How do I get my puppy to sleep in his crate without crying?

Thanks for asking about crate training your puppy. I'm a professional dog trainer.
It sounds like you are doing some of the general recommendations for crate training, like feeding in the crate and giving treats in the crate. I'm going to share with you all of my tips for crate training. But the two most important things are to ALWAYS give high value treats for going into the crate and never let him out if he's crying or barking.

For you I recommend doing this:
Step 1: Throw a handful of yummy treats in the crate and say "Crate" or whatever phrase you want to use and let him go in to eat them. While he's eating them, close the door and stand there. When he's finished eating the treats and not crying, open the door and let him out. Do this 5 times. This teaches him that he gets lots of treats in the crate. The crate is good!

Step 2: Throw the treats in the crate, say the word "Crate", let him go in and eat, close the door and walk out of site for a few seconds or a minute (very short time). Come back when he's not crying. Open the crate and let him out. Do this 5 times. This teaches him that you put him in his crate, leave and come back and let him out when he's not crying.

Step 3: Throw treats in the crate, say the word "Crate", let him go in and eat, close the door and walk away for 5 minutes. Come back when he's not crying. Open the crate and let him out. Do this 5 times. This teaches him that you stay away longer but you still come back and let him out when he's quiet.

Step 4: Do same thing for 10 minutes, 30 minutes, 1 hour and then at night.

Step 5: Now that he knows the crate is good, keep reinforcing it by always giving treats to go in. Give him a stuffed Kong or special toys that he only gets in the crate. Keep feeding him in it and don't let him out when he's crying.

More tips:

Guidelines:
1. A puppy should be able to stand up, turn around, and lie down comfortably in the crate.
2. Do not leave any extra space inside the crate where the puppy might be able to eliminate. If the crate is large, place another barrier inside that will leave just enough room for the puppy, as stated in step one.
3. Place a towel or padding in the bottom of the crate for puppy to lie on. Remove if you feel the puppy will chew or ingest it.
4. Select an area in your home to set up the crate. This should be in a room where the puppy is engaged with family activities and able to view the family. This may be the family living room or master bedroom.
5. Setup the crate and let the puppy see it in his environment and explore. Keep the door open and hide yummy treats inside, he will learn that good things happen in his crate.
6. Hold a yummy treat in your hand and lure the puppy into the crate. As the puppy enters the crate, say “Crate” or whatever word will be used as the crating cue, and praise and treat.
7. Continue to leave the door open and keep hiding treats under the crate bedding. This will encourage the puppy to explore the crate.
8. Repeat several times until she is comfortable going into the crate.

Additional Information:
• NEVER force the puppy into the crate.
• If a puppy should begin whining or barking in his crate, check your housetraing schedule to ensure the puppy does not need to potty. If the puppy just eliminated, wait until she is quiet before you let her out of the crate. Wait patiently for a split second of silence, and then open the crate door. If you let a puppy out of the crate when he is whining or barking, this will become an “I want out of the crate” cue.
• The crate should become a calm and positive environment.
• For crate training to be successful, the puppy must view the crate as a refuge and associate it with positive experiences.
• Add special yummy treats or toys that the puppy only receives when he is in the crate. Food-stuffed toys like Kong’s work well and make the crate a happier place for the puppy.
• When a puppy is left alone in his crate, play soft music in the background.