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The crystal structure of famotidine form B has been solved directly from powder diffraction data by the application of simulated annealing. The molecule crystallizes in the monoclinic space group P21/c with refined unit-cell dimensions a = 17.6547 (4), b = 5.2932 (1), c = 18.2590 (3) Å and β = 123.558 (1)° at T = 130 K. The core of this work is a systematic investigation of the influence of algorithmic, crystallographic and molecular factors on the structure solution process. With an appropriate choice of annealing schedule, molecular description and diffraction data range, the overall number of successes in solving the crystal structure is close to 100%. Other factors, including crystallographic search space restrictions and parameter sampling method, have little effect on the structure solution process. The basic principles elucidated here have been factored into the design of the DASH structure solution program.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889802007835/ks0130sup1.cif
Contains datablock I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0021889802007835/ks0130Isup2.rtv
Contains datablock I

CCDC reference: 196446

Computing details top

Data collection: BM16 instrument software; cell refinement: DASH; data reduction: BM16 instrument software; program(s) used to solve structure: DASH; program(s) used to refine structure: SR15LS.

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3-(2-(Diaminomethyleneamino)-1,3-thiazol-4-yl)methylthio)-N'- sulfamoylpropionamidine top
Crystal data top
C8H15N7O2S3V = 1421.9 Å3
Mr = ?Z = 4
Monoclinic, P21/c? radiation, λ = 0.8507473 Å
a = 17.6547 (4) ÅT = 130 K
b = 5.2932 (1) Åwhite
c = 18.2590 (3) Åcylinder, 10 × 1 mm
β = 123.558 (1)°Specimen preparation: Prepared at 130 K
Data collection top
2 circle
diffractometer
Data collection mode: transmission
Radiation source: synchrotron, ESRF BM16Scan method: step
Si 111 monochromator2θmin = 3.000°, 2θmax = 53.000°, 2θstep = 0.005°
Specimen mounting: 1.0mm borosilicate capillary
Refinement top
Least-squares matrix: full with fixed elements per cycle124 parameters
Rp = 0.1220 restraints
Rwp = 0.1250 constraints
Rexp = 0.097H-atom parameters not refined
χ2 = 1.664Weighting scheme based on measured s.u.'s
10001 data points
Profile function: Voigt with axial divergence correctionBackground function: Chebyshev polynomial
Crystal data top
C8H15N7O2S3β = 123.558 (1)°
Mr = ?V = 1421.9 Å3
Monoclinic, P21/cZ = 4
a = 17.6547 (4) Å? radiation, λ = 0.8507473 Å
b = 5.2932 (1) ÅT = 130 K
c = 18.2590 (3) Åcylinder, 10 × 1 mm
Data collection top
2 circle
diffractometer
Scan method: step
Specimen mounting: 1.0mm borosilicate capillary2θmin = 3.000°, 2θmax = 53.000°, 2θstep = 0.005°
Data collection mode: transmission
Refinement top
Rp = 0.12210001 data points
Rwp = 0.125124 parameters
Rexp = 0.0970 restraints
χ2 = 1.664H-atom parameters not refined
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
C10.3445 (4)0.5849 (7)0.1027 (5)1.25 (6)*
H20.3199 (7)0.6130 (16)0.1602 (6)3.00*
H30.3889 (5)0.6983 (7)0.0707 (9)3.00*
C40.2706 (3)0.612 (1)0.0830 (3)1.25 (6)*
C50.1866 (4)0.4661 (13)0.1504 (2)1.25 (6)*
H60.2916 (4)0.5499 (18)0.0290 (3)3.00*
H70.2563 (5)0.7757 (11)0.0850 (6)3.00*
N80.1531 (6)0.3188 (15)0.1174 (3)1.25 (6)*
N90.1611 (3)0.4861 (12)0.2326 (2)1.25 (6)*
H100.0915 (6)0.28 (2)0.162 (3)3.00*
H110.173 (3)0.344 (15)0.0577 (5)3.00*
S120.0665 (2)0.3658 (5)0.31076 (16)1.10 (5)*
O130.0128 (4)0.4249 (13)0.3100 (4)1.25 (6)*
O140.0527 (5)0.443 (1)0.3929 (3)1.25 (6)*
N150.0725 (5)0.0587 (5)0.3043 (4)1.25 (6)*
H160.088 (7)0.0012 (16)0.340 (5)3.00*
H170.115 (5)0.0124 (10)0.2487 (13)3.00*
S180.3918 (3)0.2693 (5)0.07467 (19)1.10 (5)*
C190.4647 (3)0.2692 (10)0.1171 (2)1.25 (6)*
C200.4096 (4)0.3210 (9)0.21366 (19)1.27 (6)*
H210.5076 (3)0.3894 (16)0.0895 (3)3.00*
H220.4918 (5)0.1174 (14)0.1071 (4)3.00*
C230.4299 (5)0.4943 (13)0.2553 (2)1.27 (6)*
S240.3560 (3)0.4657 (5)0.36786 (18)1.27 (6)*
C250.3049 (5)0.2044 (13)0.3524 (2)1.27 (6)*
N260.3422 (5)0.1479 (11)0.2689 (2)1.27 (6)*
H270.4767 (12)0.604 (4)0.2280 (3)3.00*
N280.2337 (4)0.0950 (12)0.4255 (2)1.25 (6)*
C290.1899 (5)0.0972 (15)0.4173 (3)1.25 (6)*
N300.2076 (5)0.1873 (12)0.3413 (3)1.25 (6)*
N310.1211 (4)0.2026 (13)0.4902 (3)1.25 (6)*
H320.270 (4)0.176 (12)0.2904 (3)3.00*
H330.158 (4)0.271 (11)0.3418 (6)3.00*
H340.097 (4)0.124 (8)0.5423 (10)3.00*
H350.101 (4)0.357 (7)0.4881 (12)3.00*
Geometric parameters (Å, º) top
S12—O131.440 (9)N15—H170.90 (3)
S12—O141.440 (6)N15—H160.89 (11)
S12—N91.612 (5)N30—H320.97 (5)
S12—N151.629 (4)N30—H330.98 (7)
S18—C11.810 (6)N31—H340.90 (3)
S18—C191.833 (8)N31—H350.90 (4)
S24—C231.728 (4)C1—C41.540 (11)
S24—C251.757 (9)C4—C51.514 (8)
N8—C51.309 (11)C19—C201.495 (4)
N9—C51.311 (5)C20—C231.360 (9)
N26—C201.395 (8)C1—H20.899 (12)
N26—C251.318 (5)C1—H30.900 (12)
N28—C251.356 (7)C4—H60.902 (7)
N28—C291.335 (11)C4—H70.898 (8)
N30—C291.331 (8)C19—H210.900 (9)
N31—C291.331 (8)C19—H220.901 (9)
N8—H100.95 (4)C23—H270.90 (2)
N8—H110.95 (2)
O13—S12—O14110.1 (5)S18—C19—C20110.3 (4)
O13—S12—N9116.3 (4)N26—C20—C19118.1 (4)
O13—S12—N15104.0 (5)N26—C20—C23115.0 (4)
O14—S12—N9107.7 (4)C19—C20—C23125.6 (5)
O14—S12—N15109.0 (4)S24—C23—C20110.3 (5)
N9—S12—N15109.6 (4)S24—C25—N26113.1 (5)
C1—S18—C19101.7 (4)N26—C25—N28129.7 (7)
C23—S24—C2589.7 (3)S24—C25—N28117.2 (4)
S12—N9—C5120.9 (5)N28—C29—N31118.2 (5)
C20—N26—C25111.6 (6)N30—C29—N31116.8 (8)
C25—N28—C29119.7 (5)N28—C29—N30124.9 (6)
H10—N8—H11122 (4)S18—C1—H2109.4 (8)
C5—N8—H10109 (4)S18—C1—H3109.4 (8)
C5—N8—H11118 (4)C4—C1—H2109.4 (11)
H16—N15—H17109 (7)C4—C1—H3109.4 (10)
S12—N15—H16110 (2)H2—C1—H3109.4 (12)
S12—N15—H17109.5 (7)C1—C4—H6109.4 (7)
C29—N30—H32118 (3)C1—C4—H7109.6 (8)
C29—N30—H33117.4 (11)C5—C4—H6109.2 (7)
H32—N30—H33125 (3)C5—C4—H7109.4 (8)
C29—N31—H34120 (3)H6—C4—H7109.4 (10)
C29—N31—H35120.1 (16)S18—C19—H21109.5 (5)
H34—N31—H35120 (3)S18—C19—H22109.5 (7)
S18—C1—C4109.7 (4)C20—C19—H21109.2 (6)
C1—C4—C5109.8 (5)C20—C19—H22109.2 (6)
N8—C5—N9128.2 (6)H21—C19—H22109.2 (9)
N8—C5—C4114.7 (4)S24—C23—H27124.9 (9)
N9—C5—C4116.8 (6)C20—C23—H27124.7 (7)
O13—S12—N9—C549.5 (7)C25—N26—C20—C19174.1 (7)
O14—S12—N9—C5173.6 (6)C25—N28—C29—N303.4 (13)
N15—S12—N9—C568.0 (7)C29—N28—C25—S24177.1 (7)
C19—S18—C1—C4172.6 (4)C29—N28—C25—N261.4 (14)
C1—S18—C19—C2059.1 (4)C25—N28—C29—N31179.1 (8)
C23—S24—C25—N28178.5 (7)S18—C1—C4—C572.7 (6)
C23—S24—C25—N260.3 (7)C1—C4—C5—N943.1 (7)
C25—S24—C23—C203.3 (6)C1—C4—C5—N8131.6 (7)
S12—N9—C5—N813.5 (12)S18—C19—C20—C23130.7 (7)
S12—N9—C5—C4172.8 (5)S18—C19—C20—N2663.0 (7)
C20—N26—C25—S243.7 (9)N26—C20—C23—S246.1 (9)
C20—N26—C25—N28174.9 (8)C19—C20—C23—S24172.7 (5)
C25—N26—C20—C236.4 (10)

Experimental details

Crystal data
Chemical formulaC8H15N7O2S3
Mr?
Crystal system, space groupMonoclinic, P21/c
Temperature (K)130
a, b, c (Å)17.6547 (4), 5.2932 (1), 18.2590 (3)
β (°) 123.558 (1)
V3)1421.9
Z4
Radiation type?, λ = 0.8507473 Å
µ (mm1)?
Specimen shape, size (mm)Cylinder, 10 × 1
Data collection
Diffractometer2 circle
diffractometer
Specimen mounting1.0mm borosilicate capillary
Data collection modeTransmission
Scan methodStep
2θ values (°)2θmin = 3.000 2θmax = 53.000 2θstep = 0.005
Refinement
R factors and goodness of fitRp = 0.122, Rwp = 0.125, Rexp = 0.097, χ2 = 1.664
No. of data points10001
No. of parameters124
H-atom treatmentH-atom parameters not refined

Computer programs: BM16 instrument software, DASH, SR15LS.

Selected geometric parameters (Å, º) top
S12—O131.440 (9)N26—C201.395 (8)
S12—O141.440 (6)N26—C251.318 (5)
S12—N91.612 (5)N28—C251.356 (7)
S12—N151.629 (4)N28—C291.335 (11)
S18—C11.810 (6)N30—C291.331 (8)
S18—C191.833 (8)N31—C291.331 (8)
S24—C231.728 (4)C1—C41.540 (11)
S24—C251.757 (9)C4—C51.514 (8)
N8—C51.309 (11)C19—C201.495 (4)
N9—C51.311 (5)C20—C231.360 (9)
O13—S12—O14110.1 (5)N8—C5—N9128.2 (6)
O13—S12—N9116.3 (4)N8—C5—C4114.7 (4)
O13—S12—N15104.0 (5)N9—C5—C4116.8 (6)
O14—S12—N9107.7 (4)S18—C19—C20110.3 (4)
O14—S12—N15109.0 (4)N26—C20—C19118.1 (4)
N9—S12—N15109.6 (4)N26—C20—C23115.0 (4)
C1—S18—C19101.7 (4)S24—C23—C20110.3 (5)
C23—S24—C2589.7 (3)S24—C25—N26113.1 (5)
S12—N9—C5120.9 (5)N26—C25—N28129.7 (7)
C20—N26—C25111.6 (6)S24—C25—N28117.2 (4)
C25—N28—C29119.7 (5)N28—C29—N31118.2 (5)
S18—C1—C4109.7 (4)N30—C29—N31116.8 (8)
C1—C4—C5109.8 (5)N28—C29—N30124.9 (6)
 

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