Iclaprim mesylate displaying a hydrogen-bonded mol­ecular tape

Iclaprim and mesylate mol­ecules are linked into a hydrogen-bonded mol­ecular tape, the central section of which is composed of fused rings.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.104
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT767_ALERT_4_A INS Embedded LIST 6 Instruction Should be LIST 4     Please Check

Author Response: Data originate from a twinned sample, processed as HKLF-5. LIST 6 is incompatible with this kind of data.

Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.079 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT793_ALERT_4_G Model has Chirality at C14         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         10 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 4-1-1)         Est.d BASF       0.26 Check
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        1.0 Low

   1 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
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2020); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

2,6-Diamino-5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]pyrimidin-1-ium methanesulfonate

Crystal data

C19H23N4O3^+·CH3O3S^−	Z = 2
Mr = 450.51	F(000) = 476
Triclinic, P1	Dx = 1.433 Mg m^−3
a = 5.4726 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8450 (4) Å	Cell parameters from 9886 reflections
c = 22.1395 (11) Å	θ = 2.3–25.3°
α = 98.094 (2)°	µ = 0.20 mm^−1
β = 93.754 (2)°	T = 223 K
γ = 98.919 (2)°	Prism, colourless
V = 1043.98 (9) Å^3	0.21 × 0.18 × 0.03 mm

Data collection

Bruker D8 QUEST PHOTON 100 diffractometer	3851 measured reflections
Radiation source: Incoatec Microfocus	3851 independent reflections
Multi layered optics monochromator	3507 reflections with I > 2σ(I)
Detector resolution: 10.4 pixels mm^-1	θmax = 25.4°, θmin = 2.4°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (TWINABS; Bruker, 2013)	k = −10→10
Tmin = 0.910, Tmax = 0.971	l = −26→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.7995P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3851 reflections	Δρmax = 0.57 e Å^−3
320 parameters	Δρmin = −0.30 e Å^−3
10 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (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	0.3058 (4)	0.7951 (2)	0.38547 (8)	0.0428 (5)
O2	0.9479 (4)	1.1480 (2)	0.33158 (8)	0.0413 (5)
O3	0.6716 (4)	1.0418 (2)	0.41560 (7)	0.0418 (5)
N1	0.0557 (4)	0.9523 (2)	0.10508 (8)	0.0239 (4)
H1N	0.015 (5)	1.042 (3)	0.1116 (12)	0.035 (7)*
N2	0.0189 (3)	0.7157 (2)	0.03914 (8)	0.0240 (4)
N3	−0.2450 (4)	0.8895 (2)	0.02407 (10)	0.0314 (5)
H3A	−0.292 (5)	0.976 (2)	0.0359 (11)	0.030 (7)*
H3B	−0.318 (5)	0.831 (3)	−0.0091 (10)	0.041 (8)*
N4	0.2945 (4)	0.5524 (2)	0.05307 (9)	0.0296 (4)
H4A	0.215 (5)	0.491 (3)	0.0214 (10)	0.042 (8)*
H4B	0.416 (4)	0.528 (3)	0.0742 (11)	0.034 (7)*
C1	0.2336 (4)	0.9125 (2)	0.14129 (10)	0.0230 (5)
H1	0.3024	0.9821	0.1765	0.028*
C2	−0.0565 (4)	0.8502 (2)	0.05556 (9)	0.0219 (4)
C3	0.2094 (4)	0.6806 (2)	0.07298 (9)	0.0216 (4)
C4	0.3182 (4)	0.7772 (2)	0.12931 (9)	0.0210 (4)
C5	0.5138 (5)	0.7290 (3)	0.17050 (10)	0.0287 (5)
H5A	0.4704	0.6177	0.1715	0.034*
H5B	0.6731	0.7464	0.1527	0.034*
C6	0.5457 (4)	0.8135 (3)	0.23546 (10)	0.0263 (5)
C7	0.7329 (4)	0.9416 (3)	0.25216 (10)	0.0280 (5)
H7	0.8359	0.9748	0.2226	0.034*
C8	0.7705 (4)	1.0212 (3)	0.31165 (10)	0.0291 (5)
C9	0.6184 (5)	0.9716 (3)	0.35590 (10)	0.0292 (5)
C10	0.4339 (5)	0.8453 (3)	0.33923 (10)	0.0289 (5)
C11	0.3909 (5)	0.7643 (3)	0.27896 (10)	0.0297 (5)
C12	0.1991 (6)	0.6280 (3)	0.26835 (13)	0.0480 (7)
H12	0.1796	0.5622	0.2305	0.058*
C13	0.0514 (6)	0.5956 (3)	0.31140 (14)	0.0506 (8)
H13	−0.0684	0.5052	0.3038	0.061*
C14	0.0691 (5)	0.6975 (4)	0.37117 (13)	0.0477 (7)
H14	−0.0506	0.7688	0.3658	0.057*
C15	0.0006 (7)	0.6284 (4)	0.42415 (16)	0.0603 (9)
H15	0.088 (6)	0.537 (3)	0.4274 (16)	0.072*
C16	−0.0784 (9)	0.7122 (6)	0.47930 (19)	0.0775 (11)
H16A	−0.051 (8)	0.687 (5)	0.5200 (11)	0.093*
H16B	−0.082 (9)	0.821 (3)	0.4736 (19)	0.093*
C17	−0.2553 (8)	0.5873 (6)	0.4384 (2)	0.0800 (12)
H17A	−0.310 (8)	0.490 (3)	0.4518 (19)	0.096*
H17B	−0.369 (7)	0.614 (5)	0.4075 (15)	0.096*
C18	1.1370 (5)	1.1840 (3)	0.29246 (12)	0.0407 (6)
H18A	1.2567	1.2718	0.3128	0.061*
H18B	1.0637	1.2093	0.2549	0.061*
H18C	1.2199	1.0953	0.2830	0.061*
C19	0.4888 (7)	1.1252 (4)	0.44003 (14)	0.0568 (8)
H19A	0.5389	1.1668	0.4827	0.085*
H19B	0.3308	1.0562	0.4368	0.085*
H19C	0.4719	1.2095	0.4172	0.085*
S1	0.73446 (11)	0.29318 (6)	0.12358 (2)	0.02483 (16)
O4	0.9826 (3)	0.26069 (18)	0.14030 (8)	0.0348 (4)
O5	0.5834 (3)	0.16098 (19)	0.08426 (8)	0.0381 (4)
O6	0.7365 (3)	0.43739 (19)	0.09992 (8)	0.0362 (4)
C20	0.5874 (5)	0.3152 (3)	0.19206 (11)	0.0339 (6)
H20A	0.5974	0.2263	0.2127	0.051*
H20B	0.4145	0.3227	0.1827	0.051*
H20C	0.6694	0.4086	0.2185	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0498 (11)	0.0446 (10)	0.0295 (9)	−0.0066 (9)	0.0072 (8)	0.0039 (8)
O2	0.0414 (11)	0.0421 (10)	0.0327 (9)	−0.0078 (8)	0.0035 (8)	−0.0043 (8)
O3	0.0470 (12)	0.0497 (11)	0.0230 (8)	0.0026 (9)	0.0004 (8)	−0.0070 (7)
N1	0.0272 (10)	0.0169 (9)	0.0275 (10)	0.0082 (8)	−0.0012 (8)	0.0003 (7)
N2	0.0252 (10)	0.0222 (9)	0.0236 (9)	0.0068 (8)	−0.0005 (8)	−0.0014 (7)
N3	0.0311 (11)	0.0299 (11)	0.0323 (11)	0.0133 (9)	−0.0084 (9)	−0.0021 (9)
N4	0.0301 (11)	0.0273 (10)	0.0288 (10)	0.0134 (9)	−0.0077 (9)	−0.0094 (8)
C1	0.0248 (11)	0.0207 (10)	0.0221 (10)	0.0037 (9)	−0.0009 (9)	−0.0002 (8)
C2	0.0227 (11)	0.0224 (10)	0.0214 (10)	0.0048 (9)	0.0037 (9)	0.0041 (8)
C3	0.0221 (11)	0.0206 (10)	0.0217 (10)	0.0036 (9)	0.0026 (9)	0.0018 (8)
C4	0.0222 (11)	0.0204 (10)	0.0201 (10)	0.0041 (9)	0.0025 (9)	0.0013 (8)
C5	0.0334 (13)	0.0278 (11)	0.0256 (11)	0.0133 (10)	−0.0025 (10)	−0.0002 (9)
C6	0.0306 (12)	0.0270 (11)	0.0226 (11)	0.0145 (10)	−0.0033 (9)	0.0003 (9)
C7	0.0283 (12)	0.0320 (12)	0.0247 (11)	0.0085 (10)	0.0025 (9)	0.0040 (9)
C8	0.0291 (13)	0.0280 (11)	0.0288 (12)	0.0052 (10)	−0.0027 (10)	0.0017 (9)
C9	0.0342 (13)	0.0318 (12)	0.0205 (11)	0.0071 (10)	−0.0019 (9)	0.0005 (9)
C10	0.0348 (13)	0.0284 (11)	0.0251 (11)	0.0090 (10)	0.0017 (10)	0.0059 (9)
C11	0.0321 (13)	0.0267 (11)	0.0291 (11)	0.0064 (10)	−0.0038 (11)	0.0020 (9)
C12	0.0526 (18)	0.0426 (15)	0.0401 (15)	−0.0066 (14)	0.0002 (14)	−0.0057 (12)
C13	0.0493 (18)	0.0459 (16)	0.0488 (17)	−0.0112 (14)	0.0013 (14)	0.0034 (13)
C14	0.0366 (15)	0.0582 (18)	0.0450 (16)	−0.0016 (13)	0.0020 (13)	0.0079 (13)
C15	0.061 (2)	0.0572 (19)	0.062 (2)	−0.0019 (17)	0.0203 (17)	0.0109 (16)
C16	0.072 (3)	0.097 (3)	0.064 (2)	0.002 (3)	0.026 (2)	0.019 (2)
C17	0.046 (2)	0.112 (3)	0.089 (3)	0.002 (2)	0.014 (2)	0.048 (3)
C18	0.0365 (15)	0.0428 (14)	0.0404 (14)	−0.0013 (12)	0.0012 (12)	0.0081 (12)
C19	0.069 (2)	0.0547 (18)	0.0415 (16)	0.0133 (17)	0.0076 (15)	−0.0144 (13)
S1	0.0219 (3)	0.0225 (3)	0.0302 (3)	0.0083 (2)	−0.0031 (2)	0.0019 (2)
O4	0.0245 (9)	0.0312 (8)	0.0486 (10)	0.0121 (7)	−0.0063 (8)	0.0022 (7)
O5	0.0330 (9)	0.0345 (9)	0.0417 (10)	0.0086 (8)	−0.0085 (8)	−0.0093 (7)
O6	0.0366 (10)	0.0325 (9)	0.0468 (10)	0.0173 (8)	0.0103 (8)	0.0150 (7)
C20	0.0357 (14)	0.0319 (12)	0.0333 (13)	0.0051 (11)	0.0015 (11)	0.0034 (10)

Geometric parameters (Å, º)

O1—C10	1.365 (3)	C10—C11	1.410 (3)
O1—C14	1.431 (3)	C11—C12	1.451 (4)
O2—C8	1.364 (3)	C12—C13	1.323 (4)
O2—C18	1.420 (3)	C12—H12	0.9400
O3—C9	1.371 (3)	C13—C14	1.481 (4)
O3—C19	1.423 (4)	C13—H13	0.9400
N1—C1	1.341 (3)	C14—C15	1.441 (4)
N1—C2	1.362 (3)	C14—H14	0.9900
N1—H1N	0.85 (3)	C15—C17	1.458 (5)
N2—C2	1.330 (3)	C15—C16	1.463 (5)
N2—C3	1.345 (3)	C15—H15	1.007 (18)
N3—C2	1.325 (3)	C16—C17	1.500 (6)
N3—H3A	0.857 (17)	C16—H16A	0.965 (19)
N3—H3B	0.869 (17)	C16—H16B	0.988 (19)
N4—C3	1.322 (3)	C17—H17A	0.958 (19)
N4—H4A	0.871 (17)	C17—H17B	0.971 (19)
N4—H4B	0.863 (17)	C18—H18A	0.9700
C1—C4	1.347 (3)	C18—H18B	0.9700
C1—H1	0.9400	C18—H18C	0.9700
C3—C4	1.444 (3)	C19—H19A	0.9700
C4—C5	1.510 (3)	C19—H19B	0.9700
C5—C6	1.510 (3)	C19—H19C	0.9700
C5—H5A	0.9800	S1—O6	1.4442 (16)
C5—H5B	0.9800	S1—O5	1.4588 (17)
C6—C7	1.394 (3)	S1—O4	1.4658 (17)
C6—C11	1.395 (3)	S1—C20	1.763 (2)
C7—C8	1.390 (3)	C20—H20A	0.9700
C7—H7	0.9400	C20—H20B	0.9700
C8—C9	1.400 (3)	C20—H20C	0.9700
C9—C10	1.375 (3)
C10—O1—C14	119.5 (2)	C12—C13—C14	122.0 (3)
C8—O2—C18	117.48 (19)	C12—C13—H13	119.0
C9—O3—C19	115.4 (2)	C14—C13—H13	119.0
C1—N1—C2	119.79 (18)	O1—C14—C15	109.1 (2)
C1—N1—H1N	121.2 (18)	O1—C14—C13	112.5 (2)
C2—N1—H1N	118.9 (18)	C15—C14—C13	118.4 (3)
C2—N2—C3	118.52 (18)	O1—C14—H14	105.2
C2—N3—H3A	119.3 (18)	C15—C14—H14	105.2
C2—N3—H3B	121.4 (19)	C13—C14—H14	105.2
H3A—N3—H3B	119 (3)	C14—C15—C17	123.6 (4)
C3—N4—H4A	118.4 (19)	C14—C15—C16	124.3 (3)
C3—N4—H4B	119.0 (18)	C17—C15—C16	61.8 (3)
H4A—N4—H4B	122 (3)	C14—C15—H15	110 (2)
N1—C1—C4	122.8 (2)	C17—C15—H15	108 (2)
N1—C1—H1	118.6	C16—C15—H15	120 (2)
C4—C1—H1	118.6	C15—C16—C17	58.9 (3)
N3—C2—N2	120.8 (2)	C15—C16—H16A	124 (3)
N3—C2—N1	117.59 (19)	C17—C16—H16A	112 (3)
N2—C2—N1	121.6 (2)	C15—C16—H16B	109 (3)
N4—C3—N2	117.50 (19)	C17—C16—H16B	118 (3)
N4—C3—C4	120.4 (2)	H16A—C16—H16B	120 (4)
N2—C3—C4	122.07 (19)	C15—C17—C16	59.3 (3)
C1—C4—C3	114.73 (19)	C15—C17—H17A	120 (3)
C1—C4—C5	123.42 (19)	C16—C17—H17A	120 (3)
C3—C4—C5	121.84 (18)	C15—C17—H17B	110 (3)
C6—C5—C4	114.54 (18)	C16—C17—H17B	120 (3)
C6—C5—H5A	108.6	H17A—C17—H17B	114 (4)
C4—C5—H5A	108.6	O2—C18—H18A	109.5
C6—C5—H5B	108.6	O2—C18—H18B	109.5
C4—C5—H5B	108.6	H18A—C18—H18B	109.5
H5A—C5—H5B	107.6	O2—C18—H18C	109.5
C7—C6—C11	119.7 (2)	H18A—C18—H18C	109.5
C7—C6—C5	119.6 (2)	H18B—C18—H18C	109.5
C11—C6—C5	120.8 (2)	O3—C19—H19A	109.5
C8—C7—C6	121.3 (2)	O3—C19—H19B	109.5
C8—C7—H7	119.3	H19A—C19—H19B	109.5
C6—C7—H7	119.3	O3—C19—H19C	109.5
O2—C8—C7	125.0 (2)	H19A—C19—H19C	109.5
O2—C8—C9	115.5 (2)	H19B—C19—H19C	109.5
C7—C8—C9	119.5 (2)	O6—S1—O5	113.41 (11)
O3—C9—C10	121.8 (2)	O6—S1—O4	113.82 (11)
O3—C9—C8	119.0 (2)	O5—S1—O4	111.29 (10)
C10—C9—C8	119.0 (2)	O6—S1—C20	105.55 (11)
O1—C10—C9	116.1 (2)	O5—S1—C20	105.63 (12)
O1—C10—C11	121.4 (2)	O4—S1—C20	106.36 (11)
C9—C10—C11	122.4 (2)	S1—C20—H20A	109.5
C6—C11—C10	118.2 (2)	S1—C20—H20B	109.5
C6—C11—C12	125.0 (2)	H20A—C20—H20B	109.5
C10—C11—C12	116.7 (2)	S1—C20—H20C	109.5
C13—C12—C11	120.6 (3)	H20A—C20—H20C	109.5
C13—C12—H12	119.7	H20B—C20—H20C	109.5
C11—C12—H12	119.7
C2—N1—C1—C4	3.6 (3)	C7—C8—C9—C10	−0.3 (3)
C3—N2—C2—N3	−179.3 (2)	C14—O1—C10—C9	161.4 (2)
C3—N2—C2—N1	0.5 (3)	C14—O1—C10—C11	−23.3 (4)
C1—N1—C2—N3	174.6 (2)	O3—C9—C10—O1	0.6 (3)
C1—N1—C2—N2	−5.3 (3)	C8—C9—C10—O1	174.7 (2)
C2—N2—C3—N4	−174.6 (2)	O3—C9—C10—C11	−174.6 (2)
C2—N2—C3—C4	5.9 (3)	C8—C9—C10—C11	−0.5 (4)
N1—C1—C4—C3	2.4 (3)	C7—C6—C11—C10	−1.3 (3)
N1—C1—C4—C5	−178.4 (2)	C5—C6—C11—C10	178.4 (2)
N4—C3—C4—C1	173.2 (2)	C7—C6—C11—C12	−176.3 (2)
N2—C3—C4—C1	−7.3 (3)	C5—C6—C11—C12	3.4 (4)
N4—C3—C4—C5	−6.0 (3)	O1—C10—C11—C6	−173.7 (2)
N2—C3—C4—C5	173.5 (2)	C9—C10—C11—C6	1.3 (4)
C1—C4—C5—C6	20.0 (3)	O1—C10—C11—C12	1.8 (4)
C3—C4—C5—C6	−160.8 (2)	C9—C10—C11—C12	176.7 (2)
C4—C5—C6—C7	−96.5 (3)	C6—C11—C12—C13	−176.0 (3)
C4—C5—C6—C11	83.8 (3)	C10—C11—C12—C13	8.9 (4)
C11—C6—C7—C8	0.5 (3)	C11—C12—C13—C14	1.7 (5)
C5—C6—C7—C8	−179.1 (2)	C10—O1—C14—C15	165.4 (3)
C18—O2—C8—C7	−12.6 (3)	C10—O1—C14—C13	31.8 (4)
C18—O2—C8—C9	167.6 (2)	C12—C13—C14—O1	−21.4 (4)
C6—C7—C8—O2	−179.5 (2)	C12—C13—C14—C15	−150.4 (3)
C6—C7—C8—C9	0.3 (3)	O1—C14—C15—C17	149.3 (4)
C19—O3—C9—C10	−70.3 (3)	C13—C14—C15—C17	−80.3 (5)
C19—O3—C9—C8	115.5 (3)	O1—C14—C15—C16	72.7 (5)
O2—C8—C9—O3	−6.2 (3)	C13—C14—C15—C16	−156.8 (4)
C7—C8—C9—O3	174.0 (2)	C14—C15—C16—C17	113.3 (4)
O2—C8—C9—C10	179.5 (2)	C14—C15—C17—C16	−114.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4^i	0.85 (3)	1.99 (3)	2.827 (2)	168 (3)
N3—H3A···O5^i	0.86 (2)	2.06 (2)	2.896 (3)	166 (2)
N3—H3B···O5^ii	0.87 (2)	2.15 (2)	2.871 (3)	140 (2)
N4—H4A···N2^ii	0.87 (2)	2.27 (2)	3.107 (3)	163 (2)
N4—H4B···O6	0.86 (2)	2.11 (2)	2.948 (3)	163 (2)

Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y+1, −z.