The Collaborative International Dictionary of English v.0.48:

Calculate \Cal"cu*late\, v. i. [imp. & p. p. Calculater; p.
   pr. & vb. n. Calculating.] [L, calculatus, p. p. of
   calculate, fr. calculus a pebble, a stone used in reckoning;
   hence, a reckoning, fr. calx, calcis, a stone used in gaming,
   limestone. See Calx.]
   1. To ascertain or determine by mathematical processes,
      usually by the ordinary rules of arithmetic; to reckon up;
      to estimate; to compute.
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            A calencar exacity calculated than any othe.
                                                  --North.
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   2. To ascertain or predict by mathematical or astrological
      computations the time, circumstances, or other conditions
      of; to forecast or compute the character or consequences
      of; as, to calculate or cast one's nativity.
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            A cunning man did calculate my birth. --Shak.
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   3. To adjust for purpose; to adapt by forethought or
      calculation; to fit or prepare by the adaptation of means
      to an end; as, to calculate a system of laws for the
      government and protection of a free people.
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            [Religion] is . . . calculated for our benefit.
                                                  --Abp.
                                                  Tillotson.
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   4. To plan; to expect; to think. [Local, U. S.]

   Syn: To compute; reckon; count; estimate; rate.

   Usage: To Calculate, Compute. Reckon, Count. These
          words indicate the means by which we arrive at a given
          result in regard to quantity. We calculate with a view
          to obtain a certain point of knowledge; as, to
          calculate an eclipse. We compute by combining given
          numbers, in order to learn the grand result. We reckon
          and count in carrying out the details of a
          computation. These words are also used in a secondary
          and figurative sense. "Calculate is rather a
          conjection from what is, as to what may be;
          computation is a rational estimate of what has been,
          from what is; reckoning is a conclusive conviction, a
          pleasing assurance that a thing will happen; counting
          indicates an expectation. We calculate on a gain; we
          compute any loss sustained, or the amount of any
          mischief done; we reckon on a promised pleasure; we
          count the hours and minutes until the time of
          enjoyment arrives" --Crabb.
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The Collaborative International Dictionary of English v.0.48:

Calculating \Cal"cu*la`ting\, a.
   1. Of or pertaining to mathematical calculations; performing
      or able to perform mathematical calculations.
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   2. Given to contrivance or forethought; forecasting;
      scheming; as, a cool calculating disposition.
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   Calculating machine, a machine for the mechanical
      performance of mathematical operations, for the most part
      invented by Charles Babbage and G. and E. Scheutz. It
      computes logarithmic and other mathematical tables of a
      high degree of intricacy, imprinting the results on a
      leaden plate, from which a stereotype plate is then
      directly made.
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The Collaborative International Dictionary of English v.0.48:

Calculating \Cal"cu*la`ting\, n.
   The act or process of making mathematical computations or of
   estimating results.
   [1913 Webster]

WordNet (r) 3.0 (2006):

calculating
    adj 1: used of persons; "the most calculating and selfish men in
           the community" [syn: calculating, calculative,
           conniving, scheming, shrewd]

Moby Thesaurus II by Grady Ward, 1.0:

76 Moby Thesaurus words for "calculating":
   Byzantine, Machiavellian, artful, canny, careful, chary, chiseling,
   circumspect, collusive, computational, computative, computing,
   connivent, conniving, considerate, conspiring, contriving,
   covinous, crafty, cunning, deceitful, designing, devious, discreet,
   disingenuous, enumerative, estimating, estimative, false,
   falsehearted, finagling, forsworn, foxy, fraudulent, furtive,
   gingerly, guarded, guileful, indirect, insidious, insincere,
   intriguing, knowing, manipulative, numerative, pawky, perjured,
   plotting, quantifying, safe, scheming, sharp, shifty, shrewd,
   slick, slippery, sly, sneaky, statistical, stratagemical, subtile,
   subtle, surreptitious, treacherous, trickish, tricky, two-faced,
   uncandid, underhand, underhanded, unfrank, unsincere, untruthful,
   up to, wary, wily