The trick to brush shearing is preparation of the brush so that it is facing the right direction and not too complex. If you want brush shearing to be simply then try and orientate the brush so that it involves the minimal amount of brush shearing directions needed.

The image above shows the brush shape you have designed and how you want to span the gap using brush shearing. The first thing you need to do is create the angled version of your shape. Take the original brush, and cut it like the one in the top right. It does not matter about how big the brush is or if it fills the right space, its just the angle that is really important.
Starting with the first brush segment, copy the one in the top right of diagram and put the brush into position. Then brush shear on one face only into position. Put the cursor on the left hand side of the brush and shear upwards into position. Because the brush is angled already the shearing operation should only be necessary on one side of the brush and not produce any errors.
Once the new brush is into position, use the new brush as the next template as it will be quicker to create the circumference from one point to the other with something partly in place already. Once you reach the middle you can either mirror around the other segments or use the middle brush as the next template and carry on brush shearing.
Once you have finished you should have something like this:

Here is the map file:
// entity 0
{
"classname" "worldspawn"
// brush 0
{
( 64 -192 0 ) ( 0 -192 0 ) ( 0 -256 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 0 -256 64 ) ( 0 -192 64 ) ( 64 -192 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 0 -256 8 ) ( 64 -256 8 ) ( 64 -256 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 64 -256 8 ) ( 64 -192 8 ) ( 64 -192 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 64 -192 8 ) ( 0 -192 8 ) ( 0 -192 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 0 -192 8 ) ( 0 -256 8 ) ( 0 -256 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 0 -208 64 ) ( 0 -192 48 ) ( 64 -208 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( 0 -256 48 ) ( 0 -240 64 ) ( 64 -256 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 1
{
( -96 -96 48 ) ( -96 -80 64 ) ( -32 -96 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -96 -48 64 ) ( -96 -32 48 ) ( -32 -48 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -32 -32 8 ) ( -96 -32 8 ) ( -96 -32 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -96 -96 8 ) ( -32 -96 8 ) ( -32 -96 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -96 -96 64 ) ( -96 -32 64 ) ( -32 -32 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -32 -32 0 ) ( -96 -32 0 ) ( -96 -96 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -32 -32 0 ) ( -40 -48 0 ) ( -32 -32 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -72 -48 0 ) ( -64 -32 0 ) ( -72 -48 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 2
{
( -128 -144 0 ) ( -136 -160 0 ) ( -128 -144 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -128 -144 0 ) ( -160 -208 0 ) ( -144 -224 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -152 -192 64 ) ( -136 -160 64 ) ( -120 -176 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -160 -208 0 ) ( -160 -208 48 ) ( -144 -224 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -128 -144 48 ) ( -128 -144 0 ) ( -112 -160 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -136 -160 64 ) ( -128 -144 48 ) ( -112 -160 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -160 -208 48 ) ( -152 -192 64 ) ( -136 -208 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -160 -136 0 ) ( -144 -128 0 ) ( -160 -136 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 3
{
( -192 -88 0 ) ( -176 -80 0 ) ( -192 -88 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -240 -112 48 ) ( -224 -104 64 ) ( -208 -136 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -192 -88 64 ) ( -176 -80 48 ) ( -160 -112 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -176 -80 48 ) ( -176 -80 0 ) ( -160 -112 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -240 -112 0 ) ( -240 -112 48 ) ( -224 -144 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -224 -104 64 ) ( -192 -88 64 ) ( -176 -120 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -176 -80 0 ) ( -240 -112 0 ) ( -224 -144 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -160 -112 0 ) ( -176 -120 0 ) ( -160 -112 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 4
{
( -184 -64 0 ) ( -200 -72 0 ) ( -184 -64 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -192 -32 0 ) ( -256 -64 0 ) ( -248 -96 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -240 -56 64 ) ( -208 -40 64 ) ( -200 -72 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -256 -64 0 ) ( -256 -64 48 ) ( -248 -96 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -192 -32 48 ) ( -192 -32 0 ) ( -184 -64 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -208 -40 64 ) ( -192 -32 48 ) ( -184 -64 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -256 -64 48 ) ( -240 -56 64 ) ( -232 -88 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -208 -40 0 ) ( -192 -32 0 ) ( -208 -40 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 5
{
( -256 64 48 ) ( -240 64 64 ) ( -256 0 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -208 64 64 ) ( -192 64 48 ) ( -208 0 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -200 64 8 ) ( -264 64 8 ) ( -264 64 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -192 0 8 ) ( -192 64 8 ) ( -192 64 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -256 0 8 ) ( -192 0 8 ) ( -192 0 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -256 64 8 ) ( -256 0 8 ) ( -256 0 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -256 64 64 ) ( -192 64 64 ) ( -192 0 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -192 0 0 ) ( -192 64 0 ) ( -256 64 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 6
{
( -96 -248 48 ) ( -88 -232 64 ) ( -56 -240 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -72 -200 64 ) ( -64 -184 48 ) ( -32 -192 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -64 -184 48 ) ( -64 -184 0 ) ( -32 -192 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -96 -248 0 ) ( -96 -248 48 ) ( -64 -256 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -88 -232 64 ) ( -72 -200 64 ) ( -40 -208 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -64 -184 0 ) ( -96 -248 0 ) ( -64 -256 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -32 -192 0 ) ( -40 -208 0 ) ( -32 -192 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -72 -200 0 ) ( -64 -184 0 ) ( -72 -200 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
// brush 7
{
( -120 -176 0 ) ( -112 -160 0 ) ( -120 -176 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -80 -176 0 ) ( -88 -192 0 ) ( -80 -176 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -112 -160 0 ) ( -144 -224 0 ) ( -112 -240 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -136 -208 64 ) ( -120 -176 64 ) ( -88 -192 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -144 -224 0 ) ( -144 -224 48 ) ( -112 -240 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -112 -160 48 ) ( -112 -160 0 ) ( -80 -176 0 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -120 -176 64 ) ( -112 -160 48 ) ( -80 -176 48 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
( -144 -224 48 ) ( -136 -208 64 ) ( -104 -224 64 ) common/caulk 0 0 0 0.500000 0.500000 0 4 0
}
}
Sock
:moo:
PS. Planetquake seems to be going up and down like a yoyo atm, so the images might need a few refreshes to see them.