In an $n$-bit $2$’s complement system, if the leftmost bit is $1$, the number is negative.
For a negative $n$-bit number, signed value $=$ unsigned value $-2^n$.
A: $1001011$ is a $7$-bit number.
Unsigned value $=64+8+2+1=75$.
Signed value $=75-2^7=75-128=-53$.
B: $11001010$ is an $8$-bit number.
Unsigned value $=128+64+8+2=202$.
Signed value $=202-2^8=202-256=-54$.
C: $111000101$ is a $9$-bit number.
Unsigned value $=256+128+64+4+1=453$.
Signed value $=453-2^9=453-512=-59$.
D: $101111$ is a $6$-bit number.
Unsigned value $=32+8+4+2+1=47$.
Signed value $=47-2^6=47-64=-17$.
Now compare the values:
A $=-53$, B $=-54$, C $=-59$, D $=-17$.
The smallest value is $-59$.
Final Answer: C.