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So I want to create a document in Chinese but there's just one problem: How do ancient and modern day chinese deal with numbered lists while in vertical format and how do they use punctuation marks in ancient and middle china? Do they have special chinese character for those or is there another way.

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There were usually no punctuation marks in ancient China. Modern punctuation marks were introduced into Chinese in the 20th century. See Wikipedia for a more detailed history and the usages of each punctuation mark (both horizontal and vertical).

For vertical numbered lists, below is an example from 康熙字典 (published in 1710-1716):

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Each item in the list is marked by the Chinese character "一" (maybe we should call this an unordered list). No punctuation marks can be seen on this page.

A more modern example with modern punctuation marks:

enter image description here

It's pretty clear how they handle vertical numbered lists and punctuation marks.

For punctuation marks, there are some differences in Mainland China and Taiwan but the main principles are similar.

There are also other possible styles for numbered lists (both horizontal and vertical).

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How do ancient and modern day chinese deal with numbered lists while in vertical format

no numbered lists was used in ancient time. the nearest one is, using characters “一” to indicate list items, as shown in another answer by betty 👍

how do they use punctuation marks in ancient and middle china

again, no punctuation marks is used in ancient time. here’re a few pages in vertical layout, dealing with number:

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enter image description here

note that the “circle” (“0”, “o” shaped symbol) does not mean zero, in the above page.

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in this page, the “circle” (“0”, “o” shaped symbol) does mean zero, that, it should be read as “大差弦四百零八”

have fun :)

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While in vertical format, write the numbers with letters - 零、壹(一)、貳(二)、參(三)、肆(四)、伍(五)、陸(六)、柒(七)、捌(八)、玖(九)、拾(十)、佰(百)、仟(千)、萬(万)、億、兆. (I think 億 and 兆 are the later inventions of the modern time to indicate numbers of the respective magnitude, such as 一億(兆), which seem to be borrowed from the ancient phrase "億兆" that indicated "多數"或"眾多". Per wiki: 億兆 means "countless"; "numerous".)

1357 - 壹仟參佰伍拾柒 (大寫); 一千三百五十七 (小寫), or simply 一三五七.

103 - 壹佰零參; 一百零三 or 一零三.

The decimal point wasn't in use until the adoption of Arabic Numbers. But in case you see a number like 一百零三點八 (一零三點八), it is equal to 103.8.

ADD: Since I am not a scholar of the Ancient Chinese Language/Literature, I wouldn't argue the notion of "no punctuation" in the ancient Chinese world. However, the text below seems to suggest otherwise and tells the ways existed and were used to understand the long paragraphs without the obvious modern punctuation marks, namely "斷句" - a skill that is taught at the advanced level of Chinese learning only.

"Chinese punctuation uses a different set of punctuation marks from European languages and has shapes that are derived from both Western and Chinese sources. Although there was a long native tradition of textual annotation to indicate the boundaries of sentences and clauses, the concept of punctuation marks being a mandatory and integral part of the text was only adapted in the written language during the 20th century due to Western influence. Before that, the concept of punctuation in Chinese literature existed mainly in the form of judou (traditional Chinese: 句讀; simplified Chinese: 句读; pinyin: jù dòu; lit. 'sentences and clauses'), a system of annotations denoting stops and pauses. However, unlike modern punctuation, judou marks were added into a text by scholars to aid comprehension and for pedagogical purposes and were not viewed as an integral part of the text. Classical texts were therefore generally transmitted without judou.2 In most cases, this did not interfere with the interpretation of a text, although there were occasionally ambiguous passages as a result of this practice.[A]

The first was given by the Han dynasty scholar Zhao Qi (趙岐) and was the traditionally accepted reading, but Song and Ming neo-Confucianists have proposed the second one.

Many ancient Chinese books contain thousands of words with no spaces between them; however, when necessary to explicitly denote a pause or break, Judou marks such as "。" (句號) and "、" (逗點) were used. Similar to the development of punctuation in Europe, there were varying types of Judou marks. For instance, a Song Dynasty print of Chronicles of Huayang used full-width spaces to denote a stop,[citation needed] whereas a print of Jingdian Shiwen from the same dynasty simply used "。" and "、" marks.[citation needed] Also, Qu Yuan's Li Sao used the character 兮 and grammatical particles to denote stops, similar to Judou marks.[3] In Chinese writing, each character conforms to a roughly square frame so that the text as a whole can fit into a grid. Because of this, East Asian punctuation marks are larger than their European counterparts, as they should occupy a square area that is the same size as the characters around them. These punctuation marks are called fullwidth to contrast them from halfwidth European punctuation marks."

https://en.wikipedia.org/wiki/Chinese_punctuation

ADD: Chinese Numerals

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    “億” & “兆” are used in ancient time, such as “蓋不可以億兆計”, “紂有億兆夷人”, “有億兆之數”. ctext.org/pre-qin-and-han/zh?searchu=億兆 Oct 18 at 4:52
  • In those articles “億” & “兆” indicated 多數 or something I don't know, but not the numbers 100,000,000 and ....
    – r13
    Oct 18 at 14:57
  • @水巷孑蠻 I suggest to read this article about Chinese Numerals - new (modern) vs old (ancient). omniglot.com/chinese/numerals.htm
    – r13
    Oct 18 at 19:37
  • thanks for the link, read 😸 Oct 19 at 5:03
  • Very good, 賞銀萬兩 :)
    – r13
    Oct 19 at 20:34

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