2-(2,6-Diisopropyl­phenyl­imino)-1-phenyl­propan-1-one

In the crystal structure of the title compound, C₂₀H₂₅NO, all bond lengths and angles show normal values. Non-classical hydrogen bonds are responsible for the deviation from a planar arrangement.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.144
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C19

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.60 Deg.
              H19  -N1   -C19     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.50 Deg.
              H16  -N1   -C16     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.20 Deg.
              H6   -N1   -C6      1.555   1.555   1.555

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COSMO/APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-(2,6-Diisopropylphenylimino)-1-phenylpropan-1-one

Crystal data

C21H25NO	F(000) = 664
Mr = 307.42	Dx = 1.114 Mg m^−3
Monoclinic, P21/n	Melting point: 362 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.9291 (4) Å	Cell parameters from 87 reflections
b = 18.5953 (6) Å	θ = 2.1–57.9°
c = 10.4394 (4) Å	µ = 0.07 mm^−1
β = 108.015 (2)°	T = 295 K
V = 1832.98 (12) Å^3	Block, yellow
Z = 4	0.26 × 0.24 × 0.15 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	Rint = 0.027
Graphite monochromator	θmax = 25.5°, θmin = 3°
φ and ω scans	h = −12→12
16097 measured reflections	k = −14→22
3408 independent reflections	l = −12→12
2508 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.2624P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.144	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.18 e Å^−3
3408 reflections	Δρmin = −0.17 e Å^−3
253 parameters

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.3268 (0.0067) x - 14.5879 (0.0085) y + 1.3560 (0.0088) z = 1.0192 (0.0051)

* -0.0017 (0.0012) C1 * 0.0004 (0.0013) C2 * 0.0015 (0.0014) C3 * -0.0020 (0.0015) C4 * 0.0007 (0.0016) C5 * 0.0011 (0.0014) C6

Rms deviation of fitted atoms = 0.0014

6.0108 (0.0071) x - 14.4760 (0.0120) y - 3.6009 (0.0087) z = 2.1547 (0.0069)

Angle to previous plane (with approximate e.s.d.) = 27.88 (0.09)

* 0.2294 (0.0009) N1 * -0.2607 (0.0011) C14 * 0.0049 (0.0011) C13 * 0.2317 (0.0013) C1 * -0.2053 (0.0008) C6

Rms deviation of fitted atoms = 0.2080

5.5970 (0.0067) x + 15.2876 (0.0086) y - 2.6116 (0.0085) z = 6.1495 (0.0053)

Angle to previous plane (with approximate e.s.d.) = 73.41 (0.05)

* 0.0092 (0.0011) C7 * -0.0095 (0.0012) C8 * 0.0025 (0.0015) C9 * 0.0051 (0.0017) C10 * -0.0055 (0.0015) C11 * -0.0018 (0.0012) C12

Rms deviation of fitted atoms = 0.0063

5.3268 (0.0067) x - 14.5879 (0.0085) y + 1.3560 (0.0088) z = 1.0192 (0.0051)

Angle to previous plane (with approximate e.s.d.) = 68.45 (0.05)

* -0.0017 (0.0012) C1 * 0.0004 (0.0013) C2 * 0.0015 (0.0014) C3 * -0.0020 (0.0015) C4 * 0.0007 (0.0016) C5 * 0.0011 (0.0014) C6

Rms deviation of fitted atoms = 0.0014

6.8547 (0.0070) x - 13.4493 (0.0128) y - 2.0630 (0.0308) z = 2.6831 (0.0082)

Angle to previous plane (with approximate e.s.d.) = 19.44 (0.15)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C13 * 0.0000 (0.0000) O1

Rms deviation of fitted atoms = 0.0000

6.7168 (0.0215) x - 13.6943 (0.0369) y - 2.2382 (0.0101) z = 2.5731 (0.0227)

Angle to previous plane (with approximate e.s.d.) = 1.68 (0.31)

* 0.0000 (0.0000) O1 * 0.0000 (0.0000) C13 * 0.0000 (0.0000) C14

Rms deviation of fitted atoms = 0.0000

9.0855 (0.0082) x - 6.7234 (0.0186) y - 4.7294 (0.0267) z = 5.6411 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 27.59 (0.23)

* 0.0000 (0.0000) N1 * 0.0000 (0.0000) C14 * 0.0000 (0.0000) C15

Rms deviation of fitted atoms = 0.0000

5.4294 (0.0055) x - 14.4150 (0.0059) y + 1.3749 (0.0088) z = 1.0681 (0.0048)

Angle to previous plane (with approximate e.s.d.) = 43.61 (0.10)

* 0.0241 (0.0013) C1 * 0.0160 (0.0014) C2 * -0.0033 (0.0014) C3 * -0.0176 (0.0016) C4 * -0.0052 (0.0016) C5 * 0.0158 (0.0016) C6 * -0.0298 (0.0010) C13

Rms deviation of fitted atoms = 0.0182

5.5010 (0.0040) x + 15.3933 (0.0049) y - 2.6648 (0.0070) z = 6.0506 (0.0039)

Angle to previous plane (with approximate e.s.d.) = 68.49 (0.03)

* 0.0305 (0.0013) C7 * -0.0071 (0.0015) C8 * -0.0090 (0.0018) C9 * -0.0023 (0.0017) C10 * 0.0055 (0.0018) C11 * 0.0240 (0.0015) C12 * -0.0317 (0.0012) C16 * -0.0100 (0.0012) C19

Rms deviation of fitted atoms = 0.0186

5.7575 (0.0179) x + 14.6435 (0.0501) y - 3.9458 (0.0589) z = 5.9245 (0.0056)

Angle to previous plane (with approximate e.s.d.) = 7.44 (0.34)

* 0.0446 (0.0042) N1 * -0.0122 (0.0031) C7 * -0.0470 (0.0020) C8 * 0.1185 (0.0075) C19 * -0.1039 (0.0073) H19

Rms deviation of fitted atoms = 0.0764

6.1041 (0.0394) x + 14.6283 (0.0520) y - 2.5476 (0.0321) z = 6.4313 (0.0295)

Angle to previous plane (with approximate e.s.d.) = 8.96 (0.54)

* -0.0895 (0.0041) N1 * 0.0761 (0.0033) C7 * 0.0180 (0.0022) C12 * -0.1584 (0.0076) C16 * 0.1537 (0.0069) H16

Rms deviation of fitted atoms = 0.1121

3.6408 (0.0562) x + 10.8278 (0.1204) y - 8.3873 (0.0551) z = 3.2404 (0.0488)

Angle to previous plane (with approximate e.s.d.) = 43.56 (0.54)

* 0.0000 (0.0000) H6 * 0.0000 (0.0000) H16 * 0.0000 (0.0000) H19 0.2689 (0.0116) N1

Rms deviation of fitted atoms = 0.0000

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

	x	y	z	Uiso*/Ueq
C1	0.56434 (16)	0.11813 (8)	−0.19561 (14)	0.0511 (4)
C2	0.5313 (2)	0.09365 (10)	−0.32760 (17)	0.0633 (5)
C3	0.4192 (2)	0.04776 (11)	−0.3804 (2)	0.0743 (5)
C4	0.3378 (2)	0.02542 (11)	−0.3035 (2)	0.0767 (6)
C5	0.3686 (2)	0.04856 (13)	−0.1734 (2)	0.0831 (6)
C6	0.48157 (19)	0.09486 (11)	−0.11884 (18)	0.0693 (5)
C7	0.83502 (16)	0.13476 (8)	0.22014 (14)	0.0503 (4)
C8	0.96145 (17)	0.09514 (9)	0.26640 (15)	0.0589 (4)
C9	1.0303 (2)	0.09418 (13)	0.40382 (19)	0.0793 (6)
C10	0.9765 (3)	0.12916 (14)	0.4921 (2)	0.0894 (7)
C11	0.8514 (3)	0.16644 (12)	0.44635 (18)	0.0794 (6)
C12	0.77725 (18)	0.17041 (9)	0.30926 (16)	0.0602 (4)
C13	0.68192 (17)	0.17072 (9)	−0.14777 (15)	0.0564 (4)
C14	0.75702 (16)	0.18324 (8)	0.00103 (15)	0.0502 (4)
C15	0.8287 (2)	0.25414 (10)	0.03802 (18)	0.0723 (5)
H15A	0.8796	0.2547	0.1326	0.109*
H15B	0.7591	0.2918	0.0176	0.109*
H15C	0.8937	0.2616	−0.0124	0.109*
C16	0.6356 (2)	0.20911 (10)	0.2613 (2)	0.0677 (5)
C17	0.6302 (3)	0.27779 (13)	0.3381 (3)	0.1089 (8)
H17A	0.6413	0.2664	0.4305	0.163*
H17B	0.5406	0.3011	0.2988	0.163*
H17C	0.7052	0.3093	0.3337	0.163*
C18	0.5157 (2)	0.15936 (13)	0.2666 (3)	0.0904 (6)
H18A	0.5172	0.1168	0.215	0.136*
H18B	0.4267	0.1836	0.2296	0.136*
H18C	0.5276	0.1463	0.3584	0.136*
C19	1.0233 (2)	0.05618 (11)	0.17015 (19)	0.0697 (5)
C20	1.1397 (4)	0.09917 (19)	0.1450 (4)	0.1522 (14)
H20A	1.1031	0.1448	0.1065	0.228*
H20B	1.1773	0.0736	0.0838	0.228*
H20C	1.2134	0.1068	0.2285	0.228*
C21	1.0740 (4)	−0.01929 (15)	0.2174 (3)	0.1255 (10)
H21A	1.1056	−0.0428	0.15	0.188*
H21B	0.9975	−0.0462	0.232	0.188*
H21C	1.1508	−0.0165	0.3	0.188*
N1	0.75912 (12)	0.13066 (7)	0.07980 (12)	0.0496 (3)
O1	0.72381 (16)	0.20434 (9)	−0.22773 (13)	0.0935 (5)
H2	0.589 (2)	0.1088 (10)	−0.3782 (19)	0.074 (6)*
H3	0.398 (2)	0.0304 (11)	−0.472 (2)	0.094 (7)*
H4	0.255 (2)	−0.0091 (13)	−0.343 (2)	0.095 (6)*
H5	0.316 (2)	0.0329 (12)	−0.118 (2)	0.098 (7)*
H6	0.503 (2)	0.1090 (9)	−0.0274 (19)	0.074 (5)*
H9	1.118 (2)	0.0656 (11)	0.436 (2)	0.088 (6)*
H10	1.024 (3)	0.1304 (12)	0.584 (2)	0.107 (7)*
H11	0.809 (2)	0.1909 (10)	0.511 (2)	0.082 (6)*
H16	0.6167 (19)	0.2221 (10)	0.1681 (19)	0.074 (5)*
H19	0.946 (2)	0.0494 (10)	0.088 (2)	0.075 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0472 (8)	0.0543 (9)	0.0468 (8)	0.0052 (7)	0.0070 (6)	0.0062 (6)
C2	0.0596 (10)	0.0722 (11)	0.0555 (9)	0.0065 (9)	0.0139 (8)	0.0010 (8)
C3	0.0720 (12)	0.0732 (12)	0.0660 (11)	0.0054 (10)	0.0041 (10)	−0.0146 (10)
C4	0.0661 (11)	0.0663 (12)	0.0813 (13)	−0.0082 (10)	−0.0010 (10)	0.0010 (10)
C5	0.0619 (11)	0.1046 (16)	0.0769 (13)	−0.0225 (11)	0.0130 (10)	0.0124 (12)
C6	0.0576 (10)	0.0929 (14)	0.0544 (10)	−0.0142 (10)	0.0127 (8)	0.0008 (9)
C7	0.0485 (8)	0.0553 (9)	0.0453 (8)	−0.0095 (7)	0.0118 (6)	0.0014 (6)
C8	0.0498 (9)	0.0716 (11)	0.0516 (9)	−0.0049 (8)	0.0102 (7)	0.0066 (8)
C9	0.0624 (12)	0.1085 (16)	0.0576 (10)	0.0029 (11)	0.0048 (9)	0.0108 (11)
C10	0.0873 (15)	0.1228 (19)	0.0463 (10)	−0.0015 (14)	0.0031 (10)	0.0016 (11)
C11	0.0929 (15)	0.0952 (15)	0.0531 (10)	−0.0084 (12)	0.0270 (10)	−0.0064 (10)
C12	0.0650 (10)	0.0630 (10)	0.0543 (9)	−0.0086 (8)	0.0210 (8)	−0.0003 (8)
C13	0.0551 (9)	0.0621 (10)	0.0512 (8)	−0.0009 (8)	0.0151 (7)	0.0097 (7)
C14	0.0461 (8)	0.0545 (9)	0.0509 (8)	−0.0033 (7)	0.0160 (6)	0.0017 (7)
C15	0.0851 (13)	0.0628 (11)	0.0691 (11)	−0.0209 (10)	0.0236 (9)	0.0016 (9)
C16	0.0764 (12)	0.0676 (11)	0.0673 (11)	0.0048 (9)	0.0339 (9)	0.0019 (9)
C17	0.132 (2)	0.0755 (14)	0.130 (2)	0.0062 (14)	0.0555 (17)	−0.0173 (14)
C18	0.0723 (13)	0.0877 (14)	0.1193 (17)	0.0016 (11)	0.0414 (12)	0.0031 (13)
C19	0.0571 (10)	0.0883 (13)	0.0625 (11)	0.0092 (10)	0.0167 (9)	0.0074 (10)
C20	0.160 (3)	0.150 (3)	0.203 (3)	−0.037 (2)	0.137 (3)	−0.026 (2)
C21	0.162 (3)	0.108 (2)	0.1092 (19)	0.0549 (19)	0.0470 (19)	0.0141 (15)
N1	0.0446 (7)	0.0551 (8)	0.0464 (7)	−0.0036 (6)	0.0101 (5)	0.0019 (6)
O1	0.1037 (11)	0.1158 (11)	0.0583 (7)	−0.0427 (9)	0.0210 (7)	0.0164 (7)

Geometric parameters (Å, º)

C1—C6	1.383 (2)	C13—C14	1.519 (2)
C1—C2	1.391 (2)	C14—N1	1.2735 (19)
C1—C13	1.486 (2)	C14—C15	1.491 (2)
C2—C3	1.375 (3)	C15—H15A	0.96
C2—H2	0.93 (2)	C15—H15B	0.96
C3—C4	1.368 (3)	C15—H15C	0.96
C3—H3	0.97 (2)	C16—C17	1.518 (3)
C4—C5	1.366 (3)	C16—C18	1.522 (3)
C4—H4	1.02 (2)	C16—N1	2.943 (2)
C5—C6	1.389 (3)	C16—H16	0.963 (19)
C5—H5	0.93 (2)	C17—H17A	0.96
C6—N1	2.967 (2)	C17—H17B	0.96
C6—H6	0.949 (18)	C17—H17C	0.96
C7—C12	1.401 (2)	C18—H18A	0.96
C7—C8	1.406 (2)	C18—H18B	0.96
C7—N1	1.4274 (18)	C18—H18C	0.96
C8—C9	1.385 (2)	C19—C20	1.493 (3)
C8—C19	1.514 (2)	C19—C21	1.521 (3)
C9—C10	1.365 (3)	C19—N1	2.856 (2)
C9—H9	0.99 (2)	C19—H19	0.97 (2)
C10—C11	1.372 (3)	C20—H20A	0.96
C10—H10	0.93 (2)	C20—H20B	0.96
C11—C12	1.394 (2)	C20—H20C	0.96
C11—H11	1.01 (2)	C21—H21A	0.96
C12—C16	1.520 (3)	C21—H21B	0.96
C13—O1	1.2147 (19)	C21—H21C	0.96
C6—C1—C2	118.12 (16)	C16—C17—H17B	109.5
C6—C1—C13	123.86 (14)	H17A—C17—H17B	109.5
C2—C1—C13	117.95 (14)	C16—C17—H17C	109.5
C3—C2—C1	120.95 (18)	H17A—C17—H17C	109.5
C3—C2—H2	121.4 (12)	H17B—C17—H17C	109.5
C1—C2—H2	117.6 (12)	C16—C18—H18A	109.5
C4—C3—C2	120.31 (19)	C16—C18—H18B	109.5
C4—C3—H3	119.4 (13)	H18A—C18—H18B	109.5
C2—C3—H3	120.2 (13)	C16—C18—H18C	109.5
C5—C4—C3	119.78 (19)	H18A—C18—H18C	109.5
C5—C4—H4	120.1 (12)	H18B—C18—H18C	109.5
C3—C4—H4	120.1 (11)	C20—C19—C8	110.80 (19)
C4—C5—C6	120.5 (2)	C20—C19—C21	110.8 (2)
C4—C5—H5	121.3 (14)	C8—C19—C21	112.81 (16)
C6—C5—H5	118.3 (14)	C20—C19—N1	111.33 (19)
C1—C6—C5	120.38 (18)	C8—C19—N1	57.83 (9)
C1—C6—N1	75.21 (10)	C21—C19—N1	137.10 (17)
C5—C6—N1	152.08 (15)	C20—C19—H19	111.2 (11)
C1—C6—H6	120.6 (11)	C8—C19—H19	106.0 (11)
C5—C6—H6	118.9 (11)	C21—C19—H19	105.1 (11)
N1—C6—H6	50.6 (11)	N1—C19—H19	51.1 (11)
C12—C7—C8	121.67 (14)	C19—C20—H20A	109.5
C12—C7—N1	120.80 (14)	C19—C20—H20B	109.5
C8—C7—N1	117.17 (13)	H20A—C20—H20B	109.5
C9—C8—C7	117.70 (17)	C19—C20—H20C	109.5
C9—C8—C19	120.61 (16)	H20A—C20—H20C	109.5
C7—C8—C19	121.67 (14)	H20B—C20—H20C	109.5
C10—C9—C8	121.5 (2)	C19—C21—H21A	109.5
C10—C9—H9	120.9 (12)	C19—C21—H21B	109.5
C8—C9—H9	117.6 (12)	H21A—C21—H21B	109.5
C9—C10—C11	120.44 (18)	C19—C21—H21C	109.5
C9—C10—H10	121.8 (15)	H21A—C21—H21C	109.5
C11—C10—H10	117.7 (15)	H21B—C21—H21C	109.5
C10—C11—C12	121.19 (19)	C14—N1—C7	121.32 (13)
C10—C11—H11	121.2 (11)	C14—N1—H19	111.6 (4)
C12—C11—H11	117.6 (11)	C7—N1—H19	80.7 (5)
C11—C12—C7	117.49 (17)	C14—N1—H6	91.4 (4)
C11—C12—C16	120.28 (16)	C7—N1—H6	128.0 (4)
C7—C12—C16	122.16 (14)	H19—N1—H6	126.5 (6)
O1—C13—C1	120.54 (14)	C14—N1—H16	79.7 (4)
O1—C13—C14	117.38 (15)	C7—N1—H16	76.7 (4)
C1—C13—C14	122.06 (13)	H19—N1—H16	157.4 (6)
N1—C14—C15	126.89 (14)	H6—N1—H16	70.5 (6)
N1—C14—C13	116.59 (14)	C14—N1—C19	114.55 (10)
C15—C14—C13	116.38 (13)	C7—N1—C19	63.09 (8)
C14—C15—H15A	109.5	H19—N1—C19	18.6 (5)
C14—C15—H15B	109.5	H6—N1—C19	141.3 (4)
H15A—C15—H15B	109.5	H16—N1—C19	139.2 (4)
C14—C15—H15C	109.5	C14—N1—C16	96.22 (10)
H15A—C15—H15C	109.5	C7—N1—C16	60.37 (9)
H15B—C15—H15C	109.5	H19—N1—C16	140.3 (5)
C17—C16—C12	113.87 (18)	H6—N1—C16	78.3 (4)
C17—C16—C18	109.66 (18)	H16—N1—C16	18.5 (4)
C12—C16—C18	110.76 (16)	C19—N1—C16	123.43 (7)
C17—C16—N1	147.92 (15)	C14—N1—C6	83.96 (9)
C12—C16—N1	56.63 (8)	C7—N1—C6	144.17 (9)
C18—C16—N1	102.02 (12)	H19—N1—C6	115.3 (5)
C17—C16—H16	107.2 (11)	H6—N1—C6	17.2 (4)
C12—C16—H16	108.8 (11)	H16—N1—C6	84.5 (4)
C18—C16—H16	106.2 (11)	C19—N1—C6	132.97 (7)
N1—C16—H16	57.6 (11)	C16—N1—C6	94.54 (7)
C16—C17—H17A	109.5
C6—C1—C2—C3	0.2 (3)	C12—C7—N1—H16	10.8 (4)
C13—C1—C2—C3	−176.73 (16)	C8—C7—N1—H16	−175.9 (4)
C1—C2—C3—C4	0.1 (3)	C12—C7—N1—C19	−176.45 (16)
C2—C3—C4—C5	−0.4 (3)	C8—C7—N1—C19	−3.24 (11)
C3—C4—C5—C6	0.3 (3)	C12—C7—N1—C16	1.42 (12)
C2—C1—C6—C5	−0.2 (3)	C8—C7—N1—C16	174.63 (16)
C13—C1—C6—C5	176.46 (17)	C12—C7—N1—C6	−49.4 (2)
C2—C1—C6—N1	154.52 (15)	C8—C7—N1—C6	123.83 (17)
C13—C1—C6—N1	−28.77 (15)	C20—C19—N1—C14	15.5 (2)
C4—C5—C6—C1	0.0 (3)	C8—C19—N1—C14	117.31 (14)
C4—C5—C6—N1	−118.3 (3)	C21—C19—N1—C14	−152.9 (2)
C12—C7—C8—C9	−2.0 (2)	C20—C19—N1—C7	−98.7 (2)
N1—C7—C8—C9	−175.11 (15)	C8—C19—N1—C7	3.16 (11)
C12—C7—C8—C19	179.56 (15)	C21—C19—N1—C7	92.9 (2)
N1—C7—C8—C19	6.4 (2)	C20—C19—N1—H19	100.6 (14)
C7—C8—C9—C10	1.3 (3)	C8—C19—N1—H19	−157.6 (14)
C19—C8—C9—C10	179.8 (2)	C21—C19—N1—H19	−67.9 (14)
C8—C9—C10—C11	0.1 (4)	C20—C19—N1—H6	143.3 (7)
C9—C10—C11—C12	−0.8 (4)	C8—C19—N1—H6	−114.9 (7)
C10—C11—C12—C7	0.2 (3)	C21—C19—N1—H6	−25.1 (7)
C10—C11—C12—C16	177.2 (2)	C20—C19—N1—H16	−87.8 (7)
C8—C7—C12—C11	1.2 (2)	C8—C19—N1—H16	14.1 (7)
N1—C7—C12—C11	174.14 (15)	C21—C19—N1—H16	103.8 (7)
C8—C7—C12—C16	−175.72 (15)	C20—C19—N1—C16	−100.87 (18)
N1—C7—C12—C16	−2.8 (2)	C8—C19—N1—C16	0.94 (13)
C6—C1—C13—O1	−158.94 (18)	C21—C19—N1—C16	90.7 (2)
C2—C1—C13—O1	17.8 (2)	C20—C19—N1—C6	121.01 (18)
C6—C1—C13—C14	22.8 (2)	C8—C19—N1—C6	−137.18 (12)
C2—C1—C13—C14	−160.47 (15)	C21—C19—N1—C6	−47.4 (2)
O1—C13—C14—N1	−150.67 (17)	C17—C16—N1—C14	−42.0 (3)
C1—C13—C14—N1	27.6 (2)	C12—C16—N1—C14	−124.01 (13)
O1—C13—C14—C15	25.3 (2)	C18—C16—N1—C14	128.91 (15)
C1—C13—C14—C15	−156.36 (16)	C17—C16—N1—C7	80.7 (3)
C11—C12—C16—C17	39.6 (2)	C12—C16—N1—C7	−1.35 (11)
C7—C12—C16—C17	−143.48 (19)	C18—C16—N1—C7	−108.43 (15)
C11—C12—C16—C18	−84.5 (2)	C17—C16—N1—H19	93.5 (8)
C7—C12—C16—C18	92.4 (2)	C12—C16—N1—H19	11.4 (7)
C11—C12—C16—N1	−175.47 (19)	C18—C16—N1—H19	−95.7 (7)
C7—C12—C16—N1	1.41 (12)	C17—C16—N1—H6	−132.1 (5)
C9—C8—C19—C20	−79.0 (3)	C12—C16—N1—H6	145.9 (4)
C7—C8—C19—C20	99.4 (3)	C18—C16—N1—H6	38.8 (4)
C9—C8—C19—C21	45.8 (3)	C17—C16—N1—H16	−69.2 (13)
C7—C8—C19—C21	−135.8 (2)	C12—C16—N1—H16	−151.2 (13)
C9—C8—C19—N1	178.2 (2)	C18—C16—N1—H16	101.7 (13)
C7—C8—C19—N1	−3.37 (12)	C17—C16—N1—C19	83.0 (3)
C15—C14—N1—C7	0.1 (2)	C12—C16—N1—C19	0.93 (13)
C13—C14—N1—C7	175.62 (13)	C18—C16—N1—C19	−106.16 (14)
C15—C14—N1—H19	−92.1 (5)	C17—C16—N1—C6	−126.4 (3)
C13—C14—N1—H19	83.4 (5)	C12—C16—N1—C6	151.59 (11)
C15—C14—N1—H6	137.4 (4)	C18—C16—N1—C6	44.50 (14)
C13—C14—N1—H6	−47.1 (4)	C1—C6—N1—C14	38.99 (13)
C15—C14—N1—H16	67.5 (4)	C5—C6—N1—C14	167.2 (3)
C13—C14—N1—H16	−116.9 (4)	C1—C6—N1—C7	177.29 (18)
C15—C14—N1—C19	−72.20 (19)	C5—C6—N1—C7	−54.5 (4)
C13—C14—N1—C19	103.35 (13)	C1—C6—N1—H19	−72.1 (5)
C15—C14—N1—C16	59.02 (18)	C5—C6—N1—H19	56.1 (6)
C13—C14—N1—C16	−125.43 (12)	C1—C6—N1—H6	154.0 (14)
C15—C14—N1—C6	152.96 (17)	C5—C6—N1—H6	−77.8 (14)
C13—C14—N1—C6	−31.50 (13)	C1—C6—N1—H16	119.2 (5)
C12—C7—N1—C14	79.87 (19)	C5—C6—N1—H16	−112.5 (6)
C8—C7—N1—C14	−106.92 (17)	C1—C6—N1—C19	−79.20 (13)
C12—C7—N1—H19	−170.4 (5)	C5—C6—N1—C19	49.0 (4)
C8—C7—N1—H19	2.8 (5)	C1—C6—N1—C16	134.78 (11)
C12—C7—N1—H6	−40.8 (6)	C5—C6—N1—C16	−97.0 (3)
C8—C7—N1—H6	132.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.95 (2)	2.47 (2)	2.967 (2)	112.3 (15)
C16—H16···N1	0.96 (2)	2.56 (2)	2.943 (2)	103.9 (13)
C19—H19···N1	0.97 (2)	2.37 (2)	2.856 (2)	110.3 (14)