2-(2,6-Diiso­propyl­phenyl­amino)­cyclo­hex-1-enyl phenyl ketone

The two independent mol­ecules of the title compound, C₂₅H₃₁NO, are linked by a pair of weak hydrogen bonds across a non-crystallographic inversion center in the monoclinic space group Cc.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.130
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C23'

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.87 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C4'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C20'
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.10
           From the CIF: _reflns_number_total               4703
           Count of symmetry unique reflns         4766
           Completeness (_total/calc)             98.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-(2,6-Diisopropylphenylamino)cyclohex-1-enyl phenyl ketone

Crystal data

C25H31NO	F(000) = 1568
Mr = 361.51	Dx = 1.114 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 946 reflections
a = 9.815 (1) Å	θ = 1.7–27.1°
b = 23.404 (3) Å	µ = 0.07 mm^−1
c = 18.777 (2) Å	T = 295 K
β = 92.002 (2)°	Block, pale yellow
V = 4310.5 (9) Å^3	0.50 × 0.48 × 0.45 mm
Z = 8

Data collection

Bruker SMART area-detector diffractometer	4021 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.1°, θmin = 1.7°
φ and ω scans	h = −12→12
13505 measured reflections	k = −29→30
4703 independent reflections	l = −23→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 0.6097P] where P = (Fo^2 + 2Fc^2)/3
4703 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.27 e Å^−3
2 restraints	Δρmin = −0.14 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.6324 (2)	0.1091 (1)	0.5000 (1)	0.0592 (5)
N1	0.5818 (2)	0.2084 (1)	0.5550 (1)	0.0430 (4)
C1	0.4662 (3)	0.0775 (1)	0.3394 (2)	0.0609 (7)
C2	0.4412 (4)	0.0330 (2)	0.2927 (2)	0.0755 (9)
C3	0.4381 (4)	−0.0222 (2)	0.3175 (2)	0.085 (1)
C4	0.4646 (4)	−0.0331 (1)	0.3880 (2)	0.081 (1)
C5	0.4918 (3)	0.0116 (1)	0.4355 (2)	0.0604 (7)
C6	0.4911 (2)	0.0671 (1)	0.4114 (1)	0.0444 (5)
C7	0.5245 (2)	0.1143 (1)	0.4638 (1)	0.0417 (5)
C8	0.4319 (2)	0.1612 (1)	0.4705 (1)	0.0401 (5)
C9	0.2931 (3)	0.1589 (1)	0.4315 (2)	0.0544 (6)
C10	0.1886 (3)	0.1970 (1)	0.4637 (2)	0.0685 (8)
C11	0.2444 (3)	0.2554 (1)	0.4758 (2)	0.0712 (9)
C12	0.3675 (3)	0.2553 (1)	0.5266 (2)	0.0545 (6)
C13	0.4642 (2)	0.2062 (1)	0.5161 (1)	0.0395 (4)
C14	0.6008 (3)	0.2521 (1)	0.6731 (1)	0.0501 (6)
C15	0.6490 (3)	0.2966 (1)	0.7162 (2)	0.0641 (7)
C16	0.7164 (3)	0.3421 (1)	0.6880 (2)	0.0697 (8)
C17	0.7376 (3)	0.3449 (1)	0.6163 (2)	0.0611 (7)
C18	0.6916 (2)	0.3014 (1)	0.5706 (1)	0.0487 (5)
C19	0.6245 (2)	0.2552 (1)	0.6001 (1)	0.0416 (5)
C20	0.5304 (3)	0.2009 (1)	0.7051 (2)	0.0644 (7)
C21	0.6344 (5)	0.1585 (2)	0.7328 (3)	0.131 (2)
C22	0.4288 (6)	0.2182 (3)	0.7599 (3)	0.134 (2)
C23	0.7184 (3)	0.3043 (1)	0.4917 (2)	0.0601 (7)
C24	0.6962 (5)	0.3647 (2)	0.4606 (2)	0.094 (1)
C25	0.8592 (5)	0.2832 (3)	0.4774 (2)	0.130 (2)
O1'	0.8732 (2)	0.1517 (1)	0.5914 (1)	0.0667 (6)
N1'	0.9261 (2)	0.0532 (1)	0.5329 (1)	0.0476 (5)
C1'	1.0077 (4)	0.1697 (2)	0.7575 (2)	0.0719 (8)
C2'	1.0262 (4)	0.2089 (2)	0.8121 (2)	0.088 (1)
C3'	1.0500 (4)	0.2641 (2)	0.7975 (2)	0.093 (1)
C4'	1.0507 (5)	0.2824 (2)	0.7290 (3)	0.098 (1)
C5'	1.0275 (4)	0.2441 (1)	0.6725 (2)	0.0720 (8)
C6'	1.0079 (2)	0.1873 (1)	0.6873 (1)	0.0494 (5)
C7'	0.9796 (2)	0.1452 (1)	0.6278 (1)	0.0470 (5)
C8'	1.0756 (2)	0.0999 (1)	0.6173 (1)	0.0448 (5)
C9'	1.2146 (3)	0.1030 (1)	0.6564 (2)	0.0562 (6)
C10'	1.3203 (3)	0.0662 (1)	0.6221 (2)	0.0571 (6)
C11'	1.2652 (3)	0.0069 (1)	0.6107 (2)	0.0597 (7)
C12'	1.1436 (3)	0.0078 (1)	0.5582 (2)	0.0557 (6)
C13'	1.0448 (2)	0.0560 (1)	0.5709 (1)	0.0426 (5)
C14'	0.8819 (2)	0.0048 (1)	0.4911 (1)	0.0441 (5)
C15'	0.8973 (3)	0.0056 (1)	0.4177 (1)	0.0524 (6)
C16'	0.8487 (3)	−0.0407 (1)	0.3788 (2)	0.0659 (7)
C17'	0.7894 (3)	−0.0862 (1)	0.4110 (2)	0.0690 (8)
C18'	0.7773 (3)	−0.0870 (1)	0.4835 (2)	0.0612 (7)
C19'	0.8223 (2)	−0.0415 (1)	0.5259 (1)	0.0487 (5)
C20'	0.9644 (3)	0.0559 (2)	0.3818 (2)	0.0701 (8)
C21'	0.8591 (5)	0.0993 (2)	0.3560 (3)	0.103 (1)
C22'	1.0555 (5)	0.0390 (3)	0.3226 (3)	0.123 (2)
C23'	0.8084 (3)	−0.0427 (1)	0.6059 (2)	0.0620 (7)
C24'	0.8283 (7)	−0.1019 (2)	0.6373 (2)	0.114 (2)
C25'	0.6744 (6)	−0.0157 (3)	0.6262 (2)	0.128 (2)
H1n	0.6351	0.1799	0.5528	0.052*
H1	0.4663	0.1149	0.3225	0.073*
H2	0.4265	0.0403	0.2444	0.091*
H3	0.4180	−0.0521	0.2863	0.103*
H4	0.4644	−0.0705	0.4045	0.097*
H5	0.5105	0.0039	0.4834	0.073*
H9a	0.3038	0.1700	0.3822	0.065*
H9b	0.2600	0.1199	0.4317	0.065*
H10a	0.1085	0.1990	0.4320	0.082*
H10b	0.1613	0.1809	0.5086	0.082*
H11a	0.1741	0.2794	0.4950	0.085*
H11b	0.2697	0.2715	0.4306	0.085*
H12a	0.4167	0.2908	0.5209	0.065*
H12b	0.3363	0.2540	0.5750	0.065*
H15	0.6351	0.2955	0.7649	0.077*
H16	0.7480	0.3714	0.7177	0.084*
H17	0.7832	0.3761	0.5978	0.073*
H20	0.4786	0.1821	0.6661	0.077*
H21a	0.6955	0.1491	0.6957	0.197*
H21b	0.5889	0.1244	0.7479	0.197*
H21c	0.6850	0.1747	0.7725	0.197*
H22a	0.3659	0.2455	0.7393	0.201*
H22b	0.4763	0.2350	0.8002	0.201*
H22c	0.3798	0.1851	0.7750	0.201*
H23	0.6534	0.2786	0.4671	0.072*
H24a	0.7129	0.3642	0.4105	0.140*
H24b	0.7578	0.3910	0.4842	0.140*
H24c	0.6040	0.3765	0.4677	0.140*
H25a	0.8702	0.2451	0.4958	0.195*
H25b	0.9253	0.3080	0.5002	0.195*
H25c	0.8721	0.2829	0.4269	0.195*
H1'n	0.8736	0.0820	0.5338	0.057*
H1'	0.9951	0.1313	0.7681	0.086*
H2'	1.0222	0.1969	0.8592	0.106*
H3'	1.0660	0.2899	0.8345	0.111*
H4'	1.0668	0.3208	0.7194	0.118*
H5'	1.0254	0.2570	0.6257	0.086*
H9'a	1.2457	0.1424	0.6570	0.067*
H9'b	1.2050	0.0909	0.7053	0.067*
H10c	1.3440	0.0826	0.5767	0.068*
H10d	1.4021	0.0647	0.6525	0.068*
H11c	1.2376	−0.0088	0.6558	0.072*
H11d	1.3360	−0.0175	0.5925	0.072*
H12c	1.1766	0.0110	0.5103	0.067*
H12d	1.0954	−0.0283	0.5613	0.067*
H16'	0.8565	−0.0408	0.3296	0.079*
H17'	0.7572	−0.1168	0.3836	0.083*
H18'	0.7381	−0.1186	0.5048	0.073*
H20'	1.0222	0.0749	0.4183	0.084*
H21d	0.9039	0.1304	0.3330	0.155*
H21e	0.8108	0.1136	0.3959	0.155*
H21f	0.7959	0.0815	0.3227	0.155*
H22d	1.0937	0.0726	0.3019	0.184*
H22e	1.0033	0.0185	0.2867	0.184*
H22f	1.1277	0.0150	0.3413	0.184*
H23'	0.8814	−0.0186	0.6264	0.074*
H24d	0.9138	−0.1172	0.6229	0.171*
H24e	0.7555	−0.1264	0.6205	0.171*
H24f	0.8282	−0.0997	0.6883	0.171*
H25d	0.6676	−0.0164	0.6771	0.192*
H25e	0.5999	−0.0367	0.6046	0.192*
H25f	0.6710	0.0232	0.6098	0.192*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.055 (1)	0.055 (1)	0.066 (1)	0.015 (1)	−0.021 (1)	−0.019 (1)
N1	0.044 (1)	0.039 (1)	0.045 (1)	0.004 (1)	−0.006 (1)	−0.009 (1)
C1	0.070 (2)	0.064 (2)	0.049 (1)	0.001 (1)	−0.002 (1)	−0.009 (1)
C2	0.074 (2)	0.091 (2)	0.060 (2)	0.011 (2)	−0.013 (2)	−0.031 (2)
C3	0.072 (2)	0.079 (2)	0.104 (3)	0.013 (2)	−0.022 (2)	−0.053 (2)
C4	0.077 (2)	0.044 (1)	0.119 (3)	0.001 (1)	−0.009 (2)	−0.022 (2)
C5	0.065 (2)	0.049 (1)	0.067 (2)	0.002 (1)	−0.004 (1)	−0.004 (1)
C6	0.041 (1)	0.045 (1)	0.047 (1)	0.000 (1)	−0.002 (1)	−0.011 (1)
C7	0.045 (1)	0.042 (1)	0.038 (1)	−0.001 (1)	−0.004 (1)	−0.006 (1)
C8	0.040 (1)	0.039 (1)	0.041 (1)	−0.002 (1)	−0.003 (1)	−0.003 (1)
C9	0.046 (1)	0.055 (1)	0.060 (2)	0.002 (1)	−0.013 (1)	−0.008 (1)
C10	0.048 (1)	0.066 (2)	0.090 (2)	0.005 (1)	−0.013 (1)	−0.011 (2)
C11	0.051 (2)	0.054 (2)	0.107 (3)	0.012 (1)	−0.016 (2)	−0.012 (2)
C12	0.048 (1)	0.046 (1)	0.069 (2)	0.006 (1)	−0.003 (1)	−0.013 (1)
C13	0.039 (1)	0.040 (1)	0.040 (1)	−0.001 (1)	0.001 (1)	−0.001 (1)
C14	0.046 (1)	0.055 (1)	0.049 (1)	−0.003 (1)	−0.002 (1)	−0.011 (1)
C15	0.064 (2)	0.079 (2)	0.049 (2)	−0.009 (1)	0.001 (1)	−0.024 (1)
C16	0.072 (2)	0.063 (2)	0.074 (2)	−0.014 (1)	−0.004 (2)	−0.032 (2)
C17	0.062 (2)	0.046 (1)	0.076 (2)	−0.012 (1)	0.001 (1)	−0.009 (1)
C18	0.044 (1)	0.048 (1)	0.054 (1)	0.002 (1)	−0.002 (1)	−0.005 (1)
C19	0.038 (1)	0.042 (1)	0.045 (1)	0.001 (1)	−0.004 (1)	−0.010 (1)
C20	0.062 (2)	0.084 (2)	0.048 (2)	−0.023 (1)	0.000 (1)	−0.004 (1)
C21	0.097 (3)	0.129 (4)	0.167 (5)	−0.029 (3)	−0.018 (3)	0.083 (4)
C22	0.127 (4)	0.173 (5)	0.106 (3)	−0.074 (4)	0.064 (3)	−0.046 (3)
C23	0.065 (2)	0.060 (2)	0.055 (2)	−0.002 (1)	0.001 (1)	0.006 (1)
C24	0.121 (3)	0.071 (2)	0.088 (3)	−0.015 (2)	−0.001 (2)	0.021 (2)
C25	0.112 (4)	0.207 (6)	0.073 (3)	0.073 (4)	0.037 (2)	0.029 (3)
O1'	0.063 (1)	0.063 (1)	0.072 (1)	0.019 (1)	−0.027 (1)	−0.022 (1)
N1'	0.044 (1)	0.044 (1)	0.054 (1)	0.006 (1)	−0.012 (1)	−0.010 (1)
C1'	0.081 (2)	0.081 (2)	0.053 (2)	0.001 (2)	−0.007 (1)	−0.003 (2)
C2'	0.095 (3)	0.117 (3)	0.052 (2)	0.022 (2)	−0.009 (2)	−0.019 (2)
C3'	0.100 (3)	0.099 (3)	0.077 (2)	0.030 (2)	−0.026 (2)	−0.046 (2)
C4'	0.124 (3)	0.059 (2)	0.110 (3)	0.013 (2)	−0.008 (3)	−0.028 (2)
C5'	0.096 (2)	0.055 (2)	0.065 (2)	0.006 (2)	−0.001 (2)	−0.010 (1)
C6'	0.045 (1)	0.055 (1)	0.049 (1)	0.007 (1)	−0.005 (1)	−0.011 (1)
C7'	0.047 (1)	0.046 (1)	0.047 (1)	0.000 (1)	−0.005 (1)	−0.005 (1)
C8'	0.042 (1)	0.048 (1)	0.045 (1)	0.001 (1)	−0.007 (1)	−0.001 (1)
C9'	0.046 (1)	0.061 (1)	0.060 (2)	0.001 (1)	−0.014 (1)	−0.012 (1)
C10'	0.040 (1)	0.062 (2)	0.068 (2)	0.000 (1)	−0.009 (1)	0.001 (1)
C11'	0.047 (1)	0.056 (1)	0.076 (2)	0.008 (1)	−0.010 (1)	−0.002 (1)
C12'	0.050 (1)	0.051 (1)	0.065 (2)	0.008 (1)	−0.010 (1)	−0.010 (1)
C13'	0.042 (1)	0.043 (1)	0.042 (1)	0.001 (1)	−0.003 (1)	0.001 (1)
C14'	0.040 (1)	0.045 (1)	0.047 (1)	0.004 (1)	−0.006 (1)	−0.010 (1)
C15'	0.044 (1)	0.065 (2)	0.048 (1)	0.001 (1)	−0.001 (1)	−0.005 (1)
C16'	0.067 (2)	0.081 (2)	0.050 (2)	0.003 (2)	−0.001 (1)	−0.020 (1)
C17'	0.074 (2)	0.062 (2)	0.070 (2)	−0.003 (1)	−0.013 (2)	−0.026 (1)
C18'	0.064 (2)	0.047 (1)	0.073 (2)	−0.005 (1)	−0.005 (1)	−0.005 (1)
C19'	0.048 (1)	0.048 (1)	0.050 (1)	0.006 (1)	−0.004 (1)	−0.004 (1)
C20'	0.061 (2)	0.089 (2)	0.060 (2)	−0.011 (2)	0.001 (1)	0.009 (2)
C21'	0.099 (3)	0.108 (3)	0.104 (3)	0.007 (2)	0.024 (3)	0.041 (3)
C22'	0.095 (3)	0.156 (5)	0.121 (4)	0.000 (3)	0.054 (3)	0.020 (3)
C23'	0.068 (2)	0.068 (2)	0.050 (2)	0.000 (1)	−0.001 (1)	0.003 (1)
C24'	0.175 (5)	0.095 (3)	0.072 (2)	0.013 (3)	−0.011 (3)	0.023 (2)
C25'	0.113 (4)	0.202 (6)	0.069 (3)	0.055 (4)	0.026 (2)	0.014 (3)

Geometric parameters (Å, º)

O1—C7	1.244 (3)	C2—H2	0.93
N1—C13	1.346 (3)	C3—H3	0.93
N1—C19	1.437 (3)	C4—H4	0.93
C1—C2	1.378 (4)	C5—H5	0.93
C1—C6	1.386 (4)	C9—H9a	0.97
C2—C3	1.373 (6)	C9—H9b	0.97
C3—C4	1.365 (6)	C10—H10a	0.97
C4—C5	1.393 (4)	C10—H10b	0.97
C5—C6	1.375 (4)	C11—H11a	0.97
C6—C7	1.510 (3)	C11—H11b	0.97
C7—C8	1.432 (3)	C12—H12a	0.97
C8—C13	1.387 (3)	C12—H12b	0.97
C8—C9	1.525 (3)	C15—H15	0.93
C9—C10	1.501 (4)	C16—H16	0.93
C10—C11	1.487 (4)	C17—H17	0.93
C11—C12	1.513 (4)	C20—H20	0.98
C12—C13	1.508 (3)	C21—H21a	0.96
C14—C15	1.393 (4)	C21—H21b	0.96
C14—C19	1.401 (3)	C21—H21c	0.96
C14—C20	1.517 (4)	C22—H22a	0.96
C15—C16	1.370 (5)	C22—H22b	0.96
C16—C17	1.372 (5)	C22—H22c	0.96
C17—C18	1.395 (4)	C23—H23	0.98
C18—C19	1.392 (3)	C24—H24a	0.96
C18—C23	1.515 (4)	C24—H24b	0.96
C20—C21	1.504 (6)	C24—H24c	0.96
C20—C22	1.513 (6)	C25—H25a	0.96
C23—C25	1.501 (5)	C25—H25b	0.96
C23—C24	1.543 (4)	C25—H25c	0.96
O1'—C7'	1.237 (3)	N1'—H1'n	0.85
N1'—C13'	1.346 (3)	C1'—H1'	0.93
N1'—C14'	1.437 (3)	C2'—H2'	0.93
C1'—C6'	1.381 (4)	C3'—H3'	0.93
C1'—C2'	1.383 (5)	C4'—H4'	0.93
C2'—C3'	1.344 (6)	C5'—H5'	0.93
C3'—C4'	1.356 (7)	C9'—H9'a	0.97
C4'—C5'	1.401 (5)	C9'—H9'b	0.97
C5'—C6'	1.373 (4)	C10'—H10c	0.97
C6'—C7'	1.508 (3)	C10'—H10d	0.97
C7'—C8'	1.437 (3)	C11'—H11c	0.97
C8'—C13'	1.375 (3)	C11'—H11d	0.97
C8'—C9'	1.528 (3)	C12'—H12c	0.97
C9'—C10'	1.510 (4)	C12'—H12d	0.97
C10'—C11'	1.501 (4)	C16'—H16'	0.93
C11'—C12'	1.521 (4)	C17'—H17'	0.93
C12'—C13'	1.512 (3)	C18'—H18'	0.93
C15'—C16'	1.381 (4)	C20'—H20'	0.98
C15'—C14'	1.391 (4)	C21'—H21d	0.96
C15'—C20'	1.518 (4)	C21'—H21e	0.96
C14'—C19'	1.404 (4)	C21'—H21f	0.96
C16'—C17'	1.365 (5)	C22'—H22d	0.96
C17'—C18'	1.371 (4)	C22'—H22e	0.96
C18'—C19'	1.392 (4)	C22'—H22f	0.96
C19'—C23'	1.513 (4)	C23'—H23'	0.98
C20'—C22'	1.505 (6)	C24'—H24d	0.96
C20'—C21'	1.517 (6)	C24'—H24e	0.96
C23'—C24'	1.517 (5)	C24'—H24f	0.96
C23'—C25'	1.519 (6)	C25'—H25d	0.96
N1—H1n	0.85	C25'—H25e	0.96
C1—H1	0.93	C25'—H25f	0.96
C13—N1—C19	125.2 (2)	C11—C12—H12a	108.7
C2—C1—C6	120.5 (3)	C13—C12—H12b	108.7
C3—C2—C1	120.1 (3)	C11—C12—H12b	108.7
C4—C3—C2	119.9 (3)	H12a—C12—H12b	107.6
C3—C4—C5	120.4 (3)	C16—C15—H15	119.5
C6—C5—C4	120.0 (3)	C14—C15—H15	119.5
C5—C6—C1	119.1 (2)	C15—C16—H16	119.7
C5—C6—C7	118.6 (2)	C17—C16—H16	119.7
C1—C6—C7	122.2 (2)	C16—C17—H17	119.6
O1—C7—C8	124.0 (2)	C18—C17—H17	119.6
O1—C7—C6	116.5 (2)	C21—C20—H20	106.9
C8—C7—C6	119.6 (2)	C22—C20—H20	106.9
C13—C8—C7	120.2 (2)	C14—C20—H20	106.9
C13—C8—C9	120.2 (2)	C20—C21—H21a	109.5
C7—C8—C9	119.4 (2)	C20—C21—H21b	109.5
C10—C9—C8	113.4 (2)	H21a—C21—H21b	109.5
C11—C10—C9	110.7 (3)	C20—C21—H21c	109.5
C10—C11—C12	112.1 (2)	H21a—C21—H21c	109.5
N1—C13—C8	122.6 (2)	H21b—C21—H21c	109.5
N1—C13—C12	115.5 (2)	C20—C22—H22a	109.5
C8—C13—C12	121.9 (2)	C20—C22—H22b	109.5
C15—C14—C19	117.7 (2)	H22a—C22—H22b	109.5
C15—C14—C20	120.8 (2)	C20—C22—H22c	109.5
C19—C14—C20	121.5 (2)	H22a—C22—H22c	109.5
C16—C15—C14	121.1 (3)	H22b—C22—H22c	109.5
C13—C12—C11	114.3 (2)	C25—C23—H23	107.6
C15—C16—C17	120.6 (2)	C18—C23—H23	107.6
C16—C17—C18	120.8 (3)	C24—C23—H23	107.6
C19—C18—C17	118.1 (2)	C23—C24—H24a	109.5
C19—C18—C23	121.6 (2)	C23—C24—H24b	109.5
C17—C18—C23	120.3 (2)	H24a—C24—H24b	109.5
C18—C19—C14	121.8 (2)	C23—C24—H24c	109.5
C18—C19—N1	119.4 (2)	H24a—C24—H24c	109.5
C14—C19—N1	118.8 (2)	H24b—C24—H24c	109.5
C21—C20—C22	113.4 (4)	C23—C25—H25a	109.5
C21—C20—C14	110.2 (3)	C23—C25—H25b	109.5
C22—C20—C14	112.2 (3)	H25a—C25—H25b	109.5
C25—C23—C18	110.7 (3)	C23—C25—H25c	109.5
C25—C23—C24	110.6 (4)	H25a—C25—H25c	109.5
C18—C23—C24	112.6 (3)	H25b—C25—H25c	109.5
C13'—N1'—C14'	124.6 (2)	C13'—N1'—H1'n	117.7
C6'—C1'—C2'	120.3 (4)	C14'—N1'—H1'n	117.7
C3'—C2'—C1'	120.4 (4)	C6'—C1'—H1'	119.8
C2'—C3'—C4'	120.3 (3)	C2'—C1'—H1'	119.8
C3'—C4'—C5'	120.6 (4)	C3'—C2'—H2'	119.8
C6'—C5'—C4'	119.2 (3)	C1'—C2'—H2'	119.8
C5'—C6'—C1'	119.1 (3)	C2'—C3'—H3'	119.9
C5'—C6'—C7'	120.4 (2)	C4'—C3'—H3'	119.9
C1'—C6'—C7'	120.4 (3)	C3'—C4'—H4'	119.7
O1'—C7'—C8'	124.0 (2)	C5'—C4'—H4'	119.7
O1'—C7'—C6'	117.4 (2)	C6'—C5'—H5'	120.4
C8'—C7'—C6'	118.6 (2)	C4'—C5'—H5'	120.4
C13'—C8'—C7'	120.6 (2)	C10'—C9'—H9'a	109.1
C13'—C8'—C9'	120.9 (2)	C8'—C9'—H9'a	109.1
C7'—C8'—C9'	118.5 (2)	C10'—C9'—H9'b	109.1
C10'—C9'—C8'	112.5 (2)	C8'—C9'—H9'b	109.1
C11'—C10'—C9'	109.8 (2)	H9'a—C9'—H9'b	107.8
C10'—C11'—C12'	110.5 (2)	C11'—C10'—H10c	109.7
C13'—C12'—C11'	113.6 (2)	C9'—C10'—H10c	109.7
N1'—C13'—C8'	122.6 (2)	C11'—C10'—H10d	109.7
N1'—C13'—C12'	115.4 (2)	C9'—C10'—H10d	109.7
C8'—C13'—C12'	122.0 (2)	H10c—C10'—H10d	108.2
C16'—C15'—C14'	117.7 (3)	C10'—C11'—H11c	109.5
C16'—C15'—C20'	121.4 (3)	C12'—C11'—H11c	109.5
C14'—C15'—C20'	120.9 (2)	C10'—C11'—H11d	109.5
C15'—C14'—C19'	122.2 (2)	C12'—C11'—H11d	109.5
C15'—C14'—N1'	119.3 (2)	H11c—C11'—H11d	108.1
C19'—C14'—N1'	118.4 (2)	C13'—C12'—H12c	108.8
C17'—C16'—C15'	121.5 (3)	C11'—C12'—H12c	108.8
C16'—C17'—C18'	120.2 (2)	C13'—C12'—H12d	108.8
C17'—C18'—C19'	121.4 (3)	C11'—C12'—H12d	108.8
C18'—C19'—C14'	116.9 (2)	H12c—C12'—H12d	107.7
C18'—C19'—C23'	121.1 (3)	C17'—C16'—H16'	119.2
C14'—C19'—C23'	122.0 (2)	C15'—C16'—H16'	119.2
C22'—C20'—C21'	110.8 (4)	C16'—C17'—H17'	119.9
C22'—C20'—C15'	113.7 (3)	C18'—C17'—H17'	119.9
C21'—C20'—C15'	111.1 (3)	C17'—C18'—H18'	119.3
C19'—C23'—C24'	112.8 (3)	C19'—C18'—H18'	119.3
C19'—C23'—C25'	110.6 (3)	C22'—C20'—H20'	106.9
C24'—C23'—C25'	112.5 (4)	C21'—C20'—H20'	106.9
C13—N1—H1n	117.4	C15'—C20'—H20'	106.9
C19—N1—H1n	117.4	C20'—C21'—H21d	109.5
C2—C1—H1	119.7	C20'—C21'—H21e	109.5
C6—C1—H1	119.7	H21d—C21'—H21e	109.5
C3—C2—H2	120.0	C20'—C21'—H21f	109.5
C1—C2—H2	120.0	H21d—C21'—H21f	109.5
C4—C3—H3	120.1	H21e—C21'—H21f	109.5
C2—C3—H3	120.1	C20'—C22'—H22d	109.5
C3—C4—H4	119.8	C20'—C22'—H22e	109.5
C5—C4—H4	119.8	H22d—C22'—H22e	109.5
C6—C5—H5	120.0	C20'—C22'—H22f	109.5
C4—C5—H5	120.0	H22d—C22'—H22f	109.5
C10—C9—H9a	108.9	H22e—C22'—H22f	109.5
C8—C9—H9a	108.9	C19'—C23'—H23'	106.9
C10—C9—H9b	108.9	C24'—C23'—H23'	106.9
C8—C9—H9b	108.9	C25'—C23'—H23'	106.9
H9a—C9—H9b	107.7	C23'—C24'—H24d	109.5
C11—C10—H10a	109.5	C23'—C24'—H24e	109.5
C9—C10—H10a	109.5	H24d—C24'—H24e	109.5
C11—C10—H10b	109.5	C23'—C24'—H24f	109.5
C9—C10—H10b	109.5	H24d—C24'—H24f	109.5
H10a—C10—H10b	108.1	H24e—C24'—H24f	109.5
C10—C11—H11a	109.2	C23'—C25'—H25d	109.5
C12—C11—H11a	109.2	C23'—C25'—H25e	109.5
C10—C11—H11b	109.2	H25d—C25'—H25e	109.5
C12—C11—H11b	109.2	C23'—C25'—H25f	109.5
H11a—C11—H11b	107.9	H25d—C25'—H25f	109.5
C13—C12—H12a	108.7	H25e—C25'—H25f	109.5
C6—C1—C2—C3	1.3 (5)	C6'—C1'—C2'—C3'	−2.7 (6)
C1—C2—C3—C4	−2.3 (6)	C1'—C2'—C3'—C4'	2.6 (6)
C2—C3—C4—C5	1.4 (6)	C2'—C3'—C4'—C5'	−0.4 (7)
C3—C4—C5—C6	0.5 (5)	C3'—C4'—C5'—C6'	−1.9 (7)
C4—C5—C6—C1	−1.5 (4)	C4'—C5'—C6'—C1'	1.8 (5)
C4—C5—C6—C7	−178.5 (3)	C4'—C5'—C6'—C7'	178.6 (3)
C2—C1—C6—C5	0.6 (4)	C2'—C1'—C6'—C5'	0.4 (5)
C2—C1—C6—C7	177.5 (3)	C2'—C1'—C6'—C7'	−176.4 (3)
C5—C6—C7—O1	52.3 (3)	C5'—C6'—C7'—O1'	−63.5 (4)
C1—C6—C7—O1	−124.6 (3)	C1'—C6'—C7'—O1'	113.2 (3)
C5—C6—C7—C8	−126.5 (3)	C5'—C6'—C7'—C8'	117.4 (3)
C1—C6—C7—C8	56.7 (3)	C1'—C6'—C7'—C8'	−65.9 (3)
O1—C7—C8—C13	4.3 (4)	O1'—C7'—C8'—C13'	−8.6 (4)
C6—C7—C8—C13	−177.0 (2)	C6'—C7'—C8'—C13'	170.5 (2)
O1—C7—C8—C9	−171.0 (2)	O1'—C7'—C8'—C9'	168.8 (3)
C6—C7—C8—C9	7.6 (3)	C6'—C7'—C8'—C9'	−12.2 (3)
C13—C8—C9—C10	−17.8 (3)	C13'—C8'—C9'—C10'	17.8 (4)
C7—C8—C9—C10	157.5 (2)	C7'—C8'—C9'—C10'	−159.6 (2)
C8—C9—C10—C11	48.9 (4)	C8'—C9'—C10'—C11'	−50.4 (3)
C9—C10—C11—C12	−60.8 (4)	C9'—C10'—C11'—C12'	64.1 (3)
C10—C11—C12—C13	40.1 (4)	C10'—C11'—C12'—C13'	−43.5 (4)
C19—N1—C13—C8	176.4 (2)	C14'—N1'—C13'—C8'	−171.5 (2)
C19—N1—C13—C12	−5.1 (3)	C14'—N1'—C13'—C12'	9.4 (3)
C7—C8—C13—N1	0.6 (3)	C7'—C8'—C13'—N1'	0.6 (4)
C9—C8—C13—N1	175.9 (2)	C9'—C8'—C13'—N1'	−176.7 (2)
C7—C8—C13—C12	−177.8 (2)	C7'—C8'—C13'—C12'	179.7 (2)
C9—C8—C13—C12	−2.5 (3)	C9'—C8'—C13'—C12'	2.4 (4)
C11—C12—C13—N1	172.9 (2)	C11'—C12'—C13'—N1'	−170.2 (2)
C11—C12—C13—C8	−8.6 (4)	C11'—C12'—C13'—C8'	10.7 (4)
C19—C14—C15—C16	0.4 (4)	C16'—C15'—C14'—C19'	1.5 (4)
C20—C14—C15—C16	178.0 (3)	C20'—C15'—C14'—C19'	−178.9 (2)
C14—C15—C16—C17	0.3 (5)	C16'—C15'—C14'—N1'	−177.5 (2)
C15—C16—C17—C18	−0.3 (5)	C20'—C15'—C14'—N1'	2.1 (4)
C16—C17—C18—C19	−0.4 (4)	C13'—N1'—C14'—C15'	−99.9 (3)
C16—C17—C18—C23	−178.6 (3)	C13'—N1'—C14'—C19'	81.1 (3)
C17—C18—C19—C14	1.1 (4)	C14'—C15'—C16'—C17'	−1.0 (4)
C23—C18—C19—C14	179.3 (2)	C20'—C15'—C16'—C17'	179.4 (3)
C17—C18—C19—N1	−177.0 (2)	C15'—C16'—C17'—C18'	−0.2 (5)
C23—C18—C19—N1	1.2 (3)	C16'—C17'—C18'—C19'	1.1 (5)
C15—C14—C19—C18	−1.1 (4)	C17'—C18'—C19'—C14'	−0.6 (4)
C20—C14—C19—C18	−178.7 (2)	C17'—C18'—C19'—C23'	179.9 (3)
C15—C14—C19—N1	177.0 (2)	C15'—C14'—C19'—C18'	−0.7 (4)
C20—C14—C19—N1	−0.5 (3)	N1'—C14'—C19'—C18'	178.3 (2)
C13—N1—C19—C18	−85.1 (3)	C15'—C14'—C19'—C23'	178.8 (2)
C13—N1—C19—C14	96.7 (3)	N1'—C14'—C19'—C23'	−2.2 (3)
C15—C14—C20—C21	−83.2 (4)	C16'—C15'—C20'—C22'	−39.5 (5)
C19—C14—C20—C21	94.2 (4)	C14'—C15'—C20'—C22'	140.9 (4)
C15—C14—C20—C22	44.1 (5)	C16'—C15'—C20'—C21'	86.4 (4)
C19—C14—C20—C22	−138.4 (4)	C14'—C15'—C20'—C21'	−93.2 (4)
C19—C18—C23—C25	−95.8 (4)	C18'—C19'—C23'—C24'	35.6 (4)
C17—C18—C23—C25	82.3 (4)	C14'—C19'—C23'—C24'	−143.9 (4)
C19—C18—C23—C24	139.7 (3)	C18'—C19'—C23'—C25'	−91.4 (4)
C17—C18—C23—C24	−42.2 (4)	C14'—C19'—C23'—C25'	89.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.85	1.93	2.598 (2)	135
N1—H1n···O1′	0.85	2.51	3.204 (3)	140
N1′—H1′n···O1′	0.85	1.96	2.614 (3)	133
N1′—H1′n···O1	0.85	2.51	3.206 (3)	140