CC on iPad Crashes with large file

Of my 200 odd files, one causes CC to crash when doing a Wireless Device transfer. CC, Calibre, iOS all at latest versions. The file is 588.6 MB, is that too big?

calibre, version 3.3.0
ERROR: Error: Error communicating with device

Device responded with incorrect information

Traceback (most recent call last):
File "site-packages/calibre/gui2/device.py", line 88, in run
File "site-packages/calibre/gui2/device.py", line 542, in _sync_booklists
File "site-packages/calibre/devices/smart_device_app/driver.py", line 50, in _synchronizer
File "site-packages/calibre/devices/smart_device_app/driver.py", line 1254, in free_space
File "site-packages/calibre/devices/smart_device_app/driver.py", line 50, in _synchronizer
File "site-packages/calibre/devices/smart_device_app/driver.py", line 633, in _call_client
File "site-packages/calibre/devices/smart_device_app/driver.py", line 675, in _receive_from_client
ControlError: Device responded with incorrect information