Saturday, December 22, 2012

#SheriSangji preliminary hearing: Day 6

Drs. Jyllian Kemsley and Michael Torrice of C&EN have posted their summary of Day 6 (the final day) of the preliminary hearing of Professor Patrick Harran on charges stemming from the death of Sheharbano (Sheri) Sangji in January 2009. It should be noted that a preliminary hearing is a determination of the quality of the prosecution's evidence in the case.

I don't plan on writing up a full review of the preliminary hearing until the first week of next year, when folks will have returned from winter breaks. But I will note a couple of really remarkable developments on Day 6. Cal/OSHA investigator Brian Baudendistel was questioned again by both the prosecution and the defense. The really illuminating questions, however, came from the defense's questioning of chemical safety expert Neal Langerman:
  • The defense attempted to get Dr. Langerman to admit that Ms. Sangji demonstrated her ability meet Dr. Langerman's personal training standards to work with pyrophorics because she performed an experiment with Grubbs II catalyst in dichloromethane in a glovebag, and that Professor Harran watched her work and declared her technique "perfect." 
  • The defense suggested that Professor Harran's postdoctoral fellow was the key person who was supervising and training her, and that it was reasonable for Professor Harran to rely on the postdoc in her training.
I surmise that Dr. Langerman was not particularly interested in going along with the defense's reasoning on this issue. You should go over there and read the transcripts that Drs. Kemsley and Torrice have provided to see if you agree. 

I find it surprising and perhaps objectionable that Grubbs II in dichloromethane has been described as "reactive" and "air sensitive". From the Chem 215 notes at Harvard authored by Myers and coworkers:
Ru-based catalysts show little sensitivity to air, moisture or minor impurities in solvents.
A variety of Google results tends to support the Myers position that Grubbs II is not particularly sensitive to air. Professor Doug Taber comes a little closer with his description that "Prolonged exposure to air and moisture deactivates the complex..." The couple of minutes that it would take to weigh out the complex and toss it into the flask doesn't count, I don't think.

What is ultimately more probative (and again, perhaps I am wrong) is that it would be difficult to immediately tell that air-sensitive technique with Grubbs II was either good or bad. Bad technique with tBuLi announces itself with a flame; bad technique with Grubbs catalyst might result in a mild color change and a poor yield.

Readers, am I nuts in thinking that this is a crazy comparison to make? The Sangji case is such a weird nexus between law and chemistry; God help us all if this makes it in front of a jury.


  1. Re: Grubbs II, check this paper:

    Still don't know why they'd use it as a stock solution instead of just the solid.

    The really crazy thing is that the judge allowed the Grubbs stuff but thought the deceased's non-fatal use of diazomethane was not relevant.

    1. The description in her lab notebook makes it sound like she was using a solid: "The grubbs II was weighed..." (

  2. Did Harran just throw his postdoc to the wolves?

    1. I'm not really sure. Let's look at what was said:

      O’Brien: And Dr. Hurley said he wouldn’t necessarily clamp the bottle, is that right?
      Langerman: Yes.
      O’Brien: And in the accident involving Ms. Sangji on 29th of December, you opined after reviewing the documents that the tert-butyllithium bottle had not been clamped, right?
      Langerman: Correct.
      O’Brien: Going back to the 14th of October, when Prof. Harran was watching Ms. Sangji conduct the transfer using a non-pyrophoric, air sensitive, Prof. Harran said that she actually clamped the bottle, is that right?
      Langerman: I believe so, yes.
      O’Brien: Also, Dr. Hurley told Mr. Baudendistel that he wouldn’t necessarily use the longer needle, which is called for in the Aldrich bulletin, to transfer the tert-butyllithium, is that right?
      Langerman: Yes.
      O’Brien: And in fact, if you look at photographs, I think we put those up last month, it indicates that Ms. Sangji in her syringe transfer was also using a needle which was a short needle, is that right?
      Langerman: That’s correct.
      O’Brien: Is that part of the reason you believe Ms. Sangji had been trained, albeit improperly, by Dr. Hurley?
      Langerman: Given Dr. Hurley’s testimony of lack of memory of doing training, it’s difficult for me to develop an opinion as to what, if anything, he actually told Ms. Sangji.
      O’Brien: And again, you mentioned this earlier, I think, there were other witness transcripts that you also reviewed, and those other witnesses observed Dr. Hurley training Ms. Sangji in dealing with tert-butyllithium, is that right?
      Langerman: I don’t believe that’s what the record reflects.
      O’Brien: Do you recall some of the witnesses in the transcript observing Dr. Hurley standing with Sheri Sangji on the 17th of October when she did this reaction with tert-butyllithium?

      Langerman: I recall the testimony, but again in reading it, the observer, the person, I think it was Dr. Ding, was not sure what they were doing. So again for me, it was not clear what was going on.

      And after some discussion of Hurley’s qualifications:

      O’Brien: Do you believe it would then be reasonable for someone like Prof. Harran to rely on Dr. Hurley, a published Ph.D. on various pyrophoric substances, to be an adequate instructor in the laboratory on the transfer of pyrophoric substances?

      Langerman: Certainly to rely on, but that doesn’t relieve the requirement to make sure the training is, is, that’s being given is appropriate.
      O’Brien: I’m not saying that at all. The question is the first part. Was it reasonable in your opinion for Dr. Harran to be able to rely on Dr. Paul Hurley to construct a proper mechanism for transferring a pyrophoric substance?
      Langerman: Yes.
      O’Brien: At the bottom of page 10 of your report, sir … you include a large citation, a large quote of Prof. Harran … and this is part of again an interview that Prof. Harran gave to Mr. Baudendistel?
      Langerman: Yes.

      O’Brien: In this quote, Prof. Harran was describing how Ms. Sangji apparently conducted the experiment, is that right?
      Langerman: Yes.
      O’Brien: And Prof. Harran said, this is the last line in this, “That’s certainly not how she did experiments when I was in the lab with her at all. Uh, and I don’t know, but I certainly hope that my personnel, my senior personnel, would not ever show someone to do an experiment that way, ever.” Is that right?
      Langerman: That’s the quote, yes.
      O’Brien: You indicated in your report that Ms. Sangji had demonstrated the ability to perform a cannula transfer, yes?
      Langerman: Yes.

    2. I've been thinking Hurley bears more than a little responsibility since this began. It's the most realistic explanation to me, but still doesn't exonerate Harran, who still bears responsibility for his own lab. Hurley wasn't charged and is now past the statute of limitations, i think.

    3. The legal statute refers to "Any employer and any employee having direction,
      management, control, or custody of any employment, place of employment, or of any other employee..." [California Labor Code Section 6425(a),].

      So legally, I don't think Hurley could be charged, because he didn't fit that description: He didn't direct her work, I doubt he was given responsibility for her timesheets, etc. AND he left the lab a month before the fire.

      Charging aside, I think whether people view him as (partly) responsible is an interesting question. It sounds like he was never trained properly, either, so didn't know better. Does the fault for that lie on him, Harran, or Hurley's PhD adviser?

  3. I am by no means a legal scholar, but I find the defense's cross-examination tactic blunt and irritating. By constructing long potentially-affirmative phrases and tagging the ends of his questions with "is that right?", he's essentially weighting the odds in favor of a simple "yes" each time.

    Does this interrogation style usually appear in testimony, or is this O'Brien's "style?"

    1. My time on a jury suggests that it is standard operating procedure, annoying as it sounds to us. The lawyer would quiz his own witness the same way; basically they construct a narrative and the witness supports it, to minimize how much latitude they get, i guess. It would be particularly grating to get the same treatment as a hostile witness, though. Not sure i could stand for it for long.

    2. My answer to loaded questions in front of a judge would be "Yes and no - It depends." Then I would go on about qualifying details. I would not allow anyone to put the words in my mouths.

      With the defense tactics - it is understandable they would try to raise a reasonable doubt - it takes just one person to hang the jury... It is very easy to make the issue of personal responsibility murky when it comes to arguing technical details. In the end, it is word of one expert against another, and the emotional impact of carefully pre-packaged "evidence" on the jury.

  4. Actually, bad technique with Grubbs II catalyst gives pretty good yield. I have used it several times in direct contact with air and moisture, (once with the direct, intentional introduction of both,)with virtually no change in yield.

  5. First off, the post-doc does not bear any legal responsibility. Give them real jobs, real pay checks, real benefits, and real training, and then yes, you can talk about managerial responsibilities. But the position they have now is just another grunt laborer.

    Second, Sangji's training was ridiculously ten miles short of adequate. It wasn't even in the city, let alone the ballpark. In an industrial lab, there would have been a multi-stage review process involving numerous people, including management, before anyone got near t-butyl lithium, let alone at that scale. There would have been a written procedure, signed off by Harran, at a bare mininum.