Stockholders' Equity (Tables)

12 Months Ended

Dec. 31, 2019

Disclosure Of Compensation Related Costs Sharebased Payments [Abstract]

Stock Option Activities of Long-Term Incentive and Option Plans

The following information relates to our long-term incentive plans:

	December 31, 2019
	2016 Plan		2008 Plan
Maximum number of securities for issuance		2,750,000
Number of awards available to be granted (1)		1,285,922
Number of unvested restricted stock/performance-based    restricted stock/restricted stock units outstanding		925,851		—
Number of options outstanding		—		124,000
Number of options exercisable		—		111,750

.

(1) Includes 2008 Plan shares canceled, forfeited, expired unexercised, which became available for reissuance under the 2016 Plan after the effective date of the 2016 Plan.

	2019
	Shares		Weighted-Average Exercise Price
Outstanding at beginning of year		124,000	$	33.86
Granted		—	$	—
Exercised		—	$	—
Forfeited or expired		—	$	—
Outstanding at end of year		124,000	$	33.86
Exercisable at end of year		111,750	$	33.91

	2019			2018			2017
Stock-based compensation expense - Cost of sales	$	122,000		$	141,000		$	317,000
Stock-based compensation expense - SG&A	$	50,000		$	71,000		$	108,000
Income tax benefit	$	(42,000	)	$	(54,000	)	$	(164,000	)
Total intrinsic value of options exercised during the year	$	—		$	—		$	—
Total fair value of options vested during the year	$	169,000		$	169,000		$	451,000
Total intrinsic value of options outstanding at end of year	$	—		$	—		$	16,000
Total intrinsic value of options exercisable at end of year	$	—		$	—		$	16,000
Total weighted-average remaining vesting period in years	0.49				1.05			1.53
Total weighted-average remaining contractual life period in years (options outstanding)	3.61				4.61			5.10
Total weighted-average remaining contractual life period in years (options exercisable)	3.47				4.31			4.44

Summary of Restricted Stock Activity

A summary of restricted stock activity during 2019 is presented below:

	Restricted Stock					Performance-Based Restricted Stock				Restricted Stock Units
	Shares			Weighted- Average Grant Date Fair Value		Shares		Weighted- Average Grant Date Fair Value		Shares			Weighted- Average Grant Date Fair Value
Unvested restricted stock outstanding at    beginning of year		739,465		$	7.79		—	$	—		68,334		$	8.23
Granted		285,956		$	4.28		221,439	$	7.26		31,833		$	5.89
Vested		(407,349	)	$	8.27		—	$	—		(13,827	)	$	13.56
Cancelled or forfeited		—		$	—		—	$	—		—		$	—
Unvested restricted stock outstanding at end    of year		618,072		$	5.42		221,439	$	7.26		86,340		$	6.51

	Restricted Stock
	2019			2018			2017
Shares of restricted stock granted		285,956			369,350			469,465
Total fair value of restricted stock granted	$	1,223,000		$	2,019,000		$	4,277,000
Weighted-average fair value per restricted stock granted during year	$	4.28		$	5.47		$	9.11
Stock-based compensation expense - Cost of sales	$	255,000		$	385,000		$	312,000
Stock-based compensation expense - SG&A (1)	$	1,263,000		$	7,574,000		$	3,987,000
Income tax benefit	$	(374,000	)	$	(398,000	)	$	(1,659,000	)
Total weighted-average remaining vesting period in years	2.18				1.78			1.95
Total fair value of restricted stock vested during the year	$	3,371,000		$	7,355,000		$	3,124,000

	Performance-Based Restricted Stock
	2019 (2)
Shares of PBRS granted		221,439
Total fair value of PBRS granted	$	1,608,000
Weighted-average fair value per PBRS granted during year	$	7.26
Stock-based compensation expense - Cost of sales	$	53,000
Stock-based compensation expense - SG&A	$	290,000
Income tax benefit	$	(84,000	)
Total weighted-average remaining vesting period in years		1.85
Total fair value of PBRS vested during the year	$	-

	Restricted Stock Units
	2019			2018			2017
Shares of RSU granted		31,833			35,511			37,992
Total fair value of RSU granted	$	187,000		$	187,000		$	375,000
Weighted-average fair value per RSU granted during year	$	5.89		$	5.28		$	9.87
Stock-based compensation expense - SG&A	$	187,000		$	187,000		$	375,000
Income tax benefit	$	(46,000	)	$	(34,000	)	$	(115,000	)
Total weighted-average remaining vesting period in years		1.57			1.75			3.05
Total fair value of RSU vested during the year	$	187,000		$	125,000		$	250,000

(1) As it relates to 2018, see Note 14-Related Party Transactions.

(2) The PBRS restricted stock grants are tied to our free cash flow, fixed costs per ton of ammonia measured annually over a three-year period and modified based on our ranking relative to total stockholder return (share price appreciation plus dividends reinvested) (“TSR”) versus the companies in our 2019 peer group (“Peer Group”) over a three-year measurement period. The actual number of shares that will vest at the end of the third year will be based on our performance against the metrics set in the award. The threshold performance for free cash flow is 70% and for fixed costs per ton of ammonia is 50% of the targeted improvement with a maximum for each of 120% of target. The TSR modifier will adjust the overall actual performance up or down by as much as 25% based on the our TSR versus the Peer Group average TSR. We estimate the fair value of each PBRS on the date of grant using a Monte Carlo simulation.