C# DataGridView Checkbox checked event

You can handle CellContentClick event of your DataGridView and put the logic for changing those cells there.

The key point is using CommitEdit(DataGridViewDataErrorContexts.Commit) to commits changes in the current cell to the data cache without ending edit mode. This way when you check for value of cell in this event, it returns current checked or unchecked value which you see in the cell currently after click:

private void dataGridView1_CellContentClick(object sender, DataGridViewCellEventArgs e)
{
    //We make DataGridCheckBoxColumn commit changes with single click
    //use index of logout column
    if(e.ColumnIndex == 4 && e.RowIndex>=0)
        this.dataGridView1.CommitEdit(DataGridViewDataErrorContexts.Commit);

    //Check the value of cell
    if((bool)this.dataGridView1.CurrentCell.Value == true)
    {
        //Use index of TimeOut column
        this.dataGridView1.Rows[e.RowIndex].Cells[3].Value = DateTime.Now;

        //Set other columns values
    }
    else
    {
        //Use index of TimeOut column
        this.dataGridView1.Rows[e.RowIndex].Cells[3].Value = DBNull.Value;

        //Set other columns values
    }
}