Why is my mac unable to connect to exchange server 2010 sp3

mac os osx yosemite version 10.10.5
outlook for mac 2011 version 14.0.0 (100825)

unable to get any messages on outlook. using exchange server 2010 sp3

error if sending unexpected data was encountered. mail could not be sent. error code 17997

things tried
Error -17997

"Unexpected Data was Encountered error
Error -17997"

Can connect to Exchange server and receive mail, but when sending, the messages hang in the Outbox with error -17997, unexpected data was encountered.

Users reported these fixes:

Option 1:

: Changed the server name to the URL of used to access OWA via the your browser.
: Tick Override default port in the Outlook 2011 settings and changed the port to 442
Option 2:

The solution I had to take was to create a new identity a second time. The first time I created a new identity didn't work. I suppose there may have been something I had done to complicate matters, but I'd be hard-pressed to say what it was. Once I was sure I had all the user's mail synced and his locally-stored messages complete, I exported an .olm file, created a new identity as the default and imported the .olm file. This time I was able to send messages from the identity.
Working Steps To Fix ‘Mac Outlook Error Code 17997’:
First of all click on all the spot light search glass and then type terminal and after that press enter to open the terminal.
Now to delete the old preferences, one has to type default delete com.Microsoft.Outlook.
In the next step type killall cfprefsd. This will surely remove the cached preferences.
Finally at last try to launch the Outlook again.

Member_2_6474242Senior Systems AdministratorAsked:
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What Rollup Update you have installed on Exchange?
Get-Command ExSetup | ForEach {$_.FileVersionInfo} 

Open in new window

to confirm.
Install Rollup Update 18.
Member_2_6474242Senior Systems AdministratorAuthor Commented:
Hi Ronin

product version: 14.03.0123.004
File Version: 14.03.0123.004
Member_2_6474242Senior Systems AdministratorAuthor Commented:
tried installing update it did not update instead got the error message below

setup wizard for update rollup 18 for exchange server 2010 sp3 KB4018588 ended prematurely because of an error. you system has not been modifed. to install this program at a later time, please run the installation again
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Have you tried running Windows Update on the server?
Go to the properties and select to deploy additional software.
Member_2_6474242Senior Systems AdministratorAuthor Commented:
it says your pc is up to date no updates are available
Seems like you're running Exchange 2010 SP3,  to confirm open Exchange MMC, HELP -> ABOUT
Post the screenshot.

If that's correct the server is almost 5 years behind on Exchange updates. If that's the case the lack of updates what is probably causing MAC not to connect.

I find it extremely strange that Windows Updates on the server doesn't show you anything.  Confirm the version as advised above and we'll continue from there. There should be events in Event Logs indicating reason to the installation failure.

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Member_2_6474242Senior Systems AdministratorAuthor Commented:
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