4,6-Dibenzoyl­isophthalic acid N,N-dimethyl­formamide disolvate

In the title compound, C₂₂H₁₄O₆·2C₃H₇NO, 4,6-dibenzoyl­isophthalic acid is linked to two N,N-dimethyl­formamide solvent mol­ecules via O—H...O hydrogen bonds. An intra­molecular three-centred C—H...O hydrogen bond is favoured by the syn conformation of both carboxyl groups.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.079
• wR factor = 0.193
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.701
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.08
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.70 e/A   
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C28
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C14    ..  O2      ..      99.00 Deg.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H14 O6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H7 N O

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.084
            Tmax scaled      0.991 Tmin scaled      0.901

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

4,6-Dibenzoylisophthalic acid N,N-dimethylformamide disolvate

Crystal data

C22H14O6·2C3H7NO	Z = 2
Mr = 520.52	F(000) = 548
Triclinic, P1	Dx = 1.281 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.998 (2) Å	Cell parameters from 25 reflections
b = 10.940 (2) Å	θ = 10–13°
c = 12.577 (3) Å	µ = 0.10 mm^−1
α = 98.06 (3)°	T = 298 K
β = 97.67 (3)°	Block, colorless
γ = 90.72 (3)°	0.20 × 0.20 × 0.10 mm
V = 1349.2 (5) Å^3

Data collection

Nonius CAD-4 diffractometer	2837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.831, Tmax = 0.913	l = 0→15
5284 measured reflections	3 standard reflections every 200 reflections
5284 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.05P)^2 + P] where P = (Fo^2 + 2Fc^2)/3
5284 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.70 e Å^−3
38 restraints	Δρmin = −0.51 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	−0.0028 (3)	0.6326 (3)	0.0940 (2)	0.1004 (8)
O2	−0.0869 (3)	0.6403 (3)	0.4872 (2)	0.1189 (11)
H2B	−0.0619	0.7069	0.5233	0.178*
O3	−0.0231 (3)	0.7296 (3)	0.3533 (2)	0.1088 (9)
O4	−0.2207 (3)	0.1419 (3)	0.0462 (3)	0.1149 (10)
O5	−0.4138 (3)	0.3066 (3)	0.3935 (3)	0.1146 (10)
H5B	−0.4683	0.2564	0.4072	0.172*
O6	−0.4067 (3)	0.1642 (3)	0.2499 (2)	0.1130 (10)
C1	0.3394 (5)	0.5076 (5)	0.3540 (4)	0.1152 (15)
H1A	0.3632	0.4621	0.4104	0.138*
C2	0.2065 (4)	0.5087 (4)	0.3073 (4)	0.0990 (12)
H2A	0.1413	0.4626	0.3319	0.119*
C3	0.1687 (4)	0.5775 (4)	0.2245 (3)	0.0818 (10)
C4	0.2674 (4)	0.6446 (4)	0.1898 (3)	0.0977 (12)
H4A	0.2447	0.6927	0.1351	0.117*
C5	0.4002 (5)	0.6409 (5)	0.2360 (4)	0.1161 (15)
H5A	0.4662	0.6855	0.2109	0.139*
C6	0.4360 (5)	0.5738 (5)	0.3167 (4)	0.1185 (16)
H6A	0.5259	0.5726	0.3470	0.142*
C7	0.0277 (4)	0.5796 (4)	0.1721 (3)	0.0825 (10)
C8	−0.0716 (4)	0.6433 (4)	0.3855 (3)	0.0866 (10)
C9	−0.1214 (4)	0.5275 (3)	0.3122 (3)	0.0793 (9)
C10	−0.0800 (4)	0.5037 (3)	0.2094 (3)	0.0790 (9)
C11	−0.1370 (4)	0.4034 (3)	0.1377 (3)	0.0825 (10)
H11A	−0.1092	0.3871	0.0696	0.099*
C12	−0.2342 (4)	0.3268 (3)	0.1647 (3)	0.0806 (10)
C13	−0.2718 (4)	0.3486 (3)	0.2686 (3)	0.0802 (10)
C14	−0.2149 (4)	0.4493 (4)	0.3404 (3)	0.0840 (10)
H14A	−0.2406	0.4642	0.4094	0.101*
C15	−0.3715 (4)	0.2662 (4)	0.3040 (4)	0.0921 (11)
C16	−0.2932 (4)	0.2240 (4)	0.0773 (3)	0.0872 (11)
C17	−0.4334 (4)	0.2318 (3)	0.0230 (3)	0.0816 (10)
C18	−0.4880 (4)	0.1347 (4)	−0.0539 (3)	0.0923 (11)
H18A	−0.4371	0.0654	−0.0694	0.111*
C19	−0.6162 (5)	0.1394 (4)	−0.1075 (4)	0.1034 (13)
H19A	−0.6520	0.0736	−0.1588	0.124*
C20	−0.6913 (5)	0.2413 (5)	−0.0851 (4)	0.1094 (14)
H20A	−0.7782	0.2446	−0.1216	0.131*
C21	−0.6390 (5)	0.3387 (4)	−0.0089 (4)	0.1072 (13)
H21A	−0.6907	0.4074	0.0064	0.129*
C22	−0.5102 (4)	0.3342 (4)	0.0447 (3)	0.0933 (11)
H22A	−0.4746	0.4004	0.0957	0.112*
O7	−0.5870 (5)	0.1744 (5)	0.4634 (4)	0.1913 (19)
N1	−0.6951 (4)	0.0120 (4)	0.4678 (4)	0.1186 (12)
C23	−0.7437 (7)	−0.1077 (6)	0.4190 (6)	0.184 (3)
H23A	−0.7108	−0.1277	0.3506	0.276*
H23B	−0.8406	−0.1098	0.4078	0.276*
H23C	−0.7125	−0.1669	0.4656	0.276*
C24	−0.7392 (7)	0.0539 (7)	0.5713 (6)	0.186 (3)
H24A	−0.7957	−0.0091	0.5900	0.279*
H24B	−0.7892	0.1277	0.5666	0.279*
H24C	−0.6619	0.0709	0.6258	0.279*
C25	−0.6127 (6)	0.0664 (6)	0.4023 (7)	0.170 (2)
H25A	−0.5852	0.0352	0.3362	0.204*
O8	−0.0181 (4)	0.8357 (4)	0.6261 (3)	0.1390 (13)
N2	−0.0786 (4)	0.9113 (4)	0.7870 (3)	0.1117 (12)
C26	−0.0797 (6)	0.8284 (6)	0.6983 (5)	0.1319 (18)
H26A	−0.1346	0.7580	0.6931	0.158*
C27	0.0006 (7)	1.0214 (6)	0.8093 (5)	0.168 (3)
H27A	0.0443	1.0318	0.7475	0.252*
H27B	0.0676	1.0174	0.8709	0.252*
H27C	−0.0560	1.0900	0.8247	0.252*
C28	−0.1515 (7)	0.8783 (7)	0.8704 (5)	0.186 (3)
H28A	−0.2012	0.8018	0.8447	0.279*
H28B	−0.2130	0.9420	0.8889	0.279*
H28C	−0.0890	0.8688	0.9334	0.279*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.100 (2)	0.115 (2)	0.0916 (19)	−0.0014 (16)	0.0153 (15)	0.0313 (17)
O2	0.163 (3)	0.106 (2)	0.0844 (19)	−0.018 (2)	0.0224 (19)	−0.0006 (16)
O3	0.126 (2)	0.093 (2)	0.107 (2)	−0.0197 (18)	0.0366 (18)	−0.0020 (16)
O4	0.106 (2)	0.098 (2)	0.129 (3)	0.0136 (18)	0.0014 (19)	−0.0107 (18)
O5	0.121 (2)	0.111 (2)	0.118 (2)	−0.0206 (18)	0.043 (2)	0.0155 (19)
O6	0.136 (3)	0.097 (2)	0.105 (2)	−0.0265 (19)	0.0202 (19)	0.0129 (17)
C1	0.095 (3)	0.137 (4)	0.118 (4)	0.017 (3)	0.013 (3)	0.031 (3)
C2	0.085 (3)	0.106 (3)	0.110 (3)	0.002 (2)	0.016 (2)	0.025 (3)
C3	0.079 (2)	0.085 (2)	0.080 (2)	0.0008 (19)	0.014 (2)	0.0066 (19)
C4	0.095 (3)	0.112 (3)	0.089 (3)	−0.009 (2)	0.018 (2)	0.019 (2)
C5	0.091 (3)	0.143 (4)	0.117 (4)	−0.017 (3)	0.020 (3)	0.023 (3)
C6	0.086 (3)	0.155 (5)	0.113 (4)	0.007 (3)	0.009 (3)	0.017 (3)
C7	0.091 (3)	0.080 (2)	0.076 (2)	0.001 (2)	0.014 (2)	0.0083 (19)
C8	0.087 (3)	0.089 (3)	0.083 (3)	0.000 (2)	0.016 (2)	0.008 (2)
C9	0.077 (2)	0.080 (2)	0.081 (2)	0.0005 (19)	0.0109 (19)	0.0102 (19)
C10	0.078 (2)	0.082 (2)	0.077 (2)	0.0004 (19)	0.0088 (19)	0.0133 (19)
C11	0.085 (2)	0.086 (2)	0.076 (2)	0.001 (2)	0.0092 (19)	0.0100 (19)
C12	0.082 (2)	0.078 (2)	0.081 (2)	0.0014 (19)	0.0071 (19)	0.0116 (19)
C13	0.077 (2)	0.080 (2)	0.084 (2)	−0.0043 (19)	0.0097 (19)	0.016 (2)
C14	0.084 (2)	0.088 (3)	0.081 (2)	0.002 (2)	0.014 (2)	0.013 (2)
C15	0.088 (3)	0.100 (3)	0.090 (3)	−0.003 (2)	0.008 (2)	0.026 (2)
C16	0.092 (3)	0.079 (3)	0.089 (3)	−0.002 (2)	0.010 (2)	0.010 (2)
C17	0.086 (3)	0.078 (2)	0.081 (2)	−0.005 (2)	0.009 (2)	0.0124 (19)
C18	0.094 (3)	0.084 (3)	0.096 (3)	−0.005 (2)	0.006 (2)	0.010 (2)
C19	0.101 (3)	0.097 (3)	0.106 (3)	−0.013 (3)	−0.001 (3)	0.006 (2)
C20	0.084 (3)	0.111 (4)	0.130 (4)	−0.008 (3)	−0.001 (3)	0.022 (3)
C21	0.094 (3)	0.099 (3)	0.127 (4)	0.006 (3)	0.013 (3)	0.013 (3)
C22	0.092 (3)	0.087 (3)	0.098 (3)	−0.001 (2)	0.009 (2)	0.007 (2)
O7	0.177 (4)	0.218 (4)	0.192 (4)	−0.016 (4)	0.054 (3)	0.049 (4)
N1	0.103 (3)	0.111 (3)	0.136 (3)	0.005 (2)	−0.006 (2)	0.020 (3)
C23	0.185 (6)	0.141 (4)	0.212 (6)	−0.042 (4)	−0.029 (5)	0.036 (4)
C24	0.181 (6)	0.192 (6)	0.197 (6)	0.042 (5)	0.042 (5)	0.052 (5)
C25	0.121 (4)	0.116 (4)	0.266 (6)	−0.040 (3)	−0.044 (4)	0.076 (4)
O8	0.161 (3)	0.143 (3)	0.104 (3)	−0.003 (3)	0.019 (2)	−0.010 (2)
N2	0.121 (3)	0.120 (3)	0.088 (3)	0.009 (2)	0.010 (2)	−0.001 (2)
C26	0.146 (5)	0.141 (5)	0.107 (4)	0.012 (4)	0.009 (4)	0.021 (4)
C27	0.199 (7)	0.125 (5)	0.161 (6)	−0.035 (5)	−0.038 (5)	0.022 (4)
C28	0.208 (7)	0.208 (7)	0.147 (6)	−0.020 (6)	0.065 (5)	0.005 (5)

Geometric parameters (Å, º)

O1—C7	1.216 (4)	C17—C22	1.382 (5)
O2—C8	1.313 (5)	C17—C18	1.385 (5)
O2—H2B	0.8200	C18—C19	1.372 (6)
O3—C8	1.199 (4)	C18—H18A	0.9300
O4—C16	1.216 (4)	C19—C20	1.369 (6)
O5—C15	1.279 (5)	C19—H19A	0.9300
O5—H5B	0.8200	C20—C21	1.376 (6)
O6—C15	1.243 (5)	C20—H20A	0.9300
C1—C6	1.370 (6)	C21—C22	1.376 (6)
C1—C2	1.380 (6)	C21—H21A	0.9300
C1—H1A	0.9300	C22—H22A	0.9300
C2—C3	1.384 (5)	C25—O7	1.319 (8)
C2—H2A	0.9300	C25—N1	1.421 (8)
C3—C4	1.376 (5)	C25—H25A	0.9300
C3—C7	1.476 (5)	N1—C23	1.417 (7)
C4—C5	1.379 (6)	N1—C24	1.445 (7)
C4—H4A	0.9300	C23—H23A	0.9600
C5—C6	1.347 (6)	C23—H23B	0.9600
C5—H5A	0.9300	C23—H23C	0.9600
C6—H6A	0.9300	C24—H24A	0.9600
C7—C10	1.513 (5)	C24—H24B	0.9600
C8—C9	1.495 (5)	C24—H24C	0.9600
C9—C14	1.374 (5)	O8—C26	1.174 (6)
C9—C10	1.400 (5)	N2—C26	1.335 (6)
C10—C11	1.382 (5)	N2—C27	1.406 (6)
C11—C12	1.382 (5)	N2—C28	1.438 (7)
C11—H11A	0.9300	C27—H27A	0.9600
C12—C13	1.396 (5)	C27—H27B	0.9600
C12—C16	1.512 (5)	C27—H27C	0.9600
C13—C14	1.386 (5)	C26—H26A	0.9300
C13—C15	1.488 (5)	C28—H28A	0.9600
C14—H14A	0.9300	C28—H28B	0.9600
C16—C17	1.484 (5)	C28—H28C	0.9600
C8—O2—H2B	109.5	C18—C17—C16	119.0 (4)
C15—O5—H5B	109.5	C19—C18—C17	120.7 (4)
C6—C1—C2	119.6 (5)	C19—C18—H18A	119.6
C6—C1—H1A	120.2	C17—C18—H18A	119.6
C2—C1—H1A	120.2	C20—C19—C18	119.8 (4)
C1—C2—C3	121.1 (4)	C20—C19—H19A	120.1
C1—C2—H2A	119.5	C18—C19—H19A	120.1
C3—C2—H2A	119.5	C19—C20—C21	120.3 (4)
C4—C3—C2	118.1 (4)	C19—C20—H20A	119.8
C4—C3—C7	119.5 (4)	C21—C20—H20A	119.8
C2—C3—C7	122.4 (4)	C20—C21—C22	119.9 (4)
C3—C4—C5	120.2 (4)	C20—C21—H21A	120.0
C3—C4—H4A	119.9	C22—C21—H21A	120.0
C5—C4—H4A	119.9	C21—C22—C17	120.3 (4)
C6—C5—C4	121.3 (5)	C21—C22—H22A	119.8
C6—C5—H5A	119.3	C17—C22—H22A	119.8
C4—C5—H5A	119.3	O7—C25—N1	98.7 (7)
C5—C6—C1	119.8 (5)	O7—C25—H25A	130.7
C5—C6—H6A	120.1	N1—C25—H25A	130.7
C1—C6—H6A	120.1	C23—N1—C25	111.6 (6)
O1—C7—C3	121.8 (4)	C23—N1—C24	115.0 (6)
O1—C7—C10	118.7 (4)	C25—N1—C24	133.4 (6)
C3—C7—C10	119.2 (3)	N1—C23—H23A	109.5
O3—C8—O2	124.1 (4)	N1—C23—H23B	109.5
O3—C8—C9	122.7 (4)	H23A—C23—H23B	109.5
O2—C8—C9	113.3 (4)	N1—C23—H23C	109.5
C14—C9—C10	119.4 (3)	H23A—C23—H23C	109.5
C14—C9—C8	121.1 (4)	H23B—C23—H23C	109.5
C10—C9—C8	119.2 (3)	N1—C24—H24A	109.5
C11—C10—C9	119.0 (3)	N1—C24—H24B	109.5
C11—C10—C7	117.1 (3)	H24A—C24—H24B	109.5
C9—C10—C7	123.8 (3)	N1—C24—H24C	109.5
C12—C11—C10	121.6 (4)	H24A—C24—H24C	109.5
C12—C11—H11A	119.2	H24B—C24—H24C	109.5
C10—C11—H11A	119.2	C26—N2—C27	124.5 (5)
C11—C12—C13	119.0 (3)	C26—N2—C28	117.1 (5)
C11—C12—C16	116.4 (3)	C27—N2—C28	118.0 (5)
C13—C12—C16	124.5 (3)	N2—C27—H27A	109.5
C14—C13—C12	119.3 (3)	N2—C27—H27B	109.5
C14—C13—C15	119.2 (4)	H27A—C27—H27B	109.5
C12—C13—C15	121.5 (4)	N2—C27—H27C	109.5
C9—C14—C13	121.5 (4)	H27A—C27—H27C	109.5
C9—C14—H14A	119.3	H27B—C27—H27C	109.5
C13—C14—H14A	119.3	O8—C26—N2	126.3 (6)
O6—C15—O5	123.7 (4)	O8—C26—H26A	116.8
O6—C15—C13	120.9 (4)	N2—C26—H26A	116.8
O5—C15—C13	115.3 (4)	N2—C28—H28A	109.5
O4—C16—C17	121.0 (4)	N2—C28—H28B	109.5
O4—C16—C12	119.0 (4)	H28A—C28—H28B	109.5
C17—C16—C12	119.6 (4)	N2—C28—H28C	109.5
C22—C17—C18	118.9 (4)	H28A—C28—H28C	109.5
C22—C17—C16	122.1 (4)	H28B—C28—H28C	109.5
C6—C1—C2—C3	−1.1 (7)	C11—C12—C13—C15	−177.3 (4)
C1—C2—C3—C4	0.1 (6)	C16—C12—C13—C15	2.9 (6)
C1—C2—C3—C7	179.3 (4)	C10—C9—C14—C13	−1.5 (6)
C2—C3—C4—C5	1.0 (6)	C8—C9—C14—C13	173.4 (4)
C7—C3—C4—C5	−178.2 (4)	C12—C13—C14—C9	−0.6 (6)
C3—C4—C5—C6	−1.2 (7)	C15—C13—C14—C9	179.4 (4)
C4—C5—C6—C1	0.2 (8)	C14—C13—C15—O6	−167.3 (4)
C2—C1—C6—C5	1.0 (8)	C12—C13—C15—O6	12.7 (6)
C4—C3—C7—O1	5.0 (6)	C14—C13—C15—O5	11.0 (6)
C2—C3—C7—O1	−174.2 (4)	C12—C13—C15—O5	−169.1 (4)
C4—C3—C7—C10	178.9 (4)	C11—C12—C16—O4	65.9 (5)
C2—C3—C7—C10	−0.3 (6)	C13—C12—C16—O4	−114.4 (5)
O3—C8—C9—C14	−157.7 (4)	C11—C12—C16—C17	−107.7 (4)
O2—C8—C9—C14	22.1 (5)	C13—C12—C16—C17	72.1 (5)
O3—C8—C9—C10	17.2 (6)	O4—C16—C17—C22	−169.2 (4)
O2—C8—C9—C10	−163.0 (4)	C12—C16—C17—C22	4.2 (6)
C14—C9—C10—C11	1.6 (5)	O4—C16—C17—C18	9.1 (6)
C8—C9—C10—C11	−173.4 (3)	C12—C16—C17—C18	−177.5 (3)
C14—C9—C10—C7	−176.6 (4)	C22—C17—C18—C19	−0.3 (6)
C8—C9—C10—C7	8.5 (6)	C16—C17—C18—C19	−178.7 (4)
O1—C7—C10—C11	62.6 (5)	C17—C18—C19—C20	0.2 (7)
C3—C7—C10—C11	−111.5 (4)	C18—C19—C20—C21	−0.2 (7)
O1—C7—C10—C9	−119.2 (4)	C19—C20—C21—C22	0.4 (7)
C3—C7—C10—C9	66.7 (5)	C20—C21—C22—C17	−0.6 (7)
C9—C10—C11—C12	0.5 (6)	C18—C17—C22—C21	0.5 (6)
C7—C10—C11—C12	178.7 (3)	C16—C17—C22—C21	178.8 (4)
C10—C11—C12—C13	−2.6 (6)	O7—C25—N1—C23	177.9 (5)
C10—C11—C12—C16	177.2 (3)	O7—C25—N1—C24	−1.4 (8)
C11—C12—C13—C14	2.6 (5)	C27—N2—C26—O8	−1.6 (9)
C16—C12—C13—C14	−177.1 (4)	C28—N2—C26—O8	−174.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O8	0.82	1.78	2.586 (5)	167
O5—H5B···O7	0.82	1.76	2.562 (6)	167
C11—H11A···O1^i	0.93	2.46	3.373 (5)	169
C14—H14A···O2	0.93	2.46	2.762 (5)	99
C14—H14A···O5	0.93	2.40	2.721 (5)	100
C23—H23B···O3^ii	0.96	2.48	3.240 (8)	136
C27—H27A···O8	0.96	2.47	2.834 (8)	102
C27—H27B···O4^iii	0.96	2.57	3.358 (7)	139

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