactions responsible for the formation of a new solid form of nicotinic acid (NA), cocrystallized with pyrogallol (PY). There are two NA–PY units in the asymmetric unit. The experimental results are compared with the results obtained from theoretical structure factors modeled using periodic boundary DFT calculations. Both refinements were carried out using the Hansen and Coppens multipolar formalism (in MoPro program). The non-centrosymmetric and polar nature of the crystal system rendered the multipolar refinement challenging which was addressed by involving the transferability principle. This study highlights the significance of the transferability principle in electron density modeling in non-routine situations. The 2:2 cocrystal of NA–PY exhibits a zigzag, brickwall and sheet-like layered structure in three dimensions and is stabilized by strong intra- and inter-molecular hydrogen bonding through N—H...O and O—H...O bonds, some of them due to the zwitterion nature of NA as well as weak interactions between the PY molecules. Ranking these interactions via topological analysis of the electron density shows the leading role of the NA–NA substructure which drives the organization of the cocrystals. These strong interactions between the NA zwitterions may explain why Z′ = 2.

Computing details

Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for IAM_SHELX. Program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54) for IAM_MoPro, multipolar_MoPro, theoretical; XL (Sheldrick, 2008) for IAM_SHELX. Molecular graphics: Olex2 (Dolomanov et al., 2009) for IAM_SHELX. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for IAM_SHELX.

(IAM_MoPro)

Crystal data

C6H5NO2·C6H6O3	Dx = 1.566 Mg m^−3
Mr = 249.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2780 reflections
a = 13.6648 (4) Å	θ = 2.3–52.2°
b = 11.9321 (3) Å	µ = 0.12 mm^−1
c = 12.9678 (4) Å	T = 100 K
V = 2114.40 (10) Å^3	Block, brown
Z = 8	0.35 × 0.29 × 0.24 mm
F(000) = 1040

Data collection

Bruker D8 Venture PHOTON II diffractometer	19169 reflections with > 2.0 σ(I)
Radiation source: Micro-focus	Rint = 0.051
ω and phi scan	θmax = 52.2°, θmin = 2.3°
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0673 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8999. The λ/2 correction factor is Not present.	h = −30→21
Tmin = 0.675, Tmax = 0.750	k = −26→24
24508 measured reflections	l = −28→28
19169 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[1.044*σ^2(Fo^2) + 0.0054*Yo^2]
S = 1.08	(Δ/σ)max = 0.062
19169 reflections	Δρmax = 0.70 e Å^−3
325 parameters	Δρmin = −0.51 e Å^−3
0 restraints	Absolute structure: Rogers (1981), 8469 Friedel pairs
Primary atom site location: structure-invariant direct methods	Rogers parameter: 1

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O1	0.68086 (4)	0.64334 (5)	0.547657 (10)	0.01537 (2)
N1	0.68878 (4)	0.35059 (4)	0.37560 (6)	0.01156 (2)
H1	0.68602	0.27497	0.41133	0.02558
C1	0.68304 (4)	0.44404 (5)	0.43321 (6)	0.01069 (2)
H1A	0.67533	0.43767	0.51612	0.02649
O2	0.68743 (5)	0.74549 (5)	0.40295 (6)	0.01747 (2)
N2	0.67958 (4)	−0.14702 (5)	0.62877 (6)	0.01136 (2)
H2	0.67978	−0.22211	0.59199	0.02593
C2	0.68697 (4)	0.54854 (5)	0.38668 (6)	0.01017 (2)
O3	0.68257 (4)	0.14659 (4)	0.45986 (5)	0.01527 (2)
C3	0.69543 (5)	0.55387 (5)	0.27945 (7)	0.01227 (2)
H3	0.69739	0.63461	0.24135	0.02621
O4	0.67781 (4)	0.24890 (5)	0.60435 (6)	0.01594 (2)
C4	0.70137 (5)	0.45585 (6)	0.22167 (7)	0.01336 (2)
H4	0.70843	0.45916	0.13854	0.02551
C5	0.69804 (5)	0.35394 (5)	0.27265 (7)	0.01292 (2)
H5	0.70291	0.27660	0.22924	0.02345
O5	0.56140 (4)	0.40688 (4)	0.68618 (6)	0.01504 (2)
H5A	0.59802	0.33631	0.68852	0.02559
O6	0.58033 (4)	0.28203 (4)	0.86706 (6)	0.01667 (2)
H6	0.57819	0.24930	0.93633	0.02326
C6	0.68415 (5)	0.65410 (5)	0.45040 (7)	0.01160 (2)
C7	0.67999 (5)	−0.05243 (5)	0.57228 (6)	0.01110 (2)
H7	0.68164	−0.05748	0.48891	0.02381
O7	0.54114 (4)	0.63229 (4)	0.69501 (6)	0.01416 (2)
H7A	0.58089	0.59771	0.64075	0.02620
O8	0.57053 (4)	1.13640 (4)	0.28397 (6)	0.01463 (2)
H8	0.60255	1.10762	0.34619	0.02487
C8	0.67814 (4)	0.05134 (5)	0.62073 (6)	0.01012 (2)
C9	0.67581 (5)	0.05484 (5)	0.72827 (7)	0.01201 (2)
H9	0.67254	0.13476	0.76771	0.02486
O9	0.54926 (4)	1.19674 (5)	0.07979 (6)	0.01550 (2)
H9A	0.52831	1.24072	0.13967	0.02641
C10	0.67769 (5)	−0.04451 (5)	0.78492 (7)	0.01266 (2)
H10	0.67795	−0.04250	0.86841	0.02400
O10	0.58565 (4)	0.91944 (4)	0.33841 (6)	0.01431 (2)
H10A	0.61352	0.84449	0.34804	0.02639
C11	0.67913 (5)	−0.14542 (5)	0.73257 (7)	0.01223 (2)
H11	0.67991	−0.22346	0.77522	0.02658
C12	0.67900 (5)	0.15763 (5)	0.55721 (7)	0.01127 (2)
C13	0.56224 (4)	0.45555 (5)	0.78110 (7)	0.01050 (2)
C14	0.57031 (4)	0.39610 (5)	0.87395 (7)	0.01132 (2)
C15	0.56852 (5)	0.45306 (6)	0.96802 (7)	0.01318 (2)
H15	0.57585	0.40694	1.03954	0.02636
C16	0.55728 (5)	0.56925 (6)	0.97010 (7)	0.01411 (3)
H16	0.55545	0.61300	1.04324	0.02659
C17	0.54835 (5)	0.62906 (5)	0.87836 (7)	0.01290 (2)
H17	0.53926	0.71921	0.87983	0.02712
C18	0.55112 (4)	0.57223 (5)	0.78478 (7)	0.01057 (2)
C19	0.56861 (4)	1.05463 (5)	0.21022 (6)	0.01017 (2)
C20	0.55772 (4)	1.08576 (5)	0.10733 (7)	0.01098 (2)
C21	0.55609 (5)	1.00464 (6)	0.02978 (7)	0.01425 (3)
H21	0.54768	1.02901	−0.05018	0.02647
C22	0.56525 (5)	0.89210 (6)	0.05631 (7)	0.01582 (3)
H22	0.56529	0.82899	−0.00371	0.02600
C23	0.57457 (5)	0.85924 (5)	0.15926 (7)	0.01369 (2)
H23	0.58033	0.77133	0.17915	0.02656
C24	0.57653 (4)	0.94088 (5)	0.23588 (7)	0.01049 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0243 (2)	0.01114 (17)	0.01064 (17)	−0.00074 (14)	0.00434 (15)	−0.00181 (13)
N1	0.01403 (16)	0.00894 (16)	0.01171 (17)	−0.00040 (12)	0.00030 (14)	−0.00081 (13)
H1	0.03895	0.01701	0.02077	0.00008	0.00127	0.00250
C1	0.01405 (19)	0.00871 (18)	0.00931 (17)	0.00010 (14)	0.00013 (14)	−0.00005 (14)
H1A	0.03980	0.02492	0.01473	0.00040	0.00213	0.00041
O2	0.0267 (2)	0.00858 (16)	0.0171 (2)	0.00236 (15)	0.00211 (17)	0.00226 (14)
N2	0.01452 (18)	0.00911 (16)	0.01043 (17)	0.00083 (13)	0.00008 (13)	0.00020 (13)
H2	0.03877	0.01714	0.02187	−0.00073	−0.00055	−0.00296
C2	0.01268 (17)	0.00885 (17)	0.00897 (17)	0.00076 (13)	0.00055 (13)	0.00032 (13)
O3	0.0261 (2)	0.01096 (17)	0.00878 (15)	−0.00198 (15)	−0.00167 (14)	0.00048 (12)
C3	0.01538 (19)	0.0117 (2)	0.00973 (18)	−0.00020 (15)	0.00025 (16)	0.00120 (15)
H3	0.03908	0.01726	0.02229	0.00049	0.00065	0.00380
O4	0.0258 (2)	0.00874 (15)	0.01332 (17)	−0.00051 (15)	0.00021 (15)	−0.00238 (13)
C4	0.0160 (2)	0.0147 (2)	0.00942 (18)	−0.00140 (17)	0.00121 (16)	−0.00154 (16)
H4	0.03677	0.02522	0.01455	0.00046	0.00126	0.00000
C5	0.01462 (19)	0.0124 (2)	0.0117 (2)	−0.00106 (15)	0.00122 (15)	−0.00260 (16)
H5	0.03025	0.01899	0.02110	0.00494	−0.00072	−0.00064
O5	0.0237 (2)	0.01214 (16)	0.00931 (15)	0.00291 (14)	−0.00265 (14)	−0.00175 (13)
H5A	0.03699	0.01790	0.02187	0.00093	0.00087	−0.00484
O6	0.0253 (2)	0.01035 (16)	0.01441 (18)	−0.00019 (15)	−0.00086 (16)	0.00238 (14)
H6	0.03171	0.02153	0.01654	0.00030	0.00123	0.00207
C6	0.01474 (19)	0.00867 (18)	0.01138 (19)	0.00103 (14)	0.00199 (15)	−0.00032 (14)
C7	0.0148 (2)	0.00941 (18)	0.00906 (17)	−0.00002 (14)	−0.00041 (14)	−0.00050 (14)
H7	0.03050	0.02259	0.01834	0.00474	0.00370	−0.00120
O7	0.02105 (19)	0.01195 (16)	0.00948 (15)	0.00349 (14)	0.00309 (13)	0.00212 (12)
H7A	0.03827	0.02492	0.01542	−0.00022	0.00007	−0.00079
O8	0.0244 (2)	0.00914 (15)	0.01038 (15)	0.00040 (13)	−0.00383 (15)	−0.00146 (13)
H8	0.03440	0.02145	0.01874	0.00412	−0.00433	0.00058
C8	0.01295 (18)	0.00882 (17)	0.00858 (17)	−0.00023 (14)	−0.00049 (13)	−0.00023 (13)
C9	0.0157 (2)	0.01124 (19)	0.00905 (18)	−0.00025 (15)	0.00012 (15)	−0.00124 (15)
H9	0.03523	0.02041	0.01895	0.00352	0.00206	−0.00199
O9	0.0228 (2)	0.01210 (17)	0.01160 (16)	0.00234 (15)	0.00050 (14)	0.00303 (13)
H9A	0.03903	0.01756	0.02263	0.00032	0.00076	−0.00407
C10	0.0158 (2)	0.0134 (2)	0.00884 (17)	0.00060 (15)	0.00067 (15)	0.00079 (16)
H10	0.03339	0.01774	0.02085	0.00506	−0.00027	0.00034
O10	0.02229 (19)	0.01115 (16)	0.00950 (15)	0.00196 (14)	0.00033 (14)	0.00129 (12)
H10A	0.03845	0.02538	0.01535	−0.00071	0.00009	0.00011
C11	0.01425 (19)	0.01153 (19)	0.0109 (2)	0.00115 (15)	0.00053 (15)	0.00190 (15)
H11	0.03862	0.01788	0.02324	−0.00089	−0.00043	0.00466
C12	0.01537 (19)	0.00888 (18)	0.00957 (17)	−0.00059 (14)	−0.00136 (15)	−0.00045 (14)
C13	0.01265 (17)	0.01040 (18)	0.00845 (16)	0.00014 (13)	−0.00084 (14)	−0.00005 (14)
C14	0.01310 (18)	0.01128 (18)	0.00959 (17)	−0.00047 (14)	−0.00041 (14)	0.00160 (15)
C15	0.0156 (2)	0.0154 (2)	0.00860 (18)	−0.00070 (17)	−0.00002 (15)	0.00107 (16)
H15	0.03769	0.02408	0.01731	0.00164	−0.00069	0.00415
C16	0.0173 (2)	0.0161 (2)	0.00891 (18)	−0.00026 (17)	0.00134 (16)	−0.00136 (16)
H16	0.03836	0.02448	0.01693	0.00192	0.00020	−0.00470
C17	0.0160 (2)	0.01226 (19)	0.01043 (18)	0.00023 (16)	0.00197 (16)	−0.00155 (16)
H17	0.04021	0.01660	0.02457	0.00338	−0.00003	−0.00083
C18	0.01268 (17)	0.01020 (17)	0.00883 (16)	0.00045 (14)	0.00112 (14)	0.00006 (14)
C19	0.01243 (17)	0.00948 (17)	0.00861 (17)	0.00009 (13)	−0.00086 (13)	−0.00036 (13)
C20	0.01230 (17)	0.01156 (19)	0.00907 (16)	0.00131 (15)	−0.00070 (14)	0.00055 (15)
C21	0.0170 (2)	0.0166 (2)	0.00916 (18)	0.00398 (18)	−0.00117 (15)	−0.00189 (16)
H21	0.03813	0.02520	0.01608	0.00221	−0.00174	0.00266
C22	0.0200 (2)	0.0153 (2)	0.0121 (2)	0.00426 (19)	−0.00217 (18)	−0.00439 (18)
H22	0.03732	0.02102	0.01965	0.00179	−0.00033	−0.00504
C23	0.0174 (2)	0.0108 (2)	0.0129 (2)	0.00195 (16)	−0.00102 (17)	−0.00289 (16)
H23	0.03935	0.01617	0.02415	0.00233	−0.00057	0.00205
C24	0.01267 (17)	0.00932 (17)	0.00948 (17)	0.00018 (14)	0.00001 (14)	−0.00048 (14)

Geometric parameters (Å, º)

O1—C6	1.2685 (9)	C8—C12	1.5123 (8)
N1—C1	1.3444 (8)	C8—C9	1.3956 (8)
N1—C5	1.3416 (9)	C9—C10	1.3948 (9)
N1—H1	1.0150	C9—H9	1.0830
C1—C2	1.3863 (8)	O9—C20	1.3763 (8)
C1—H1A	1.0830	O9—H9A	0.9800
O2—C6	1.2529 (8)	C10—C11	1.3825 (9)
N2—C7	1.3455 (8)	C10—H10	1.0830
N2—C11	1.3463 (8)	O10—C24	1.3597 (8)
N2—H2	1.0150	O10—H10A	0.9800
C2—C6	1.5068 (9)	C11—H11	1.0830
C2—C3	1.3968 (9)	C13—C18	1.4013 (8)
O3—C12	1.2702 (8)	C13—C14	1.4019 (8)
C3—C4	1.3914 (9)	C14—C15	1.3967 (9)
C3—H3	1.0830	C15—C16	1.3951 (10)
O4—C12	1.2490 (8)	C15—H15	1.0830
C4—C5	1.3849 (10)	C16—C17	1.3927 (10)
C4—H4	1.0830	C16—H16	1.0830
C5—H5	1.0830	C17—C18	1.3907 (9)
O5—C13	1.3611 (8)	C17—H17	1.0830
O5—H5A	0.9800	C19—C20	1.3930 (8)
O6—C14	1.3709 (8)	C19—C24	1.4016 (8)
O6—H6	0.9800	C20—C21	1.3960 (9)
C7—C8	1.3887 (8)	C21—C22	1.3919 (11)
C7—H7	1.0830	C21—H21	1.0830
O7—C18	1.3739 (8)	C22—C23	1.3972 (10)
O7—H7A	0.9800	C22—H22	1.0830
O8—C19	1.3665 (8)	C23—C24	1.3917 (9)
O8—H8	0.9800	C23—H23	1.0830
C1—N1—C5	122.26 (5)	N2—C11—C10	120.22 (5)
C1—N1—H1	118.78 (5)	N2—C11—H11	119.89 (6)
C5—N1—H1	118.96 (6)	C10—C11—H11	119.89 (5)
N1—C1—C2	120.13 (5)	O4—C12—O3	125.27 (5)
N1—C1—H1A	119.95 (5)	O4—C12—C8	117.68 (5)
C2—C1—H1A	119.93 (5)	O3—C12—C8	117.04 (5)
C7—N2—C11	122.18 (5)	O5—C13—C18	116.99 (5)
C7—N2—H2	118.99 (5)	O5—C13—C14	124.16 (5)
C11—N2—H2	118.83 (6)	C18—C13—C14	118.81 (5)
C6—C2—C1	120.81 (5)	O6—C14—C13	117.02 (5)
C6—C2—C3	120.66 (5)	O6—C14—C15	122.81 (5)
C1—C2—C3	118.52 (5)	C13—C14—C15	120.17 (5)
C2—C3—C4	120.18 (5)	C14—C15—C16	120.15 (5)
C2—C3—H3	119.79 (6)	C14—C15—H15	119.94 (6)
C4—C3—H3	120.04 (5)	C16—C15—H15	119.91 (5)
C5—C4—C3	118.63 (5)	C17—C16—C15	120.16 (6)
C5—C4—H4	120.67 (5)	C17—C16—H16	119.94 (6)
C3—C4—H4	120.70 (5)	C15—C16—H16	119.90 (5)
N1—C5—C4	120.28 (5)	C18—C17—C16	119.54 (5)
N1—C5—H5	119.85 (6)	C18—C17—H17	120.19 (6)
C4—C5—H5	119.87 (5)	C16—C17—H17	120.27 (6)
C13—O5—H5A	109.52 (5)	O7—C18—C13	120.01 (5)
C14—O6—H6	109.45 (5)	O7—C18—C17	118.84 (5)
O2—C6—O1	125.28 (6)	C13—C18—C17	121.15 (5)
O2—C6—C2	117.21 (5)	O8—C19—C20	118.81 (5)
O1—C6—C2	117.48 (5)	O8—C19—C24	121.59 (5)
N2—C7—C8	120.10 (5)	C20—C19—C24	119.60 (5)
N2—C7—H7	119.79 (5)	O9—C20—C19	120.94 (5)
C8—C7—H7	120.11 (5)	O9—C20—C21	118.61 (5)
C18—O7—H7A	109.50 (5)	C19—C20—C21	120.45 (5)
C19—O8—H8	109.55 (5)	C20—C21—C22	119.30 (6)
C12—C8—C7	120.08 (5)	C20—C21—H21	120.35 (6)
C12—C8—C9	121.28 (5)	C22—C21—H21	120.35 (6)
C7—C8—C9	118.64 (5)	C21—C22—C23	121.01 (6)
C8—C9—C10	120.02 (5)	C21—C22—H22	119.55 (6)
C8—C9—H9	119.95 (6)	C23—C22—H22	119.44 (6)
C10—C9—H9	120.02 (5)	C24—C23—C22	119.17 (6)
C20—O9—H9A	109.52 (5)	C24—C23—H23	120.43 (6)
C11—C10—C9	118.81 (5)	C22—C23—H23	120.40 (6)
C11—C10—H10	120.67 (5)	O10—C24—C19	114.92 (5)
C9—C10—H10	120.52 (5)	O10—C24—C23	124.62 (5)
C24—O10—H10A	109.39 (5)	C19—C24—C23	120.46 (5)
O1—C6—C2—C1	1.93 (9)	O7—C18—C13—C14	−178.74 (8)
O1—C6—C2—C3	−176.88 (9)	O7—C18—C17—C16	179.30 (8)
N1—C1—C2—C6	−177.87 (8)	O7—C18—C17—H17	−0.65
N1—C1—C2—C3	0.96 (8)	H7A—O7—C18—C13	−34.86
N1—C5—C4—C3	0.33 (8)	H7A—O7—C18—C17	146.16
N1—C5—C4—H4	−179.65	O8—C19—C20—O9	0.17 (8)
H1—N1—C1—C2	179.75	O8—C19—C20—C21	179.57 (8)
H1—N1—C1—H1A	−0.25	O8—C19—C24—O10	0.27 (8)
H1—N1—C5—C4	179.58	O8—C19—C24—C23	−179.87 (9)
H1—N1—C5—H5	−0.39	H8—O8—C19—C20	−158.55
C1—N1—C5—C4	−0.45 (8)	H8—O8—C19—C24	21.97
C1—N1—C5—H5	179.58	C8—C7—N2—C11	−1.19 (9)
C1—C2—C6—O2	−179.60 (9)	C8—C9—C10—C11	−1.76 (9)
C1—C2—C3—C4	−1.06 (9)	C8—C9—C10—H10	178.28
C1—C2—C3—H3	178.97	C9—C10—C11—H11	−179.42
H1A—C1—N1—C5	179.78	H9—C9—C8—C12	1.70
H1A—C1—C2—C6	2.14	H9—C9—C10—C11	178.24
H1A—C1—C2—C3	−179.03	H9—C9—C10—H10	−1.72
O2—C6—C2—C3	1.59 (9)	O9—C20—C19—C24	179.66 (8)
N2—C7—C8—C12	179.76 (8)	O9—C20—C21—C22	179.56 (9)
N2—C7—C8—C9	−0.03 (8)	O9—C20—C21—H21	−0.54
N2—C11—C10—C9	0.57 (8)	H9A—O9—C20—C19	−20.60
N2—C11—C10—H10	−179.47	H9A—O9—C20—C21	159.99
H2—N2—C7—C8	178.97	C10—C9—C8—C12	−178.29 (9)
H2—N2—C7—H7	−0.93	H10—C10—C11—H11	0.54
H2—N2—C11—C10	−179.24	O10—C24—C19—C20	−179.21 (8)
H2—N2—C11—H11	0.75	O10—C24—C23—C22	−179.74 (9)
C2—C1—N1—C5	−0.22 (8)	O10—C24—C23—H23	0.15
C2—C3—C4—C5	0.43 (9)	H10A—O10—C24—C19	−160.04
C2—C3—C4—H4	−179.59	H10A—O10—C24—C23	20.11
O3—C12—C8—C7	−0.77 (9)	C13—C18—C17—C16	0.33 (8)
O3—C12—C8—C9	179.02 (9)	C13—C18—C17—H17	−179.62
C3—C4—C5—H5	−179.69	C13—C14—C15—C16	0.92 (8)
H3—C3—C2—C6	−2.19	C13—C14—C15—H15	−179.10
H3—C3—C4—C5	−179.60	C14—C13—C18—C17	0.22 (8)
H3—C3—C4—H4	0.37	C14—C15—C16—C17	−0.36 (9)
O4—C12—C8—C7	−179.61 (9)	C14—C15—C16—H16	179.59
O4—C12—C8—C9	0.17 (9)	C15—C14—C13—C18	−0.84 (8)
C4—C3—C2—C6	177.77 (9)	C15—C16—C17—C18	−0.26 (9)
H4—C4—C5—H5	0.33	C15—C16—C17—H17	179.69
O5—C13—C18—O7	−0.74 (8)	H15—C15—C16—C17	179.65
O5—C13—C18—C17	178.21 (8)	H15—C15—C16—H16	−0.39
O5—C13—C14—O6	1.66 (8)	H16—C16—C17—C18	179.79
O5—C13—C14—C15	−178.68 (8)	H16—C16—C17—H17	−0.27
H5A—O5—C13—C18	154.23	C19—C20—C21—C22	0.15 (9)
H5A—O5—C13—C14	−27.89	C19—C20—C21—H21	−179.96
O6—C14—C13—C18	179.51 (8)	C19—C24—C23—C22	0.41 (9)
O6—C14—C15—C16	−179.45 (9)	C19—C24—C23—H23	−179.70
O6—C14—C15—H15	0.54	C20—C19—C24—C23	0.66 (9)
H6—O6—C14—C13	−173.99	C20—C21—C22—C23	0.94 (9)
H6—O6—C14—C15	6.36	C20—C21—C22—H22	−178.94
C7—N2—C11—C10	0.92 (8)	C21—C20—C19—C24	−0.94 (9)
C7—N2—C11—H11	−179.09	C21—C22—C23—C24	−1.22 (10)
C7—C8—C9—C10	1.50 (9)	C21—C22—C23—H23	178.89
C7—C8—C9—H9	−178.50	H21—C21—C22—C23	−178.96
H7—C7—N2—C11	178.91	H21—C21—C22—H22	1.16
H7—C7—C8—C12	−0.35	H22—C22—C23—C24	178.67
H7—C7—C8—C9	179.86	H22—C22—C23—H23	−1.22

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	1.01	1.71	2.7137 (7)	172
N2—H2···O2^i	1.01	2.48	3.1987 (9)	127
N2—H2···C6^i	1.01	2.36	3.3145 (9)	157
C5—H5···O8^i	1.08	2.56	3.1297 (8)	112
C7—H7···O2^i	1.08	2.60	3.2628 (9)	119
C7—H7···O10^i	1.08	2.37	3.3124 (8)	145
O6—H6···O9^ii	0.98	2.00	2.9708 (8)	169
C15—H15···O9^ii	1.08	2.59	3.3947 (8)	131
N1—H1···O3	1.01	1.66	2.6696 (7)	175
N1—H1···O4	1.01	2.53	3.2085 (9)	124
N1—H1···C12	1.01	2.36	3.2963 (9)	154
C1—H1A···O4	1.08	2.53	3.2175 (8)	121
O5—H5A···O4	0.98	1.86	2.6851 (8)	140
O5—H5A···O6	0.98	2.42	2.7908 (8)	102
O7—H7A···O1	0.98	1.90	2.7045 (7)	137
O8—H8···O10	0.98	2.26	2.6913 (7)	105
C9—H9···O6	1.08	2.52	3.5056 (9)	151
O9—H9A···O8	0.98	2.32	2.7593 (8)	106
O10—H10A···O2	0.98	1.71	2.6349 (8)	156
O8—H8···O3^iii	0.98	1.89	2.7498 (8)	144
C11—H11···O2^iv	1.08	2.48	3.1465 (9)	118
C5—H5···O4^v	1.08	2.32	3.0351 (9)	122
C15—H15···O7^vi	1.08	2.62	3.4564 (9)	134
C16—H16···O5^vi	1.08	2.46	3.2500 (8)	129
O9—H9A···O7^vii	0.98	1.93	2.8143 (7)	149
C21—H21···O10^vii	1.08	2.40	3.2758 (8)	136
C17—H17···O8^viii	1.08	2.60	3.4596 (8)	136

Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2.

(multipolar_MoPro)

Crystal data

C6H5NO2·C6H6O3	Dx = 1.566 Mg m^−3
Mr = 249.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2780 reflections
a = 13.6648 (4) Å	θ = 2.3–52.2°
b = 11.9321 (3) Å	µ = 0.12 mm^−1
c = 12.9678 (4) Å	T = 100 K
V = 2114.40 (10) Å^3	Block, brown
Z = 8	0.35 × 0.29 × 0.24 mm
F(000) = 1040

Data collection

Bruker D8 Venture PHOTON II diffractometer	19169 reflections with > 2.0 σ(I)
ω and phi scan	Rint = 0.051
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0673 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8999. The λ/2 correction factor is Not present.	θmax = 52.2°, θmin = 2.3°
Tmin = 0.675, Tmax = 0.750	h = −30→21
101259 measured reflections	k = −26→24
19169 independent reflections	l = −28→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.046	w = 1/[1.223*σ^2(Fo^2) + 0.0001*Yo^2]
S = 1.01	(Δ/σ)max = 0.027
19169 reflections	Δρmax = 0.34 e Å^−3
1075 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Absolute structure: Rogers (1981), 8469 Friedel pairs
Primary atom site location: structure-invariant direct methods	Rogers parameter: 1

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O1	0.68090 (2)	0.64338 (3)	0.547620 (6)	0.015210 (14)
N1	0.68875 (2)	0.35065 (3)	0.37576 (4)	0.011509 (13)
H1	0.68420	0.27141	0.41620	0.02558
C1	0.68309 (3)	0.44392 (3)	0.43328 (4)	0.010812 (14)
H1A	0.66960	0.42702	0.51436	0.02649
O2	0.68742 (2)	0.74541 (3)	0.40319 (4)	0.017211 (15)
N2	0.67965 (2)	−0.14701 (3)	0.62887 (3)	0.011375 (13)
H2	0.67924	−0.22524	0.58805	0.02593
C2	0.68698 (2)	0.54858 (3)	0.38670 (4)	0.010287 (14)
O3	0.68263 (2)	0.14660 (3)	0.46002 (3)	0.015081 (14)
C3	0.69544 (3)	0.55390 (3)	0.27960 (4)	0.012285 (15)
H3	0.70080	0.63357	0.23922	0.02621
O4	0.67786 (2)	0.24881 (3)	0.60438 (4)	0.015723 (13)
C4	0.70135 (3)	0.45585 (3)	0.22178 (4)	0.013279 (16)
H4	0.71476	0.45861	0.13934	0.02551
C5	0.69796 (3)	0.35401 (3)	0.27262 (4)	0.012910 (16)
H5	0.70442	0.27493	0.23204	0.02345
O5	0.56144 (2)	0.40676 (2)	0.68628 (3)	0.014828 (13)
H5A	0.59914	0.33578	0.68516	0.02559
O6	0.58028 (2)	0.28220 (2)	0.86722 (4)	0.016431 (13)
H6	0.57488	0.24894	0.93655	0.02326
C6	0.68411 (3)	0.65407 (3)	0.45043 (4)	0.011740 (15)
C7	0.68004 (3)	−0.05256 (3)	0.57242 (4)	0.011191 (15)
H7	0.68071	−0.06829	0.49002	0.02381
O7	0.54119 (2)	0.63227 (2)	0.69511 (3)	0.013985 (12)
H7A	0.58036	0.59732	0.63949	0.02620
O8	0.57053 (2)	1.13634 (2)	0.28401 (3)	0.014451 (12)
H8	0.60116	1.10197	0.34559	0.02487
C8	0.67818 (2)	0.05129 (3)	0.62078 (4)	0.010193 (14)
C9	0.67578 (3)	0.05494 (3)	0.72828 (4)	0.012078 (15)
H9	0.67177	0.13523	0.76801	0.02486
O9	0.54931 (2)	1.19663 (2)	0.07989 (4)	0.015353 (13)
H9A	0.52751	1.24376	0.13812	0.02641
C10	0.67774 (3)	−0.04438 (3)	0.78495 (4)	0.012692 (15)
H10	0.67737	−0.04356	0.86869	0.02400
O10	0.58562 (2)	0.91928 (2)	0.33847 (3)	0.014056 (13)
H10A	0.61384	0.84387	0.35324	0.02639
C11	0.67919 (3)	−0.14549 (3)	0.73257 (4)	0.012351 (15)
H11	0.68115	−0.22669	0.77022	0.02658
C12	0.67898 (3)	0.15756 (3)	0.55730 (4)	0.011442 (15)
C13	0.56219 (2)	0.45555 (3)	0.78113 (4)	0.010470 (13)
C14	0.57028 (2)	0.39612 (3)	0.87400 (4)	0.011408 (14)
C15	0.56856 (3)	0.45315 (3)	0.96799 (4)	0.013364 (16)
H15	0.57734	0.40278	1.03727	0.02636
C16	0.55731 (3)	0.56930 (3)	0.97008 (4)	0.014164 (16)
H16	0.55366	0.61271	1.04369	0.02659
C17	0.54835 (3)	0.62915 (3)	0.87837 (4)	0.012971 (15)
H17	0.53055	0.71786	0.87439	0.02712
C18	0.55113 (2)	0.57221 (3)	0.78479 (4)	0.010619 (13)
C19	0.56858 (2)	1.05468 (3)	0.21025 (4)	0.010177 (14)
C20	0.55765 (2)	1.08586 (3)	0.10726 (4)	0.011211 (14)
C21	0.55605 (3)	1.00476 (3)	0.02999 (4)	0.014420 (17)
H21	0.54060	1.03286	−0.04810	0.02647
C22	0.56525 (3)	0.89216 (4)	0.05637 (4)	0.016084 (17)
H22	0.56100	0.82864	−0.00360	0.02600
C23	0.57464 (3)	0.85922 (3)	0.15933 (4)	0.013821 (16)
H23	0.58265	0.77247	0.18401	0.02656
C24	0.57651 (3)	0.94088 (3)	0.23599 (4)	0.010626 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.02419 (13)	0.01087 (11)	0.01058 (11)	−0.00067 (9)	0.00410 (9)	−0.00163 (8)
N1	0.01425 (10)	0.00881 (11)	0.01146 (11)	−0.00052 (8)	0.00022 (9)	−0.00081 (9)
H1	0.03895	0.01701	0.02077	0.00008	0.00127	0.00250
C1	0.01457 (12)	0.00884 (12)	0.00903 (11)	0.00000 (9)	0.00024 (9)	0.00014 (9)
H1A	0.03980	0.02492	0.01473	0.00040	0.00213	0.00041
O2	0.02650 (13)	0.00853 (10)	0.01661 (13)	0.00223 (9)	0.00198 (10)	0.00208 (9)
N2	0.01487 (11)	0.00893 (11)	0.01032 (11)	0.00079 (9)	0.00019 (9)	0.00004 (9)
H2	0.03877	0.01714	0.02187	−0.00073	−0.00055	−0.00296
C2	0.01306 (11)	0.00854 (11)	0.00926 (12)	0.00066 (9)	0.00060 (9)	0.00024 (9)
O3	0.02558 (13)	0.01055 (11)	0.00911 (10)	−0.00177 (9)	−0.00177 (9)	0.00041 (8)
C3	0.01592 (12)	0.01146 (13)	0.00948 (12)	−0.00022 (9)	0.00051 (10)	0.00114 (11)
H3	0.03908	0.01726	0.02229	0.00049	0.00065	0.00380
O4	0.02531 (13)	0.00856 (10)	0.01329 (11)	−0.00050 (9)	0.00021 (10)	−0.00215 (9)
C4	0.01663 (13)	0.01420 (14)	0.00900 (12)	−0.00131 (10)	0.00125 (10)	−0.00125 (10)
H4	0.03677	0.02522	0.01455	0.00046	0.00126	0.00000
C5	0.01509 (12)	0.01172 (13)	0.01192 (14)	−0.00118 (10)	0.00166 (10)	−0.00292 (10)
H5	0.03025	0.01899	0.02110	0.00494	−0.00072	−0.00064
O5	0.02301 (12)	0.01218 (10)	0.00930 (10)	0.00285 (9)	−0.00268 (9)	−0.00170 (8)
H5A	0.03699	0.01790	0.02187	0.00093	0.00087	−0.00484
O6	0.02442 (12)	0.01080 (10)	0.01407 (11)	−0.00029 (9)	−0.00089 (10)	0.00227 (9)
H6	0.03171	0.02153	0.01654	0.00030	0.00123	0.00207
C6	0.01570 (12)	0.00855 (12)	0.01097 (12)	0.00095 (10)	0.00196 (10)	0.00022 (10)
C7	0.01545 (13)	0.00932 (12)	0.00880 (11)	0.00008 (10)	−0.00036 (10)	−0.00090 (9)
H7	0.03050	0.02259	0.01834	0.00474	0.00370	−0.00120
O7	0.02046 (11)	0.01166 (10)	0.00984 (10)	0.00334 (9)	0.00276 (9)	0.00183 (8)
H7A	0.03827	0.02492	0.01542	−0.00022	0.00007	−0.00079
O8	0.02360 (11)	0.00921 (9)	0.01054 (9)	0.00039 (8)	−0.00356 (10)	−0.00151 (8)
H8	0.03440	0.02145	0.01874	0.00412	−0.00433	0.00058
C8	0.01337 (12)	0.00879 (12)	0.00842 (11)	−0.00035 (9)	−0.00048 (9)	−0.00025 (9)
C9	0.01624 (13)	0.01110 (12)	0.00889 (12)	−0.00016 (10)	0.00012 (10)	−0.00092 (10)
H9	0.03523	0.02041	0.01895	0.00352	0.00206	−0.00199
O9	0.02226 (12)	0.01255 (11)	0.01125 (10)	0.00244 (9)	0.00034 (9)	0.00280 (8)
H9A	0.03903	0.01756	0.02263	0.00032	0.00076	−0.00407
C10	0.01621 (13)	0.01338 (13)	0.00849 (11)	0.00053 (10)	0.00059 (11)	0.00066 (11)
H10	0.03339	0.01774	0.02085	0.00506	−0.00027	0.00034
O10	0.02160 (11)	0.01085 (10)	0.00972 (10)	0.00193 (9)	0.00043 (9)	0.00120 (8)
H10A	0.03845	0.02538	0.01535	−0.00071	0.00009	0.00011
C11	0.01498 (12)	0.01117 (13)	0.01090 (13)	0.00111 (10)	0.00040 (10)	0.00185 (10)
H11	0.03862	0.01788	0.02324	−0.00089	−0.00043	0.00466
C12	0.01627 (12)	0.00863 (12)	0.00943 (12)	−0.00071 (10)	−0.00124 (10)	−0.00051 (9)
C13	0.01329 (11)	0.00987 (11)	0.00825 (10)	0.00019 (9)	−0.00089 (9)	0.00007 (10)
C14	0.01361 (11)	0.01111 (12)	0.00950 (11)	−0.00042 (9)	−0.00055 (10)	0.00130 (10)
C15	0.01608 (13)	0.01538 (14)	0.00863 (11)	−0.00056 (11)	−0.00007 (10)	0.00106 (10)
H15	0.03769	0.02408	0.01731	0.00164	−0.00069	0.00415
C16	0.01809 (13)	0.01565 (14)	0.00876 (11)	−0.00005 (11)	0.00133 (11)	−0.00138 (10)
H16	0.03836	0.02448	0.01693	0.00192	0.00020	−0.00470
C17	0.01675 (13)	0.01198 (13)	0.01018 (12)	0.00059 (10)	0.00215 (11)	−0.00129 (10)
H17	0.04021	0.01660	0.02457	0.00338	−0.00003	−0.00083
C18	0.01325 (11)	0.00990 (11)	0.00871 (10)	0.00060 (9)	0.00111 (10)	0.00007 (10)
C19	0.01269 (11)	0.00938 (12)	0.00846 (11)	0.00008 (9)	−0.00089 (9)	−0.00032 (9)
C20	0.01304 (11)	0.01185 (13)	0.00874 (11)	0.00127 (10)	−0.00071 (9)	0.00047 (10)
C21	0.01743 (14)	0.01667 (15)	0.00916 (11)	0.00397 (11)	−0.00129 (10)	−0.00194 (10)
H21	0.03813	0.02520	0.01608	0.00221	−0.00174	0.00266
C22	0.02131 (15)	0.01483 (14)	0.01211 (13)	0.00414 (12)	−0.00250 (12)	−0.00449 (11)
H22	0.03732	0.02102	0.01965	0.00179	−0.00033	−0.00504
C23	0.01756 (13)	0.01077 (13)	0.01313 (13)	0.00189 (10)	−0.00117 (11)	−0.00288 (10)
H23	0.03935	0.01617	0.02415	0.00233	−0.00057	0.00205
C24	0.01310 (11)	0.00947 (12)	0.00930 (11)	0.00031 (9)	−0.00010 (9)	−0.00044 (9)

Geometric parameters (Å, º)

O1—C6	1.2675 (5)	C8—C12	1.5117 (5)
N1—C1	1.3420 (5)	C8—C9	1.3952 (5)
N1—C5	1.3440 (5)	C9—C10	1.3947 (5)
N1—H1	1.0829	C9—H9	1.0892
C1—C2	1.3883 (5)	O9—C20	1.3733 (5)
C1—H1A	1.0863	O9—H9A	0.9874
O2—C6	1.2511 (5)	C10—C11	1.3846 (5)
N2—C7	1.3439 (5)	C10—H10	1.0860
N2—C11	1.3449 (5)	O10—C24	1.3595 (5)
N2—H2	1.0731	O10—H10A	0.9975
C2—C6	1.5063 (5)	C11—H11	1.0853
C2—C3	1.3951 (5)	C13—C18	1.4009 (5)
O3—C12	1.2693 (5)	C13—C14	1.4020 (5)
C3—C4	1.3920 (5)	C14—C15	1.3961 (5)
C3—H3	1.0877	C15—C16	1.3947 (6)
O4—C12	1.2484 (5)	C15—H15	1.0875
C4—C5	1.3832 (6)	C16—C17	1.3926 (6)
C4—H4	1.0852	C16—H16	1.0872
C5—H5	1.0840	C17—C18	1.3913 (5)
O5—C13	1.3609 (5)	C17—H17	1.0873
O5—H5A	0.9914	C19—C20	1.3945 (5)
O6—C14	1.3690 (5)	C19—C24	1.4025 (5)
O6—H6	0.9855	C20—C21	1.3931 (5)
C7—C8	1.3890 (5)	C21—C22	1.3921 (6)
C7—H7	1.0850	C21—H21	1.0874
O7—C18	1.3728 (5)	C22—C23	1.3976 (6)
O7—H7A	0.9903	C22—H22	1.0876
O8—C19	1.3657 (4)	C23—C24	1.3921 (5)
O8—H8	0.9905	C23—H23	1.0890
C1—N1—C5	122.26 (3)	N2—C11—C10	120.16 (3)
C1—N1—H1	116.84	N2—C11—H11	115.95
C5—N1—H1	120.89	C10—C11—H11	123.88
N1—C1—C2	120.13 (3)	O4—C12—O3	125.19 (3)
N1—C1—H1A	113.20	O4—C12—C8	117.73 (3)
C2—C1—H1A	126.48	O3—C12—C8	117.07 (3)
C7—N2—C11	122.23 (3)	O5—C13—C18	117.06 (3)
C7—N2—H2	117.43	O5—C13—C14	124.10 (3)
C11—N2—H2	120.33	C18—C13—C14	118.81 (3)
C6—C2—C1	120.80 (3)	O6—C14—C13	117.06 (3)
C6—C2—C3	120.68 (3)	O6—C14—C15	122.80 (3)
C1—C2—C3	118.51 (3)	C13—C14—C15	120.14 (3)
C2—C3—C4	120.18 (3)	C14—C15—C16	120.21 (3)
C2—C3—H3	121.64	C14—C15—H15	116.74
C4—C3—H3	118.12	C16—C15—H15	123.05
C5—C4—C3	118.67 (3)	C17—C16—C15	120.18 (3)
C5—C4—H4	120.12	C17—C16—H16	120.09
C3—C4—H4	120.99	C15—C16—H16	119.71
N1—C5—C4	120.24 (3)	C18—C17—C16	119.47 (3)
N1—C5—H5	117.69	C18—C17—H17	116.11
C4—C5—H5	122.05	C16—C17—H17	124.02
C13—O5—H5A	112.01	O7—C18—C13	120.04 (3)
C14—O6—H6	109.50	O7—C18—C17	118.77 (3)
O2—C6—O1	125.16 (3)	C13—C18—C17	121.18 (3)
O2—C6—C2	117.28 (3)	O8—C19—C20	118.85 (3)
O1—C6—C2	117.54 (3)	O8—C19—C24	121.51 (3)
N2—C7—C8	120.14 (3)	C20—C19—C24	119.64 (3)
N2—C7—H7	113.04	O9—C20—C19	120.87 (3)
C8—C7—H7	126.81	O9—C20—C21	118.78 (3)
C18—O7—H7A	110.11	C19—C20—C21	120.35 (3)
C19—O8—H8	106.11	C20—C21—C22	119.48 (3)
C12—C8—C7	120.15 (3)	C20—C21—H21	117.30
C12—C8—C9	121.20 (3)	C22—C21—H21	122.96
C7—C8—C9	118.64 (3)	C21—C22—C23	120.96 (3)
C8—C9—C10	119.97 (3)	C21—C22—H22	119.47
C8—C9—H9	120.08	C23—C22—H22	119.48
C10—C9—H9	119.94	C24—C23—C22	119.14 (3)
C20—O9—H9A	112.05	C24—C23—H23	116.97
C11—C10—C9	118.82 (3)	C22—C23—H23	123.87
C11—C10—H10	119.90	O10—C24—C19	115.04 (3)
C9—C10—H10	121.27	O10—C24—C23	124.55 (3)
C24—O10—H10A	113.21	C19—C24—C23	120.41 (3)
O1—C6—C2—C1	1.99 (5)	O7—C18—C13—C14	−178.78 (4)
O1—C6—C2—C3	−176.82 (5)	O7—C18—C17—C16	179.34 (4)
N1—C1—C2—C6	−177.94 (5)	O7—C18—C17—H17	6.29
N1—C1—C2—C3	0.88 (5)	H7A—O7—C18—C13	−34.06
N1—C5—C4—C3	0.25 (5)	H7A—O7—C18—C17	146.99
N1—C5—C4—H4	174.97	O8—C19—C20—O9	0.24 (5)
H1—N1—C1—C2	−179.09	O8—C19—C20—C21	179.55 (5)
H1—N1—C1—H1A	−3.84	O8—C19—C24—O10	0.30 (4)
H1—N1—C5—C4	178.46	O8—C19—C24—C23	−179.79 (5)
H1—N1—C5—H5	−3.10	H8—O8—C19—C20	−160.67
C1—N1—C5—C4	−0.38 (5)	H8—O8—C19—C24	19.86
C1—N1—C5—H5	178.06	C8—C7—N2—C11	−1.17 (5)
C1—C2—C6—O2	−179.65 (5)	C8—C9—C10—C11	−1.87 (5)
C1—C2—C3—C4	−1.00 (5)	C8—C9—C10—H10	178.79
C1—C2—C3—H3	−178.31	C9—C10—C11—H11	179.65
H1A—C1—N1—C5	175.05	H9—C9—C8—C12	2.22
H1A—C1—C2—C6	7.49	H9—C9—C10—C11	177.63
H1A—C1—C2—C3	−173.68	H9—C9—C10—H10	−1.71
O2—C6—C2—C3	1.55 (5)	O9—C20—C19—C24	179.73 (5)
N2—C7—C8—C12	179.79 (5)	O9—C20—C21—C22	179.46 (5)
N2—C7—C8—C9	−0.09 (5)	O9—C20—C21—H21	−6.22
N2—C11—C10—C9	0.65 (5)	H9A—O9—C20—C19	−21.35
N2—C11—C10—H10	180.00	H9A—O9—C20—C21	159.33
H2—N2—C7—C8	178.44	C10—C9—C8—C12	−178.28 (5)
H2—N2—C7—H7	−0.64	H10—C10—C11—H11	−1.00
H2—N2—C11—C10	−178.71	O10—C24—C19—C20	−179.17 (4)
H2—N2—C11—H11	2.21	O10—C24—C23—C22	−179.79 (5)
C2—C1—N1—C5	−0.20 (5)	O10—C24—C23—H23	−1.35
C2—C3—C4—C5	0.45 (5)	H10A—O10—C24—C19	−159.93
C2—C3—C4—H4	−174.22	H10A—O10—C24—C23	20.17
O3—C12—C8—C7	−0.87 (5)	C13—C18—C17—C16	0.40 (5)
O3—C12—C8—C9	179.00 (5)	C13—C18—C17—H17	−172.65
C3—C4—C5—H5	−178.12	C13—C14—C15—C16	0.96 (5)
H3—C3—C2—C6	0.52	C13—C14—C15—H15	−178.22
H3—C3—C4—C5	177.84	C14—C13—C18—C17	0.15 (5)
H3—C3—C4—H4	3.18	C14—C15—C16—C17	−0.41 (5)
O4—C12—C8—C7	−179.55 (5)	C14—C15—C16—H16	178.01
O4—C12—C8—C9	0.32 (5)	C15—C14—C13—C18	−0.83 (5)
C4—C3—C2—C6	177.83 (5)	C15—C16—C17—C18	−0.27 (5)
H4—C4—C5—H5	−3.40	C15—C16—C17—H17	172.20
O5—C13—C18—O7	−0.67 (4)	H15—C15—C16—C17	178.72
O5—C13—C18—C17	178.26 (5)	H15—C15—C16—H16	−2.86
O5—C13—C14—O6	1.57 (4)	H16—C16—C17—C18	−178.68
O5—C13—C14—C15	−178.80 (5)	H16—C16—C17—H17	−6.21
H5A—O5—C13—C18	152.88	C19—C20—C21—C22	0.14 (5)
H5A—O5—C13—C14	−29.12	C19—C20—C21—H21	174.46
O6—C14—C13—C18	179.54 (5)	C19—C24—C23—C22	0.31 (5)
O6—C14—C15—C16	−179.43 (5)	C19—C24—C23—H23	178.75
O6—C14—C15—H15	1.39	C20—C19—C24—C23	0.74 (5)
H6—O6—C14—C13	−171.20	C20—C21—C22—C23	0.94 (5)
H6—O6—C14—C15	9.18	C20—C21—C22—H22	177.49
C7—N2—C11—C10	0.88 (5)	C21—C20—C19—C24	−0.96 (5)
C7—N2—C11—H11	−178.19	C21—C22—C23—C24	−1.16 (6)
C7—C8—C9—C10	1.59 (5)	C21—C22—C23—H23	−179.48
C7—C8—C9—H9	−177.90	H21—C21—C22—C23	−173.05
H7—C7—N2—C11	179.75	H21—C21—C22—H22	3.51
H7—C7—C8—C12	−1.27	H22—C22—C23—C24	−177.71
H7—C7—C8—C9	178.85	H22—C22—C23—H23	3.97

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	1.07	1.65	2.7140 (4)	169 (1)
N2—H2···O2^i	1.07	2.42	3.1975 (5)	128 (1)
N2—H2···C6^i	1.07	2.29	3.3153 (5)	158 (1)
C5—H5···O8^i	1.08	2.56	3.1304 (5)	112
C7—H7···O2^i	1.09	2.49	3.2615 (5)	126
C7—H7···O10^i	1.09	2.36	3.3138 (5)	145
O6—H6···O9^ii	0.99	1.99	2.9711 (5)	172 (1)
C15—H15···O9^ii	1.09	2.55	3.3975 (5)	134
N1—H1···O3	1.08	1.59	2.6700 (4)	172 (1)
N1—H1···O4	1.08	2.46	3.2075 (5)	125 (1)
N1—H1···C12	1.08	2.28	3.2968 (5)	156 (1)
C1—H1A···O4	1.09	2.43	3.2168 (5)	128
O5—H5A···O4	0.99	1.83	2.6853 (4)	143 (1)
O7—H7A···O1	0.99	1.90	2.7056 (4)	137 (1)
O8—H8···O10	0.99	2.19	2.6925 (4)	110 (1)
C9—H9···O6	1.09	2.51	3.5076 (5)	151
O9—H9A···O8	0.99	2.36	2.7582 (4)	103 (1)
O10—H10A···O2	1.00	1.68	2.6350 (4)	160 (1)
O8—H8···O3^iii	0.99	1.93	2.7515 (4)	138
C11—H11···O2^iv	1.09	2.51	3.1485 (5)	116
C5—H5···O4^v	1.08	2.33	3.0356 (5)	121
C16—H16···O5^vi	1.09	2.44	3.2519 (5)	130
O9—H9A···O7^vii	0.99	1.90	2.8160 (4)	153 (1)
C21—H21···O10^vii	1.09	2.34	3.2767 (5)	143
C17—H17···O8^viii	1.09	2.51	3.4592 (5)	145

Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2.

(IAM_SHELX)

Crystal data

C6H5NO2·C6H6O3	Dx = 1.566 Mg m^−3
Mr = 249.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2780 reflections
a = 13.6648 (4) Å	θ = 2.3–52.2°
b = 11.9321 (3) Å	µ = 0.12 mm^−1
c = 12.9678 (4) Å	T = 100 K
V = 2114.40 (10) Å^3	Block, brown
Z = 8	0.35 × 0.29 × 0.24 mm
F(000) = 1040

Data collection

Bruker D8 Venture PHOTON II diffractometer	18901 reflections with > 2.0 σ(I)
ω and phi scan	Rint = 0.051
Absorption correction: analytical SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0673 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8999. The λ/2 correction factor is Not present.	θmax = 52.2°, θmin = 2.3°
Tmin = 0.675, Tmax = 0.750	h = −30→21
101259 measured reflections	k = −26→24
23980 independent reflections	l = −28→28

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.052P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.108	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.60 e Å^−3
23980 reflections	Δρmin = −0.29 e Å^−3
337 parameters	Absolute structure: Flack x determined using 7550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.33 (13)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.68082 (5)	0.64347 (5)	0.54764 (5)	0.01535 (10)
N1	0.68877 (5)	0.35064 (5)	0.37566 (6)	0.01162 (8)
H1	0.686355	0.285033	0.406564	0.014*
C1	0.68307 (5)	0.44402 (6)	0.43316 (6)	0.01072 (9)
H1A	0.676324	0.438433	0.505889	0.013*
O2	0.68742 (5)	0.74545 (5)	0.40301 (6)	0.01741 (11)
N2	0.67966 (5)	−0.14702 (5)	0.62883 (5)	0.01139 (8)
H2	0.679790	−0.212087	0.596891	0.014*
C2	0.68700 (5)	0.54851 (5)	0.38668 (5)	0.01018 (9)
O3	0.68259 (5)	0.14651 (5)	0.45988 (5)	0.01530 (9)
C3	0.69544 (5)	0.55387 (6)	0.27962 (6)	0.01225 (9)
H3	0.697158	0.624623	0.246069	0.015*
O4	0.67779 (5)	0.24879 (5)	0.60445 (5)	0.01592 (9)
C4	0.70134 (6)	0.45578 (6)	0.22175 (6)	0.01330 (10)
H4	0.707518	0.458712	0.148835	0.016*
C5	0.69803 (5)	0.35398 (6)	0.27269 (6)	0.01294 (10)
H5A	0.702336	0.286143	0.234608	0.016*
O5	0.56137 (5)	0.40691 (5)	0.68616 (5)	0.01506 (9)
H5	0.5908 (13)	0.3478 (16)	0.6884 (3)	0.023*
O6	0.58033 (5)	0.28210 (5)	0.86705 (5)	0.01673 (10)
H6	0.5771 (13)	0.2562 (8)	0.9213 (16)	0.025*
C6	0.68414 (5)	0.65411 (6)	0.45048 (6)	0.01154 (9)
C7	0.67999 (5)	−0.05258 (6)	0.57240 (6)	0.01108 (9)
H7A	0.681475	−0.056849	0.499266	0.013*
O7	0.54108 (5)	0.63227 (5)	0.69503 (5)	0.01410 (9)
H7	0.5731 (12)	0.6035 (12)	0.6504 (12)	0.021*
O8	0.57046 (5)	1.13643 (5)	0.28395 (5)	0.01470 (9)
H8	0.5982 (12)	1.1132 (8)	0.3349 (14)	0.022*
C8	0.67815 (5)	0.05133 (6)	0.62076 (5)	0.01010 (9)
C9	0.67580 (5)	0.05490 (6)	0.72827 (6)	0.01197 (9)
H9A	0.672934	0.124988	0.762886	0.014*
O9	0.54934 (5)	1.19671 (5)	0.07977 (5)	0.01553 (9)
H9	0.5312 (13)	1.2341 (10)	0.1306 (13)	0.023*
C10	0.67766 (5)	−0.04442 (6)	0.78492 (6)	0.01265 (10)
H10A	0.677895	−0.042770	0.858163	0.015*
O10	0.58561 (5)	0.91940 (5)	0.33843 (5)	0.01431 (9)
H10	0.6080 (13)	0.8565 (15)	0.34655 (19)	0.021*
C11	0.67915 (5)	−0.14535 (6)	0.73254 (6)	0.01221 (10)
H11	0.679823	−0.213800	0.769956	0.015*
C12	0.67897 (5)	0.15765 (6)	0.55722 (6)	0.01125 (9)
C13	0.56221 (5)	0.45548 (5)	0.78113 (6)	0.01051 (8)
C14	0.57028 (5)	0.39613 (6)	0.87398 (6)	0.01125 (9)
C15	0.56847 (6)	0.45310 (7)	0.96798 (6)	0.01328 (10)
H15	0.574919	0.412630	1.030703	0.016*
C16	0.55723 (6)	0.56921 (7)	0.97011 (6)	0.01410 (10)
H16	0.555671	0.607600	1.034274	0.017*
C17	0.54828 (6)	0.62910 (6)	0.87831 (6)	0.01287 (9)
H17	0.540313	0.708177	0.879637	0.015*
C18	0.55110 (5)	0.57222 (6)	0.78476 (6)	0.01052 (8)
C19	0.56865 (5)	1.05461 (6)	0.21035 (5)	0.01024 (9)
C20	0.55768 (5)	1.08585 (6)	0.10737 (6)	0.01107 (9)
C21	0.55606 (6)	1.00465 (7)	0.02986 (6)	0.01446 (11)
H21	0.548736	1.026000	−0.040289	0.017*
C22	0.56529 (6)	0.89208 (7)	0.05642 (7)	0.01591 (11)
H22	0.565218	0.836771	0.003723	0.019*
C23	0.57464 (6)	0.85923 (6)	0.15926 (6)	0.01364 (10)
H23	0.579661	0.782124	0.176734	0.016*
C24	0.57650 (5)	0.94088 (6)	0.23589 (5)	0.01050 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0241 (3)	0.01132 (19)	0.0106 (2)	−0.00069 (17)	0.00425 (17)	−0.00178 (15)
N1	0.0142 (2)	0.00903 (18)	0.0116 (2)	−0.00026 (15)	0.00022 (16)	−0.00081 (16)
C1	0.0141 (2)	0.0088 (2)	0.0093 (2)	0.00005 (17)	0.00028 (17)	0.00001 (16)
O2	0.0268 (3)	0.00857 (18)	0.0169 (2)	0.00219 (18)	0.0020 (2)	0.00232 (17)
N2	0.0147 (2)	0.00907 (19)	0.0104 (2)	0.00089 (15)	0.00014 (16)	0.00003 (15)
C2	0.0127 (2)	0.0088 (2)	0.0090 (2)	0.00076 (16)	0.00055 (16)	0.00022 (15)
O3	0.0262 (3)	0.01100 (19)	0.00868 (19)	−0.00197 (17)	−0.00171 (17)	0.00046 (14)
C3	0.0155 (2)	0.0115 (2)	0.0098 (2)	−0.00032 (17)	0.00033 (19)	0.00107 (18)
O4	0.0254 (3)	0.00895 (18)	0.0134 (2)	−0.00066 (17)	0.00003 (18)	−0.00244 (16)
C4	0.0160 (2)	0.0149 (3)	0.0090 (2)	−0.0014 (2)	0.00129 (19)	−0.00155 (18)
C5	0.0146 (2)	0.0123 (2)	0.0119 (2)	−0.00104 (18)	0.00137 (19)	−0.00284 (18)
O5	0.0235 (2)	0.01238 (19)	0.00926 (18)	0.00303 (17)	−0.00269 (16)	−0.00188 (15)
O6	0.0257 (3)	0.01043 (18)	0.0140 (2)	−0.00018 (17)	−0.00106 (19)	0.00247 (16)
C6	0.0147 (2)	0.0087 (2)	0.0112 (2)	0.00105 (17)	0.00180 (18)	−0.00041 (16)
C7	0.0149 (2)	0.0095 (2)	0.0088 (2)	−0.00018 (17)	−0.00033 (17)	−0.00063 (16)
O7	0.0211 (2)	0.01177 (18)	0.00942 (18)	0.00354 (17)	0.00307 (16)	0.00203 (14)
O8	0.0246 (2)	0.00936 (17)	0.01017 (18)	0.00046 (16)	−0.00411 (18)	−0.00161 (15)
C8	0.0129 (2)	0.0090 (2)	0.0084 (2)	−0.00027 (16)	−0.00043 (16)	−0.00028 (15)
C9	0.0154 (2)	0.0113 (2)	0.0091 (2)	−0.00031 (18)	0.00018 (17)	−0.00114 (17)
O9	0.0231 (2)	0.01198 (19)	0.01149 (19)	0.00270 (18)	0.00054 (17)	0.00284 (16)
C10	0.0156 (2)	0.0134 (2)	0.0089 (2)	0.00050 (18)	0.00061 (19)	0.00089 (18)
O10	0.0222 (2)	0.01103 (18)	0.00970 (18)	0.00224 (17)	0.00031 (16)	0.00134 (14)
C11	0.0143 (2)	0.0114 (2)	0.0110 (2)	0.00107 (18)	0.00054 (18)	0.00195 (17)
C12	0.0154 (2)	0.0088 (2)	0.0095 (2)	−0.00066 (17)	−0.00140 (18)	−0.00056 (16)
C13	0.0126 (2)	0.0105 (2)	0.00843 (19)	0.00008 (16)	−0.00084 (17)	−0.00004 (17)
C14	0.0131 (2)	0.0110 (2)	0.0096 (2)	−0.00061 (16)	−0.00037 (17)	0.00152 (18)
C15	0.0157 (2)	0.0156 (3)	0.0085 (2)	−0.0008 (2)	0.00000 (18)	0.00107 (19)
C16	0.0172 (3)	0.0162 (3)	0.0090 (2)	−0.0001 (2)	0.00149 (19)	−0.00142 (19)
C17	0.0162 (2)	0.0120 (2)	0.0104 (2)	0.00054 (18)	0.00199 (19)	−0.00148 (18)
C18	0.0127 (2)	0.0103 (2)	0.00860 (18)	0.00042 (16)	0.00097 (17)	0.00027 (17)
C19	0.0125 (2)	0.0095 (2)	0.0087 (2)	0.00006 (16)	−0.00072 (16)	−0.00031 (15)
C20	0.0126 (2)	0.0116 (2)	0.0089 (2)	0.00133 (17)	−0.00060 (16)	0.00054 (17)
C21	0.0174 (3)	0.0169 (3)	0.0091 (2)	0.0040 (2)	−0.00108 (19)	−0.00193 (19)
C22	0.0202 (3)	0.0153 (3)	0.0122 (2)	0.0041 (2)	−0.0023 (2)	−0.0045 (2)
C23	0.0173 (3)	0.0107 (2)	0.0130 (2)	0.00187 (19)	−0.0010 (2)	−0.00283 (18)
C24	0.0127 (2)	0.0094 (2)	0.0094 (2)	0.00024 (17)	−0.00003 (16)	−0.00045 (16)

Geometric parameters (Å, º)

O1—C6	1.2672 (10)	C8—C9	1.3951 (10)
N1—H1	0.8800	C8—C12	1.5128 (10)
N1—C1	1.3429 (9)	C9—H9A	0.9500
N1—C5	1.3419 (10)	C9—C10	1.3945 (10)
C1—H1A	0.9500	O9—H9	0.83 (2)
C1—C2	1.3859 (9)	O9—C20	1.3751 (9)
O2—C6	1.2525 (10)	C10—H10A	0.9500
N2—H2	0.8800	C10—C11	1.3829 (11)
N2—C7	1.3436 (9)	O10—H10	0.818 (18)
N2—C11	1.3450 (10)	O10—C24	1.3599 (9)
C2—C3	1.3946 (10)	C11—H11	0.9500
C2—C6	1.5079 (10)	C13—C14	1.4012 (10)
O3—C12	1.2703 (9)	C13—C18	1.4020 (9)
C3—H3	0.9500	C14—C15	1.3960 (10)
C3—C4	1.3926 (10)	C15—H15	0.9500
O4—C12	1.2481 (9)	C15—C16	1.3942 (11)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.3835 (11)	C16—C17	1.3938 (11)
C5—H5A	0.9500	C17—H17	0.9500
O5—H5	0.812 (18)	C17—C18	1.3906 (10)
O5—C13	1.3611 (9)	C19—C20	1.3945 (10)
O6—H6	0.77 (2)	C19—C24	1.4010 (9)
O6—C14	1.3704 (9)	C20—C21	1.3962 (10)
C7—H7A	0.9500	C21—H21	0.9500
C7—C8	1.3897 (10)	C21—C22	1.3924 (12)
O7—H7	0.80 (2)	C22—H22	0.9500
O7—C18	1.3733 (9)	C22—C23	1.3960 (12)
O8—H8	0.81 (2)	C23—H23	0.9500
O8—C19	1.3655 (9)	C23—C24	1.3918 (10)
C1—N1—H1	118.9	N2—C11—C10	120.27 (7)
C5—N1—H1	118.9	N2—C11—H11	119.9
C5—N1—C1	122.23 (6)	C10—C11—H11	119.9
N1—C1—H1A	119.9	O3—C12—C8	116.99 (6)
N1—C1—C2	120.18 (7)	O4—C12—O3	125.40 (7)
C2—C1—H1A	119.9	O4—C12—C8	117.60 (7)
C7—N2—H2	118.9	O5—C13—C14	124.26 (6)
C7—N2—C11	122.16 (7)	O5—C13—C18	116.90 (6)
C11—N2—H2	118.9	C14—C13—C18	118.80 (6)
C1—C2—C3	118.52 (6)	O6—C14—C13	116.96 (6)
C1—C2—C6	120.81 (6)	O6—C14—C15	122.85 (7)
C3—C2—C6	120.66 (6)	C15—C14—C13	120.19 (6)
C2—C3—H3	119.9	C14—C15—H15	119.9
C4—C3—C2	120.17 (6)	C16—C15—C14	120.21 (7)
C4—C3—H3	119.9	C16—C15—H15	119.9
C3—C4—H4	120.7	C15—C16—H16	119.9
C5—C4—C3	118.61 (7)	C17—C16—C15	120.14 (7)
C5—C4—H4	120.7	C17—C16—H16	119.9
N1—C5—C4	120.29 (7)	C16—C17—H17	120.2
N1—C5—H5A	119.9	C18—C17—C16	119.50 (7)
C4—C5—H5A	119.9	C18—C17—H17	120.2
C13—O5—H5	109.5	O7—C18—C13	120.05 (6)
C14—O6—H6	109.5	O7—C18—C17	118.80 (6)
O1—C6—C2	117.56 (6)	C17—C18—C13	121.15 (6)
O2—C6—O1	125.25 (7)	O8—C19—C20	118.70 (6)
O2—C6—C2	117.17 (7)	O8—C19—C24	121.73 (6)
N2—C7—H7A	119.9	C20—C19—C24	119.57 (6)
N2—C7—C8	120.16 (7)	O9—C20—C19	121.02 (6)
C8—C7—H7A	119.9	O9—C20—C21	118.61 (7)
C18—O7—H7	109.5	C19—C20—C21	120.37 (7)
C19—O8—H8	109.5	C20—C21—H21	120.3
C7—C8—C9	118.59 (6)	C22—C21—C20	119.34 (7)
C7—C8—C12	120.15 (6)	C22—C21—H21	120.3
C9—C8—C12	121.26 (6)	C21—C22—H22	119.5
C8—C9—H9A	120.0	C21—C22—C23	121.03 (7)
C10—C9—C8	120.00 (7)	C23—C22—H22	119.5
C10—C9—H9A	120.0	C22—C23—H23	120.4
C20—O9—H9	109.5	C24—C23—C22	119.15 (7)
C9—C10—H10A	120.6	C24—C23—H23	120.4
C11—C10—C9	118.79 (7)	O10—C24—C19	114.88 (6)
C11—C10—H10A	120.6	O10—C24—C23	124.59 (7)
C24—O10—H10	109.5	C23—C24—C19	120.53 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.88	1.79	2.6706 (9)	175
N1—H1···O4	0.88	2.60	3.2095 (10)	126
C1—H1A···O4	0.95	2.60	3.2196 (10)	123
N2—H2···O1^i	0.88	1.84	2.7127 (9)	172
N2—H2···O2^i	0.88	2.57	3.1989 (10)	129
C5—H5A···O4^ii	0.95	2.39	3.0356 (10)	124
C5—H5A···O8^i	0.95	2.62	3.1303 (9)	114
O5—H5···O4	0.81	2.00	2.6859 (9)	142
O6—H6···O9^iii	0.77	2.21	2.9710 (9)	171
C7—H7A···O10^i	0.95	2.48	3.3137 (10)	146
O7—H7···O1	0.80	2.04	2.7050 (9)	139
O8—H8···O3^iv	0.81	2.03	2.7508 (9)	148
O9—H9···O7^v	0.83	2.05	2.8152 (9)	151
O10—H10···O2	0.82	1.86	2.6353 (9)	157
C11—H11···O2^vi	0.95	2.55	3.1478 (10)	121
C21—H21···O10^v	0.95	2.50	3.2760 (10)	138

Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y, z−1/2; (iii) x, y−1, z+1; (iv) x, y+1, z; (v) −x+1, −y+2, z−1/2; (vi) −x+3/2, y−1, z+1/2.

(theoretical)

Crystal data

C24H22N2O10	c = 12.9678 (4) Å
Mr = 498.42	V = 2114.40 (10) Å^3
Orthorhombic, Pca21	Z = 4
Hall symbol: P ?	F(000) = 1040
a = 13.6648 (4) Å	Dx = 1.566 Mg m^−3
b = 11.9321 (3) Å	Mo Kα radiation, λ = 0.71073 Å

Data collection

Radiation source: fine-focus sealed tube	h = 0→30
24319 independent reflections	k = 0→26
24319 reflections with > 2.0σ(I)	l = −28→28
θmax = 52.2°, θmin = 1.7°

Refinement

Refinement on F	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.005	H-atom parameters constrained
wR(F^2) = 0.005	Weighting scheme based on measured s.u.'s
S = 0.09	(Δ/σ)max = −0.193
24319 reflections	Δρmax = 0.15 e Å^−3
707 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Absolute structure: Rogers (1981), 11836 Friedel pairs
Primary atom site location: structure-invariant direct methods	Rogers parameter: 1

Special details

Refinement. Refinement of F¹ against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O1	0.68089	0.64338	0.59216	0
N1	0.68879	0.35067	0.42022	0
H1	0.68542	0.26970	0.45767	0
C1	0.68310	0.44394	0.47777	0
H1A	0.67264	0.43149	0.55994	0
O2	0.68751	0.74535	0.44775	0
N2	0.67968	−0.14699	0.67341	0
H2	0.68142	−0.22544	0.63292	0
C2	0.68699	0.54859	0.43124	0
O3	0.68262	0.14656	0.50446	0
C3	0.69545	0.55391	0.32407	0
H3	0.69961	0.63472	0.28540	0
O4	0.67793	0.24873	0.64886	0
C4	0.70137	0.45578	0.26628	0
H4	0.71005	0.46010	0.18309	0
C5	0.69796	0.35402	0.31714	0
H5	0.70276	0.27447	0.27700	0
O5	0.56142	0.40687	0.73084	0
H5A	0.59770	0.33497	0.72808	0
O6	0.58031	0.28227	0.91177	0
H6	0.57567	0.25490	0.98322	0
C6	0.68413	0.65409	0.49492	0
C7	0.68004	−0.05258	0.61693	0
H7	0.68028	−0.06381	0.53381	0
O7	0.54118	0.63227	0.73962	0
H7A	0.57965	0.59878	0.68262	0
O8	0.57046	1.13640	0.32854	0
H8	0.59802	1.10558	0.39316	0
C8	0.67825	0.05126	0.66529	0
C9	0.67576	0.05491	0.77276	0
H9	0.67291	0.13636	0.81048	0
O9	0.54934	1.19663	0.12436	0
H9A	0.52812	1.24270	0.18345	0
C10	0.67775	−0.04442	0.82949	0
H10	0.67840	−0.04237	0.91312	0
O10	0.58559	0.91926	0.38292	0
H10A	0.61285	0.84288	0.39514	0
C11	0.67917	−0.14552	0.77705	0
H11	0.68115	−0.22717	0.81377	0
C12	0.67900	0.15754	0.60179	0
C13	0.56219	0.45555	0.82561	0
C14	0.57020	0.39610	0.91852	0
C15	0.56854	0.45320	1.01247	0
H15	0.57417	0.40514	1.08339	0
C16	0.55733	0.56933	1.01458	0
H16	0.55363	0.61002	1.08941	0
C17	0.54836	0.62918	0.92287	0
H17	0.53691	0.71936	0.92107	0
C18	0.55110	0.57225	0.82929	0
C19	0.56857	1.05467	0.25473	0
C20	0.55770	1.08588	0.15179	0
C21	0.55608	1.00477	0.07452	0
H21	0.54382	1.03094	−0.00484	0
C22	0.56524	0.89209	0.10087	0
H22	0.56226	0.82760	0.04160	0
C23	0.57463	0.85923	0.20385	0
H23	0.58124	0.77089	0.22372	0
C24	0.57652	0.94092	0.28045	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0	0	0	0	0	0
N1	0	0	0	0	0	0
H1	0	0	0	0	0	0
C1	0	0	0	0	0	0
H1A	0	0	0	0	0	0
O2	0	0	0	0	0	0
N2	0	0	0	0	0	0
H2	0	0	0	0	0	0
C2	0	0	0	0	0	0
O3	0	0	0	0	0	0
C3	0	0	0	0	0	0
H3	0	0	0	0	0	0
O4	0	0	0	0	0	0
C4	0	0	0	0	0	0
H4	0	0	0	0	0	0
C5	0	0	0	0	0	0
H5	0	0	0	0	0	0
O5	0	0	0	0	0	0
H5A	0	0	0	0	0	0
O6	0	0	0	0	0	0
H6	0	0	0	0	0	0
C6	0	0	0	0	0	0
C7	0	0	0	0	0	0
H7	0	0	0	0	0	0
O7	0	0	0	0	0	0
H7A	0	0	0	0	0	0
O8	0	0	0	0	0	0
H8	0	0	0	0	0	0
C8	0	0	0	0	0	0
C9	0	0	0	0	0	0
H9	0	0	0	0	0	0
O9	0	0	0	0	0	0
H9A	0	0	0	0	0	0
C10	0	0	0	0	0	0
H10	0	0	0	0	0	0
O10	0	0	0	0	0	0
H10A	0	0	0	0	0	0
C11	0	0	0	0	0	0
H11	0	0	0	0	0	0
C12	0	0	0	0	0	0
C13	0	0	0	0	0	0
C14	0	0	0	0	0	0
C15	0	0	0	0	0	0
H15	0	0	0	0	0	0
C16	0	0	0	0	0	0
H16	0	0	0	0	0	0
C17	0	0	0	0	0	0
H17	0	0	0	0	0	0
C18	0	0	0	0	0	0
C19	0	0	0	0	0	0
C20	0	0	0	0	0	0
C21	0	0	0	0	0	0
H21	0	0	0	0	0	0
C22	0	0	0	0	0	0
H22	0	0	0	0	0	0
C23	0	0	0	0	0	0
H23	0	0	0	0	0	0
C24	0	0	0	0	0	0

Geometric parameters (Å, º)

O1—C6	1.2682	C8—C12	1.5120
N1—C1	1.3421	C8—C9	1.3948
N1—C5	1.3432	C9—C10	1.3953
N1—H1	1.0824	C9—H9	1.0887
C1—C2	1.3879	O9—C20	1.3733
C1—H1A	1.0854	O9—H9A	0.9866
O2—C6	1.2498	C10—C11	1.3848
N2—C7	1.3436	C10—H10	1.0848
N2—C11	1.3441	O10—C24	1.3593
N2—H2	1.0736	O10—H10A	0.9973
C2—C6	1.5061	C11—H11	1.0848
C2—C3	1.3960	C13—C18	1.4015
O3—C12	1.2700	C13—C14	1.4025
C3—C4	1.3926	C14—C15	1.3960
C3—H3	1.0883	C15—C16	1.3944
O4—C12	1.2478	C15—H15	1.0866
C4—C5	1.3826	C16—C17	1.3926
C4—H4	1.0865	C16—H16	1.0862
C5—H5	1.0845	C17—C18	1.3913
O5—C13	1.3594	C17—H17	1.0876
O5—H5A	0.9914	C19—C20	1.3938
O6—C14	1.3681	C19—C24	1.4020
O6—H6	0.9845	C20—C21	1.3933
C7—C8	1.3890	C21—C22	1.3928
C7—H7	1.0862	C21—H21	1.0885
O7—C18	1.3724	C22—C23	1.3977
O7—H7A	0.9912	C22—H22	1.0884
O8—C19	1.3666	C23—C24	1.3920
O8—H8	0.9896	C23—H23	1.0889
C1—N1—C5	122.279	N2—C11—C10	120.159
C1—N1—H1	119.229	N2—C11—H11	115.280
C5—N1—H1	118.490	C10—C11—H11	124.553
N1—C1—C2	120.140	O4—C12—O3	125.211
N1—C1—H1A	116.106	O4—C12—C8	117.703
C2—C1—H1A	123.709	O3—C12—C8	117.071
C7—N2—C11	122.285	O5—C13—C18	117.040
C7—N2—H2	117.668	O5—C13—C14	124.133
C11—N2—H2	120.033	C18—C13—C14	118.795
C6—C2—C1	120.840	O6—C14—C13	117.070
C6—C2—C3	120.668	O6—C14—C15	122.822
C1—C2—C3	118.482	C13—C14—C15	120.106
C2—C3—C4	120.154	C14—C15—C16	120.260
C2—C3—H3	120.219	C14—C15—H15	118.681
C4—C3—H3	119.603	C16—C15—H15	121.039
C5—C4—C3	118.668	C17—C16—C15	120.167
C5—C4—H4	121.270	C17—C16—H16	121.976
C3—C4—H4	120.049	C15—C16—H16	117.829
N1—C5—C4	120.269	C18—C17—C16	119.480
N1—C5—H5	117.213	C18—C17—H17	117.921
C4—C5—H5	122.518	C16—C17—H17	122.571
C13—O5—H5A	113.485	O7—C18—C13	120.017
C14—O6—H6	105.222	O7—C18—C17	118.791
O2—C6—O1	125.152	C13—C18—C17	121.184
O2—C6—C2	117.313	O8—C19—C20	118.825
O1—C6—C2	117.512	O8—C19—C24	121.519
N2—C7—C8	120.115	C20—C19—C24	119.655
N2—C7—H7	115.947	O9—C20—C19	120.932
C8—C7—H7	123.926	O9—C20—C21	118.743
C18—O7—H7A	111.661	C19—C20—C21	120.322
C19—O8—H8	109.579	C20—C21—C22	119.517
C12—C8—C7	120.145	C20—C21—H21	118.887
C12—C8—C9	121.208	C22—C21—H21	121.517
C7—C8—C9	118.646	C21—C22—C23	120.897
C8—C9—C10	119.985	C21—C22—H22	120.389
C8—C9—H9	118.533	C23—C22—H22	118.669
C10—C9—H9	121.479	C24—C23—C22	119.147
C20—O9—H9A	111.064	C24—C23—H23	120.493
C11—C10—C9	118.775	C22—C23—H23	120.356
C11—C10—H10	120.691	O10—C24—C19	115.066
C9—C10—H10	120.533	O10—C24—C23	124.485
C24—O10—H10A	111.293	C19—C24—C23	120.448
O1—C6—C2—C1	1.97	O7—C18—C13—C14	−178.74
O1—C6—C2—C3	−176.83	O7—C18—C17—C16	179.36
N1—C1—C2—C6	−177.93	O7—C18—C17—H17	1.23
N1—C1—C2—C3	0.90	H7A—O7—C18—C13	−33.88
N1—C5—C4—C3	0.21	H7A—O7—C18—C17	147.10
N1—C5—C4—H4	178.91	O8—C19—C20—O9	0.23
H1—N1—C1—C2	−179.81	O8—C19—C20—C21	179.61
H1—N1—C1—H1A	−2.14	O8—C19—C24—O10	0.30
H1—N1—C5—C4	179.24	O8—C19—C24—C23	−179.85
H1—N1—C5—H5	−1.02	H8—O8—C19—C20	−162.99
C1—N1—C5—C4	−0.34	H8—O8—C19—C24	17.52
C1—N1—C5—H5	179.40	C8—C7—N2—C11	−1.08
C1—C2—C6—O2	−179.71	C8—C9—C10—C11	−1.95
C1—C2—C3—C4	−1.01	C8—C9—C10—H10	177.85
C1—C2—C3—H3	−179.22	C9—C10—C11—H11	179.65
H1A—C1—N1—C5	177.43	H9—C9—C8—C12	1.19
H1A—C1—C2—C6	4.59	H9—C9—C10—C11	178.59
H1A—C1—C2—C3	−176.58	H9—C9—C10—H10	−1.61
O2—C6—C2—C3	1.49	O9—C20—C19—C24	179.73
N2—C7—C8—C12	179.79	O9—C20—C21—C22	179.49
N2—C7—C8—C9	−0.20	O9—C20—C21—H21	−3.67
N2—C11—C10—C9	0.70	H9A—O9—C20—C19	−20.77
N2—C11—C10—H10	−179.10	H9A—O9—C20—C21	159.85
H2—N2—C7—C8	−179.75	C10—C9—C8—C12	−178.29
H2—N2—C7—H7	1.45	H10—C10—C11—H11	−0.14
H2—N2—C11—C10	179.47	O10—C24—C19—C20	−179.19
H2—N2—C11—H11	0.42	O10—C24—C23—C22	−179.82
C2—C1—N1—C5	−0.23	O10—C24—C23—H23	−0.53
C2—C3—C4—C5	0.47	H10A—O10—C24—C19	−160.94
C2—C3—C4—H4	−178.25	H10A—O10—C24—C23	19.21
O3—C12—C8—C7	−0.90	C13—C18—C17—C16	0.35
O3—C12—C8—C9	179.09	C13—C18—C17—H17	−177.78
C3—C4—C5—H5	−179.50	C13—C14—C15—C16	1.04
H3—C3—C2—C6	−0.39	C13—C14—C15—H15	179.43
H3—C3—C4—C5	178.69	C14—C13—C18—C17	0.26
H3—C3—C4—H4	−0.03	C14—C15—C16—C17	−0.42
O4—C12—C8—C7	−179.57	C14—C15—C16—H16	177.70
O4—C12—C8—C9	0.43	C15—C14—C13—C18	−0.95
C4—C3—C2—C6	177.82	C15—C16—C17—C18	−0.28
H4—C4—C5—H5	−0.81	C15—C16—C17—H17	177.77
O5—C13—C18—O7	−0.72	H15—C15—C16—C17	−178.76
O5—C13—C18—C17	178.28	H15—C15—C16—H16	−0.65
O5—C13—C14—O6	1.73	H16—C16—C17—C18	−178.31
O5—C13—C14—C15	−178.82	H16—C16—C17—H17	−0.27
H5A—O5—C13—C18	153.93	C19—C20—C21—C22	0.11
H5A—O5—C13—C14	−28.17	C19—C20—C21—H21	176.95
O6—C14—C13—C18	179.60	C19—C24—C23—C22	0.34
O6—C14—C15—C16	−179.54	C19—C24—C23—H23	179.63
O6—C14—C15—H15	−1.16	C20—C19—C24—C23	0.67
H6—O6—C14—C13	−172.49	C20—C21—C22—C23	0.92
H6—O6—C14—C15	8.08	C20—C21—C22—H22	178.44
C7—N2—C11—C10	0.83	C21—C20—C19—C24	−0.90
C7—N2—C11—H11	−178.22	C21—C22—C23—C24	−1.15
C7—C8—C9—C10	1.70	C21—C22—C23—H23	179.57
C7—C8—C9—H9	−178.82	H21—C21—C22—C23	−175.83
H7—C7—N2—C11	−179.88	H21—C21—C22—H22	1.68
H7—C7—C8—C12	−1.51	H22—C22—C23—C24	−178.70
H7—C7—C8—C9	178.49	H22—C22—C23—H23	2.01

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	1.07	1.65	2.7142	169
N2—H2···O2^i	1.07	2.43	3.1977	128
N2—H2···C6^i	1.07	2.30	3.3158	158
C5—H5···O8^i	1.09	2.54	3.1305	114
C7—H7···O2^i	1.09	2.54	3.2615	123
C7—H7···O10^i	1.09	2.36	3.3148	147
O6—H6···O9^ii	0.98	1.99	2.9704	173
C15—H15···O9^ii	1.09	2.57	3.3980	133
N1—H1···O3	1.08	1.59	2.6705	176
N1—H1···O4	1.08	2.49	3.2082	123
N1—H1···C12	1.08	2.30	3.2974	152
C1—H1A···O4	1.09	2.47	3.2177	125
O5—H5A···O4	0.99	1.82	2.6880	144
O7—H7A···O1	0.99	1.89	2.7054	138
O8—H8···O10	0.99	2.23	2.6931	107
C9—H9···O6	1.09	2.52	3.5085	150
O9—H9A···O8	0.99	2.34	2.7587	105
O10—H10A···O2	1.00	1.69	2.6368	157
O8—H8···O3^iii	0.99	1.91	2.7510	141
C11—H11···O2^iv	1.09	2.52	3.1487	116
C5—H5···O4^v	1.09	2.35	3.0359	120
C15—H15···O7^vi	1.09	2.61	3.4590	135
C16—H16···O5^vi	1.09	2.42	3.2525	132
O9—H9A···O7^vii	0.99	1.91	2.8164	151
C21—H21···O10^vii	1.09	2.37	3.2776	140
C17—H17···O8^viii	1.09	2.56	3.4578	139

Symmetry codes: (i) x, y−1, z; (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+3/2, y−1, z+1/2; (v) −x+3/2, y, z−1/2; (vi) −x+1, −y+1, z+1/2; (vii) −x+1, −y+2, z−1/2; (viii) −x+1, −y+2, z+1/2.