SELECT `user`.`email`
FROM `order`
  LEFT JOIN `click` ON `order`.`click_id` = `click`.`id`
  LEFT JOIN `shop` ON `click`.`shop_id` = `shop`.`id`
  LEFT JOIN `shop_country` ON `shop`.`id` = `shop_country`.`shop_id`
  LEFT JOIN `user` ON `click`.`user_id` = `user`.`id`
WHERE (`order`.`date_create` < '2018-06-08 00:00:00') AND
      (`shop`.`id` IN (SELECT `c`.`shop_id`
                       FROM `shop_country` `c`
                       WHERE `c`.`country_id` = '1'))