[flake8-simplify] Fix raw string handling in SIM905 for embedded quotes (#19591)

## Summary

When splitting triple-quoted, raw strings one has to take care before attempting to make each item have single-quotes.

Fixes #19577

---------

Co-authored-by: dylwil3 <dylwil3@gmail.com>

crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM905.py

@@ -129,4 +129,35 @@ print(" x ".rsplit(maxsplit=0))
 print(" x ".rsplit(maxsplit=0))
 print(" x ".rsplit(sep=None, maxsplit=0))
 print("  x  ".rsplit(maxsplit=0))
-print("  x  ".rsplit(sep=None, maxsplit=0))
+print("  x  ".rsplit(sep=None, maxsplit=0))
+
+# https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
+r"""simple@example.com
+very.common@example.com
+FirstName.LastName@EasierReading.org
+x@example.com
+long.email-address-with-hyphens@and.subdomains.example.com
+user.name+tag+sorting@example.com
+name/surname@example.com
+xample@s.example
+" "@example.org
+"john..doe"@example.org
+mailhost!username@example.org
+"very.(),:;<>[]\".VERY.\"very@\\ \"very\".unusual"@strange.example.com
+user%example.com@example.org
+user-@example.org
+I❤️CHOCOLATE@example.com
+this\ still\"not\\allowed@example.com
+stellyamburrr985@example.com
+Abc.123@example.com
+user+mailbox/department=shipping@example.com
+!#$%&'*+-/=?^_`.{|}~@example.com
+"Abc@def"@example.com
+"Fred\ Bloggs"@example.com
+"Joe.\\Blow"@example.com""".split("\n")
+
+
+r"""first
+'no need' to escape
+"swap" quote style
+"use' ugly triple quotes""".split("\n")

crates/ruff_linter/src/rules/flake8_simplify/rules/split_static_string.rs

@@ -1,6 +1,7 @@
 use std::cmp::Ordering;
 
 use ruff_macros::{ViolationMetadata, derive_message_formats};
+use ruff_python_ast::StringFlags;
 use ruff_python_ast::{
     Expr, ExprCall, ExprContext, ExprList, ExprUnaryOp, StringLiteral, StringLiteralFlags,
     StringLiteralValue, UnaryOp, str::TripleQuotes,
@@ -116,26 +117,50 @@ pub(crate) fn split_static_string(
     }
 }
 
+fn replace_flags(elt: &str, flags: StringLiteralFlags) -> StringLiteralFlags {
+    // In the ideal case we can wrap the element in _single_ quotes of the same
+    // style. For example, both of these are okay:
+    //
+    // ```python
+    // """itemA
+    // itemB
+    // itemC""".split() # -> ["itemA", "itemB", "itemC"]
+    // ```
+    //
+    // ```python
+    // r"""itemA
+    // 'single'quoted
+    // """.split() # -> [r"itemA",r"'single'quoted'"]
+    // ```
+    if !flags.prefix().is_raw() || !elt.contains(flags.quote_style().as_char()) {
+        flags.with_triple_quotes(TripleQuotes::No)
+    }
+    // If we have a raw string containing a quotation mark of the same style,
+    // then we have to swap the style of quotation marks used
+    else if !elt.contains(flags.quote_style().opposite().as_char()) {
+        flags
+            .with_quote_style(flags.quote_style().opposite())
+            .with_triple_quotes(TripleQuotes::No)
+    } else
+    // If both types of quotes are used in the raw, triple-quoted string, then
+    // we are forced to either add escapes or keep the triple quotes. We opt for
+    // the latter.
+    {
+        flags
+    }
+}
+
 fn construct_replacement(elts: &[&str], flags: StringLiteralFlags) -> Expr {
     Expr::List(ExprList {
         elts: elts
             .iter()
             .map(|elt| {
+                let element_flags = replace_flags(elt, flags);
                 Expr::from(StringLiteral {
                     value: Box::from(*elt),
                     range: TextRange::default(),
                     node_index: ruff_python_ast::AtomicNodeIndex::dummy(),
-                    // intentionally omit the triple quote flag, if set, to avoid strange
-                    // replacements like
-                    //
-                    // ```python
-                    // """
-                    // itemA
-                    // itemB
-                    // itemC
-                    // """.split() # -> ["""itemA""", """itemB""", """itemC"""]
-                    // ```
-                    flags: flags.with_triple_quotes(TripleQuotes::No),
+                    flags: element_flags,
                 })
             })
             .collect(),

crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM905_SIM905.py.snap

@@ -1226,6 +1226,7 @@ SIM905.py:130:7: SIM905 [*] Consider using a list literal instead of `str.split`
     130 |+print([" x"])
 131 131 | print("  x  ".rsplit(maxsplit=0))
 132 132 | print("  x  ".rsplit(sep=None, maxsplit=0))
+133 133 | 
 
 SIM905.py:131:7: SIM905 [*] Consider using a list literal instead of `str.split`
     |
@@ -1244,6 +1245,8 @@ SIM905.py:131:7: SIM905 [*] Consider using a list literal instead of `str.split`
 131     |-print("  x  ".rsplit(maxsplit=0))
     131 |+print(["  x"])
 132 132 | print("  x  ".rsplit(sep=None, maxsplit=0))
+133 133 | 
+134 134 | # https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
 
 SIM905.py:132:7: SIM905 [*] Consider using a list literal instead of `str.split`
     |
@@ -1251,6 +1254,8 @@ SIM905.py:132:7: SIM905 [*] Consider using a list literal instead of `str.split`
 131 | print("  x  ".rsplit(maxsplit=0))
 132 | print("  x  ".rsplit(sep=None, maxsplit=0))
     |       ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ SIM905
+133 |
+134 | # https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
     |
     = help: Replace with list literal
 
@@ -1260,3 +1265,88 @@ SIM905.py:132:7: SIM905 [*] Consider using a list literal instead of `str.split`
 131 131 | print("  x  ".rsplit(maxsplit=0))
 132     |-print("  x  ".rsplit(sep=None, maxsplit=0))
     132 |+print(["  x"])
+133 133 | 
+134 134 | # https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
+135 135 | r"""simple@example.com
+
+SIM905.py:135:1: SIM905 [*] Consider using a list literal instead of `str.split`
+    |
+134 |   # https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
+135 | / r"""simple@example.com
+136 | | very.common@example.com
+137 | | FirstName.LastName@EasierReading.org
+138 | | x@example.com
+139 | | long.email-address-with-hyphens@and.subdomains.example.com
+140 | | user.name+tag+sorting@example.com
+141 | | name/surname@example.com
+142 | | xample@s.example
+143 | | " "@example.org
+144 | | "john..doe"@example.org
+145 | | mailhost!username@example.org
+146 | | "very.(),:;<>[]\".VERY.\"very@\\ \"very\".unusual"@strange.example.com
+147 | | user%example.com@example.org
+148 | | user-@example.org
+149 | | I❤️CHOCOLATE@example.com
+150 | | this\ still\"not\\allowed@example.com
+151 | | stellyamburrr985@example.com
+152 | | Abc.123@example.com
+153 | | user+mailbox/department=shipping@example.com
+154 | | !#$%&'*+-/=?^_`.{|}~@example.com
+155 | | "Abc@def"@example.com
+156 | | "Fred\ Bloggs"@example.com
+157 | | "Joe.\\Blow"@example.com""".split("\n")
+    | |_______________________________________^ SIM905
+    |
+    = help: Replace with list literal
+
+ℹ Safe fix
+132 132 | print("  x  ".rsplit(sep=None, maxsplit=0))
+133 133 | 
+134 134 | # https://github.com/astral-sh/ruff/issues/19581 - embedded quotes in raw strings
+135     |-r"""simple@example.com
+136     |-very.common@example.com
+137     |-FirstName.LastName@EasierReading.org
+138     |-x@example.com
+139     |-long.email-address-with-hyphens@and.subdomains.example.com
+140     |-user.name+tag+sorting@example.com
+141     |-name/surname@example.com
+142     |-xample@s.example
+143     |-" "@example.org
+144     |-"john..doe"@example.org
+145     |-mailhost!username@example.org
+146     |-"very.(),:;<>[]\".VERY.\"very@\\ \"very\".unusual"@strange.example.com
+147     |-user%example.com@example.org
+148     |-user-@example.org
+149     |-I❤️CHOCOLATE@example.com
+150     |-this\ still\"not\\allowed@example.com
+151     |-stellyamburrr985@example.com
+152     |-Abc.123@example.com
+153     |-user+mailbox/department=shipping@example.com
+154     |-!#$%&'*+-/=?^_`.{|}~@example.com
+155     |-"Abc@def"@example.com
+156     |-"Fred\ Bloggs"@example.com
+157     |-"Joe.\\Blow"@example.com""".split("\n")
+    135 |+[r"simple@example.com", r"very.common@example.com", r"FirstName.LastName@EasierReading.org", r"x@example.com", r"long.email-address-with-hyphens@and.subdomains.example.com", r"user.name+tag+sorting@example.com", r"name/surname@example.com", r"xample@s.example", r'" "@example.org', r'"john..doe"@example.org', r"mailhost!username@example.org", r'"very.(),:;<>[]\".VERY.\"very@\\ \"very\".unusual"@strange.example.com', r"user%example.com@example.org", r"user-@example.org", r"I❤️CHOCOLATE@example.com", r'this\ still\"not\\allowed@example.com', r"stellyamburrr985@example.com", r"Abc.123@example.com", r"user+mailbox/department=shipping@example.com", r"!#$%&'*+-/=?^_`.{|}~@example.com", r'"Abc@def"@example.com', r'"Fred\ Bloggs"@example.com', r'"Joe.\\Blow"@example.com']
+158 136 | 
+159 137 | 
+160 138 | r"""first
+
+SIM905.py:160:1: SIM905 [*] Consider using a list literal instead of `str.split`
+    |
+160 | / r"""first
+161 | | 'no need' to escape
+162 | | "swap" quote style
+163 | | "use' ugly triple quotes""".split("\n")
+    | |_______________________________________^ SIM905
+    |
+    = help: Replace with list literal
+
+ℹ Safe fix
+157 157 | "Joe.\\Blow"@example.com""".split("\n")
+158 158 | 
+159 159 | 
+160     |-r"""first
+161     |-'no need' to escape
+162     |-"swap" quote style
+163     |-"use' ugly triple quotes""".split("\n")
+    160 |+[r"first", r"'no need' to escape", r'"swap" quote style', r""""use' ugly triple quotes"""]