Cabergoline, form VII

Bednář, R.; Cvak, L.; Čejka, J.; Kratochvíl, B.; Císařová, I.; Jegorov, A.

doi:10.1107/S1600536804013777

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Cabergoline, form VII

R. Bednár, L. Cvak, J. Cejka, B. Kratochvíl, I. Císarová and A. Jegorov

A new crystal structure of cabergoline (C₂₆H₃₇N₅O₂), polymorph form VII, is reported. It crystallizes in the same space group, P2₁, as the more stable form I, but there are two independent molecules in form VII. The molecular packing and the hydrogen-bond networks are, consequently, completely different.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013777/cf6348sup1.cif Contains datablocks CRYSTALS_cabergo7, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013777/cf6348Isup2.hkl Contains datablock I

CCDC reference: 245288

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.037
wR factor = 0.044
Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.45 Ratio

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.71 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.47 Ratio
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        N81

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT213_ALERT_2_C Atom C82     has ADP max/min Ratio .............       3.50 prolat
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.85 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N71
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N31
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H442   ..  H572    ..       1.98 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.13 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C26 H37 N5 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C26 H37 N5 O2

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               6104
           Count of symmetry unique reflns         6119
           Completeness (_total/calc)             99.75%
           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

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1996); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.

N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-allyl ergoline-8β-carboxamide top

Crystal data top

C₂₆H₃₇N₅O₂	F(000) = 976.000
M_r = 451.61	D_x = 1.168 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.9448 (2) Å	Cell parameters from 6047 reflections
b = 15.1406 (2) Å	θ = 1–27°
c = 15.6896 (3) Å	µ = 0.08 mm⁻¹
β = 99.1231 (9)°	T = 150 K
V = 2567.23 (8) Å³	Prism, white
Z = 4	0.37 × 0.23 × 0.21 mm

Data collection top

Enraf Nonius Kappa CCD diffractometer	R_int = 0.01
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
φ and ω scans	h = −14→14
46767 measured reflections	k = −19→19
6104 independent reflections	l = −20→20
5301 reflections with I > 1.96σ(I)

Refinement top

Refinement on F	Primary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.044	Modified Chebychev polynomial (Watkin, 1994) with coefficients 0.912 0.735 0.593
S = 1.13	(Δ/σ)_max = 0.001
5301 reflections	Δρ_max = 0.26 e Å⁻³
626 parameters	Δρ_min = −0.22 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.20444 (16)	0.19446 (13)	0.48752 (12)	0.0355
C2	0.20251 (19)	0.12340 (15)	0.43103 (14)	0.0350
C3	0.08522 (17)	0.08961 (13)	0.41383 (12)	0.0275
C4	0.02631 (17)	0.01398 (13)	0.36022 (13)	0.0281
C5	−0.11669 (16)	0.02154 (12)	0.34398 (11)	0.0230
N6	−0.17238 (13)	−0.0633 (1)	0.31149 (9)	0.0224
C7	−0.30798 (16)	−0.05798 (12)	0.29235 (12)	0.0252
C8	−0.36061 (16)	−0.03857 (13)	0.37543 (12)	0.0247
C9	−0.31173 (17)	0.04999 (13)	0.41053 (13)	0.0268
C10	−0.17047 (16)	0.04641 (12)	0.42702 (11)	0.0229
C11	−0.11124 (17)	0.12891 (13)	0.47005 (12)	0.0261
C12	−0.1612 (2)	0.18834 (15)	0.52233 (14)	0.0349
C13	−0.0866 (2)	0.25590 (15)	0.56545 (14)	0.0384
C14	0.0377 (2)	0.26593 (14)	0.56037 (13)	0.0335
C15	0.08755 (18)	0.20580 (13)	0.50763 (13)	0.0286
C16	0.01313 (17)	0.14051 (13)	0.46269 (12)	0.0258
C17	−0.12306 (19)	−0.09876 (14)	0.23637 (13)	0.0316
C18	−0.1720 (2)	−0.18981 (15)	0.21319 (14)	0.0346
C19	−0.2212 (3)	−0.21515 (19)	0.13538 (17)	0.0536
C20	−0.50066 (16)	−0.04135 (13)	0.35916 (12)	0.0270
O21	−0.56208 (14)	0.02502 (11)	0.36307 (12)	0.0400
N22	−0.55977 (14)	−0.12025 (11)	0.3327 (1)	0.0251
C23	−0.49827 (18)	−0.20403 (13)	0.33940 (12)	0.0276
O24	−0.41231 (14)	−0.2195 (1)	0.3972 (1)	0.0366
N25	−0.54363 (18)	−0.26213 (12)	0.27894 (13)	0.0383
C26	−0.4887 (3)	−0.35038 (16)	0.2792 (2)	0.0537
C27	−0.5234 (3)	−0.40809 (19)	0.3484 (3)	0.0713
C28	−0.69459 (16)	−0.11484 (14)	0.30426 (13)	0.0283
C29	−0.73227 (18)	−0.06473 (14)	0.21936 (14)	0.0332
C30	−0.6656 (2)	−0.09369 (15)	0.14669 (13)	0.0355
N31	−0.6832 (2)	−0.18701 (14)	0.12386 (12)	0.0462
C32	−0.5943 (5)	−0.2111 (3)	0.0669 (2)	0.0849
C33	−0.8095 (4)	−0.2031 (3)	0.0816 (2)	0.0770
N41	−0.27803 (16)	0.01204 (13)	0.00893 (12)	0.0352
C42	−0.25946 (18)	0.07310 (14)	0.07541 (13)	0.0310
C43	−0.37040 (16)	0.10981 (13)	0.08608 (12)	0.0257
C44	−0.40977 (16)	0.17690 (13)	0.14626 (12)	0.0261
C45	−0.54924 (16)	0.16741 (12)	0.15107 (11)	0.0230
N46	−0.59133 (14)	0.24336 (11)	0.1984 (1)	0.0272
C47	−0.72303 (17)	0.23578 (14)	0.20565 (14)	0.0313
C48	−0.80189 (16)	0.23706 (13)	0.11641 (14)	0.0297
C49	−0.76739 (16)	0.15825 (13)	0.06482 (13)	0.0274
C50	−0.62917 (15)	0.16295 (13)	0.05967 (12)	0.0241
C51	−0.58635 (17)	0.08920 (13)	0.00561 (12)	0.0265
C52	−0.65599 (19)	0.04190 (15)	−0.06097 (13)	0.0325
C53	−0.5973 (2)	−0.02202 (16)	−0.10734 (14)	0.0392
C54	−0.4717 (2)	−0.03930 (15)	−0.09095 (14)	0.0380
C55	−0.40194 (19)	0.00915 (14)	−0.02475 (13)	0.0310
C56	−0.46048 (17)	0.07021 (13)	0.02236 (12)	0.0264
C57	−0.5202 (2)	0.25400 (15)	0.28583 (13)	0.0341
C58	−0.5480 (2)	0.34082 (16)	0.32461 (15)	0.0414
C59	−0.5637 (4)	0.3525 (2)	0.4047 (2)	0.0711
C60	−0.93693 (17)	0.23359 (14)	0.12846 (15)	0.0333
O61	−0.98642 (15)	0.16278 (11)	0.13743 (16)	0.0531
N62	−1.00038 (13)	0.31103 (11)	0.1395 (1)	0.0256
C63	−0.96299 (17)	0.39614 (13)	0.11510 (13)	0.0289
O64	−0.90236 (14)	0.40511 (11)	0.05580 (12)	0.0419
N65	−1.00180 (16)	0.46320 (12)	0.15916 (13)	0.0350
C66	−0.9650 (2)	0.55382 (15)	0.1426 (2)	0.0492
C67	−0.8397 (3)	0.5762 (2)	0.1953 (3)	0.0689
C68	−1.12100 (16)	0.29935 (13)	0.16988 (13)	0.0281
C69	−1.1083 (2)	0.27484 (16)	0.26559 (15)	0.0393
C70	−1.0452 (4)	0.3407 (4)	0.3279 (3)	0.0515	0.6000
N71	−1.1085 (5)	0.4279 (7)	0.3159 (6)	0.0451	0.6000
C72	−1.0425 (9)	0.4932 (5)	0.3733 (3)	0.0854	0.6000
C73	−1.2335 (5)	0.4233 (4)	0.3334 (3)	0.0669	0.6000
C80	−1.1480 (6)	0.3534 (4)	0.3207 (4)	0.0428	0.4000
C82	−0.9416 (11)	0.4127 (8)	0.3681 (5)	0.0997	0.4000
N81	−1.0591 (9)	0.429 (1)	0.3216 (8)	0.0558	0.4000
C83	−1.1236 (17)	0.5068 (12)	0.3556 (13)	0.126 (6)*	0.4000
H21	0.27569	0.10018	0.40720	0.0413*
H41	0.05044	−0.04261	0.39124	0.0326*
H42	0.05673	0.01390	0.30339	0.0326*
H51	−0.13797	0.07001	0.30090	0.0273*
H71	−0.34221	−0.11513	0.26700	0.0291*
H72	−0.33194	−0.00917	0.25005	0.0291*
H81	−0.33337	−0.08537	0.41932	0.0282*
H91	−0.34301	0.06269	0.46578	0.0320*
H92	−0.33997	0.09751	0.36764	0.0320*
H101	−0.14775	−0.00244	0.46946	0.0273*
H121	−0.2500	0.18309	0.52965	0.0419*
H131	−0.1252	0.29847	0.60198	0.0463*
H141	0.0893	0.31379	0.59189	0.0384*
H171	−0.03074	−0.10160	0.25004	0.0371*
H172	−0.14779	−0.05849	0.18608	0.0371*
H181	−0.1680	−0.23421	0.26073	0.0408*
H191	−0.2525	−0.27691	0.12502	0.0609*
H192	−0.2268	−0.17256	0.08620	0.0609*
H261	−0.5182	−0.37888	0.2221	0.0652*
H262	−0.3966	−0.34436	0.2876	0.0652*
H271	−0.4840	−0.46741	0.3457	0.0830*
H272	−0.6154	−0.41496	0.3404	0.0830*
H273	−0.4938	−0.38044	0.4058	0.0830*
H281	−0.73233	−0.08445	0.35035	0.0330*
H282	−0.72789	−0.17631	0.29640	0.0330*
H291	−0.82311	−0.07331	0.20046	0.0381*
H292	−0.71464	−0.00061	0.23058	0.0381*
H301	−0.6970	−0.05734	0.09459	0.0423*
H302	−0.5751	−0.08270	0.16450	0.0423*
H321	−0.6045	−0.2747	0.0502	0.1052*
H322	−0.6072	−0.1736	0.0138	0.1052*
H323	−0.5091	−0.2011	0.0992	0.1052*
H331	−0.8208	−0.2670	0.0660	0.0854*
H332	−0.8677	−0.1864	0.1221	0.0854*
H333	−0.8270	−0.1663	0.0282	0.0854*
H421	−0.17747	0.08895	0.10978	0.0359*
H441	−0.39345	0.23746	0.12525	0.0312*
H442	−0.36104	0.16783	0.20512	0.0312*
H451	−0.56019	0.11084	0.18188	0.0266*
H471	−0.74664	0.28674	0.24018	0.0373*
H472	−0.73764	0.17924	0.23541	0.0373*
H481	−0.78770	0.29206	0.08408	0.0343*
H491	−0.81667	0.15947	0.00544	0.0329*
H492	−0.78516	0.10233	0.09448	0.0329*
H501	−0.61644	0.21925	0.02892	0.0291*
H521	−0.74704	0.05262	−0.07579	0.0380*
H531	−0.6494	−0.05589	−0.15437	0.0454*
H541	−0.4327	−0.08423	−0.12484	0.0461*
H571	−0.5422	0.20517	0.32356	0.0417*
H572	−0.4299	0.25114	0.28230	0.0417*
H581	−0.5548	0.39401	0.28637	0.0510*
H591	−0.5821	0.4126	0.4258	0.0914*
H592	−0.5577	0.3008	0.4448	0.0914*
H661	−1.0287	0.59600	0.1575	0.0576*
H662	−0.9589	0.55935	0.0799	0.0576*
H671	−0.8162	0.6380	0.1823	0.0838*
H672	−0.8453	0.5710	0.2581	0.0838*
H673	−0.7755	0.5343	0.1806	0.0838*
H681	−1.16813	0.35603	0.16052	0.0333*
H682	−1.16799	0.25147	0.13504	0.0333*
H6911	−1.1933	0.26508	0.27950	0.0440*	0.6000
H6912	−1.0601	0.21856	0.27428	0.0440*	0.6000
H6921	−1.1625	0.22289	0.27201	0.0440*	0.4000
H6922	−1.0201	0.25902	0.28729	0.0440*	0.4000
H701	−1.0465	0.3192	0.3880	0.0487*	0.6000
H702	−0.9575	0.3475	0.3183	0.0487*	0.6000
H801	−1.2327	0.3740	0.2952	0.0598*	0.4000
H802	−1.1484	0.3332	0.3814	0.0598*	0.4000
H721	−1.0853	0.5517	0.3653	0.0774*	0.6000
H722	−1.0392	0.4732	0.4343	0.0774*	0.6000
H723	−0.9565	0.4991	0.3601	0.0774*	0.6000
H731	−1.2745	0.4824	0.3257	0.0743*	0.6000
H732	−1.2327	0.4024	0.3939	0.0743*	0.6000
H733	−1.2801	0.3802	0.2922	0.0743*	0.6000
H821	−0.8874	0.4654	0.3650	0.0967*	0.4000
H822	−0.9452	0.3986	0.4299	0.0967*	0.4000
H823	−0.9069	0.3610	0.3402	0.0967*	0.4000
H831	−1.0655	0.5580	0.3564	0.1190*	0.4000
H832	−1.2038	0.5214	0.3183	0.1190*	0.4000
H833	−1.1386	0.4944	0.4157	0.1190*	0.4000
H651	−1.03402	0.45644	0.21031	0.0500*
H411	−0.21547	−0.01725	−0.00801	0.0500*
H11	0.27645	0.21792	0.51745	0.0500*
H251	−0.59605	−0.23570	0.22909	0.0500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0262 (8)	0.0367 (9)	0.0430 (9)	−0.0060 (7)	0.0036 (7)	−0.0091 (8)
C2	0.0275 (9)	0.033 (1)	0.0450 (11)	−0.0019 (8)	0.0064 (8)	−0.0080 (9)
C3	0.0247 (8)	0.0264 (9)	0.0322 (9)	−0.0018 (7)	0.0065 (7)	−0.0038 (7)
C4	0.0231 (8)	0.0262 (9)	0.0359 (9)	0.0004 (7)	0.0076 (7)	−0.0076 (8)
C5	0.0253 (8)	0.0197 (8)	0.0242 (8)	0.0010 (6)	0.0049 (6)	−0.0024 (6)
N6	0.0223 (7)	0.0198 (7)	0.0255 (7)	0.0005 (5)	0.0049 (5)	−0.0040 (6)
C7	0.0257 (8)	0.0231 (8)	0.0264 (8)	0.0024 (7)	0.0030 (6)	−0.0030 (7)
C8	0.0238 (8)	0.0222 (8)	0.0285 (8)	−0.0012 (7)	0.0054 (6)	−0.0050 (7)
C9	0.0230 (8)	0.0235 (8)	0.0345 (9)	−0.0016 (7)	0.0065 (7)	−0.0073 (7)
C10	0.0236 (8)	0.0216 (8)	0.0243 (8)	0.0011 (6)	0.0059 (6)	−0.0033 (7)
C11	0.0273 (8)	0.0245 (8)	0.0267 (8)	−0.0001 (7)	0.0053 (7)	−0.0034 (7)
C12	0.033 (1)	0.034 (1)	0.0403 (11)	−0.0058 (8)	0.0138 (8)	−0.0147 (9)
C13	0.0439 (11)	0.0348 (11)	0.0395 (11)	−0.0057 (9)	0.0156 (9)	−0.0161 (9)
C14	0.0406 (11)	0.0280 (9)	0.0318 (9)	−0.0056 (8)	0.0056 (8)	−0.0078 (8)
C15	0.0312 (9)	0.0244 (9)	0.0293 (9)	−0.0028 (7)	0.0023 (7)	−0.0009 (7)
C16	0.0270 (9)	0.0244 (8)	0.0254 (8)	0.0000 (7)	0.0024 (6)	−0.0024 (7)
C17	0.036 (1)	0.031 (1)	0.0295 (9)	−0.0017 (8)	0.0118 (8)	−0.0078 (8)
C18	0.0409 (11)	0.030 (1)	0.033 (1)	0.0023 (9)	0.0079 (8)	−0.0108 (8)
C19	0.0726 (18)	0.0456 (14)	0.0409 (12)	−0.0094 (12)	0.0033 (12)	−0.0179 (11)
C20	0.0242 (8)	0.0251 (9)	0.0325 (9)	−0.0004 (7)	0.0073 (7)	−0.0048 (7)
O21	0.0269 (7)	0.0281 (7)	0.065 (1)	0.0008 (6)	0.0085 (7)	−0.0123 (7)
N22	0.0222 (7)	0.0238 (8)	0.0289 (8)	−0.0006 (6)	0.0028 (6)	−0.0001 (6)
C23	0.0298 (9)	0.0220 (8)	0.0310 (9)	−0.0002 (7)	0.0042 (7)	0.0023 (7)
O24	0.0380 (8)	0.0262 (7)	0.0413 (8)	0.0009 (6)	−0.0064 (6)	0.0037 (6)
N25	0.045 (1)	0.0245 (8)	0.0422 (9)	0.0027 (7)	−0.0038 (8)	−0.0047 (7)
C26	0.0601 (15)	0.0273 (11)	0.0685 (17)	0.009 (1)	−0.0062 (13)	−0.0118 (11)
C27	0.074 (2)	0.0323 (13)	0.101 (3)	−0.0044 (13)	−0.0056 (18)	0.0065 (15)
C28	0.0212 (8)	0.0313 (9)	0.0334 (9)	−0.0021 (7)	0.0075 (7)	−0.0012 (8)
C29	0.0266 (9)	0.032 (1)	0.040 (1)	0.0042 (8)	0.0020 (8)	0.0011 (8)
C30	0.039 (1)	0.0367 (11)	0.030 (1)	0.0005 (9)	0.0041 (8)	0.0028 (8)
N31	0.0701 (14)	0.036 (1)	0.0299 (9)	0.005 (1)	0.0009 (8)	−0.0061 (8)
C32	0.142 (4)	0.074 (2)	0.0453 (16)	0.036 (2)	0.0340 (19)	−0.0075 (15)
C33	0.096 (3)	0.0628 (19)	0.0587 (17)	−0.0222 (18)	−0.0273 (17)	−0.0056 (15)
N41	0.0280 (8)	0.0345 (9)	0.046 (1)	0.0043 (7)	0.0144 (7)	−0.0031 (8)
C42	0.0275 (9)	0.0270 (9)	0.039 (1)	0.0035 (7)	0.0067 (7)	0.0013 (8)
C43	0.0232 (8)	0.0244 (8)	0.0297 (9)	0.0003 (7)	0.0050 (7)	0.0017 (7)
C44	0.0207 (8)	0.0268 (9)	0.0306 (9)	−0.0011 (7)	0.0029 (6)	−0.0009 (7)
C45	0.0232 (8)	0.0192 (8)	0.0266 (8)	0.0009 (6)	0.0035 (6)	0.0006 (6)
N46	0.0231 (7)	0.0252 (8)	0.0343 (8)	−0.0012 (6)	0.0074 (6)	−0.0055 (7)
C47	0.0259 (9)	0.0289 (9)	0.042 (1)	−0.0024 (7)	0.0133 (8)	−0.0078 (8)
C48	0.0218 (8)	0.0224 (8)	0.0461 (11)	0.0000 (7)	0.0091 (7)	0.0025 (8)
C49	0.0205 (8)	0.0283 (9)	0.0332 (9)	−0.0008 (7)	0.0037 (6)	0.0005 (7)
C50	0.0186 (7)	0.0257 (8)	0.0280 (8)	−0.0000 (6)	0.0038 (6)	0.0034 (7)
C51	0.0254 (8)	0.0262 (9)	0.0284 (9)	−0.0030 (7)	0.0060 (7)	0.0010 (7)
C52	0.0314 (9)	0.035 (1)	0.0309 (9)	−0.0068 (8)	0.0055 (7)	−0.0020 (8)
C53	0.0451 (12)	0.0385 (11)	0.035 (1)	−0.013 (1)	0.0080 (9)	−0.0099 (9)
C54	0.0468 (12)	0.031 (1)	0.0396 (11)	−0.0057 (9)	0.0182 (9)	−0.0085 (9)
C55	0.033 (1)	0.0269 (9)	0.035 (1)	−0.0008 (8)	0.0124 (8)	−0.0001 (8)
C56	0.0273 (8)	0.0230 (8)	0.0302 (9)	0.0001 (7)	0.0079 (7)	0.0016 (7)
C57	0.034 (1)	0.0356 (11)	0.0324 (9)	−0.0034 (8)	0.0058 (8)	−0.0045 (8)
C58	0.0508 (13)	0.0377 (12)	0.0378 (11)	−0.010 (1)	0.013 (1)	−0.0099 (9)
C59	0.104 (3)	0.0614 (18)	0.0570 (17)	−0.0158 (18)	0.0395 (18)	−0.0190 (15)
C60	0.0204 (8)	0.0268 (9)	0.0536 (12)	0.0003 (7)	0.0088 (8)	0.0007 (9)
O61	0.0297 (8)	0.0257 (8)	0.1093 (16)	−0.0038 (6)	0.0276 (9)	0.0003 (9)
N62	0.0179 (6)	0.0258 (8)	0.0336 (8)	−0.0009 (6)	0.0062 (6)	0.0028 (6)
C63	0.0206 (8)	0.0268 (9)	0.039 (1)	0.0007 (7)	0.0031 (7)	0.0072 (8)
O64	0.0360 (8)	0.0349 (8)	0.060 (1)	0.0063 (6)	0.0226 (7)	0.0178 (7)
N65	0.0358 (9)	0.0225 (8)	0.047 (1)	−0.0011 (7)	0.0078 (7)	0.0029 (7)
C66	0.0458 (13)	0.024 (1)	0.0778 (18)	0.0015 (9)	0.0099 (12)	0.0060 (11)
C67	0.0613 (18)	0.0464 (16)	0.096 (2)	−0.0209 (14)	0.0044 (16)	−0.0023 (16)
C68	0.0180 (8)	0.0278 (9)	0.039 (1)	−0.0019 (7)	0.0067 (7)	−0.0010 (8)
C69	0.037 (1)	0.0402 (12)	0.0430 (11)	−0.0054 (9)	0.0122 (9)	0.011 (1)
C70	0.043 (2)	0.074 (3)	0.036 (2)	−0.006 (2)	−0.0008 (16)	0.013 (2)
N71	0.045 (3)	0.059 (3)	0.029 (2)	−0.001 (3)	0.000 (3)	−0.0064 (19)
C72	0.125 (6)	0.094 (5)	0.039 (3)	−0.039 (5)	0.020 (3)	−0.035 (3)
C73	0.070 (3)	0.084 (4)	0.050 (3)	0.013 (3)	0.020 (2)	−0.006 (3)
C80	0.059 (4)	0.041 (3)	0.030 (3)	−0.002 (3)	0.013 (2)	0.001 (2)
C82	0.140 (9)	0.104 (8)	0.038 (4)	−0.088 (8)	−0.039 (5)	0.022 (4)
N81	0.084 (7)	0.051 (4)	0.033 (4)	−0.022 (7)	0.010 (6)	−0.011 (3)

Geometric parameters (Å, º) top

N1—C2	1.392 (3)	N46—C57	1.475 (3)
N1—C15	1.376 (3)	C47—C48	1.524 (3)
N1—H11	0.922	C47—H471	1.000
C2—C3	1.368 (3)	C47—H472	1.000
C2—H21	1.000	C48—C49	1.523 (3)
C3—C4	1.504 (3)	C48—C60	1.520 (2)
C3—C16	1.413 (3)	C48—H481	1.000
C4—C5	1.550 (2)	C49—C50	1.529 (2)
C4—H41	1.000	C49—H491	1.000
C4—H42	1.000	C49—H492	1.000
C5—N6	1.477 (2)	C50—C51	1.521 (3)
C5—C10	1.558 (2)	C50—H501	1.000
C5—H51	1.000	C51—C52	1.390 (3)
N6—C7	1.469 (2)	C51—C56	1.391 (3)
N6—C17	1.473 (2)	C52—C53	1.424 (3)
C7—C8	1.535 (2)	C52—H521	1.000
C7—H71	1.000	C53—C54	1.382 (3)
C7—H72	1.000	C53—H531	1.000
C8—C9	1.515 (2)	C54—C55	1.396 (3)
C8—C20	1.514 (2)	C54—H541	1.000
C8—H81	1.000	C55—C56	1.401 (3)
C9—C10	1.528 (2)	C57—C58	1.500 (3)
C9—H91	1.000	C57—H571	1.000
C9—H92	1.000	C57—H572	1.000
C10—C11	1.516 (2)	C58—C59	1.306 (4)
C10—H101	1.000	C58—H581	1.000
C11—C12	1.387 (3)	C59—H591	1.000
C11—C16	1.395 (3)	C59—H592	1.000
C12—C13	1.413 (3)	C60—O61	1.219 (3)
C12—H121	1.000	C60—N62	1.387 (3)
C13—C14	1.383 (3)	N62—C63	1.423 (2)
C13—H131	1.000	N62—C68	1.484 (2)
C14—C15	1.398 (3)	C63—O64	1.233 (3)
C14—H141	1.000	C63—N65	1.335 (3)
C15—C16	1.398 (3)	N65—C66	1.465 (3)
C17—C18	1.503 (3)	N65—H651	0.932
C17—H171	1.000	C66—C67	1.523 (4)
C17—H172	1.000	C66—H661	1.000
C18—C19	1.311 (3)	C66—H662	1.000
C18—H181	1.000	C67—H671	1.000
C19—H191	1.000	C67—H672	1.000
C19—H192	1.000	C67—H673	1.000
C20—O21	1.216 (2)	C68—C69	1.532 (3)
C20—N22	1.390 (2)	C68—H681	1.000
N22—C23	1.432 (2)	C68—H682	1.000
N22—C28	1.475 (2)	C69—C70	1.488 (5)
C23—O24	1.222 (2)	C69—C80	1.572 (7)
C23—N25	1.331 (3)	C69—H6911	1.000
N25—C26	1.465 (3)	C69—H6912	1.000
N25—H251	0.979	C69—H6921	1.000
C26—C27	1.489 (5)	C69—H6922	1.000
C26—H261	1.000	C70—N71	1.490 (11)
C26—H262	1.000	C70—C80	1.130 (8)
C27—H271	1.000	C70—C82	1.627 (9)
C27—H272	1.000	C70—N81	1.354 (16)
C27—H273	1.000	C70—H701	1.000
C28—C29	1.532 (3)	C70—H702	1.000
C28—H281	1.000	N71—C72	1.45 (1)
C28—H282	1.000	N71—C73	1.439 (8)
C29—C30	1.512 (3)	N71—C80	1.215 (12)
C29—H291	1.000	N71—N81	0.53 (1)
C29—H292	1.000	N71—C83	1.37 (2)
C30—N31	1.463 (3)	C72—C82	1.656 (17)
C30—H301	1.000	C72—N81	1.256 (14)
C30—H302	1.000	C72—C83	0.910 (17)
N31—C32	1.467 (4)	C72—H721	1.000
N31—C33	1.456 (4)	C72—H722	1.000
C32—H321	1.000	C72—H723	1.000
C32—H322	1.000	C72—H831	1.04 (2)
C32—H323	1.000	C73—C80	1.448 (9)
C33—H331	1.000	C73—H801	0.958 (8)
C33—H332	1.000	C73—H731	1.000
C33—H333	1.000	C73—H732	1.000
N41—C42	1.385 (3)	C73—H733	1.000
N41—C55	1.376 (3)	C80—N81	1.507 (13)
N41—H411	0.891	C80—H801	1.000
C42—C43	1.370 (3)	C80—H802	1.000
C42—H421	1.000	C82—N81	1.398 (16)
C43—C44	1.496 (3)	C82—H702	1.254 (12)
C43—C56	1.421 (3)	C82—H821	1.000
C44—C45	1.547 (2)	C82—H822	1.000
C44—H441	1.000	C82—H823	1.000
C44—H442	1.000	N81—C83	1.51 (2)
C45—N46	1.481 (2)	C83—H721	0.80 (2)
C45—C50	1.558 (2)	C83—H831	1.000
C45—H451	1.000	C83—H832	1.000
N46—C47	1.468 (2)	C83—H833	1.000

C2—N1—C15	108.76 (16)	H441—C44—H442	109.5
C2—N1—H11	123.2	C44—C45—N46	109.88 (14)
C15—N1—H11	125.9	C44—C45—C50	111.92 (14)
N1—C2—C3	109.49 (17)	N46—C45—C50	108.72 (14)
N1—C2—H21	125.3	C44—C45—H451	107.33
C3—C2—H21	125.2	N46—C45—H451	110.6
C2—C3—C4	134.47 (17)	C50—C45—H451	108.4
C2—C3—C16	106.03 (17)	C45—N46—C47	111.43 (14)
C4—C3—C16	119.47 (16)	C45—N46—C57	113.00 (15)
C3—C4—C5	111.59 (14)	C47—N46—C57	108.42 (15)
C3—C4—H41	108.9	N46—C47—C48	110.33 (16)
C5—C4—H41	109.0	N46—C47—H471	108.8
C3—C4—H42	109.0	C48—C47—H471	109.3
C5—C4—H42	108.9	N46—C47—H472	109.6
H41—C4—H42	109.5	C48—C47—H472	109.3
C4—C5—N6	110.08 (14)	H471—C47—H472	109.5
C4—C5—C10	112.70 (14)	C47—C48—C49	109.05 (15)
N6—C5—C10	107.99 (14)	C47—C48—C60	107.78 (16)
C4—C5—H51	106.6	C49—C48—C60	111.53 (16)
N6—C5—H51	111.5	C47—C48—H481	111.5
C10—C5—H51	108.0	C49—C48—H481	108.1
C5—N6—C7	111.79 (13)	C60—C48—H481	108.9
C5—N6—C17	114.18 (14)	C48—C49—C50	108.81 (15)
C7—N6—C17	110.05 (14)	C48—C49—H491	109.8
N6—C7—C8	109.87 (14)	C50—C49—H491	110.0
N6—C7—H71	109.7	C48—C49—H492	109.5
C8—C7—H71	109.6	C50—C49—H492	109.3
N6—C7—H72	109.0	H491—C49—H492	109.5
C8—C7—H72	109.1	C45—C50—C49	111.66 (14)
H71—C7—H72	109.5	C45—C50—C51	111.56 (14)
C7—C8—C9	108.64 (15)	C49—C50—C51	112.97 (15)
C7—C8—C20	110.96 (14)	C45—C50—H501	107.8
C9—C8—C20	112.07 (14)	C49—C50—H501	106.2
C7—C8—H81	109.8	C51—C50—H501	106.1
C9—C8—H81	109.1	C50—C51—C52	128.08 (17)
C20—C8—H81	106.2	C50—C51—C56	115.46 (16)
C8—C9—C10	108.66 (14)	C52—C51—C56	116.37 (18)
C8—C9—H91	109.6	C51—C52—C53	119.74 (19)
C10—C9—H91	109.7	C51—C52—H521	119.9
C8—C9—H92	109.8	C53—C52—H521	120.4
C10—C9—H92	109.6	C52—C53—C54	123.34 (19)
H91—C9—H92	109.5	C52—C53—H531	118.3
C5—C10—C9	111.92 (14)	C54—C53—H531	118.3
C5—C10—C11	112.34 (14)	C53—C54—C55	116.70 (19)
C9—C10—C11	113.34 (14)	C53—C54—H541	121.7
C5—C10—H101	106.9	C55—C54—H541	121.6
C9—C10—H101	106.1	N41—C55—C54	133.80 (19)
C11—C10—H101	105.6	N41—C55—C56	106.37 (17)
C10—C11—C12	128.11 (17)	C54—C55—C56	119.83 (19)
C10—C11—C16	114.88 (15)	C43—C56—C51	127.00 (17)
C12—C11—C16	116.65 (17)	C43—C56—C55	108.99 (16)
C11—C12—C13	120.04 (19)	C51—C56—C55	123.98 (18)
C11—C12—H121	119.9	N46—C57—C58	111.22 (18)
C13—C12—H121	120.1	N46—C57—H571	109.2
C12—C13—C14	123.44 (19)	C58—C57—H571	108.9
C12—C13—H131	118.4	N46—C57—H572	108.9
C14—C13—H131	118.1	C58—C57—H572	109.1
C13—C14—C15	116.25 (18)	H571—C57—H572	109.5
C13—C14—H141	122.3	C57—C58—C59	125.0 (3)
C15—C14—H141	121.5	C57—C58—H581	117.6
N1—C15—C14	132.94 (18)	C59—C58—H581	117.4
N1—C15—C16	106.53 (17)	C58—C59—H591	120.3
C14—C15—C16	120.52 (18)	C58—C59—H592	119.7
C3—C16—C11	127.76 (17)	H591—C59—H592	120.0
C3—C16—C15	109.18 (16)	C48—C60—O61	120.20 (18)
C11—C16—C15	123.03 (17)	C48—C60—N62	120.14 (17)
N6—C17—C18	111.49 (16)	O61—C60—N62	119.23 (17)
N6—C17—H171	109.3	C60—N62—C63	124.11 (15)
C18—C17—H171	108.8	C60—N62—C68	115.34 (15)
N6—C17—H172	108.7	C63—N62—C68	120.19 (15)
C18—C17—H172	109.1	N62—C63—O64	121.00 (18)
H171—C17—H172	109.5	N62—C63—N65	114.89 (17)
C17—C18—C19	124.9 (2)	O64—C63—N65	124.08 (19)
C17—C18—H181	117.7	C63—N65—C66	120.10 (19)
C19—C18—H181	117.4	C63—N65—H651	123.9
C18—C19—H191	120.3	C66—N65—H651	114.1
C18—C19—H192	119.7	N65—C66—C67	111.2 (2)
H191—C19—H192	120.0	N65—C66—H661	109.6
C8—C20—O21	121.43 (17)	C67—C66—H661	109.4
C8—C20—N22	119.01 (15)	N65—C66—H662	108.4
O21—C20—N22	119.37 (16)	C67—C66—H662	108.8
C20—N22—C23	123.24 (15)	H661—C66—H662	109.5
C20—N22—C28	116.01 (15)	C66—C67—H671	109.6
C23—N22—C28	120.50 (15)	C66—C67—H672	109.1
N22—C23—O24	121.48 (17)	H671—C67—H672	109.5
N22—C23—N25	114.54 (17)	C66—C67—H673	109.8
O24—C23—N25	123.98 (19)	H671—C67—H673	109.5
C23—N25—C26	119.64 (19)	H672—C67—H673	109.5
C23—N25—H251	113.9	N62—C68—C69	113.38 (16)
C26—N25—H251	124.3	N62—C68—H681	108.4
N25—C26—C27	112.7 (3)	C69—C68—H681	108.5
N25—C26—H261	108.5	N62—C68—H682	108.5
C27—C26—H261	108.4	C69—C68—H682	108.6
N25—C26—H262	108.8	H681—C68—H682	109.5
C27—C26—H262	109.0	C68—C69—C70	116.3 (2)
H261—C26—H262	109.5	C68—C69—C80	111.5 (3)
C26—C27—H271	109.6	C68—C69—H6911	107.9
C26—C27—H272	109.7	C70—C69—H6911	107.9
H271—C27—H272	109.5	C68—C69—H6912	107.7
C26—C27—H273	109.1	C70—C69—H6912	107.5
H271—C27—H273	109.5	H6911—C69—H6912	109.5
H272—C27—H273	109.5	C68—C69—H6921	109.1
N22—C28—C29	114.15 (16)	C80—C69—H6921	108.6
N22—C28—H281	108.4	C68—C69—H6922	108.9
C29—C28—H281	108.4	C80—C69—H6922	109.3
N22—C28—H282	108.3	H6921—C69—H6922	109.5
C29—C28—H282	108.1	C69—C70—N71	110.6 (4)
H281—C28—H282	109.5	C69—C70—H701	109.1
C28—C29—C30	114.62 (17)	N71—C70—H701	109.4
C28—C29—H291	108.2	C69—C70—H702	109.1
C30—C29—H291	108.3	N71—C70—H702	109.1
C28—C29—H292	108.1	H701—C70—H702	109.5
C30—C29—H292	108.2	C70—N71—C72	110.5 (6)
H291—C29—H292	109.5	C70—N71—C73	111.8 (7)
C29—C30—N31	113.86 (19)	C72—N71—C73	108.0 (7)
C29—C30—H301	108.2	N71—C72—H721	110.4
N31—C30—H301	108.5	N71—C72—H722	109.1
C29—C30—H302	108.4	H721—C72—H722	109.5
N31—C30—H302	108.4	N71—C72—H723	108.9
H301—C30—H302	109.5	H721—C72—H723	109.5
C30—N31—C32	108.4 (3)	H722—C72—H723	109.5
C30—N31—C33	110.6 (2)	N71—C73—H731	110.9
C32—N31—C33	110.8 (3)	N71—C73—H732	109.4
N31—C32—H321	110.0	H731—C73—H732	109.5
N31—C32—H322	110.4	N71—C73—H733	108.1
H321—C32—H322	109.5	H731—C73—H733	109.5
N31—C32—H323	108.0	H732—C73—H733	109.5
H321—C32—H323	109.5	C69—C80—N81	110.4 (7)
H322—C32—H323	109.5	C69—C80—H801	109.7
N31—C33—H331	110.2	N81—C80—H801	108.7
N31—C33—H332	108.9	C69—C80—H802	109.7
H331—C33—H332	109.5	N81—C80—H802	108.9
N31—C33—H333	109.3	H801—C80—H802	109.5
H331—C33—H333	109.5	N81—C82—H821	109.5
H332—C33—H333	109.5	N81—C82—H822	111.7
C42—N41—C55	109.19 (16)	H821—C82—H822	109.5
C42—N41—H411	122.0	N81—C82—H823	107.2
C55—N41—H411	128.8	H821—C82—H823	109.5
N41—C42—C43	109.63 (17)	H822—C82—H823	109.5
N41—C42—H421	125.3	C80—N81—C82	114.0 (11)
C43—C42—H421	125.0	C80—N81—C83	105.1 (10)
C42—C43—C44	134.61 (18)	C82—N81—C83	113.6 (12)
C42—C43—C56	105.82 (17)	N81—C83—H831	105.9
C44—C43—C56	119.57 (15)	N81—C83—H832	112.4
C43—C44—C45	110.67 (14)	H831—C83—H832	109.5
C43—C44—H441	109.3	N81—C83—H833	110.0
C45—C44—H441	109.3	H831—C83—H833	109.5
C43—C44—H442	109.0	H832—C83—H833	109.5
C45—C44—H442	109.2

Hydrogen-bond networks in Cabergoline forms I and VII (Å, °) top

Cabergoline form I^a	D···A	D-H···A
N4-H20···N5	2.887	161
N1-H1···N2ⁱ	2.956	167
Cabergoline form VII^b
N25-H251···N31	2.893 (3)	173
N65-H651···N71	2.934 (9)	174
N65-H651···N81	2.768 (12)	165
N1-H11···O24ⁱⁱ	2.973 (2)	167
N41-H411···O64ⁱⁱⁱ	2.861 (2)	171
C14-H141···N6ⁱⁱ	3.458 (3)	166
C2-H21···O21^iv	3.296 (3)	171
C42-H421···O61^iv	3.286 (3)	156

Note: (a) (Sabatino et al. (1995); (b) this work. Symmetry codes: (i) -x,1/2+y,2-z; (ii) -x,1/2+y,1-z; (iii) -1-x,-1/2+y,-z; (iv) 1+x,y,z.

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