11,11a,13a-Trimethyl-2,3,3a,3b,4,5,5a,6,11,11a,11b,12,13,13a-tetra­deca­hydro-1H-7-aza­indeno[5,4-a]anthracen-1-ol methanol solvate

In the title compound, C₂₃H₃₃NO·CH₄O, the asymmetric unit consists of one mol­ecule of C₂₃H₃₃NO and one methanol solvent mol­ecule, which are connected through O—H...N and O—H...O hydrogen bonds leading to the formation of zigzag-like chains parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.119
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01

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           27.48
           From the CIF: _reflns_number_total               2825
           Count of symmetry unique reflns         2829
           Completeness (_total/calc)             99.86%
           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
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

11,11a,13a-Trimethyl-2,3,3a,3 b,4,5,5a,6,11,11a,11b,12,13,13a- tetradecahydro-1H-7-azaindeno[5,4-a]anthracen-1-ol methanol solvate

Crystal data

C23H33NO·CH4O	F(000) = 816
Mr = 371.55	Dx = 1.147 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15292 reflections
a = 7.4389 (19) Å	θ = 3.0–27.5°
b = 10.599 (4) Å	µ = 0.07 mm^−1
c = 27.299 (8) Å	T = 298 K
V = 2152.4 (12) Å^3	Chunk, colorless
Z = 4	0.46 × 0.42 × 0.33 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2825 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (Higashi, 1995)	k = 0→13
Tmin = 0.957, Tmax = 0.966	l = 0→35
4930 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.4327P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
2825 reflections	Δρmax = 0.18 e Å^−3
251 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

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	0.3560 (3)	0.18461 (19)	0.17123 (6)	0.0760 (6)
H1	0.3040	0.2370	0.1543	0.114*
O2	0.2137 (4)	0.3808 (2)	0.11792 (10)	0.1034 (9)
H2	0.2832	0.4147	0.0987	0.155*
N1	0.0501 (4)	0.5610 (3)	0.54401 (8)	0.0748 (7)
C1	0.3877 (3)	0.2759 (2)	0.35081 (7)	0.0440 (5)
H1A	0.3432	0.1923	0.3601	0.053*
C2	0.5405 (3)	0.3136 (3)	0.38550 (8)	0.0578 (6)
H2A	0.6316	0.2481	0.3854	0.069*
H2B	0.5956	0.3909	0.3738	0.069*
C3	0.4732 (3)	0.3332 (3)	0.43754 (8)	0.0579 (6)
H3A	0.4313	0.2534	0.4506	0.069*
H3B	0.5717	0.3622	0.4579	0.069*
C4	0.3211 (3)	0.4289 (2)	0.43956 (8)	0.0460 (5)
H4	0.3693	0.5089	0.4272	0.055*
C5	0.2630 (4)	0.4518 (3)	0.49291 (9)	0.0594 (7)
H5A	0.2524	0.3709	0.5093	0.071*
H5B	0.3567	0.4992	0.5094	0.071*
C6	0.0885 (4)	0.5216 (2)	0.49836 (8)	0.0556 (6)
C7	−0.1066 (5)	0.6190 (4)	0.55142 (12)	0.0901 (11)
H7	−0.1347	0.6450	0.5830	0.108*
C8	−0.2278 (5)	0.6421 (3)	0.51508 (12)	0.0857 (10)
H8	−0.3352	0.6836	0.5217	0.103*
C9	−0.1876 (4)	0.6026 (3)	0.46817 (11)	0.0696 (8)
H9	−0.2682	0.6171	0.4427	0.084*
C10	−0.0263 (3)	0.5412 (2)	0.45917 (8)	0.0527 (6)
C11	0.0239 (3)	0.5035 (2)	0.40711 (8)	0.0459 (5)
H11	−0.0863	0.4728	0.3914	0.055*
C12	0.1600 (3)	0.3932 (2)	0.40631 (7)	0.0405 (5)
C13	0.2329 (3)	0.3708 (2)	0.35360 (7)	0.0398 (5)
H13	0.2834	0.4518	0.3430	0.048*
C14	0.0850 (3)	0.3388 (2)	0.31622 (8)	0.0496 (5)
H14A	0.0298	0.2592	0.3252	0.060*
H14B	−0.0072	0.4035	0.3175	0.060*
C15	0.1569 (3)	0.3292 (2)	0.26374 (7)	0.0512 (6)
H15A	0.0604	0.3032	0.2421	0.061*
H15B	0.1981	0.4116	0.2531	0.061*
C16	0.3108 (3)	0.2355 (2)	0.26000 (8)	0.0458 (5)
C17	0.4266 (4)	0.2442 (2)	0.21351 (8)	0.0564 (6)
H17	0.4469	0.3335	0.2060	0.068*
C18	0.6061 (4)	0.1846 (3)	0.22786 (9)	0.0709 (8)
H18A	0.7051	0.2313	0.2135	0.085*
H18B	0.6121	0.0980	0.2166	0.085*
C19	0.6157 (4)	0.1899 (3)	0.28429 (10)	0.0660 (7)
H19A	0.6056	0.1062	0.2984	0.079*
H19B	0.7273	0.2281	0.2952	0.079*
C20	0.4545 (3)	0.2715 (2)	0.29797 (7)	0.0453 (5)
H20	0.4896	0.3582	0.2900	0.054*
C21	0.0823 (4)	0.6220 (2)	0.37891 (9)	0.0605 (7)
H21A	0.0018	0.6902	0.3863	0.091*
H21B	0.0793	0.6051	0.3444	0.091*
H21C	0.2022	0.6448	0.3884	0.091*
C22	0.0653 (4)	0.2752 (2)	0.42594 (8)	0.0531 (6)
H22A	0.0212	0.2914	0.4584	0.080*
H22B	0.1489	0.2062	0.4269	0.080*
H22C	−0.0334	0.2539	0.4049	0.080*
C23	0.2427 (4)	0.1002 (2)	0.26620 (10)	0.0649 (7)
H23A	0.1876	0.0913	0.2978	0.097*
H23B	0.3418	0.0426	0.2635	0.097*
H23C	0.1560	0.0819	0.2411	0.097*
C24	0.0802 (6)	0.4634 (3)	0.13003 (12)	0.0892 (11)
H24A	0.0119	0.4299	0.1569	0.134*
H24B	0.0026	0.4756	0.1023	0.134*
H24C	0.1321	0.5427	0.1394	0.134*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1071 (16)	0.0743 (11)	0.0466 (9)	0.0164 (13)	−0.0117 (10)	−0.0164 (9)
O2	0.124 (2)	0.0797 (15)	0.1064 (18)	0.0227 (17)	0.0340 (16)	0.0372 (13)
N1	0.0857 (17)	0.0875 (17)	0.0513 (12)	0.0076 (16)	0.0100 (13)	−0.0154 (12)
C1	0.0424 (11)	0.0483 (12)	0.0413 (10)	0.0036 (10)	−0.0054 (9)	−0.0028 (9)
C2	0.0403 (11)	0.0824 (17)	0.0507 (12)	0.0134 (13)	−0.0125 (10)	−0.0114 (13)
C3	0.0522 (13)	0.0739 (16)	0.0476 (12)	0.0091 (14)	−0.0158 (11)	−0.0079 (12)
C4	0.0446 (12)	0.0530 (12)	0.0403 (10)	−0.0012 (11)	−0.0057 (10)	−0.0039 (9)
C5	0.0623 (16)	0.0723 (16)	0.0437 (12)	0.0043 (15)	−0.0062 (12)	−0.0087 (11)
C6	0.0634 (15)	0.0566 (13)	0.0469 (11)	−0.0018 (14)	0.0064 (12)	−0.0071 (11)
C7	0.103 (3)	0.101 (3)	0.0663 (18)	0.019 (2)	0.026 (2)	−0.0199 (17)
C8	0.080 (2)	0.094 (2)	0.083 (2)	0.023 (2)	0.0244 (19)	−0.0195 (18)
C9	0.0635 (16)	0.0754 (18)	0.0699 (16)	0.0131 (16)	0.0110 (14)	−0.0057 (15)
C10	0.0521 (13)	0.0508 (12)	0.0552 (13)	−0.0017 (12)	0.0098 (12)	−0.0042 (11)
C11	0.0420 (11)	0.0510 (12)	0.0446 (11)	0.0023 (11)	−0.0005 (10)	−0.0031 (9)
C12	0.0393 (10)	0.0446 (11)	0.0375 (9)	−0.0024 (10)	−0.0019 (9)	0.0004 (9)
C13	0.0377 (10)	0.0439 (11)	0.0379 (9)	−0.0015 (9)	−0.0015 (9)	−0.0003 (8)
C14	0.0375 (11)	0.0636 (13)	0.0476 (11)	0.0043 (12)	−0.0054 (10)	−0.0058 (11)
C15	0.0504 (12)	0.0620 (13)	0.0412 (10)	0.0046 (13)	−0.0111 (10)	−0.0061 (10)
C16	0.0510 (12)	0.0453 (11)	0.0411 (10)	−0.0022 (11)	−0.0040 (10)	−0.0046 (9)
C17	0.0705 (16)	0.0554 (14)	0.0433 (11)	0.0035 (14)	0.0033 (12)	−0.0092 (10)
C18	0.0662 (17)	0.0855 (19)	0.0611 (15)	0.0137 (17)	0.0065 (14)	−0.0155 (15)
C19	0.0488 (13)	0.0855 (19)	0.0638 (15)	0.0164 (15)	−0.0039 (12)	−0.0177 (14)
C20	0.0404 (11)	0.0514 (12)	0.0440 (11)	0.0008 (11)	−0.0028 (10)	−0.0070 (9)
C21	0.0692 (16)	0.0524 (13)	0.0598 (14)	0.0103 (14)	0.0032 (14)	0.0077 (11)
C22	0.0584 (14)	0.0514 (13)	0.0495 (12)	−0.0083 (12)	0.0037 (12)	0.0018 (10)
C23	0.0763 (19)	0.0520 (14)	0.0663 (16)	−0.0087 (15)	−0.0047 (15)	−0.0087 (12)
C24	0.121 (3)	0.0641 (17)	0.082 (2)	0.018 (2)	−0.003 (2)	−0.0044 (16)

Geometric parameters (Å, º)

O1—C17	1.416 (3)	C12—C13	1.556 (3)
O1—H1	0.8200	C13—C14	1.538 (3)
O2—C24	1.364 (4)	C13—H13	0.9800
O2—H2	0.8200	C14—C15	1.532 (3)
N1—C7	1.333 (4)	C14—H14A	0.9700
N1—C6	1.345 (3)	C14—H14B	0.9700
C1—C20	1.526 (3)	C15—C16	1.520 (3)
C1—C13	1.531 (3)	C15—H15A	0.9700
C1—C2	1.532 (3)	C15—H15B	0.9700
C1—H1A	0.9800	C16—C23	1.530 (3)
C2—C3	1.521 (3)	C16—C17	1.536 (3)
C2—H2A	0.9700	C16—C20	1.537 (3)
C2—H2B	0.9700	C17—C18	1.528 (4)
C3—C4	1.520 (3)	C17—H17	0.9800
C3—H3A	0.9700	C18—C19	1.543 (3)
C3—H3B	0.9700	C18—H18A	0.9700
C4—C5	1.538 (3)	C18—H18B	0.9700
C4—C12	1.551 (3)	C19—C20	1.525 (3)
C4—H4	0.9800	C19—H19A	0.9700
C5—C6	1.502 (4)	C19—H19B	0.9700
C5—H5A	0.9700	C20—H20	0.9800
C5—H5B	0.9700	C21—H21A	0.9600
C6—C10	1.384 (3)	C21—H21B	0.9600
C7—C8	1.363 (5)	C21—H21C	0.9600
C7—H7	0.9300	C22—H22A	0.9600
C8—C9	1.380 (4)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.388 (4)	C23—H23A	0.9600
C9—H9	0.9300	C23—H23B	0.9600
C10—C11	1.522 (3)	C23—H23C	0.9600
C11—C21	1.536 (3)	C24—H24A	0.9600
C11—C12	1.547 (3)	C24—H24B	0.9600
C11—H11	0.9800	C24—H24C	0.9600
C12—C22	1.532 (3)
C17—O1—H1	109.5	C15—C14—C13	112.68 (18)
C24—O2—H2	109.5	C15—C14—H14A	109.1
C7—N1—C6	118.0 (3)	C13—C14—H14A	109.1
C20—C1—C13	108.18 (17)	C15—C14—H14B	109.1
C20—C1—C2	110.53 (19)	C13—C14—H14B	109.1
C13—C1—C2	110.85 (18)	H14A—C14—H14B	107.8
C20—C1—H1A	109.1	C16—C15—C14	111.65 (18)
C13—C1—H1A	109.1	C16—C15—H15A	109.3
C2—C1—H1A	109.1	C14—C15—H15A	109.3
C3—C2—C1	111.7 (2)	C16—C15—H15B	109.3
C3—C2—H2A	109.3	C14—C15—H15B	109.3
C1—C2—H2A	109.3	H15A—C15—H15B	108.0
C3—C2—H2B	109.3	C15—C16—C23	110.8 (2)
C1—C2—H2B	109.3	C15—C16—C17	115.99 (19)
H2A—C2—H2B	108.0	C23—C16—C17	109.5 (2)
C4—C3—C2	111.73 (19)	C15—C16—C20	108.42 (17)
C4—C3—H3A	109.3	C23—C16—C20	112.9 (2)
C2—C3—H3A	109.3	C17—C16—C20	98.76 (18)
C4—C3—H3B	109.3	O1—C17—C18	110.4 (2)
C2—C3—H3B	109.3	O1—C17—C16	116.0 (2)
H3A—C3—H3B	107.9	C18—C17—C16	104.66 (19)
C3—C4—C5	110.40 (19)	O1—C17—H17	108.5
C3—C4—C12	113.02 (18)	C18—C17—H17	108.5
C5—C4—C12	112.0 (2)	C16—C17—H17	108.5
C3—C4—H4	107.0	C17—C18—C19	106.4 (2)
C5—C4—H4	107.0	C17—C18—H18A	110.5
C12—C4—H4	107.0	C19—C18—H18A	110.5
C6—C5—C4	114.5 (2)	C17—C18—H18B	110.5
C6—C5—H5A	108.6	C19—C18—H18B	110.5
C4—C5—H5A	108.6	H18A—C18—H18B	108.7
C6—C5—H5B	108.6	C20—C19—C18	103.2 (2)
C4—C5—H5B	108.6	C20—C19—H19A	111.1
H5A—C5—H5B	107.6	C18—C19—H19A	111.1
N1—C6—C10	122.6 (3)	C20—C19—H19B	111.1
N1—C6—C5	115.4 (2)	C18—C19—H19B	111.1
C10—C6—C5	122.0 (2)	H19A—C19—H19B	109.1
N1—C7—C8	123.4 (3)	C19—C20—C1	120.3 (2)
N1—C7—H7	118.3	C19—C20—C16	103.91 (17)
C8—C7—H7	118.3	C1—C20—C16	114.73 (18)
C7—C8—C9	118.5 (3)	C19—C20—H20	105.6
C7—C8—H8	120.7	C1—C20—H20	105.6
C9—C8—H8	120.7	C16—C20—H20	105.6
C8—C9—C10	119.6 (3)	C11—C21—H21A	109.5
C8—C9—H9	120.2	C11—C21—H21B	109.5
C10—C9—H9	120.2	H21A—C21—H21B	109.5
C6—C10—C9	117.8 (2)	C11—C21—H21C	109.5
C6—C10—C11	122.1 (2)	H21A—C21—H21C	109.5
C9—C10—C11	120.0 (2)	H21B—C21—H21C	109.5
C10—C11—C21	108.84 (19)	C12—C22—H22A	109.5
C10—C11—C12	111.82 (18)	C12—C22—H22B	109.5
C21—C11—C12	115.19 (19)	H22A—C22—H22B	109.5
C10—C11—H11	106.8	C12—C22—H22C	109.5
C21—C11—H11	106.8	H22A—C22—H22C	109.5
C12—C11—H11	106.8	H22B—C22—H22C	109.5
C22—C12—C11	108.14 (18)	C16—C23—H23A	109.5
C22—C12—C4	110.47 (18)	C16—C23—H23B	109.5
C11—C12—C4	108.25 (17)	H23A—C23—H23B	109.5
C22—C12—C13	111.05 (17)	C16—C23—H23C	109.5
C11—C12—C13	110.89 (16)	H23A—C23—H23C	109.5
C4—C12—C13	108.01 (17)	H23B—C23—H23C	109.5
C1—C13—C14	111.10 (17)	O2—C24—H24A	109.5
C1—C13—C12	114.11 (16)	O2—C24—H24B	109.5
C14—C13—C12	113.45 (17)	H24A—C24—H24B	109.5
C1—C13—H13	105.8	O2—C24—H24C	109.5
C14—C13—H13	105.8	H24A—C24—H24C	109.5
C12—C13—H13	105.8	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.94	2.750 (3)	170
O2—H2···N1^i	0.82	1.96	2.746 (3)	161

Symmetry code: (i) −x+1/2, −y+1, z−1/2.