Crystal structure of 2-chloro-1,3-bis­(2,6-diiso­propyl­phen­yl)-1,3,2-di­aza­phospho­lidine 2-oxide

The synthesis, spectroscopic and crystal structure of 2-chloro-1,3-bis­(2,6-diiso­propyl­phen­yl)-1,3,2-di­aza­phospho­lidine 2-oxide are reported.

Key indicators

• Single-crystal X-ray study
• T = 104 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.109
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CL1     ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  CL1     ..       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O1      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25C   ..  O1      ..       2.61 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.822 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         93 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine 2-oxide

Crystal data

C26H38ClN2OP	F(000) = 992
Mr = 461.00	Dx = 1.198 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 19.984 (3) Å	Cell parameters from 4093 reflections
b = 6.6328 (11) Å	θ = 2.5–24.5°
c = 20.140 (3) Å	µ = 0.23 mm^−1
β = 106.818 (2)°	T = 104 K
V = 2555.4 (7) Å^3	Block, colourless
Z = 4	0.25 × 0.21 × 0.17 mm

Data collection

Siemens/Bruker APEXII diffractometer	4640 reflections with I > 2σ(I)
Detector resolution: 66 pixels mm^-1	Rint = 0.073
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −26→26
Tmin = 0.578, Tmax = 0.746	k = −8→8
30194 measured reflections	l = −26→26
6307 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.5837P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6307 reflections	Δρmax = 0.43 e Å^−3
288 parameters	Δρmin = −0.33 e Å^−3
0 restraints

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
CL1	0.60905 (2)	0.77730 (7)	0.42592 (2)	0.02113 (12)
P1	0.70785 (2)	0.65590 (7)	0.46135 (2)	0.01383 (11)
O1	0.75532 (6)	0.81335 (17)	0.45109 (6)	0.0181 (3)
N1	0.71214 (7)	0.5695 (2)	0.53850 (7)	0.0149 (3)
N2	0.70937 (7)	0.4369 (2)	0.42630 (7)	0.0147 (3)
C1	0.72101 (10)	0.3487 (3)	0.54424 (9)	0.0196 (4)
H1A	0.692450	0.290717	0.572321	0.024*
H1B	0.770625	0.312993	0.566036	0.024*
C2	0.69615 (9)	0.2713 (3)	0.46958 (9)	0.0183 (4)
H2A	0.722531	0.149108	0.464119	0.022*
H2B	0.645730	0.237947	0.456523	0.022*
C3	0.71736 (9)	0.6963 (2)	0.59765 (8)	0.0149 (3)
C4	0.78155 (9)	0.7887 (3)	0.63099 (9)	0.0189 (4)
C5	0.78352 (10)	0.9197 (3)	0.68551 (9)	0.0245 (4)
H5	0.825951	0.987103	0.708089	0.029*
C6	0.72518 (11)	0.9539 (3)	0.70750 (10)	0.0273 (4)
H6	0.727763	1.044273	0.744756	0.033*
C7	0.66305 (10)	0.8570 (3)	0.67543 (9)	0.0256 (4)
H7	0.623418	0.879569	0.691479	0.031*
C8	0.65767 (9)	0.7266 (3)	0.61984 (9)	0.0192 (4)
C9	0.84815 (9)	0.7422 (3)	0.61222 (9)	0.0223 (4)
H9	0.834851	0.662355	0.568225	0.027*
C10	0.88538 (10)	0.9329 (3)	0.59894 (11)	0.0314 (5)
H10A	0.926952	0.895280	0.585271	0.047*
H10B	0.899393	1.014211	0.641348	0.047*
H10C	0.853666	1.011382	0.561687	0.047*
C11	0.89651 (10)	0.6108 (3)	0.66826 (11)	0.0309 (5)
H11A	0.938829	0.578975	0.655073	0.046*
H11B	0.872366	0.485491	0.673151	0.046*
H11C	0.909329	0.683572	0.712499	0.046*
C12	0.58966 (9)	0.6166 (3)	0.58712 (10)	0.0247 (4)
H12	0.593698	0.549291	0.544010	0.030*
C13	0.52710 (11)	0.7590 (4)	0.56644 (11)	0.0407 (6)
H13A	0.535887	0.864893	0.536069	0.061*
H13B	0.520044	0.820457	0.608159	0.061*
H13C	0.485179	0.683169	0.541819	0.061*
C14	0.57816 (11)	0.4518 (4)	0.63611 (11)	0.0373 (5)
H14A	0.535680	0.375892	0.613176	0.056*
H14B	0.573101	0.513955	0.678539	0.056*
H14C	0.618349	0.360144	0.647930	0.056*
C15	0.72566 (9)	0.4045 (2)	0.36189 (9)	0.0155 (4)
C16	0.67152 (9)	0.3889 (2)	0.29983 (9)	0.0172 (4)
C17	0.68940 (10)	0.3713 (3)	0.23813 (9)	0.0197 (4)
H17	0.653475	0.361779	0.195399	0.024*
C18	0.75855 (10)	0.3673 (3)	0.23807 (9)	0.0203 (4)
H18	0.769988	0.359264	0.195532	0.024*
C19	0.81087 (10)	0.3752 (3)	0.30022 (9)	0.0196 (4)
H19	0.858228	0.368268	0.299803	0.023*
C20	0.79627 (9)	0.3931 (3)	0.36346 (9)	0.0173 (4)
C21	0.59508 (9)	0.3881 (3)	0.29800 (9)	0.0188 (4)
H21	0.592775	0.410635	0.346382	0.023*
C22	0.55404 (10)	0.5564 (3)	0.25268 (10)	0.0295 (5)
H22A	0.555477	0.537843	0.204835	0.044*
H22B	0.574841	0.686840	0.270126	0.044*
H22C	0.505386	0.552822	0.253905	0.044*
C23	0.56189 (11)	0.1827 (3)	0.27379 (11)	0.0306 (5)
H23A	0.513339	0.182330	0.275382	0.046*
H23B	0.588161	0.076821	0.304337	0.046*
H23C	0.562927	0.157514	0.226146	0.046*
C24	0.85570 (9)	0.3942 (3)	0.43053 (9)	0.0195 (4)
H24	0.834454	0.399067	0.469768	0.023*
C25	0.90220 (10)	0.5797 (3)	0.43636 (10)	0.0270 (4)
H25A	0.925377	0.576285	0.399635	0.041*
H25B	0.937539	0.580306	0.481732	0.041*
H25C	0.873536	0.701785	0.431455	0.041*
C26	0.89855 (11)	0.2004 (3)	0.43818 (10)	0.0289 (5)
H26A	0.867806	0.083879	0.435911	0.043*
H26B	0.934841	0.201006	0.482942	0.043*
H26C	0.920487	0.191919	0.400596	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.0179 (2)	0.0199 (2)	0.0225 (2)	0.00405 (17)	0.00101 (17)	0.00066 (17)
P1	0.0146 (2)	0.0125 (2)	0.0134 (2)	0.00099 (17)	0.00254 (17)	0.00000 (17)
O1	0.0209 (7)	0.0144 (6)	0.0190 (6)	−0.0012 (5)	0.0058 (5)	0.0009 (5)
N1	0.0180 (8)	0.0122 (7)	0.0139 (7)	0.0010 (6)	0.0035 (6)	−0.0002 (6)
N2	0.0183 (8)	0.0135 (7)	0.0129 (7)	−0.0003 (6)	0.0054 (6)	−0.0011 (6)
C1	0.0260 (10)	0.0132 (9)	0.0198 (9)	0.0013 (7)	0.0068 (8)	0.0021 (7)
C2	0.0230 (9)	0.0135 (9)	0.0187 (9)	−0.0013 (7)	0.0066 (7)	0.0008 (7)
C3	0.0191 (9)	0.0131 (8)	0.0111 (8)	0.0009 (7)	0.0024 (7)	−0.0003 (6)
C4	0.0231 (9)	0.0170 (9)	0.0153 (8)	−0.0007 (7)	0.0034 (7)	0.0017 (7)
C5	0.0304 (11)	0.0233 (10)	0.0156 (9)	−0.0080 (8)	−0.0001 (8)	−0.0017 (8)
C6	0.0406 (12)	0.0220 (10)	0.0185 (9)	0.0009 (9)	0.0074 (9)	−0.0056 (8)
C7	0.0286 (11)	0.0297 (11)	0.0196 (10)	0.0059 (9)	0.0088 (8)	−0.0023 (8)
C8	0.0197 (9)	0.0214 (9)	0.0157 (9)	0.0017 (7)	0.0039 (7)	0.0006 (7)
C9	0.0166 (9)	0.0291 (11)	0.0185 (9)	−0.0024 (8)	0.0008 (7)	0.0016 (8)
C10	0.0215 (10)	0.0386 (12)	0.0308 (11)	−0.0073 (9)	0.0023 (9)	0.0077 (9)
C11	0.0242 (11)	0.0321 (12)	0.0318 (11)	−0.0004 (9)	0.0007 (9)	0.0051 (9)
C12	0.0181 (10)	0.0374 (12)	0.0192 (9)	−0.0009 (8)	0.0062 (8)	−0.0030 (8)
C13	0.0225 (11)	0.0671 (17)	0.0309 (12)	0.0118 (11)	0.0052 (9)	−0.0062 (11)
C14	0.0280 (12)	0.0538 (15)	0.0309 (12)	−0.0152 (10)	0.0096 (9)	0.0020 (10)
C15	0.0209 (9)	0.0115 (8)	0.0155 (8)	0.0002 (7)	0.0072 (7)	−0.0014 (7)
C16	0.0217 (9)	0.0119 (8)	0.0191 (9)	−0.0007 (7)	0.0076 (7)	−0.0019 (7)
C17	0.0253 (10)	0.0162 (9)	0.0160 (9)	−0.0010 (7)	0.0035 (8)	−0.0017 (7)
C18	0.0275 (10)	0.0175 (9)	0.0190 (9)	−0.0004 (8)	0.0116 (8)	−0.0024 (7)
C19	0.0211 (9)	0.0159 (9)	0.0237 (9)	0.0004 (7)	0.0097 (8)	−0.0007 (7)
C20	0.0203 (9)	0.0128 (8)	0.0196 (9)	−0.0011 (7)	0.0070 (7)	−0.0004 (7)
C21	0.0177 (9)	0.0220 (10)	0.0151 (9)	−0.0019 (7)	0.0021 (7)	−0.0018 (7)
C22	0.0210 (10)	0.0392 (12)	0.0280 (11)	0.0049 (9)	0.0068 (9)	0.0092 (9)
C23	0.0312 (11)	0.0328 (12)	0.0304 (11)	−0.0131 (9)	0.0130 (9)	−0.0099 (9)
C24	0.0163 (9)	0.0225 (10)	0.0199 (9)	0.0013 (7)	0.0056 (7)	0.0004 (7)
C25	0.0213 (10)	0.0251 (10)	0.0305 (11)	−0.0029 (8)	0.0010 (8)	0.0019 (8)
C26	0.0305 (11)	0.0273 (11)	0.0270 (11)	0.0081 (9)	0.0052 (9)	0.0032 (9)

Geometric parameters (Å, º)

CL1—P1	2.0592 (7)	C13—H13A	0.9800
P1—O1	1.4652 (12)	C13—H13B	0.9800
P1—N2	1.6192 (14)	C13—H13C	0.9800
P1—N1	1.6348 (14)	C14—H14A	0.9800
N1—C3	1.437 (2)	C14—H14B	0.9800
N1—C1	1.476 (2)	C14—H14C	0.9800
N2—C15	1.442 (2)	C15—C16	1.400 (2)
N2—C2	1.473 (2)	C15—C20	1.404 (2)
C1—C2	1.529 (2)	C16—C17	1.394 (2)
C1—H1A	0.9900	C16—C21	1.517 (2)
C1—H1B	0.9900	C17—C18	1.382 (3)
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—C19	1.380 (3)
C3—C8	1.404 (2)	C18—H18	0.9500
C3—C4	1.405 (2)	C19—C20	1.392 (2)
C4—C5	1.392 (2)	C19—H19	0.9500
C4—C9	1.517 (2)	C20—C24	1.519 (2)
C5—C6	1.380 (3)	C21—C22	1.523 (3)
C5—H5	0.9500	C21—C23	1.532 (3)
C6—C7	1.381 (3)	C21—H21	1.0000
C6—H6	0.9500	C22—H22A	0.9800
C7—C8	1.394 (2)	C22—H22B	0.9800
C7—H7	0.9500	C22—H22C	0.9800
C8—C12	1.515 (3)	C23—H23A	0.9800
C9—C11	1.529 (3)	C23—H23B	0.9800
C9—C10	1.530 (3)	C23—H23C	0.9800
C9—H9	1.0000	C24—C25	1.526 (3)
C10—H10A	0.9800	C24—C26	1.527 (3)
C10—H10B	0.9800	C24—H24	1.0000
C10—H10C	0.9800	C25—H25A	0.9800
C11—H11A	0.9800	C25—H25B	0.9800
C11—H11B	0.9800	C25—H25C	0.9800
C11—H11C	0.9800	C26—H26A	0.9800
C12—C13	1.526 (3)	C26—H26B	0.9800
C12—C14	1.534 (3)	C26—H26C	0.9800
C12—H12	1.0000
O1—P1—N2	118.91 (7)	C12—C13—H13A	109.5
O1—P1—N1	121.71 (7)	C12—C13—H13B	109.5
N2—P1—N1	95.60 (7)	H13A—C13—H13B	109.5
O1—P1—CL1	105.51 (5)	C12—C13—H13C	109.5
N2—P1—CL1	109.68 (6)	H13A—C13—H13C	109.5
N1—P1—CL1	104.35 (5)	H13B—C13—H13C	109.5
C3—N1—C1	122.51 (14)	C12—C14—H14A	109.5
C3—N1—P1	123.66 (12)	C12—C14—H14B	109.5
C1—N1—P1	113.22 (11)	H14A—C14—H14B	109.5
C15—N2—C2	123.16 (13)	C12—C14—H14C	109.5
C15—N2—P1	124.30 (11)	H14A—C14—H14C	109.5
C2—N2—P1	112.45 (11)	H14B—C14—H14C	109.5
N1—C1—C2	105.00 (13)	C16—C15—C20	121.87 (15)
N1—C1—H1A	110.7	C16—C15—N2	119.78 (15)
C2—C1—H1A	110.7	C20—C15—N2	118.34 (15)
N1—C1—H1B	110.7	C17—C16—C15	118.09 (16)
C2—C1—H1B	110.7	C17—C16—C21	119.61 (16)
H1A—C1—H1B	108.8	C15—C16—C21	122.30 (15)
N2—C2—C1	105.58 (13)	C18—C17—C16	121.10 (17)
N2—C2—H2A	110.6	C18—C17—H17	119.5
C1—C2—H2A	110.6	C16—C17—H17	119.5
N2—C2—H2B	110.6	C19—C18—C17	119.58 (16)
C1—C2—H2B	110.6	C19—C18—H18	120.2
H2A—C2—H2B	108.8	C17—C18—H18	120.2
C8—C3—C4	121.87 (15)	C18—C19—C20	121.92 (17)
C8—C3—N1	118.87 (15)	C18—C19—H19	119.0
C4—C3—N1	119.25 (15)	C20—C19—H19	119.0
C5—C4—C3	117.57 (16)	C19—C20—C15	117.35 (16)
C5—C4—C9	119.80 (16)	C19—C20—C24	119.82 (16)
C3—C4—C9	122.55 (16)	C15—C20—C24	122.81 (15)
C6—C5—C4	121.46 (18)	C16—C21—C22	112.06 (15)
C6—C5—H5	119.3	C16—C21—C23	110.57 (15)
C4—C5—H5	119.3	C22—C21—C23	110.65 (16)
C5—C6—C7	120.12 (17)	C16—C21—H21	107.8
C5—C6—H6	119.9	C22—C21—H21	107.8
C7—C6—H6	119.9	C23—C21—H21	107.8
C6—C7—C8	120.96 (18)	C21—C22—H22A	109.5
C6—C7—H7	119.5	C21—C22—H22B	109.5
C8—C7—H7	119.5	H22A—C22—H22B	109.5
C7—C8—C3	117.96 (16)	C21—C22—H22C	109.5
C7—C8—C12	119.95 (16)	H22A—C22—H22C	109.5
C3—C8—C12	122.05 (16)	H22B—C22—H22C	109.5
C4—C9—C11	110.16 (15)	C21—C23—H23A	109.5
C4—C9—C10	112.46 (16)	C21—C23—H23B	109.5
C11—C9—C10	111.41 (16)	H23A—C23—H23B	109.5
C4—C9—H9	107.5	C21—C23—H23C	109.5
C11—C9—H9	107.5	H23A—C23—H23C	109.5
C10—C9—H9	107.5	H23B—C23—H23C	109.5
C9—C10—H10A	109.5	C20—C24—C25	111.98 (15)
C9—C10—H10B	109.5	C20—C24—C26	110.92 (15)
H10A—C10—H10B	109.5	C25—C24—C26	111.09 (15)
C9—C10—H10C	109.5	C20—C24—H24	107.5
H10A—C10—H10C	109.5	C25—C24—H24	107.5
H10B—C10—H10C	109.5	C26—C24—H24	107.5
C9—C11—H11A	109.5	C24—C25—H25A	109.5
C9—C11—H11B	109.5	C24—C25—H25B	109.5
H11A—C11—H11B	109.5	H25A—C25—H25B	109.5
C9—C11—H11C	109.5	C24—C25—H25C	109.5
H11A—C11—H11C	109.5	H25A—C25—H25C	109.5
H11B—C11—H11C	109.5	H25B—C25—H25C	109.5
C8—C12—C13	112.45 (17)	C24—C26—H26A	109.5
C8—C12—C14	110.23 (15)	C24—C26—H26B	109.5
C13—C12—C14	110.69 (17)	H26A—C26—H26B	109.5
C8—C12—H12	107.8	C24—C26—H26C	109.5
C13—C12—H12	107.8	H26A—C26—H26C	109.5
C14—C12—H12	107.8	H26B—C26—H26C	109.5
O1—P1—N1—C3	46.64 (16)	C5—C4—C9—C11	71.0 (2)
N2—P1—N1—C3	175.81 (13)	C3—C4—C9—C11	−105.6 (2)
CL1—P1—N1—C3	−72.20 (13)	C5—C4—C9—C10	−53.9 (2)
O1—P1—N1—C1	−124.54 (12)	C3—C4—C9—C10	129.42 (18)
N2—P1—N1—C1	4.63 (13)	C7—C8—C12—C13	52.4 (2)
CL1—P1—N1—C1	116.61 (11)	C3—C8—C12—C13	−130.01 (18)
O1—P1—N2—C15	−31.45 (16)	C7—C8—C12—C14	−71.7 (2)
N1—P1—N2—C15	−162.56 (14)	C3—C8—C12—C14	106.0 (2)
CL1—P1—N2—C15	90.01 (14)	C2—N2—C15—C16	88.2 (2)
O1—P1—N2—C2	145.24 (11)	P1—N2—C15—C16	−95.46 (18)
N1—P1—N2—C2	14.13 (13)	C2—N2—C15—C20	−93.0 (2)
CL1—P1—N2—C2	−93.30 (11)	P1—N2—C15—C20	83.39 (19)
C3—N1—C1—C2	168.22 (14)	C20—C15—C16—C17	−3.1 (3)
P1—N1—C1—C2	−20.48 (17)	N2—C15—C16—C17	175.75 (15)
C15—N2—C2—C1	149.38 (15)	C20—C15—C16—C21	176.14 (16)
P1—N2—C2—C1	−27.36 (17)	N2—C15—C16—C21	−5.0 (2)
N1—C1—C2—N2	28.46 (18)	C15—C16—C17—C18	0.6 (3)
C1—N1—C3—C8	−86.2 (2)	C21—C16—C17—C18	−178.65 (16)
P1—N1—C3—C8	103.40 (17)	C16—C17—C18—C19	1.9 (3)
C1—N1—C3—C4	94.7 (2)	C17—C18—C19—C20	−1.9 (3)
P1—N1—C3—C4	−75.66 (19)	C18—C19—C20—C15	−0.5 (3)
C8—C3—C4—C5	−2.7 (3)	C18—C19—C20—C24	177.98 (16)
N1—C3—C4—C5	176.29 (15)	C16—C15—C20—C19	3.0 (3)
C8—C3—C4—C9	173.98 (16)	N2—C15—C20—C19	−175.83 (15)
N1—C3—C4—C9	−7.0 (2)	C16—C15—C20—C24	−175.40 (16)
C3—C4—C5—C6	1.8 (3)	N2—C15—C20—C24	5.8 (2)
C9—C4—C5—C6	−175.06 (17)	C17—C16—C21—C22	−58.1 (2)
C4—C5—C6—C7	0.1 (3)	C15—C16—C21—C22	122.71 (18)
C5—C6—C7—C8	−1.2 (3)	C17—C16—C21—C23	65.9 (2)
C6—C7—C8—C3	0.2 (3)	C15—C16—C21—C23	−113.34 (19)
C6—C7—C8—C12	177.92 (17)	C19—C20—C24—C25	65.7 (2)
C4—C3—C8—C7	1.8 (3)	C15—C20—C24—C25	−115.96 (19)
N1—C3—C8—C7	−177.25 (16)	C19—C20—C24—C26	−59.0 (2)
C4—C3—C8—C12	−175.87 (16)	C15—C20—C24—C26	119.31 (18)
N1—C3—C8—C12	5.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1	1.00	2.91	3.543 (2)	122
C21—H21···Cl1	1.00	2.88	3.6006 (19)	130
C9—H9···O1	1.00	2.63	3.273 (2)	122
C25—H25C···O1	0.98	2.61	3.407 (2)	138
C9—H9···N1	1.00	2.43	2.927 (2)	110
C12—H12···N1	1.00	2.41	2.904 (2)	110
C21—H21···N2	1.00	2.42	2.930 (2)	111
C24—H24···N2	1.00	2.41	2.915 (2)	110
C2—H2A···O1^i	0.99	2.36	3.319 (2)	164

Symmetry code: (i) x, y−1, z.