Sending multiple values to limited emails using recursion with Python?

I have the below input, where I have limited email Ids, but many ticket IDs. I would like to know how to write a condition that would enable me to send tickets to whatever email IDs are available. Plus would also want to install a condition that would say that if email IDs are more than tickets, then the recipients would get a "No tickets available" message.

I get the following error. "com_error: (-2147352567, 'Exception occurred.', (4096, 'Microsoft Outlook', 'Outlook does not recognize one or more names. ', None, 0, -2147467259), None).

What I tried:

    e = pd.read_csv('combo.csv')
    emails = e['1'].values
    ticket_number = e['2'].values
    desc_value = e['3'].values 
    for i in range(len(emails)):
    # if the email is not valid (i.e. NaN), skip the sending for this ticket
      if emails[i] == None:
        continue
        outlook = win32com.client.Dispatch("Outlook.Application")
        message = f'Hello the ticket number {ticket_number[i]} with the Description {desc_value[i]} has been assigned to ' \
                  f'you. '
        mail = outlook.CreateItem(0)
        mail.To = emails[i]
        mail.Subject = 'This is a test'
        mail.HTMLBody = message
        mail.Send()


Entire Code:

    import pandas as pd
    from selenium import webdriver
    from getpass import getpass
    from openpyxl import load_workbook
    import re
    import os
    import fnmatch
    from win32com.client import Dispatch
    import getpass
    import datetime
    import time
    import datetime as dt
    import csv
    import win32com.client
    import shutil
    
    # login to the website
    
    user_name = "username"
    password = "password"
    
    chrome_options = webdriver.ChromeOptions()
    chrome_options.add_argument("--incognito")
    
    driver = webdriver.Chrome(".\chromedriver", options=chrome_options)
    driver.get("http://drtracker.roc.com/")
    
    user_name_textbox = driver.find_element_by_id("user")
    user_name_textbox.send_keys(user_name)
    
    password_textbox = driver.find_element_by_id("pw")
    password_textbox.send_keys(password)
    
    login_button = driver.find_element_by_class_name("btn-lg")
    login_button.submit()
    
    download_csv = driver.find_element_by_link_text("export to excel")
    download_csv.click()
    
    driver.close()
    
    # move files from downloads to the working folder
    
    source = os.listdir("C:/Users/u0167154/Downloads")
    destination = "C:/Users/u0167154/PycharmProjects/Scraping"
    for files in source:
        if files.endswith(".csv"):
            shutil.move(files, destination)
    
    # Extract emails from folder in outlook
    
    Todays_Mail = dt.datetime.now() - dt.timedelta(hours=24)
    Todays_Mail = Todays_Mail.strftime('%m/%d/%Y %H:%M %p')
    # Connect to Outlook inbox
    outlook = Dispatch("Outlook.Application")
    mapi = outlook.GetNamespace("MAPI")
    
    your_folder = mapi.Folders['sunith.kokku@email.com'].Folders['Blah']
    
    blah_inbox = your_folder.Items
    
    blah_inbox = blah_inbox.Restrict("[ReceivedTime] >= '" + Todays_Mail + "'")
    
    f = open("email.csv", "w")
    f.write('Index,Emails\n')
    
    index = 0
    for message in blah_inbox:
        if message.Class == 43:
            if message.SenderEmailType == 'EX':
                print(message.Sender.GetExchangeUser().PrimarySmtpAddress)
                f.write(str(index) + ',' + message.Sender.GetExchangeUser().PrimarySmtpAddress + '\n')
                index = index + 1
    
            else:
                print(message.SenderEmailAddress)
    f.close()
    
    # pandas code to import the data, extract the IDs and Email and then combine into one csv.
    
    for file in os.listdir('./'):
        if fnmatch.fnmatch(file, '*.csv'):
            os.rename(file, 'data.csv')
            print(file)
    
    df = pd.read_csv('data.csv')
    print(df[['id', 'desc', 'assigned to']])
    df = df.fillna("NA")
    cols = ['id', 'desc', 'assigned to']
    df_list = df[cols]
    F = df_list[0:49]
    F.to_csv('extracted_ids.csv')
    
    # joining the emails and the extracted ticket IDs together into a combo file
    
    email_ids = pd.read_csv('email.csv')
    tickets = pd.read_csv('extracted_ids.csv')
    
    df1 = pd.DataFrame(email_ids)
    df2 = pd.DataFrame(tickets)
    df2.drop(df2.columns[[0]], axis=1, inplace=True)
    
    combo = df1.join(df2)
    combo.drop(combo.columns[[0]], axis=1, inplace=True)
    # nan_value = float("NaN")
    combo.to_csv('combo.csv')
    e = pd.read_csv('combo.csv')
    
    # send the mails
    
    e = pd.read_csv('combo.csv')
    emails = e['1'].values
    ticket_number = e['2'].values
    desc_value = e['3'].values
    for i in range(len(emails)):
        outlook = win32com.client.Dispatch("Outlook.Application")
        message = f'Hello the ticket number {ticket_number[i]} with the Description {desc_value[i]} has been assigned to ' \
                  f'you. '
        mail = outlook.CreateItem(0)
        mail.To = emails[i]
        mail.Subject = 'This is a test'
        mail.HTMLBody = message
        mail.Send()
    
    # save to master file
    
    df3 = pd.read_csv('combo.csv')
    writer = pd.ExcelWriter('master.xlsx', engine='openpyxl')
    # try to open an existing workbook
    writer.book = load_workbook('master.xlsx')
    # copy existing sheets
    writer.sheets = dict((ws.title, ws) for ws in writer.book.worksheets)
    # read existing file
    reader = pd.read_excel(r'master.xlsx')
    # write out the new sheet
    df3.to_excel(writer, index=False, header=False, startrow=len(reader) + 1)
    
    writer.close()
    
    # delete all CSV files
    
    dir_name = "C:/Users/u0167154/PycharmProjects/Scraping"
    delete_all = os.listdir(dir_name)
    
    for item in delete_all:
        if item.endswith(".csv"):
            os.remove(os.path.join(dir_name, item))
    
    f.close()