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1 cup whole wheat berries (7 ounces)
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3 cups water
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1 large tomatopeeled, seeded and chopped
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3 chipotle chiles in adobo sauce, seeded and chopped, plus 1 tablespoon of the sauce
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1/2 cup tomato paste
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2 tablespoons fresh lemon juice
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2 teaspoons honey
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1 large garlic clove, minced
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1/2 teaspoon cinnamon
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1/4 teaspoon ground cumin
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3 tablespoons plus 1 teaspoon extra-virgin olive oil
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Salt and freshly ground pepper
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One 2-pound sirloin steak
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2 teaspoons white wine vinegar
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16 cherry tomatoes, halved (1/2 pound)
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1 medium cucumberpeeled, seeded and cut into 1-inch dice
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2 tablespoons coarsely chopped flat-leaf parsley
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In a medium saucepan, combine the wheat berries with the water and bring to a boil. Cover and simmer over low heat until the wheat berries are tender but still chewy, about 2 hours.. Drain and let cool to room temperature.
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Meanwhile, in a mini food processor, puree the chopped tomato with the chipotles and adobo sauce. Transfer to a medium bowl. Stir in the tomato paste, lemon juice, honey, garlic, cinnamon and cumin. Add 3 tablespoons of the olive oil; season with salt and pepper.
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Put the steak in a shallow dish and coat with 1/4 cup of the tomato-chipotle sauce. Stir the wheat berries into the remaining sauce and season with salt. Cover and refrigerate the steak and wheat berries overnight.
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Light a grill or preheat a grill pan. Bring the steak and wheat berries to room temperature. Oil the grill and cook the steak over a medium-hot fire for about 4 minutes per side, or until lightly charred on both sides and medium rare within. Transfer the steak to a cutting board and let rest for 5 minutes.
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In a medium bowl, mix the vinegar with the remaining 1 teaspoon of olive oil. Add the cherry tomatoes, cucumber and parsley, season with salt and pepper and toss well. Slice the steak 1/4 inch thick and serve with the wheat berries and the tomato salad.
Make Ahead
The tomato-chipotle sauce and the wheat berry salad can be refrigerated for up to 3 days.
Suggested Pairing
The rare steak and intense tomato dressing point to an equally rich red wine, with plenty of ripe fruit.