Crystal structures of 2′-benzoyl-1′-(4-methyl­phenyl)-1,1′,2,2′,5′,6′,7′,7a′-octa­hydro­spiro­[indole-3,3′-pyrrolizin]-2-one and 2′-(4-bromo­benzoyl)-1′-(2-chloro­phen­yl)-1,1′,2,2′,5′,6′,7′,7a′-octa­hydro­spiro­[indole-3,3′-pyrrolizin]-2-one

The chemical modifications in terms of changes in substituents in the title compounds have not affected the type nor strength of two defining inter­molecular inter­actions present in both crystal structures.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.113
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT900_ALERT_1_A No Matching Reflection File (FCF) Found ........     Please Check

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su    0.000
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C18 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C26 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C25 Check
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C22    -C27           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00473 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O2      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19    ..  O2      ..       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  O2      ..       2.65 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT792_ALERT_1_G The Model has Chirality at C2      (Polar  SPGR)          S Verify
PLAT792_ALERT_1_G The Model has Chirality at C12     (Polar  SPGR)          S Verify
PLAT792_ALERT_1_G The Model has Chirality at C13     (Polar  SPGR)          S Verify
PLAT792_ALERT_1_G The Model has Chirality at C14     (Polar  SPGR)          R Verify

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

   6 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level A
PLAT900_ALERT_1_A No Matching Reflection File (FCF) Found ........     Please Check

Alert level C
PLAT431_ALERT_2_C Short Inter HL..A  Contact Br1    ..  O1      ..       3.19 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25    ..  O2      ..       2.61 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C12     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C13     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C14     (Centro SPGR)          R Verify

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

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

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013/1 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLUTON (Spek, 2009), Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) 2'-Benzoyl-1'-(4-methylphenyl)-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizin]-2-one

Crystal data

C28H26N2O2	Dx = 1.270 Mg m^−3
Mr = 422.51	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 3325 reflections
a = 36.030 (2) Å	θ = 2.0–26.8°
b = 24.2248 (16) Å	µ = 0.08 mm^−1
c = 10.1301 (6) Å	T = 295 K
V = 8841.7 (9) Å^3	Needle, colourless
Z = 16	0.26 × 0.18 × 0.15 mm
F(000) = 3584

Data collection

Bruker SMART APEX CCD diffractometer	3325 reflections with I > 2σ(I)
ω scans	Rint = 0.108
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.9°, θmin = 2.0°
Tmin = 0.98, Tmax = 0.99	h = −45→45
36903 measured reflections	k = −30→30
4649 independent reflections	l = −11→12

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0652P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max < 0.001
wR(F^2) = 0.113	Δρmax = 0.18 e Å^−3
S = 0.98	Δρmin = −0.14 e Å^−3
4649 reflections	Extinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
291 parameters	Extinction coefficient: 0.00076 (15)
1 restraint	Absolute structure: Refined as a perfect inversion twin
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.5

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.

Refinement. Refined as a 2-component perfect inversion twin.

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

	x	y	z	Uiso*/Ueq
O1	0.27285 (7)	1.01345 (8)	−0.0201 (2)	0.0579 (6)
O2	0.31457 (6)	0.81610 (7)	−0.0631 (2)	0.0509 (6)
N1	0.25279 (7)	0.96268 (9)	−0.1968 (2)	0.0418 (6)
H1	0.2547	0.9874	−0.2574	0.050*
N2	0.23589 (7)	0.92646 (10)	0.1303 (2)	0.0429 (6)
C1	0.26150 (8)	0.97090 (11)	−0.0689 (3)	0.0398 (7)
C2	0.25557 (8)	0.91652 (11)	0.0062 (3)	0.0362 (6)
C3	0.23874 (7)	0.88025 (11)	−0.0999 (3)	0.0358 (6)
C4	0.22634 (8)	0.82631 (11)	−0.0999 (3)	0.0416 (7)
H4	0.2247	0.8067	−0.0212	0.050*
C5	0.21643 (9)	0.80184 (12)	−0.2170 (3)	0.0502 (8)
H5	0.2079	0.7656	−0.2174	0.060*
C6	0.21893 (11)	0.83025 (13)	−0.3325 (4)	0.0613 (10)
H6	0.2123	0.8128	−0.4109	0.074*
C7	0.23109 (10)	0.88454 (13)	−0.3362 (3)	0.0556 (9)
H7	0.2330	0.9038	−0.4154	0.067*
C8	0.24016 (8)	0.90845 (11)	−0.2186 (3)	0.0385 (6)
C9	0.19502 (10)	0.92472 (16)	0.1279 (4)	0.0621 (9)
H9A	0.1862	0.9034	0.0531	0.074*
H9B	0.1848	0.9617	0.1227	0.074*
C10	0.18444 (10)	0.89746 (17)	0.2557 (4)	0.0717 (11)
H10A	0.1828	0.9243	0.3265	0.086*
H10B	0.1608	0.8785	0.2476	0.086*
C11	0.21532 (10)	0.85747 (14)	0.2801 (4)	0.0605 (9)
H11A	0.2118	0.8238	0.2298	0.073*
H11B	0.2171	0.8483	0.3731	0.073*
C12	0.24949 (9)	0.88832 (12)	0.2339 (3)	0.0431 (7)
H12	0.2593	0.9101	0.3076	0.052*
C13	0.28144 (8)	0.85597 (11)	0.1704 (3)	0.0392 (6)
H13	0.2707	0.8227	0.1309	0.047*
C14	0.29306 (7)	0.89341 (10)	0.0576 (3)	0.0358 (6)
H14	0.3077	0.9240	0.0937	0.043*
C15	0.31537 (8)	0.86578 (11)	−0.0504 (3)	0.0371 (6)
C16	0.33632 (8)	0.90084 (12)	−0.1443 (3)	0.0396 (7)
C17	0.33895 (12)	0.88417 (14)	−0.2743 (3)	0.0659 (10)
H17	0.3277	0.8516	−0.3016	0.079*
C18	0.35827 (14)	0.91583 (17)	−0.3632 (4)	0.0878 (15)
H18	0.3592	0.9052	−0.4513	0.105*
C19	0.37602 (11)	0.96247 (15)	−0.3241 (4)	0.0748 (12)
H19	0.3895	0.9832	−0.3849	0.090*
C20	0.37413 (10)	0.97879 (15)	−0.1964 (4)	0.0646 (10)
H20	0.3866	1.0104	−0.1691	0.078*
C21	0.35373 (9)	0.94869 (13)	−0.1071 (4)	0.0539 (8)
H21	0.3517	0.9610	−0.0204	0.065*
C22	0.31168 (8)	0.83740 (11)	0.2623 (3)	0.0422 (7)
C23	0.34826 (9)	0.85341 (14)	0.2504 (3)	0.0528 (8)
H23	0.3548	0.8785	0.1849	0.063*
C24	0.37553 (10)	0.83296 (15)	0.3336 (3)	0.0604 (9)
H24	0.4000	0.8444	0.3219	0.072*
C25	0.36741 (10)	0.79638 (13)	0.4324 (4)	0.0591 (9)
C26	0.33129 (12)	0.78139 (15)	0.4451 (4)	0.0812 (13)
H26	0.3247	0.7571	0.5123	0.097*
C27	0.30406 (11)	0.80081 (15)	0.3620 (4)	0.0717 (12)
H27	0.2798	0.7888	0.3738	0.086*
C28	0.39708 (13)	0.77479 (18)	0.5240 (5)	0.0886 (13)
H28A	0.3891	0.7404	0.5617	0.133*
H28B	0.4014	0.8011	0.5932	0.133*
H28C	0.4196	0.7691	0.4753	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0879 (17)	0.0324 (11)	0.0535 (14)	−0.0049 (11)	−0.0031 (12)	−0.0084 (10)
O2	0.0626 (14)	0.0343 (11)	0.0557 (14)	0.0041 (9)	0.0017 (11)	−0.0077 (10)
N1	0.0564 (15)	0.0294 (12)	0.0396 (14)	−0.0016 (10)	−0.0034 (12)	0.0051 (11)
N2	0.0423 (14)	0.0501 (14)	0.0362 (13)	0.0055 (11)	0.0054 (11)	−0.0007 (12)
C1	0.0459 (17)	0.0316 (14)	0.0418 (17)	0.0040 (12)	0.0038 (14)	−0.0050 (13)
C2	0.0410 (16)	0.0315 (14)	0.0363 (15)	0.0007 (11)	0.0010 (12)	−0.0033 (12)
C3	0.0367 (15)	0.0341 (14)	0.0366 (16)	0.0005 (11)	−0.0011 (12)	0.0011 (12)
C4	0.0475 (17)	0.0360 (14)	0.0412 (18)	−0.0057 (13)	−0.0043 (14)	0.0077 (13)
C5	0.061 (2)	0.0368 (15)	0.053 (2)	−0.0125 (14)	−0.0122 (16)	0.0033 (15)
C6	0.089 (3)	0.0481 (18)	0.047 (2)	−0.0194 (17)	−0.0194 (19)	−0.0005 (16)
C7	0.081 (2)	0.0445 (17)	0.0416 (18)	−0.0116 (16)	−0.0134 (17)	0.0076 (15)
C8	0.0418 (16)	0.0317 (13)	0.0421 (15)	−0.0025 (12)	−0.0041 (13)	0.0034 (13)
C9	0.044 (2)	0.087 (3)	0.055 (2)	0.0102 (18)	0.0091 (16)	0.001 (2)
C10	0.051 (2)	0.095 (3)	0.069 (3)	−0.0107 (19)	0.0129 (19)	−0.005 (2)
C11	0.061 (2)	0.065 (2)	0.055 (2)	−0.0094 (17)	0.0143 (18)	0.0090 (17)
C12	0.0486 (17)	0.0467 (17)	0.0341 (15)	−0.0052 (14)	0.0018 (13)	−0.0039 (13)
C13	0.0449 (16)	0.0350 (14)	0.0378 (15)	−0.0046 (12)	−0.0015 (13)	−0.0005 (12)
C14	0.0389 (15)	0.0325 (13)	0.0360 (15)	−0.0032 (11)	−0.0007 (12)	−0.0027 (12)
C15	0.0369 (15)	0.0356 (14)	0.0389 (15)	0.0012 (12)	−0.0051 (12)	−0.0056 (12)
C16	0.0377 (15)	0.0410 (16)	0.0402 (16)	0.0061 (13)	0.0050 (13)	−0.0038 (12)
C17	0.094 (3)	0.0537 (19)	0.050 (2)	−0.0063 (19)	0.020 (2)	−0.0125 (17)
C18	0.129 (4)	0.080 (3)	0.055 (2)	−0.005 (3)	0.043 (3)	−0.014 (2)
C19	0.082 (3)	0.057 (2)	0.085 (3)	0.0034 (19)	0.037 (2)	0.006 (2)
C20	0.058 (2)	0.059 (2)	0.077 (3)	−0.0122 (17)	0.0173 (19)	−0.003 (2)
C21	0.0531 (19)	0.0514 (18)	0.0570 (19)	−0.0089 (16)	0.0083 (16)	−0.0089 (16)
C22	0.0506 (17)	0.0346 (15)	0.0414 (16)	−0.0035 (12)	−0.0056 (14)	−0.0020 (13)
C23	0.051 (2)	0.066 (2)	0.0412 (18)	−0.0021 (16)	−0.0008 (15)	0.0062 (15)
C24	0.050 (2)	0.078 (2)	0.052 (2)	0.0026 (17)	−0.0111 (16)	−0.0037 (19)
C25	0.071 (2)	0.0485 (17)	0.057 (2)	0.0037 (17)	−0.0218 (19)	−0.0026 (17)
C26	0.091 (3)	0.067 (2)	0.086 (3)	−0.023 (2)	−0.033 (2)	0.038 (2)
C27	0.065 (2)	0.071 (2)	0.079 (3)	−0.0256 (19)	−0.024 (2)	0.036 (2)
C28	0.095 (3)	0.084 (3)	0.086 (3)	0.013 (2)	−0.041 (3)	0.004 (2)

Geometric parameters (Å, º)

O1—C1	1.214 (3)	C13—C22	1.502 (4)
O2—C15	1.211 (3)	C13—C14	1.518 (4)
N1—C1	1.348 (4)	C13—H13	0.9800
N1—C8	1.408 (3)	C14—C15	1.514 (4)
N1—H1	0.8600	C14—H14	0.9800
N2—C2	1.463 (4)	C15—C16	1.481 (4)
N2—C9	1.473 (4)	C16—C21	1.371 (4)
N2—C12	1.482 (4)	C16—C17	1.381 (4)
C1—C2	1.537 (4)	C17—C18	1.372 (5)
C2—C3	1.515 (4)	C17—H17	0.9300
C2—C14	1.552 (4)	C18—C19	1.357 (6)
C3—C4	1.381 (4)	C18—H18	0.9300
C3—C8	1.384 (4)	C19—C20	1.354 (6)
C4—C5	1.373 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.375 (5)
C5—C6	1.360 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.387 (4)	C22—C27	1.371 (5)
C6—H6	0.9300	C22—C23	1.379 (4)
C7—C8	1.365 (5)	C23—C24	1.386 (5)
C7—H7	0.9300	C23—H23	0.9300
C9—C10	1.503 (5)	C24—C25	1.369 (5)
C9—H9A	0.9700	C24—H24	0.9300
C9—H9B	0.9700	C25—C26	1.357 (5)
C10—C11	1.496 (5)	C25—C28	1.509 (5)
C10—H10A	0.9700	C26—C27	1.376 (5)
C10—H10B	0.9700	C26—H26	0.9300
C11—C12	1.515 (4)	C27—H27	0.9300
C11—H11A	0.9700	C28—H28A	0.9600
C11—H11B	0.9700	C28—H28B	0.9600
C12—C13	1.534 (4)	C28—H28C	0.9600
C12—H12	0.9800
C1—N1—C8	111.3 (2)	C22—C13—C14	116.5 (2)
C1—N1—H1	124.3	C22—C13—C12	115.9 (2)
C8—N1—H1	124.3	C14—C13—C12	102.6 (2)
C2—N2—C9	117.7 (2)	C22—C13—H13	107.1
C2—N2—C12	110.2 (2)	C14—C13—H13	107.1
C9—N2—C12	108.9 (2)	C12—C13—H13	107.1
O1—C1—N1	126.6 (3)	C15—C14—C13	115.2 (2)
O1—C1—C2	124.9 (3)	C15—C14—C2	112.3 (2)
N1—C1—C2	108.5 (2)	C13—C14—C2	103.2 (2)
N2—C2—C3	120.7 (2)	C15—C14—H14	108.6
N2—C2—C1	110.6 (2)	C13—C14—H14	108.6
C3—C2—C1	101.6 (2)	C2—C14—H14	108.6
N2—C2—C14	101.1 (2)	O2—C15—C16	120.9 (3)
C3—C2—C14	112.1 (2)	O2—C15—C14	120.2 (3)
C1—C2—C14	110.7 (2)	C16—C15—C14	118.7 (2)
C4—C3—C8	118.6 (3)	C21—C16—C17	118.5 (3)
C4—C3—C2	132.7 (2)	C21—C16—C15	122.8 (3)
C8—C3—C2	108.4 (2)	C17—C16—C15	118.6 (3)
C5—C4—C3	119.5 (3)	C18—C17—C16	119.8 (3)
C5—C4—H4	120.3	C18—C17—H17	120.1
C3—C4—H4	120.3	C16—C17—H17	120.1
C6—C5—C4	120.5 (3)	C19—C18—C17	120.8 (4)
C6—C5—H5	119.8	C19—C18—H18	119.6
C4—C5—H5	119.8	C17—C18—H18	119.6
C5—C6—C7	121.6 (3)	C20—C19—C18	119.9 (4)
C5—C6—H6	119.2	C20—C19—H19	120.1
C7—C6—H6	119.2	C18—C19—H19	120.1
C8—C7—C6	117.0 (3)	C19—C20—C21	120.0 (3)
C8—C7—H7	121.5	C19—C20—H20	120.0
C6—C7—H7	121.5	C21—C20—H20	120.0
C7—C8—C3	122.7 (3)	C16—C21—C20	120.8 (3)
C7—C8—N1	127.6 (3)	C16—C21—H21	119.6
C3—C8—N1	109.7 (3)	C20—C21—H21	119.6
N2—C9—C10	104.6 (3)	C27—C22—C23	116.0 (3)
N2—C9—H9A	110.8	C27—C22—C13	120.3 (3)
C10—C9—H9A	110.8	C23—C22—C13	123.7 (3)
N2—C9—H9B	110.8	C22—C23—C24	121.6 (3)
C10—C9—H9B	110.8	C22—C23—H23	119.2
H9A—C9—H9B	108.9	C24—C23—H23	119.2
C11—C10—C9	103.8 (3)	C25—C24—C23	121.7 (3)
C11—C10—H10A	111.0	C25—C24—H24	119.2
C9—C10—H10A	111.0	C23—C24—H24	119.2
C11—C10—H10B	111.0	C26—C25—C24	116.6 (3)
C9—C10—H10B	111.0	C26—C25—C28	121.9 (4)
H10A—C10—H10B	109.0	C24—C25—C28	121.5 (4)
C10—C11—C12	103.5 (3)	C25—C26—C27	122.3 (4)
C10—C11—H11A	111.1	C25—C26—H26	118.8
C12—C11—H11A	111.1	C27—C26—H26	118.8
C10—C11—H11B	111.1	C22—C27—C26	121.9 (4)
C12—C11—H11B	111.1	C22—C27—H27	119.0
H11A—C11—H11B	109.0	C26—C27—H27	119.0
N2—C12—C11	104.9 (3)	C25—C28—H28A	109.5
N2—C12—C13	105.6 (2)	C25—C28—H28B	109.5
C11—C12—C13	119.2 (2)	H28A—C28—H28B	109.5
N2—C12—H12	108.9	C25—C28—H28C	109.5
C11—C12—H12	108.9	H28A—C28—H28C	109.5
C13—C12—H12	108.9	H28B—C28—H28C	109.5
C8—N1—C1—O1	−179.4 (3)	C11—C12—C13—C22	−92.7 (4)
C8—N1—C1—C2	1.9 (3)	N2—C12—C13—C14	21.7 (3)
C9—N2—C2—C3	−28.9 (4)	C11—C12—C13—C14	139.3 (3)
C12—N2—C2—C3	96.9 (3)	C22—C13—C14—C15	71.3 (3)
C9—N2—C2—C1	89.4 (3)	C12—C13—C14—C15	−161.0 (2)
C12—N2—C2—C1	−144.8 (2)	C22—C13—C14—C2	−165.9 (2)
C9—N2—C2—C14	−153.2 (2)	C12—C13—C14—C2	−38.3 (3)
C12—N2—C2—C14	−27.5 (3)	N2—C2—C14—C15	165.2 (2)
O1—C1—C2—N2	46.5 (4)	C3—C2—C14—C15	35.2 (3)
N1—C1—C2—N2	−134.8 (2)	C1—C2—C14—C15	−77.5 (3)
O1—C1—C2—C3	175.9 (3)	N2—C2—C14—C13	40.5 (2)
N1—C1—C2—C3	−5.4 (3)	C3—C2—C14—C13	−89.5 (3)
O1—C1—C2—C14	−64.8 (3)	C1—C2—C14—C13	157.8 (2)
N1—C1—C2—C14	113.9 (3)	C13—C14—C15—O2	19.7 (4)
N2—C2—C3—C4	−56.6 (4)	C2—C14—C15—O2	−98.0 (3)
C1—C2—C3—C4	−179.3 (3)	C13—C14—C15—C16	−163.7 (2)
C14—C2—C3—C4	62.4 (4)	C2—C14—C15—C16	78.6 (3)
N2—C2—C3—C8	129.8 (3)	O2—C15—C16—C21	−146.6 (3)
C1—C2—C3—C8	7.1 (3)	C14—C15—C16—C21	36.8 (4)
C14—C2—C3—C8	−111.2 (3)	O2—C15—C16—C17	32.3 (4)
C8—C3—C4—C5	1.2 (4)	C14—C15—C16—C17	−144.3 (3)
C2—C3—C4—C5	−172.0 (3)	C21—C16—C17—C18	−0.9 (6)
C3—C4—C5—C6	0.3 (5)	C15—C16—C17—C18	−179.9 (4)
C4—C5—C6—C7	−0.7 (6)	C16—C17—C18—C19	2.4 (7)
C5—C6—C7—C8	−0.5 (6)	C17—C18—C19—C20	−1.3 (7)
C6—C7—C8—C3	2.1 (5)	C18—C19—C20—C21	−1.2 (6)
C6—C7—C8—N1	−179.5 (3)	C17—C16—C21—C20	−1.6 (5)
C4—C3—C8—C7	−2.4 (5)	C15—C16—C21—C20	177.3 (3)
C2—C3—C8—C7	172.2 (3)	C19—C20—C21—C16	2.6 (6)
C4—C3—C8—N1	178.9 (3)	C14—C13—C22—C27	−176.0 (3)
C2—C3—C8—N1	−6.4 (3)	C12—C13—C22—C27	63.2 (4)
C1—N1—C8—C7	−175.7 (3)	C14—C13—C22—C23	1.4 (4)
C1—N1—C8—C3	2.9 (3)	C12—C13—C22—C23	−119.4 (3)
C2—N2—C9—C10	141.9 (3)	C27—C22—C23—C24	0.8 (5)
C12—N2—C9—C10	15.5 (3)	C13—C22—C23—C24	−176.7 (3)
N2—C9—C10—C11	−33.1 (4)	C22—C23—C24—C25	−0.7 (5)
C9—C10—C11—C12	37.9 (4)	C23—C24—C25—C26	−0.3 (5)
C2—N2—C12—C11	−122.7 (3)	C23—C24—C25—C28	−179.2 (3)
C9—N2—C12—C11	8.0 (3)	C24—C25—C26—C27	1.2 (6)
C2—N2—C12—C13	4.1 (3)	C28—C25—C26—C27	−179.9 (4)
C9—N2—C12—C13	134.7 (3)	C23—C22—C27—C26	0.1 (6)
C10—C11—C12—N2	−28.3 (3)	C13—C22—C27—C26	177.7 (4)
C10—C11—C12—C13	−146.2 (3)	C25—C26—C27—C22	−1.2 (7)
N2—C12—C13—C22	149.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2^i	0.93	2.65	3.441 (4)	144
C19—H19···O2^ii	0.93	2.70	3.301 (5)	123
C20—H20···O2^ii	0.93	2.65	3.278 (4)	125
N1—H1···N2^iii	0.86	2.40	3.232 (3)	163
C7—H7···O1^iii	0.93	2.28	3.098 (4)	147

Symmetry codes: (i) −x+1/2, −y+3/2, z; (ii) −x+3/4, y+1/4, z−1/4; (iii) −x+1/2, −y+2, z−1/2.

(II) 2'-(4-Bromobenzoyl)-1'-(2-chlorophenyl)-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizin]-2-one

Crystal data

C27H22BrClN2O2	F(000) = 1064
Mr = 521.82	Dx = 1.475 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.7280 (4) Å	Cell parameters from 3446 reflections
b = 9.7793 (4) Å	θ = 2.0–26.0°
c = 22.6746 (9) Å	µ = 1.89 mm^−1
β = 98.972 (1)°	T = 295 K
V = 2349.74 (16) Å^3	Needle, colourless
Z = 4	0.25 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer	3446 reflections with I > 2σ(I)
ω scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.3°, θmin = 2.0°
Tmin = 0.89, Tmax = 0.97	h = −13→13
22593 measured reflections	k = −12→12
4740 independent reflections	l = −28→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.9581P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4740 reflections	Δρmax = 0.64 e Å^−3
298 parameters	Δρmin = −0.63 e Å^−3

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
Br1	0.07782 (3)	1.20198 (4)	0.80288 (2)	0.06695 (15)
Cl1	0.77846 (8)	0.56854 (9)	1.02506 (3)	0.0637 (2)
O1	0.63821 (17)	0.92263 (17)	0.73698 (7)	0.0378 (4)
O2	0.57612 (18)	0.8610 (2)	0.95502 (8)	0.0471 (5)
N1	0.72258 (19)	1.10554 (19)	0.79346 (9)	0.0312 (5)
H1	0.7099	1.1686	0.7668	0.037*
N2	0.82778 (19)	0.78758 (19)	0.82501 (9)	0.0305 (5)
C1	0.6915 (2)	0.9728 (2)	0.78339 (10)	0.0283 (5)
C2	0.7382 (2)	0.8914 (2)	0.84101 (10)	0.0266 (5)
C3	0.7894 (2)	1.0043 (2)	0.88401 (10)	0.0272 (5)
C4	0.8386 (2)	1.0042 (3)	0.94381 (11)	0.0364 (6)
H4	0.8452	0.9230	0.9654	0.044*
C5	0.8783 (3)	1.1264 (3)	0.97153 (12)	0.0419 (7)
H5	0.9118	1.1271	1.0119	0.050*
C6	0.8685 (3)	1.2472 (3)	0.93957 (12)	0.0393 (6)
H6	0.8962	1.3282	0.9587	0.047*
C7	0.8182 (3)	1.2497 (2)	0.87969 (11)	0.0350 (6)
H7	0.8115	1.3309	0.8581	0.042*
C8	0.7784 (2)	1.1277 (2)	0.85324 (10)	0.0278 (5)
C9	0.9619 (3)	0.8258 (3)	0.82865 (15)	0.0489 (7)
H9A	0.9835	0.8996	0.8570	0.059*
H9B	0.9803	0.8543	0.7899	0.059*
C10	1.0337 (3)	0.6969 (3)	0.84945 (15)	0.0517 (8)
H10A	1.1173	0.7183	0.8704	0.062*
H10B	1.0414	0.6371	0.8161	0.062*
C11	0.9524 (2)	0.6323 (3)	0.89115 (13)	0.0458 (7)
H11A	0.9675	0.6747	0.9303	0.055*
H11B	0.9684	0.5349	0.8954	0.055*
C12	0.8189 (2)	0.6601 (2)	0.85977 (10)	0.0283 (5)
H12	0.7919	0.5849	0.8322	0.034*
C13	0.7161 (2)	0.6880 (2)	0.89799 (10)	0.0265 (5)
H13	0.7562	0.7282	0.9358	0.032*
C14	0.6354 (2)	0.7997 (2)	0.86225 (10)	0.0262 (5)
H14	0.5834	0.7582	0.8275	0.031*
C15	0.5499 (2)	0.8689 (2)	0.90140 (11)	0.0298 (5)
C16	0.4334 (2)	0.9432 (2)	0.87449 (11)	0.0313 (5)
C17	0.3551 (2)	0.9935 (3)	0.91299 (12)	0.0406 (6)
H17	0.3749	0.9766	0.9537	0.049*
C18	0.2489 (3)	1.0680 (3)	0.89154 (13)	0.0470 (7)
H18	0.1969	1.1008	0.9175	0.056*
C19	0.2204 (2)	1.0934 (3)	0.83125 (13)	0.0430 (7)
C20	0.2941 (3)	1.0426 (3)	0.79221 (13)	0.0510 (8)
H20	0.2730	1.0587	0.7515	0.061*
C21	0.4005 (3)	0.9672 (3)	0.81402 (12)	0.0431 (7)
H21	0.4505	0.9321	0.7876	0.052*
C22	0.6459 (2)	0.5618 (2)	0.91200 (11)	0.0344 (6)
C23	0.5596 (3)	0.4974 (3)	0.86931 (15)	0.0517 (7)
H23	0.5428	0.5342	0.8311	0.062*
C24	0.4973 (3)	0.3791 (4)	0.88206 (19)	0.0724 (10)
H24	0.4393	0.3376	0.8527	0.087*
C25	0.5221 (4)	0.3242 (4)	0.9380 (2)	0.0744 (12)
H25	0.4804	0.2450	0.9466	0.089*
C26	0.6058 (3)	0.3830 (3)	0.98101 (17)	0.0630 (10)
H26	0.6217	0.3450	1.0190	0.076*
C27	0.6681 (3)	0.5007 (3)	0.96804 (13)	0.0434 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.04738 (19)	0.0747 (3)	0.0810 (3)	0.02523 (17)	0.01691 (17)	0.02584 (19)
Cl1	0.0790 (6)	0.0694 (5)	0.0416 (4)	0.0123 (4)	0.0053 (4)	0.0191 (4)
O1	0.0523 (11)	0.0352 (10)	0.0250 (10)	−0.0092 (8)	0.0030 (8)	0.0001 (8)
O2	0.0537 (12)	0.0633 (13)	0.0253 (10)	0.0179 (10)	0.0087 (8)	0.0015 (9)
N1	0.0468 (12)	0.0211 (10)	0.0254 (11)	0.0009 (9)	0.0049 (9)	0.0051 (8)
N2	0.0343 (11)	0.0227 (10)	0.0366 (12)	0.0016 (9)	0.0127 (9)	0.0015 (9)
C1	0.0334 (12)	0.0286 (13)	0.0243 (12)	−0.0004 (10)	0.0087 (10)	0.0003 (10)
C2	0.0339 (12)	0.0206 (12)	0.0258 (12)	0.0011 (10)	0.0061 (10)	0.0017 (9)
C3	0.0321 (12)	0.0211 (12)	0.0280 (12)	0.0025 (10)	0.0034 (10)	−0.0002 (10)
C4	0.0485 (15)	0.0274 (13)	0.0308 (14)	−0.0036 (12)	−0.0015 (11)	0.0027 (11)
C5	0.0513 (16)	0.0397 (16)	0.0313 (15)	−0.0010 (13)	−0.0039 (12)	−0.0037 (12)
C6	0.0477 (15)	0.0273 (13)	0.0426 (16)	−0.0048 (12)	0.0061 (12)	−0.0099 (12)
C7	0.0486 (15)	0.0203 (12)	0.0374 (15)	0.0016 (11)	0.0103 (12)	0.0016 (11)
C8	0.0333 (12)	0.0228 (12)	0.0285 (13)	0.0020 (10)	0.0086 (10)	−0.0019 (10)
C9	0.0403 (15)	0.0387 (16)	0.073 (2)	−0.0053 (12)	0.0263 (15)	0.0014 (14)
C10	0.0353 (14)	0.0495 (18)	0.071 (2)	0.0010 (13)	0.0122 (14)	−0.0018 (15)
C11	0.0386 (15)	0.0458 (17)	0.0521 (18)	0.0064 (13)	0.0042 (13)	0.0085 (14)
C12	0.0351 (13)	0.0215 (12)	0.0282 (13)	0.0005 (10)	0.0046 (10)	0.0003 (10)
C13	0.0326 (12)	0.0208 (12)	0.0263 (12)	0.0007 (9)	0.0050 (10)	0.0017 (9)
C14	0.0314 (12)	0.0232 (12)	0.0241 (12)	−0.0005 (10)	0.0051 (9)	−0.0003 (9)
C15	0.0350 (13)	0.0255 (13)	0.0300 (14)	−0.0014 (10)	0.0086 (10)	−0.0012 (10)
C16	0.0344 (13)	0.0286 (13)	0.0316 (14)	0.0005 (10)	0.0072 (10)	−0.0026 (10)
C17	0.0447 (15)	0.0470 (16)	0.0315 (14)	0.0062 (13)	0.0106 (11)	−0.0032 (12)
C18	0.0455 (16)	0.0503 (18)	0.0487 (18)	0.0137 (14)	0.0187 (13)	−0.0024 (14)
C19	0.0355 (14)	0.0411 (16)	0.0534 (18)	0.0087 (12)	0.0104 (12)	0.0103 (13)
C20	0.0442 (16)	0.071 (2)	0.0386 (16)	0.0147 (15)	0.0092 (13)	0.0115 (15)
C21	0.0421 (15)	0.0562 (18)	0.0330 (15)	0.0135 (13)	0.0120 (12)	−0.0020 (13)
C22	0.0391 (14)	0.0252 (13)	0.0417 (15)	0.0021 (11)	0.0147 (12)	0.0036 (11)
C23	0.0572 (18)	0.0378 (16)	0.0604 (19)	−0.0119 (14)	0.0100 (15)	−0.0032 (14)
C24	0.068 (2)	0.052 (2)	0.099 (3)	−0.0265 (18)	0.017 (2)	−0.011 (2)
C25	0.082 (3)	0.0393 (19)	0.113 (3)	−0.0122 (18)	0.050 (3)	0.013 (2)
C26	0.079 (2)	0.0428 (19)	0.077 (2)	0.0060 (18)	0.043 (2)	0.0208 (17)
C27	0.0505 (16)	0.0317 (14)	0.0530 (18)	0.0096 (13)	0.0237 (13)	0.0100 (13)

Geometric parameters (Å, º)

Br1—C19	1.891 (3)	C11—H11A	0.9700
Cl1—C27	1.743 (3)	C11—H11B	0.9700
O1—C1	1.220 (3)	C12—C13	1.530 (3)
O2—C15	1.207 (3)	C12—H12	0.9800
N1—C1	1.351 (3)	C13—C22	1.505 (3)
N1—C8	1.411 (3)	C13—C14	1.542 (3)
N1—H1	0.8600	C13—H13	0.9800
N2—C9	1.476 (3)	C14—C15	1.530 (3)
N2—C2	1.482 (3)	C14—H14	0.9800
N2—C12	1.486 (3)	C15—C16	1.492 (3)
C1—C2	1.545 (3)	C16—C21	1.382 (3)
C2—C3	1.518 (3)	C16—C17	1.392 (3)
C2—C14	1.555 (3)	C17—C18	1.375 (4)
C3—C4	1.376 (3)	C17—H17	0.9300
C3—C8	1.390 (3)	C18—C19	1.376 (4)
C4—C5	1.386 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.369 (4)
C5—C6	1.381 (4)	C20—C21	1.383 (4)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.381 (4)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.383 (4)
C7—C8	1.373 (3)	C22—C27	1.391 (4)
C7—H7	0.9300	C23—C24	1.388 (4)
C9—C10	1.514 (4)	C23—H23	0.9300
C9—H9A	0.9700	C24—C25	1.366 (6)
C9—H9B	0.9700	C24—H24	0.9300
C10—C11	1.520 (4)	C25—C26	1.347 (5)
C10—H10A	0.9700	C25—H25	0.9300
C10—H10B	0.9700	C26—C27	1.385 (4)
C11—C12	1.521 (3)	C26—H26	0.9300
C1—N1—C8	111.52 (19)	N2—C12—H12	109.1
C1—N1—H1	124.2	C11—C12—H12	109.1
C8—N1—H1	124.2	C13—C12—H12	109.1
C9—N2—C2	118.47 (19)	C22—C13—C12	113.70 (19)
C9—N2—C12	108.97 (19)	C22—C13—C14	115.66 (19)
C2—N2—C12	110.33 (17)	C12—C13—C14	102.94 (18)
O1—C1—N1	127.1 (2)	C22—C13—H13	108.1
O1—C1—C2	124.7 (2)	C12—C13—H13	108.1
N1—C1—C2	108.25 (19)	C14—C13—H13	108.1
N2—C2—C3	118.18 (19)	C15—C14—C13	110.26 (19)
N2—C2—C1	106.45 (18)	C15—C14—C2	116.27 (18)
C3—C2—C1	101.86 (18)	C13—C14—C2	101.78 (18)
N2—C2—C14	101.48 (17)	C15—C14—H14	109.4
C3—C2—C14	115.06 (19)	C13—C14—H14	109.4
C1—C2—C14	114.00 (19)	C2—C14—H14	109.4
C4—C3—C8	119.0 (2)	O2—C15—C16	119.5 (2)
C4—C3—C2	132.6 (2)	O2—C15—C14	119.3 (2)
C8—C3—C2	108.38 (19)	C16—C15—C14	121.2 (2)
C3—C4—C5	119.3 (2)	C21—C16—C17	118.4 (2)
C3—C4—H4	120.3	C21—C16—C15	123.9 (2)
C5—C4—H4	120.3	C17—C16—C15	117.7 (2)
C6—C5—C4	120.4 (2)	C18—C17—C16	120.9 (3)
C6—C5—H5	119.8	C18—C17—H17	119.6
C4—C5—H5	119.8	C16—C17—H17	119.6
C5—C6—C7	121.2 (2)	C17—C18—C19	119.4 (2)
C5—C6—H6	119.4	C17—C18—H18	120.3
C7—C6—H6	119.4	C19—C18—H18	120.3
C8—C7—C6	117.5 (2)	C20—C19—C18	121.0 (2)
C8—C7—H7	121.3	C20—C19—Br1	120.1 (2)
C6—C7—H7	121.3	C18—C19—Br1	118.8 (2)
C7—C8—C3	122.6 (2)	C19—C20—C21	119.3 (3)
C7—C8—N1	127.6 (2)	C19—C20—H20	120.3
C3—C8—N1	109.8 (2)	C21—C20—H20	120.3
N2—C9—C10	104.5 (2)	C16—C21—C20	121.0 (2)
N2—C9—H9A	110.8	C16—C21—H21	119.5
C10—C9—H9A	110.8	C20—C21—H21	119.5
N2—C9—H9B	110.8	C23—C22—C27	116.4 (3)
C10—C9—H9B	110.8	C23—C22—C13	121.9 (2)
H9A—C9—H9B	108.9	C27—C22—C13	121.7 (2)
C9—C10—C11	103.1 (2)	C22—C23—C24	121.7 (3)
C9—C10—H10A	111.1	C22—C23—H23	119.2
C11—C10—H10A	111.1	C24—C23—H23	119.2
C9—C10—H10B	111.1	C25—C24—C23	119.4 (4)
C11—C10—H10B	111.1	C25—C24—H24	120.3
H10A—C10—H10B	109.1	C23—C24—H24	120.3
C10—C11—C12	103.0 (2)	C26—C25—C24	121.0 (3)
C10—C11—H11A	111.2	C26—C25—H25	119.5
C12—C11—H11A	111.2	C24—C25—H25	119.5
C10—C11—H11B	111.2	C25—C26—C27	119.4 (3)
C12—C11—H11B	111.2	C25—C26—H26	120.3
H11A—C11—H11B	109.1	C27—C26—H26	120.3
N2—C12—C11	105.35 (19)	C26—C27—C22	122.1 (3)
N2—C12—C13	105.19 (18)	C26—C27—Cl1	116.9 (2)
C11—C12—C13	118.5 (2)	C22—C27—Cl1	120.9 (2)
C8—N1—C1—O1	177.4 (2)	N2—C12—C13—C14	24.7 (2)
C8—N1—C1—C2	−4.1 (3)	C11—C12—C13—C14	142.1 (2)
C9—N2—C2—C3	−25.9 (3)	C22—C13—C14—C15	71.0 (2)
C12—N2—C2—C3	100.6 (2)	C12—C13—C14—C15	−164.34 (18)
C9—N2—C2—C1	87.7 (3)	C22—C13—C14—C2	−164.97 (19)
C12—N2—C2—C1	−145.73 (19)	C12—C13—C14—C2	−40.4 (2)
C9—N2—C2—C14	−152.7 (2)	N2—C2—C14—C15	160.34 (19)
C12—N2—C2—C14	−26.2 (2)	C3—C2—C14—C15	31.5 (3)
O1—C1—C2—N2	58.4 (3)	C1—C2—C14—C15	−85.7 (2)
N1—C1—C2—N2	−120.2 (2)	N2—C2—C14—C13	40.5 (2)
O1—C1—C2—C3	−177.2 (2)	C3—C2—C14—C13	−88.3 (2)
N1—C1—C2—C3	4.2 (2)	C1—C2—C14—C13	154.52 (19)
O1—C1—C2—C14	−52.7 (3)	C13—C14—C15—O2	20.2 (3)
N1—C1—C2—C14	128.7 (2)	C2—C14—C15—O2	−94.9 (3)
N2—C2—C3—C4	−68.0 (3)	C13—C14—C15—C16	−158.4 (2)
C1—C2—C3—C4	175.8 (3)	C2—C14—C15—C16	86.4 (3)
C14—C2—C3—C4	52.0 (3)	O2—C15—C16—C21	174.7 (3)
N2—C2—C3—C8	113.3 (2)	C14—C15—C16—C21	−6.7 (4)
C1—C2—C3—C8	−2.9 (2)	O2—C15—C16—C17	−3.9 (4)
C14—C2—C3—C8	−126.7 (2)	C14—C15—C16—C17	174.7 (2)
C8—C3—C4—C5	−1.3 (4)	C21—C16—C17—C18	−1.4 (4)
C2—C3—C4—C5	−179.9 (2)	C15—C16—C17—C18	177.3 (2)
C3—C4—C5—C6	0.1 (4)	C16—C17—C18—C19	−0.3 (4)
C4—C5—C6—C7	0.5 (4)	C17—C18—C19—C20	1.8 (5)
C5—C6—C7—C8	0.0 (4)	C17—C18—C19—Br1	−177.5 (2)
C6—C7—C8—C3	−1.3 (4)	C18—C19—C20—C21	−1.4 (5)
C6—C7—C8—N1	178.9 (2)	Br1—C19—C20—C21	177.8 (2)
C4—C3—C8—C7	1.9 (4)	C17—C16—C21—C20	1.7 (4)
C2—C3—C8—C7	−179.2 (2)	C15—C16—C21—C20	−176.8 (3)
C4—C3—C8—N1	−178.2 (2)	C19—C20—C21—C16	−0.4 (5)
C2—C3—C8—N1	0.7 (3)	C12—C13—C22—C23	−73.0 (3)
C1—N1—C8—C7	−177.9 (2)	C14—C13—C22—C23	45.8 (3)
C1—N1—C8—C3	2.2 (3)	C12—C13—C22—C27	104.4 (3)
C2—N2—C9—C10	144.5 (2)	C14—C13—C22—C27	−136.8 (2)
C12—N2—C9—C10	17.3 (3)	C27—C22—C23—C24	0.9 (4)
N2—C9—C10—C11	−34.6 (3)	C13—C22—C23—C24	178.4 (3)
C9—C10—C11—C12	38.6 (3)	C22—C23—C24—C25	−0.3 (5)
C9—N2—C12—C11	6.9 (3)	C23—C24—C25—C26	0.0 (6)
C2—N2—C12—C11	−124.8 (2)	C24—C25—C26—C27	−0.3 (5)
C9—N2—C12—C13	132.8 (2)	C25—C26—C27—C22	0.9 (5)
C2—N2—C12—C13	1.2 (2)	C25—C26—C27—Cl1	−178.2 (3)
C10—C11—C12—N2	−28.2 (3)	C23—C22—C27—C26	−1.2 (4)
C10—C11—C12—C13	−145.4 (2)	C13—C22—C27—C26	−178.7 (2)
N2—C12—C13—C22	150.6 (2)	C23—C22—C27—Cl1	177.9 (2)
C11—C12—C13—C22	−92.0 (3)	C13—C22—C27—Cl1	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2^i	0.93	2.60	3.292 (3)	132
C25—H25···O2^ii	0.93	2.61	3.327 (4)	134
N1—H1···N2^iii	0.86	2.36	3.198 (3)	164
C7—H7···O1^iii	0.93	2.47	3.235 (3)	139
C21—H21···O1	0.93	2.47	3.337 (3)	155

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