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There are no rules, as such, but there is an accepted convention that has been in use for the past few hundred years.

The only real rules relate to the original system used by Romans themselves. Firstly, each symbol has a value that never changes: I=1, V=5, X=10, L=50, C=100, D=500 and M=1000. Numerals are created by writing these symbols in descending order (from left to right). To read a numeral, convert each symbol to its corresponding value and add the values together.

The Romans also used a shorthand for the values 4, 9, 40, 90, 400 and 900, denoted by symbolic pairings IV, IX, XL, XC, CD and CM respectively. Note that the symbols in each of these pairs are in ascending order (not descending order). This means that rather than adding the values together, the smaller of the two values is negated, such that IV = -1 + 5 = 4. These pairing are known as subtractive pairs.

The Romans themselves rarely used IV and IX, preferring the longhand notations IIII and VIIII, however either form is acceptable today. They did use the other 4 pairings more consistently, but there occasional instances of longhand, or a mixture of the two in the same numeral.

Regardless, the 6 subtractive pairs are each treated as if they were one symbol. Thus we now have 13 symbols at our disposal: I=1, IV=4, V=5, IX=9, X=10, XL=40, L=50, XC=90, C=100, CD=400, D=500, CM=900 and M=1000.

To convert a number to a Roman numeral, subtract the largest value symbol that is less than or equal to the number, write it down, and repeat with the remainder. For example, if our value is 1999, we would carry out the following steps:

  1. M (1000) is the largest value that is less than or equal to 1999, leaving 999.
  2. CM (900) is the largest value that is less than or equal to 999, leaving 99.
  3. XC (90) is the largest value that is less than or equal to 99, leaving 9.
  4. IX (9) is the largest value that is less than or equal to 9, leaving zero.

Thus the Roman numeral for 1999 is MCMXCIX. The Romans themselves would have more likely written MCMXCVIIII, but either form is acceptable.

Note that you will often find examples that bend the rules slightly. For instance, the number 1999 can also be represented by the Roman numeral MIM, even though IM (-1+1000=999) is not an acceptable subtractive pair.

The accepted convention states that no symbol may be repeated more than three times in succession (meaning IV is the preferred version of IIIII, etc), that V, L and D may never repeat (because VV can be simplified to X), and that subtractive pairs may never repeat (IXIV is not permitted). Also, although there is no rule that states IM is not permitted for the value 999, the accepted convention states that I may only be subtracted from V and X, X may only be subtracted from L and C, and C may only be subtracted from D and M. This is simply in keeping with the original Roman rules.

Under this convention, all the values in the range 1-3999 can be represented in only one unique way.

Numbers larger than 3999 can be represented using Middle Age notation. However, the notation is relatively unknown so few will understand its meaning, even if they understand the standard Roman numerals. Numbers such as 4000 are easier to understand as just MMMM, however the larger the number, the more difficult it becomes to notate. For instance, one million would require one thousand Ms, which is clearly unacceptable. But just as we'd write "1 million" today, the Romans would have written "M mille" (one thousand thousands), or even just "I million" (million being a Latin word for a thousand thousands).

Middle Age notation has two forms. The first uses overlines and vertical bars to multiply a number by 100, 1,000 or 100,000. An overline multiples by 1000, while vertical bars either side of a numeral multiply by 100. Combining the two multiplies by 100,000. To notate the least-significant portion of a number, we simply need to leave a space and notate it using the standard notation. Using this convention, we can cater for values up to one thousand million but, as previously stated, few people will understand the notation.

The second form of notation uses the original symbols for M and D, which were CIƆ and IƆ, and extends them such that CCIƆƆ means 10,000 and IƆƆ means 5000. The two forms can also be combined such that CCIƆƆƆ means 10,500 and CCIƆƆƆƆ means 15,000. Although this convention allows a greater range, there's still the problem of readability. Few will understand it, but extremely large numbers would still be extremely unwieldy. However, the symbols can be written using shorthand, such that CIƆ is written ↀ, CCIƆƆ is written ↂ, IƆ is written D (which is what it became anyway) and IƆƆ is written ↁ. Even using shorthand, extremely large numbers become so cryptic that it's really not worth the effort. The Romans themselves never wrote extremely large numbers out in full (it was implied by the context), so why should we?

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