Stereochemistry of the methyl­idene-bridged quinazoline-iso­quinoline alkaloid 3-{[6,7-dimeth­oxy-1-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­isoquinolin-2-yl]methyl­idene}-1,2,3,9-tetra­hydro­pyrrolo­[2,1-b]quinazolin-9-one methanol monosolvate

The main residue and the solvent mol­ecule aggregate to discrete pairs via a classical O—H...O hydrogen bond, while non-classical C—H...O inter­actions lead to the formation of an extended network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.061
• wR factor = 0.164
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0043 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.288 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

3-{[6,7-Dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate

Crystal data

C29H26N4O5·CH4O	F(000) = 1144
Mr = 542.58	Dx = 1.376 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.326 (4) Å	Cell parameters from 1353 reflections
b = 8.0566 (19) Å	θ = 3.0–19.8°
c = 20.565 (5) Å	µ = 0.10 mm^−1
β = 104.497 (6)°	T = 100 K
V = 2618.9 (11) Å^3	Rod, yellow
Z = 4	0.55 × 0.09 × 0.08 mm

Data collection

Bruker APEX CCD diffractometer	4821 independent reflections
Radiation source: microsource	2918 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.114
ω scans	θmax = 25.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→19
Tmin = 0.665, Tmax = 0.745	k = −9→9
25889 measured reflections	l = −24→24

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 0.4688P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4821 reflections	Δρmax = 0.39 e Å^−3
367 parameters	Δρmin = −0.35 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
O1	0.08305 (12)	1.1111 (2)	0.65060 (10)	0.0267 (5)
O2	0.14565 (12)	1.0007 (2)	0.77066 (9)	0.0256 (5)
O4	0.71000 (15)	1.2323 (3)	0.94869 (12)	0.0522 (7)
O3	0.60907 (14)	1.4105 (3)	0.94156 (11)	0.0385 (6)
O5	0.70612 (13)	0.3657 (3)	0.50686 (10)	0.0303 (5)
N1	0.63699 (17)	1.2806 (4)	0.92532 (13)	0.0338 (7)
N2	0.46055 (15)	0.8631 (3)	0.66495 (12)	0.0238 (6)
N19	0.59083 (15)	0.4135 (3)	0.66290 (12)	0.0260 (6)
N24A	0.62119 (15)	0.5026 (3)	0.56116 (12)	0.0241 (6)
C1	0.42173 (18)	0.8773 (4)	0.72189 (14)	0.0221 (7)
H1	0.4208	0.7639	0.7415	0.026*
C3	0.44128 (19)	1.0014 (4)	0.61757 (15)	0.0266 (7)
H3B	0.4754	0.9925	0.5841	0.032*
H3A	0.4551	1.1081	0.6418	0.032*
C4	0.34774 (18)	0.9951 (4)	0.58261 (14)	0.0269 (7)
H4B	0.3321	1.0936	0.5534	0.032*
H4A	0.3356	0.8947	0.5540	0.032*
C4A	0.29609 (19)	0.9915 (4)	0.63407 (14)	0.0236 (7)
C5	0.21208 (19)	1.0482 (4)	0.61679 (15)	0.0248 (7)
H5	0.1879	1.0853	0.5723	0.030*
C6	0.16455 (18)	1.0508 (4)	0.66287 (15)	0.0237 (7)
C7	0.19881 (18)	0.9950 (3)	0.72862 (14)	0.0226 (7)
C8	0.28131 (19)	0.9378 (3)	0.74592 (14)	0.0226 (7)
H8	0.3048	0.8982	0.7902	0.027*
C8A	0.33064 (18)	0.9374 (3)	0.69924 (14)	0.0213 (7)
C9	0.0470 (2)	1.1711 (4)	0.58366 (15)	0.0331 (8)
H9B	0.0804	1.2652	0.5743	0.050*
H9C	−0.0114	1.2071	0.5798	0.050*
H9A	0.0474	1.0821	0.5513	0.050*
C10	0.1823 (2)	0.9721 (4)	0.84092 (15)	0.0346 (9)
H10B	0.2047	0.8588	0.8474	0.052*
H10C	0.1389	0.9865	0.8659	0.052*
H10A	0.2283	1.0515	0.8574	0.052*
C11	0.47684 (18)	0.9873 (4)	0.77600 (14)	0.0213 (7)
C12	0.55019 (19)	0.9188 (4)	0.81757 (15)	0.0279 (8)
H12	0.5636	0.8057	0.8123	0.033*
C13	0.6034 (2)	1.0145 (4)	0.86629 (15)	0.0297 (8)
H13	0.6534	0.9687	0.8945	0.036*
C14	0.58186 (19)	1.1787 (4)	0.87291 (15)	0.0258 (7)
C15	0.51115 (19)	1.2512 (4)	0.83252 (14)	0.0262 (7)
H15	0.4986	1.3649	0.8375	0.031*
C16	0.45834 (19)	1.1526 (4)	0.78389 (14)	0.0256 (7)
H16	0.4087	1.1997	0.7556	0.031*
C17	0.50221 (18)	0.7246 (4)	0.65647 (15)	0.0223 (7)
H17	0.5061	0.6442	0.6909	0.027*
C18	0.53988 (18)	0.6787 (4)	0.60744 (15)	0.0238 (7)
C18A	0.58472 (18)	0.5214 (4)	0.61466 (14)	0.0223 (7)
C19A	0.64138 (18)	0.2763 (4)	0.66009 (15)	0.0239 (7)
C20	0.6513 (2)	0.1578 (4)	0.71145 (16)	0.0303 (8)
H20	0.6216	0.1704	0.7454	0.036*
C21	0.7038 (2)	0.0237 (4)	0.71301 (17)	0.0381 (9)
H21	0.7100	−0.0558	0.7480	0.046*
C22	0.7478 (2)	0.0034 (5)	0.66366 (18)	0.0440 (10)
H22	0.7848	−0.0886	0.6657	0.053*
C23	0.7382 (2)	0.1152 (4)	0.61231 (17)	0.0343 (8)
H23	0.7675	0.0995	0.5783	0.041*
C23A	0.68515 (18)	0.2530 (4)	0.60979 (15)	0.0258 (7)
C24	0.67353 (18)	0.3723 (4)	0.55492 (15)	0.0250 (7)
C25	0.59868 (19)	0.6360 (4)	0.51134 (15)	0.0279 (8)
H25B	0.5610	0.5943	0.4690	0.033*
H25A	0.6499	0.6847	0.5014	0.033*
C26	0.55278 (19)	0.7643 (4)	0.54499 (14)	0.0262 (7)
H26A	0.5876	0.8656	0.5571	0.031*
H26B	0.4978	0.7955	0.5146	0.031*
C27	0.8885 (3)	0.3496 (6)	0.4479 (2)	0.0611 (12)
H27A	0.9489	0.3688	0.4521	0.092*
H27B	0.8599	0.3294	0.4007	0.092*
H27C	0.8814	0.2527	0.4748	0.092*
O6	0.85271 (16)	0.4911 (3)	0.47115 (13)	0.0523 (7)
H6	0.8044 (18)	0.458 (5)	0.4864 (18)	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0260 (12)	0.0294 (13)	0.0210 (11)	0.0026 (10)	−0.0010 (9)	0.0009 (10)
O2	0.0272 (12)	0.0292 (13)	0.0193 (11)	0.0022 (10)	0.0034 (9)	0.0007 (10)
O4	0.0356 (15)	0.0495 (17)	0.0555 (17)	−0.0046 (13)	−0.0185 (13)	0.0101 (14)
O3	0.0387 (14)	0.0441 (16)	0.0304 (13)	−0.0057 (12)	0.0045 (11)	−0.0113 (12)
O5	0.0311 (12)	0.0356 (14)	0.0269 (12)	−0.0003 (10)	0.0123 (10)	−0.0025 (11)
N1	0.0309 (17)	0.0416 (19)	0.0256 (16)	−0.0090 (14)	0.0007 (13)	0.0040 (14)
N2	0.0272 (14)	0.0218 (15)	0.0218 (14)	0.0028 (12)	0.0054 (11)	0.0016 (12)
N19	0.0301 (15)	0.0237 (15)	0.0247 (15)	0.0019 (12)	0.0076 (12)	0.0005 (12)
N24A	0.0232 (14)	0.0241 (15)	0.0235 (14)	0.0000 (12)	0.0032 (11)	0.0004 (12)
C1	0.0255 (16)	0.0211 (17)	0.0191 (16)	0.0013 (13)	0.0047 (13)	0.0037 (14)
C3	0.0306 (18)	0.0245 (19)	0.0249 (17)	0.0010 (15)	0.0070 (14)	0.0035 (15)
C4	0.0306 (18)	0.0263 (19)	0.0219 (17)	−0.0025 (15)	0.0029 (14)	−0.0001 (15)
C4A	0.0318 (18)	0.0168 (17)	0.0211 (17)	−0.0018 (14)	0.0047 (14)	−0.0020 (14)
C5	0.0304 (18)	0.0218 (18)	0.0185 (16)	−0.0018 (14)	−0.0012 (14)	−0.0003 (14)
C6	0.0239 (17)	0.0189 (17)	0.0235 (17)	−0.0003 (14)	−0.0029 (14)	0.0006 (14)
C7	0.0268 (18)	0.0162 (16)	0.0233 (17)	−0.0028 (14)	0.0036 (14)	−0.0006 (14)
C8	0.0331 (18)	0.0146 (16)	0.0168 (16)	−0.0017 (14)	0.0002 (14)	−0.0009 (13)
C8A	0.0230 (16)	0.0158 (16)	0.0213 (17)	−0.0038 (13)	−0.0016 (13)	−0.0025 (13)
C9	0.0310 (18)	0.039 (2)	0.0235 (18)	0.0068 (16)	−0.0032 (15)	−0.0002 (16)
C10	0.039 (2)	0.043 (2)	0.0218 (18)	0.0109 (17)	0.0081 (15)	0.0058 (16)
C11	0.0216 (16)	0.0244 (18)	0.0172 (16)	−0.0012 (13)	0.0037 (13)	0.0020 (14)
C12	0.0292 (18)	0.0254 (19)	0.0283 (18)	0.0042 (15)	0.0061 (15)	0.0049 (15)
C13	0.0260 (18)	0.032 (2)	0.0265 (18)	−0.0008 (15)	−0.0017 (14)	0.0081 (16)
C14	0.0252 (17)	0.030 (2)	0.0207 (17)	−0.0049 (14)	0.0021 (14)	−0.0015 (15)
C15	0.0281 (18)	0.0268 (19)	0.0236 (17)	0.0010 (15)	0.0063 (15)	−0.0001 (15)
C16	0.0257 (17)	0.0284 (19)	0.0214 (17)	−0.0017 (15)	0.0034 (14)	0.0014 (15)
C17	0.0230 (16)	0.0179 (17)	0.0235 (17)	−0.0009 (13)	0.0011 (14)	0.0011 (14)
C18	0.0225 (16)	0.0240 (18)	0.0242 (17)	−0.0027 (13)	0.0044 (14)	−0.0005 (14)
C18A	0.0199 (16)	0.0237 (18)	0.0226 (17)	−0.0038 (13)	0.0038 (13)	−0.0040 (14)
C19A	0.0203 (16)	0.0202 (18)	0.0290 (18)	−0.0054 (13)	0.0023 (14)	−0.0048 (15)
C20	0.0304 (18)	0.033 (2)	0.0269 (18)	0.0010 (16)	0.0062 (15)	−0.0002 (16)
C21	0.043 (2)	0.037 (2)	0.035 (2)	0.0123 (17)	0.0106 (17)	0.0080 (17)
C22	0.048 (2)	0.042 (2)	0.043 (2)	0.0239 (19)	0.0138 (19)	0.0072 (19)
C23	0.037 (2)	0.034 (2)	0.034 (2)	0.0098 (16)	0.0120 (16)	0.0017 (17)
C23A	0.0213 (16)	0.0265 (18)	0.0282 (18)	0.0010 (14)	0.0036 (14)	−0.0012 (15)
C24	0.0207 (16)	0.0246 (18)	0.0279 (18)	−0.0036 (14)	0.0025 (14)	−0.0063 (15)
C25	0.0280 (17)	0.032 (2)	0.0231 (17)	−0.0015 (15)	0.0052 (14)	0.0017 (15)
C26	0.0265 (17)	0.0252 (18)	0.0260 (18)	−0.0002 (14)	0.0049 (14)	0.0027 (15)
C27	0.060 (3)	0.072 (3)	0.048 (3)	0.019 (2)	0.007 (2)	−0.011 (2)
O6	0.0492 (17)	0.0592 (19)	0.0511 (17)	−0.0084 (14)	0.0174 (14)	−0.0151 (14)

Geometric parameters (Å, º)

O1—C6	1.379 (3)	C10—H10C	0.9800
O1—C9	1.439 (4)	C10—H10A	0.9800
O2—C7	1.371 (3)	C11—C16	1.384 (4)
O2—C10	1.438 (3)	C11—C12	1.399 (4)
O4—N1	1.232 (3)	C12—C13	1.384 (4)
O3—N1	1.221 (3)	C12—H12	0.9500
O5—C24	1.236 (3)	C13—C14	1.384 (4)
N1—C14	1.470 (4)	C13—H13	0.9500
N2—C17	1.341 (4)	C14—C15	1.373 (4)
N2—C3	1.462 (4)	C15—C16	1.394 (4)
N2—C1	1.469 (3)	C15—H15	0.9500
N19—C18A	1.304 (4)	C16—H16	0.9500
N19—C19A	1.389 (4)	C17—C18	1.357 (4)
N24A—C24	1.379 (4)	C17—H17	0.9500
N24A—C18A	1.384 (3)	C18—C18A	1.452 (4)
N24A—C25	1.467 (4)	C18—C26	1.518 (4)
C1—C8A	1.522 (4)	C19A—C20	1.403 (4)
C1—C11	1.527 (4)	C19A—C23A	1.409 (4)
C1—H1	1.0000	C20—C21	1.374 (4)
C3—C4	1.517 (4)	C20—H20	0.9500
C3—H3B	0.9900	C21—C22	1.393 (4)
C3—H3A	0.9900	C21—H21	0.9500
C4—C4A	1.510 (4)	C22—C23	1.367 (5)
C4—H4B	0.9900	C22—H22	0.9500
C4—H4A	0.9900	C23—C23A	1.401 (4)
C4A—C8A	1.388 (4)	C23—H23	0.9500
C4A—C5	1.404 (4)	C23A—C24	1.458 (4)
C5—C6	1.367 (4)	C25—C26	1.539 (4)
C5—H5	0.9500	C25—H25B	0.9900
C6—C7	1.402 (4)	C25—H25A	0.9900
C7—C8	1.383 (4)	C26—H26A	0.9900
C8—C8A	1.399 (4)	C26—H26B	0.9900
C8—H8	0.9500	C27—O6	1.418 (4)
C9—H9B	0.9800	C27—H27A	0.9800
C9—H9C	0.9800	C27—H27B	0.9800
C9—H9A	0.9800	C27—H27C	0.9800
C10—H10B	0.9800	O6—H6	0.957 (18)
C6—O1—C9	116.0 (2)	C13—C12—H12	119.7
C7—O2—C10	117.3 (2)	C11—C12—H12	119.7
O3—N1—O4	123.7 (3)	C14—C13—C12	118.4 (3)
O3—N1—C14	118.5 (3)	C14—C13—H13	120.8
O4—N1—C14	117.7 (3)	C12—C13—H13	120.8
C17—N2—C3	125.4 (2)	C15—C14—C13	122.9 (3)
C17—N2—C1	120.2 (2)	C15—C14—N1	118.3 (3)
C3—N2—C1	114.1 (2)	C13—C14—N1	118.8 (3)
C18A—N19—C19A	115.6 (2)	C14—C15—C16	117.8 (3)
C24—N24A—C18A	123.9 (3)	C14—C15—H15	121.1
C24—N24A—C25	123.0 (2)	C16—C15—H15	121.1
C18A—N24A—C25	113.1 (2)	C11—C16—C15	121.2 (3)
N2—C1—C8A	111.4 (2)	C11—C16—H16	119.4
N2—C1—C11	109.5 (2)	C15—C16—H16	119.4
C8A—C1—C11	113.0 (2)	N2—C17—C18	131.5 (3)
N2—C1—H1	107.6	N2—C17—H17	114.3
C8A—C1—H1	107.6	C18—C17—H17	114.3
C11—C1—H1	107.6	C17—C18—C18A	118.2 (3)
N2—C3—C4	108.2 (2)	C17—C18—C26	133.6 (3)
N2—C3—H3B	110.0	C18A—C18—C26	108.0 (2)
C4—C3—H3B	110.0	N19—C18A—N24A	124.4 (3)
N2—C3—H3A	110.0	N19—C18A—C18	126.9 (3)
C4—C3—H3A	110.0	N24A—C18A—C18	108.7 (3)
H3B—C3—H3A	108.4	N19—C19A—C20	117.9 (3)
C4A—C4—C3	109.9 (2)	N19—C19A—C23A	123.5 (3)
C4A—C4—H4B	109.7	C20—C19A—C23A	118.5 (3)
C3—C4—H4B	109.7	C21—C20—C19A	120.4 (3)
C4A—C4—H4A	109.7	C21—C20—H20	119.8
C3—C4—H4A	109.7	C19A—C20—H20	119.8
H4B—C4—H4A	108.2	C20—C21—C22	120.5 (3)
C8A—C4A—C5	118.8 (3)	C20—C21—H21	119.7
C8A—C4A—C4	121.3 (3)	C22—C21—H21	119.7
C5—C4A—C4	119.9 (3)	C23—C22—C21	120.3 (3)
C6—C5—C4A	121.2 (3)	C23—C22—H22	119.8
C6—C5—H5	119.4	C21—C22—H22	119.8
C4A—C5—H5	119.4	C22—C23—C23A	120.1 (3)
C5—C6—O1	124.6 (3)	C22—C23—H23	120.0
C5—C6—C7	120.3 (3)	C23A—C23—H23	120.0
O1—C6—C7	115.0 (3)	C23—C23A—C19A	120.1 (3)
O2—C7—C8	125.3 (3)	C23—C23A—C24	120.7 (3)
O2—C7—C6	115.8 (3)	C19A—C23A—C24	119.2 (3)
C8—C7—C6	118.9 (3)	O5—C24—N24A	120.5 (3)
C7—C8—C8A	121.0 (3)	O5—C24—C23A	126.3 (3)
C7—C8—H8	119.5	N24A—C24—C23A	113.2 (3)
C8A—C8—H8	119.5	N24A—C25—C26	104.1 (2)
C4A—C8A—C8	119.8 (3)	N24A—C25—H25B	110.9
C4A—C8A—C1	121.7 (3)	C26—C25—H25B	110.9
C8—C8A—C1	118.5 (3)	N24A—C25—H25A	110.9
O1—C9—H9B	109.5	C26—C25—H25A	110.9
O1—C9—H9C	109.5	H25B—C25—H25A	109.0
H9B—C9—H9C	109.5	C18—C26—C25	105.2 (2)
O1—C9—H9A	109.5	C18—C26—H26A	110.7
H9B—C9—H9A	109.5	C25—C26—H26A	110.7
H9C—C9—H9A	109.5	C18—C26—H26B	110.7
O2—C10—H10B	109.5	C25—C26—H26B	110.7
O2—C10—H10C	109.5	H26A—C26—H26B	108.8
H10B—C10—H10C	109.5	O6—C27—H27A	109.5
O2—C10—H10A	109.5	O6—C27—H27B	109.5
H10B—C10—H10A	109.5	H27A—C27—H27B	109.5
H10C—C10—H10A	109.5	O6—C27—H27C	109.5
C16—C11—C12	119.1 (3)	H27A—C27—H27C	109.5
C16—C11—C1	122.5 (3)	H27B—C27—H27C	109.5
C12—C11—C1	118.3 (3)	C27—O6—H6	109 (2)
C13—C12—C11	120.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O5	0.96	1.91	2.8581 (7)	171
C1—H1···O1^i	1.00	2.55	3.4040 (8)	143
C1—H1···O2^i	1.00	2.37	3.2444 (8)	146
C4—H4A···O5^ii	0.99	2.45	3.4346 (8)	172
C9—H9B···O6^iii	0.98	2.54	3.5042 (9)	169
C15—H15···O1^iv	0.95	2.44	3.3402 (8)	159
C16—H16···O2^iv	0.95	2.59	3.3246 (8)	134
C17—H17···N19	0.95	2.47	2.8805 (7)	106
C25—H25A···O4^v	0.99	2.29	3.1224 (8)	141

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