Sertraline hydro­chloride form II

A second polymorph of sertraline hydro­chloride {systematic name: [(1S-cis)-4-(3,4-dichloro­phen­yl)-1,2,3,4-tetra­hydro-1-naphthy]methyl­ammonium chloride}, a potent anti­depressant drug, C₁₇H₁₈Cl₂N⁺·Cl^-, crystallizes in the same ortho­rhom­bic space group as form I. The mol­ecules in both forms exhibit nearly identical bond distances and angles, but some aspects of the mol­ecular conformation are significantly different. Hydrogen bonds involving N atoms and Cl^- anions form chains in both forms.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.119
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           25.00
           From the CIF: _reflns_number_total               3114
           Count of symmetry unique reflns         1838
           Completeness (_total/calc)            169.42%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1276
           Fraction of Friedel pairs measured     0.694
           Are heavy atom types Z>Si present        yes

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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: SHELXTL/PC (Sheldrick, 1990) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97.

[(1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthy]methylammonium chloride

Crystal data

C17H18Cl2N^+·Cl^−	F(000) = 712
Mr = 342.67	Dx = 1.293 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3254 reflections
a = 7.289 (6) Å	θ = 2.5–21.2°
b = 7.396 (7) Å	µ = 0.51 mm^−1
c = 32.66 (3) Å	T = 273 K
V = 1761 (3) Å^3	Block, colorless
Z = 4	0.14 × 0.10 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2815 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.0°, θmin = 1.3°
ω scans	h = −8→8
12731 measured reflections	k = −8→8
3114 independent reflections	l = −38→38

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0675P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
3114 reflections	Δρmax = 0.33 e Å^−3
191 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1276 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (8)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	−0.11069 (16)	0.52445 (16)	0.23080 (4)	0.0806 (4)
Cl2	−0.42035 (12)	0.22432 (17)	0.22326 (3)	0.0650 (3)
N1	0.4010 (3)	−0.0508 (3)	0.02078 (7)	0.0374 (6)
H1A	0.4246	−0.1698	0.0183	0.045*
H1B	0.2803	−0.0383	0.0258	0.045*
C1	0.5076 (4)	0.0228 (4)	0.05695 (8)	0.0376 (7)
H1	0.6383	0.0164	0.0501	0.045*
C2	0.4612 (5)	0.2212 (4)	0.06517 (9)	0.0462 (8)
H2A	0.5573	0.2750	0.0817	0.055*
H2B	0.4559	0.2861	0.0394	0.055*
C3	0.2791 (5)	0.2400 (4)	0.08716 (9)	0.0444 (8)
H3A	0.1833	0.1820	0.0713	0.053*
H3B	0.2483	0.3670	0.0900	0.053*
C4	0.2905 (4)	0.1528 (4)	0.12940 (9)	0.0367 (7)
H4	0.3787	0.2253	0.1450	0.044*
C5	0.3593 (4)	−0.1524 (4)	0.16192 (9)	0.0399 (7)
H5	0.2886	−0.1169	0.1842	0.048*
C6	0.4512 (5)	−0.3169 (5)	0.16338 (10)	0.0478 (8)
H6	0.4418	−0.3896	0.1865	0.057*
C7	0.5558 (5)	−0.3722 (5)	0.13082 (10)	0.0537 (9)
H7	0.6186	−0.4815	0.1318	0.064*
C8	0.5667 (5)	−0.2637 (4)	0.09654 (9)	0.0471 (8)
H8	0.6360	−0.3023	0.0743	0.057*
C9	0.4761 (4)	−0.0968 (4)	0.09438 (8)	0.0358 (7)
C10	0.3707 (4)	−0.0388 (4)	0.12771 (8)	0.0344 (7)
C11	0.1087 (4)	0.1687 (4)	0.15217 (9)	0.0396 (7)
C12	0.0801 (4)	0.3151 (4)	0.17803 (9)	0.0430 (7)
H12	0.1724	0.4008	0.1813	0.052*
C13	−0.0832 (5)	0.3354 (5)	0.19907 (9)	0.0438 (8)
C14	−0.2187 (4)	0.2082 (5)	0.19498 (9)	0.0437 (8)
C15	−0.1926 (4)	0.0613 (5)	0.16927 (11)	0.0541 (9)
H15	−0.2841	−0.0255	0.1667	0.065*
C16	−0.0316 (4)	0.0434 (5)	0.14752 (10)	0.0517 (9)
H16	−0.0169	−0.0532	0.1296	0.062*
C17	0.4448 (6)	0.0391 (5)	−0.01846 (9)	0.0565 (9)
H17A	0.3979	0.1604	−0.0181	0.085*
H17B	0.3894	−0.0268	−0.0406	0.085*
H17C	0.5754	0.0419	−0.0222	0.085*
Cl3	−0.02654 (11)	−0.06728 (10)	0.01830 (3)	0.0477 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0743 (7)	0.0820 (8)	0.0856 (7)	−0.0040 (6)	0.0195 (6)	−0.0460 (6)
Cl2	0.0412 (5)	0.1034 (8)	0.0503 (5)	0.0013 (5)	0.0073 (4)	−0.0112 (5)
N1	0.0402 (13)	0.0393 (14)	0.0328 (13)	−0.0002 (11)	0.0034 (11)	−0.0023 (11)
C1	0.0316 (15)	0.0464 (17)	0.0348 (15)	−0.0060 (13)	0.0018 (12)	−0.0041 (13)
C2	0.063 (2)	0.0376 (16)	0.0380 (16)	−0.0173 (16)	0.0089 (15)	−0.0029 (13)
C3	0.059 (2)	0.0357 (17)	0.0387 (16)	0.0059 (15)	−0.0006 (14)	−0.0077 (15)
C4	0.0335 (15)	0.0421 (17)	0.0345 (15)	−0.0065 (13)	−0.0028 (13)	−0.0045 (14)
C5	0.0353 (16)	0.0490 (19)	0.0353 (16)	−0.0074 (14)	0.0001 (13)	0.0001 (14)
C6	0.054 (2)	0.0457 (18)	0.0435 (17)	−0.0137 (17)	−0.0103 (16)	0.0091 (15)
C7	0.067 (2)	0.0373 (17)	0.057 (2)	0.0051 (17)	−0.0122 (19)	−0.0016 (16)
C8	0.052 (2)	0.0487 (19)	0.0406 (17)	0.0050 (16)	−0.0013 (15)	−0.0100 (15)
C9	0.0329 (15)	0.0372 (16)	0.0374 (16)	−0.0045 (14)	−0.0025 (13)	−0.0042 (12)
C10	0.0269 (14)	0.0437 (18)	0.0326 (15)	−0.0083 (13)	−0.0032 (11)	−0.0013 (13)
C11	0.0355 (16)	0.0469 (18)	0.0362 (16)	0.0019 (15)	−0.0037 (13)	−0.0047 (14)
C12	0.0401 (17)	0.0439 (18)	0.0451 (17)	−0.0075 (15)	−0.0007 (14)	−0.0016 (15)
C13	0.0477 (19)	0.0479 (18)	0.0358 (16)	0.0052 (16)	−0.0013 (14)	−0.0064 (14)
C14	0.0349 (17)	0.063 (2)	0.0329 (16)	0.0056 (16)	−0.0011 (13)	−0.0021 (16)
C15	0.0345 (17)	0.064 (2)	0.064 (2)	−0.0107 (17)	−0.0016 (16)	−0.014 (2)
C16	0.0382 (17)	0.058 (2)	0.059 (2)	−0.0078 (16)	−0.0033 (16)	−0.0240 (17)
C17	0.080 (3)	0.055 (2)	0.0352 (18)	−0.0119 (18)	−0.0007 (18)	0.0048 (16)
Cl3	0.0406 (4)	0.0437 (4)	0.0587 (5)	−0.0015 (3)	0.0020 (4)	−0.0084 (4)

Geometric parameters (Å, º)

Cl1—C13	1.751 (3)	C5—H5	0.930
Cl2—C14	1.740 (3)	C6—C7	1.371 (5)
N1—C17	1.479 (4)	C6—H6	0.930
N1—C1	1.515 (4)	C7—C8	1.380 (5)
N1—H1A	0.900	C7—H7	0.930
N1—H1B	0.900	C8—C9	1.401 (4)
C1—C9	1.526 (4)	C8—H8	0.930
C1—C2	1.529 (5)	C9—C10	1.400 (4)
C1—H1	0.980	C11—C16	1.388 (4)
C2—C3	1.515 (5)	C11—C12	1.389 (4)
C2—H2A	0.970	C12—C13	1.383 (5)
C2—H2B	0.970	C12—H12	0.930
C3—C4	1.525 (4)	C13—C14	1.371 (5)
C3—H3A	0.970	C14—C15	1.386 (5)
C3—H3B	0.970	C15—C16	1.378 (5)
C4—C11	1.524 (4)	C15—H15	0.930
C4—C10	1.533 (5)	C16—H16	0.930
C4—H4	0.980	C17—H17A	0.960
C5—C6	1.389 (5)	C17—H17B	0.960
C5—C10	1.400 (4)	C17—H17C	0.960
C17—N1—C1	113.8 (2)	C6—C7—C8	119.2 (3)
C17—N1—H1A	108.8	C6—C7—H7	120.4
C1—N1—H1A	108.8	C8—C7—H7	120.4
C17—N1—H1B	108.8	C7—C8—C9	121.7 (3)
C1—N1—H1B	108.8	C7—C8—H8	119.1
H1A—N1—H1B	107.7	C9—C8—H8	119.1
N1—C1—C9	109.8 (2)	C10—C9—C8	119.3 (3)
N1—C1—C2	111.6 (3)	C10—C9—C1	121.8 (3)
C9—C1—C2	112.5 (2)	C8—C9—C1	118.7 (3)
N1—C1—H1	107.6	C9—C10—C5	118.0 (3)
C9—C1—H1	107.6	C9—C10—C4	121.4 (3)
C2—C1—H1	107.6	C5—C10—C4	120.2 (3)
C3—C2—C1	111.4 (3)	C16—C11—C12	118.4 (3)
C3—C2—H2A	109.3	C16—C11—C4	122.4 (3)
C1—C2—H2A	109.3	C12—C11—C4	119.2 (3)
C3—C2—H2B	109.3	C13—C12—C11	121.1 (3)
C1—C2—H2B	109.3	C13—C12—H12	119.5
H2A—C2—H2B	108.0	C11—C12—H12	119.5
C2—C3—C4	110.0 (3)	C14—C13—C12	119.8 (3)
C2—C3—H3A	109.7	C14—C13—Cl1	121.6 (2)
C4—C3—H3A	109.7	C12—C13—Cl1	118.6 (3)
C2—C3—H3B	109.7	C13—C14—C15	119.9 (3)
C4—C3—H3B	109.7	C13—C14—Cl2	120.6 (3)
H3A—C3—H3B	108.2	C15—C14—Cl2	119.4 (3)
C11—C4—C3	111.2 (3)	C16—C15—C14	120.3 (3)
C11—C4—C10	114.8 (3)	C16—C15—H15	119.8
C3—C4—C10	112.3 (2)	C14—C15—H15	119.8
C11—C4—H4	105.9	C15—C16—C11	120.5 (3)
C3—C4—H4	105.9	C15—C16—H16	119.8
C10—C4—H4	105.9	C11—C16—H16	119.8
C6—C5—C10	121.6 (3)	N1—C17—H17A	109.5
C6—C5—H5	119.2	N1—C17—H17B	109.5
C10—C5—H5	119.2	H17A—C17—H17B	109.5
C7—C6—C5	120.2 (3)	N1—C17—H17C	109.5
C7—C6—H6	119.9	H17A—C17—H17C	109.5
C5—C6—H6	119.9	H17B—C17—H17C	109.5
C17—N1—C1—C9	−171.1 (3)	C11—C4—C10—C9	148.7 (3)
C17—N1—C1—C2	63.4 (3)	C3—C4—C10—C9	20.4 (4)
N1—C1—C2—C3	77.9 (3)	C11—C4—C10—C5	−39.4 (4)
C9—C1—C2—C3	−46.0 (4)	C3—C4—C10—C5	−167.7 (3)
C1—C2—C3—C4	64.0 (3)	C3—C4—C11—C16	86.3 (4)
C2—C3—C4—C11	−179.7 (3)	C10—C4—C11—C16	−42.5 (4)
C2—C3—C4—C10	−49.5 (3)	C3—C4—C11—C12	−92.6 (3)
C10—C5—C6—C7	−0.2 (5)	C10—C4—C11—C12	138.6 (3)
C5—C6—C7—C8	−0.7 (5)	C16—C11—C12—C13	0.6 (5)
C6—C7—C8—C9	1.1 (5)	C4—C11—C12—C13	179.6 (3)
C7—C8—C9—C10	−0.4 (4)	C11—C12—C13—C14	1.0 (5)
C7—C8—C9—C1	174.9 (3)	C11—C12—C13—Cl1	−179.4 (2)
N1—C1—C9—C10	−108.7 (3)	C12—C13—C14—C15	−1.1 (5)
C2—C1—C9—C10	16.3 (4)	Cl1—C13—C14—C15	179.4 (3)
N1—C1—C9—C8	76.1 (3)	C12—C13—C14—Cl2	176.5 (3)
C2—C1—C9—C8	−159.0 (3)	Cl1—C13—C14—Cl2	−3.1 (4)
C8—C9—C10—C5	−0.5 (4)	C13—C14—C15—C16	−0.6 (5)
C1—C9—C10—C5	−175.7 (2)	Cl2—C14—C15—C16	−178.1 (3)
C8—C9—C10—C4	171.5 (3)	C14—C15—C16—C11	2.2 (6)
C1—C9—C10—C4	−3.7 (4)	C12—C11—C16—C15	−2.3 (5)
C6—C5—C10—C9	0.9 (4)	C4—C11—C16—C15	178.8 (3)
C6—C5—C10—C4	−171.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3^i	0.90	2.31	3.144 (3)	154
N1—H1B···Cl3	0.90	2.26	3.120 (4)	160
C1—H1···Cl3^ii	0.98	2.73	3.683 (4)	166
C2—H2B···Cl3^iii	0.97	2.81	3.741 (4)	161

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